PUBLISHED BY THE AMERICAN CHEMICAL SOCIETY

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CENEAR 89 (29) 1–40 • ISSN 0009-2347

VOLUME 89, NUMBER 29

JULY 18, 2011

COVER: Courtesy of Kerry Maloney for the Louisiana Seafood Promotion & Marketing Board

“When we try to make new molecules, we can’t predict whether one will be a safe one and one will be a bad one. We’d like to be able to do that.”LAURENCE E. FRIED, CHEMIST, LAWRENCE

LIVERMORE NATIONAL

LABORATORY’S

HIGH EXPLOSIVES

APPLICATIONS

FACILITY PAGE 32

32 EXPLOSIVE R&D Collaborators test all aspects of explosives under one roof.

29 POLYMER-BASED ARTConservators grapple with plastics preservation.

35 “A CUBIC MILE OF OIL”Authors offer a logical, nonpolitical plan to address energy challenges before us.

27 CONCENTRATES

23 CANCER FIGHTEven with improved research methods, the road to a cure is still a long one.

25 STREAMLINING TOXICITY TESTSEPA moves toward faster chemical safety assessments.

24 CONCENTRATES

21 COSMETICS RESEARCHScientists are using plant stem cells to develop new skin care products.

19 ALGAE FIRMS DIVERSIFYCompanies probe nonfuel markets for higher profit margins.

17 CONCENTRATES

11 DRUG SUPPLY OVERSIGHTReport cites measures that could mitigate risks in the global pharmaceutical supply chain.

11 MATERIALS ADVANCEElectrochemical cell based on same-metal electrodes—one doped with a dye—is a first.

10 PROBING NUCLEAR PLANT SAFETYU.S. nuclear power plants require additional safeguards against natural disasters, expert panel says.

10 SIMPLIFYING RISK EVALUATIONEPA says it will abbreviate and clarify scientific reasoning behind chemical risk assessments.

9 BLAMING DUPONTSafety board finds the company negligent in a series of accidents, one fatal, in 2010.

9 LONZA TO BUY ARCH CHEMICALSMove will cushion Swiss firm’s pharmaceutical ingredients business, nab a share of market for antimicrobials.

8 INK-JET ELECTRONICSOrganic flexible electronics can now be produced with ink-jet printers, researchers show.

8 NEW ATTACK ON HIVNIH program will pair academic researchers with industry labs to redouble the fight.

7 CASCADE OF NATURAL PRODUCTSCollective synthesis produces complex targets in fewer steps than ever before.

SEAFOOD SCRUTINY

One year after the Gulf oil spill, fishing waters are

open and sample analyses detect few problems,

but not everyone is reassured. PAGE 12

QUOTE OF THE WEEK

COVER STORY

NEWS OF THE WEEK

BUSINESS

GOVERNMENT & POLICY

SCIENCE & TECHNOLOGY

BOOKS

40 NEWSCRIPTS37 OBITUARIES

38 CLASSIFIEDS4 LETTERS3 EDITOR’S PAGE

THE DEPARTMENTS

▶

29

32

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3WWW.CEN-ONLINE.ORG JULY 18, 2011

FROM THE EDITOR

Views expressed on this page are those of the author and not necessarily those of ACS.

Editor-in-chief

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Copyright 2011, American Chemical SocietyCanadian GST Reg. No. R127571347

Volume 89, Number 29

WHAT KIND of nation do we want to live in? That’s really the fundamental question that underlies the epic debate over raising the U.S. debt ceiling and future budgets.

It’s not about freedom. The citizens of Germany, France, and the U.K.—all nations with social welfare systems that are more developed than that of the U.S.—are as free as U.S. citizens are. They are less free in some ways, more free in others. It balances out. They have better health care; we have more guns. It all depends on what matters to you.

Here is the kind of country we’re mov-ing toward: On June 16, the Washington Post reported that, in order to reduce the deficit, the House of Representatives ap-proved $750 million to fund a food safety law passed by the previous Congress, $205 million less than President Obama had re-quested and $87 million less than the Food & Drug Administration is currently receiv-ing to guard the nation’s food supply. The House also voted to cut $35 million from the Department of Agriculture’s food safety inspection service.

The Post reported that Rep. Jack Kings-ton (R-Ga.) said the cuts were justified be-cause the nation’s food supply was “99.99 percent safe.”

For simplicity’s sake, let’s say there are 300 million U.S. citizens, and they eat three meals and a snack per day. That’s 1.2 billion “eating events” per day, or 438 billion eat-ing events per year. According to the Post , the Centers for Disease Control & Preven-tion estimates that 48 million Americans get sick from tainted food each year. If we define “safe” as 48 million cases of disease per 438 billion eating events, with 28,000 of those who get sick winding up in the hospi-tal and 3,000 dying, then the nation’s food supply is, in fact, 99.989% safe.

Do you think that this definition of a safe food supply, in which as many people die each year as died in the 9/11 attacks, is adequate?

The June 6 New York Times had an article entitled “In State Parks, the Sharpest Ax Is the Budget’s.” States are closing parks permanently in response to budget deficits. States that previously didn’t charge for en-try to state parks now are. Among park of-ficials, the Times reports, “The resignation

some feel … is rooted in a broader sense nationwide that the status of parks has per-manently changed. … [S]ome officials also worry that rising fees, rising gas prices and a need to ‘market’ parks to people who will spend money will keep those with lower incomes from enjoying public lands.”

It’s so Milton Friedmanesque. There’s no need for government to pay for or offset the costs of common goods and services in this crabbed world. If people want some-thing, they’ll pay for it. If they don’t, they won’t. If they would like to, say, take their kids to a state park but they can’t afford to pay the entrance fee, well, they’re out of luck.

One more example: Last week, the House Committee on Appropriations’ Sub-committee on Commerce, Justice, Science & Related Agencies funded NASA at $16.8 billion in 2012, $1.6 billion below the 2011 budget and $1.9 billion below President Obama’s request. The subcommittee’s bill “terminates funding for the James Webb Space Telescope, which is billions of dollars over budget and plagued by poor manage-ment,” according to the subcommittee.

The new telescope (JWST) is a techno-logical marvel that will be 100 times more powerful than the Hubble Space Telescope, which revolutionized our view of the cos-mos. An independent review of the JWST program last year concluded that it is about $1.5 billion over its $5 billion budget and one to three years behind schedule. That’s not ideal, obviously, but it’s also not un-common for projects such as the JWST. Killing the telescope—which is well along toward being built—reflects a lack of imagi-nation and belief in the future of scientific exploration.

The U.S. is not broke. It is still the rich-est nation on Earth. As a nation, however, we seem to be in the process of losing our faith in the future and unwilling to protect our citizens from bad food and substandard drugs, invest in infrastructure, and con-tinue to advance science. It’s a shame.

Thanks for reading.

What Kind Of Nation?

4WWW.CEN-ONLINE.ORG JULY 18, 2011

THIS WEEKONLINE

cen-online.org/thisweek

LETTERS

How Dirty Is The Yellow School Bus?As yellow buses transport children to and from school, their diesel engines deliver heavy doses of air pollutants. In response, school districts have started

retrofitting their buses to cut tailpipe emissions. A new study shows that while these measures may help clean outdoor air, they have virtually no im-pact on the air inside bus cabins.cenm.ag/env46

Greening Mortar With Olive WasteThe cement industry is one of the world’s largest producers of atmo-spheric carbon dioxide. Now research-ers have shown that they can replace up to 10% of the cement in mortar mix-tures without harming the strength of the widely used masonry paste. The ce-ment's replacement is environmentally friendly, to boot: a waste product from olive oil production.cenm.ag/env47

Zafgen’s Obesity Drug Shows PromiseDespite FDA’s rejection of high-profile weight-loss drugs in the past year, phar-maceutical company Zafgen scored $33 million in venture financing to help move its experimental obesity drug ZGN-433 through clinical trials. Guest blogger SeeArrOh, an industry chemist, guesses at how the drug may work in the body and describes some unusual chemical features of the molecule.cenm.ag/blg25

Algal Oil Spreads Its WingsFresh off his company’s raising $227 million in its initial public offering, So-lazyme executive Cameron Byers de-scribes to C&EN the algae firm’s strate-gies for being both environmentally and economically sustainable. He tells of the advantages of designer oils from algae serving as feedstocks for manu-facturers of chemicals and personal care products.cenm.ag/blg24

SH

UT

TE

RS

TO

CK

USEFUL INFORMATION ON BISPHENOL A

I COMMEND C&EN on the outstanding cover story articles by Stephen Ritter on BPA ( C&EN, June 6, page 13 ). They cer-tainly helped put the issues in perspective. That many cash-register printouts contain BPA was news to me. This mode of contact with BPA suggests that a study of cashiers, who have the greatest exposure, and their health records is long overdue.Sandra G. RosenthalErdenheim, Pa.

THANK YOU for Ritter’s articles on BPA. This is the best material I have found on the Web, in terms of completeness and balance, on this difficult topic. One potentially sig-nificant source of ingested BPA that was not mentioned, however, could represent one of the most prevalent sources of continuous low-dose ingested BPA: The standard liner used for water tanks is BPA-based epoxy.

These liners continuously leach BPA into the water they contain. In addition, these epoxy liners break down over time, and the particulates from the disintegrat-ing epoxy also enter the water systems they supply. As a result of the deterioration of these linings, the tanks periodically need to be emptied, scraped, cleaned, and relined with more epoxy.

Visualize these water tanks baking in the hot sunlight and consider the evidence of how heat increases the amount of BPA leached into the contents of cans, bottles, and other plastic containers. This applies to municipal water tanks as well as indus-trial water tanks, including those used in the food-processing industry.

Everyone drinking, cooking with, and bathing or showering in water from munici-pal systems is continually ingesting and be-ing bathed in BPA-laced water. Also, all food processed in water from epoxy-lined tanks is being laced with BPA, even if it might not be packed in water and even if it is pack-aged in BPA-free containers. This makes it almost impossible for most people to avoid ingesting low doses of BPA. I don’t find it at all surprising that BPA “shows up at low lev-els in the urine of essentially everyone.”

This struck a chord with me because of my past experience as a city official (city council and mayor), during which time our municipal water tank needed to be relined and the only option offered to replace the deteriorated epoxy lining was epoxy. That

was many years ago, long before I had any awareness that BPA might present any prob-lems. If you can do anything to help bring this aspect of the BPA issue to light, it would be a very valuable service. And I bring this up even though I’m not hooked up to a mu-nicipal water system; I have my own well.Carl KarastiWinton, Minn.

THE ARTICLES on BPA and a follow-up in Latest News were most welcome and informative. As a health researcher, I would like to comment on this debate. Although BPA toxicity is of concern for human health (hence the voluminous ongoing research), exposures are low as currently measured using urinary biomarkers—the medians in virtually all study populations are around 2–3 µg/L.

Moreover, the range is quite small, and limited variability in exposure poses prob-lems for epidemiologic investigations. First, narrow variability alters statistical power. Next, it is possible that specimen contamination may be responsible for part of low measured levels, although as the article mentions, dietary and other sources may also account for some of the body burden. Adequate precautions to limit or to measure contamination during specimen preparation have been taken in few if any human exposure studies.

Urinary biomarkers overcome some but not all contamination issues, while blood biomarkers of BPA likely represent only contamination. In addition, low measure-ment levels result in more noise in the ex-posure variable (by definition a multiple of method noise), which may lead to unusual statistical associations, including inverse relationships if the exposure measure is es-sentially a small numerator (exposure bio-marker) divided by a larger denominator

ACS BOARD OF DIRECTORS OPEN SESSION

The ACS Board of Directors will hold its Open Session on Sunday, Aug. 28, from noon to 1 PM in the Colorado Convention Center, Room 201/203. You are invited to participate in a lunchtime discussion with the board on the topic, “What the ACS is doing to assist members who are facing employment challenges in uncertain eco-nomic times.” The board welcomes your observations and suggestions. Sandwich-es and soft drinks will be available.

5WWW.CEN-ONLINE.ORG JULY 18, 2011

(urinary dilution factor), tantamount to 1/x.Furthermore, some study designs may

not be appropriate to examine a hypothesis about BPA and health; for example, vari-ous reports of BPA in relation to health use convenience cross-sectional data sets. Existing knowledge of exposure patterns as well as biomarker pharmacokinetics and consistency over time makes it difficult to comprehend how concurrently measured BPA represents exposure across the latency period of a chronic disease. BPA levels in urine are correlated with numerous other contaminants; therefore, BPA urinary bio-markers may be a surrogate for correlated urinary metabolites and may signify rela-tionships with multiple body contaminants.

A great advance for health research has been to exploit new technology to measure very low levels of exposure, but more at-tention should be paid to whether such measures are realistic for epidemiology or toxicology.Mary S. WolffNew York City

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news of the week

BY COMBINING small-molecule organic cataly-sis and “cascade reactions”—domino reactions performed in a single shot—researchers have

achieved “collective total synthesis,” the production of several complex synthetic targets from a com-mon molecular branch point (Nature, DOI: 10.1038/na ture10232 ).

Chemistry professor David W. C. MacMillan and coworkers at Princeton University devised the ap-proach, which could ease the large-scale production of natural products and natural-product-like com-pounds for drug discovery and other applications.

Synthesizing complex organic molecules is tradi-tionally a one-at-a-time affair, with obstacles progres-sively overcome to reach single target structures, often created in only modest yields. Collective total synthesis uses small-molecule organocatalysts and cascade reactions to surpass the time and yield limita-tions of conventional synthesis.

The Princeton team used collective total synthe-sis to produce the neurotoxin strychnine and five other compounds in three families of alkaloid natural products, some in a record low number of synthetic steps. For example, they made (−)-strychnine in 12 steps from commercially available starting materials, compared with 25 steps in the best previous catalytic asymmetric synthesis.

They used two imidazolidinone-catalyzed organo-cascade cycles to convert tryptamine and propynal starting materials to a common tetracyclic intermedi-ate. They then elaborated the tetracycle into the six alkaloids—two each from Strychnos, Aspidosperma, and Kopsia plants.

Some of the team’s endgames—tailoring of the common intermediate into final products—began in the middle of others, minimizing the total number of steps to produce all of the products together. The re-searchers note that the collective synthesis of the six alkaloids took a total of 34 steps, compared with 76 for the shortest previous comparable syntheses.

Advancing a common intermediate to several natural products is not new, and the researchers’ end-games were based on previously established proce-dures. But achieving uniquely short syntheses of natu-

ral products by combining the common-intermediate concept with organocatalysis and cascade reactions is novel.

The work “clearly demonstrates for the first time the synthetic value of a combination of organocas-cade catalysis with the use of a common intermediate, a ‘synthetic joint,’ to reach a variety of related natural-product targets,” comments Dieter Enders , an or-ganocatalysis expert at RWTH Aachen University, in Germany. “The elegance of the synthetic protocols and the drastic shortening of the number of synthetic steps toward the final alkaloids, as compared to the previous methodology, is most impressive.”

The combination of cascade catalysis and collec-tive total synthesis “demonstrates advantages over the classical stop-and-go approach and is clearly the future of small-molecule synthesis,” says former MacMillan postdoc Christoph Grondal, a specialist in organocascade reactions, now at Bayer CropScience in Germany.

MacMillan and coworkers hope to extend the ap-proach to additional families of natural products and natural-product-like compounds. —STU BORMAN

TOTAL SYNTHESIS: Organocatalyzed domino reactions speed assembly

of multiple natural products

A CASCADE OF NATURAL PRODUCTS

JULY 18, 2011 EDITED BY WILLIAM G. SCHULZ & KIMBERLY R. TWAMBLY

Im = iminium-activated cascade, H+ = protonation-induced cascade, R = 1-naphthyl, R = butoxycarbonyl, R´ = benzyl or p-methoxybenzyl

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COLLECTIVE SYNTHESIS Approach yields alkaloids more e� ciently than ever before.

THE NATIONAL INSTITUTES of Health is provid-ing three research teams—each consisting of an academic and an industry partner—with up to

five years of funding to develop new strategies for com-bating HIV. The agency plans to spend as much as $70 million to support the new anti-HIV research program.

Merck & Co. will participate in two of the three projects, joining forces with the University of North Carolina, Chapel Hill, and the University of California, San Francisco, which will receive $6.3 million and $4.2 million, respectively, in the first year of the project. The third project pairs Sangamo Biosciences with the Fred Hutchinson Cancer Research Center , in Seattle, which will receive $4.1 million in the first year.

Each team will take a different approach to battling

HIV that resists treatment with antiretroviral therapy. The first step to finding better medicine is improving understanding of the complex biology of the infection, according to Daria J. Hazuda, head of discovery for in-fectious disease at Merck Research Laboratories.

Hazuda says the scientists plan to explore several fun-damental questions, including why the virus persists de-spite highly effective therapy, whether current therapy is less effective in specific cells or tissues, and what mecha-nisms the virus uses to remain silent in cells and then activate after a patient has stopped therapy. The groups will attempt to develop better animal models, which have been “one of the biggest gaps in the field,” she says.

By pairing academics who have expertise in clinical virology, mouse-model systems, and pharmacology with industry partners that are skilled in translating re-search findings into drugs, the programs are expected to overcome some of the historical barriers to progress in fighting HIV, Hazuda adds.

“This will be an important model for many disease ar-eas moving forward,” Hazuda says. “We’re at a point now where we’re trying to tackle many diseases, like HIV, where there are significant gaps in the underlying biolo-gy. We really need to work together with external experts in the field to move these areas along.” —LISA JARVIS

PARTNERING: Merck, Sangamo, and NIH will join universities to

combat HIV drug resistance

A NEW PUSH AGAINST HIV

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NEWS OF THE WEEK

A B

A B

ORGANIC FLEXIBLE ELECTRONICS—a class of circuits that scientists are developing for radio-frequency identification tags, sensors,

and computer displays—can now be produced with a simple ink-jet printing method that’s faster and more chemically versatile than previous methods, according

to a letter in Nature (DOI: 10.1038/nature10313 ).A research team led by Tatsuo Hasegawa of the National Institute of Advanced Industrial Sci-ence & Technology, in Tsukuba, Japan, has suc-

cessfully printed thin single-crystal films of a semicon-ducting benzothiophene-based molecule on a silicon dioxide surface. The research-

ers accomplished the feat by floating the molecule on top of an evaporating droplet on the patterned SiO2 surface.

Although single-crystal semiconducting thin

films have been patterned onto surfaces previously, via vapor- and solution-phase approaches, the rapid new ink-jet method will broaden the range of organic compounds researchers can explore for use in flexible electronics, says Antonio Facchetti , chief technology officer at electronic materials supplier Polyera Corp. , in Illinois. “Single-crystal-based devices represent the ultimate in performance for semiconductors because of the absence of grain boundaries,” which interrupt the flow of charge carriers, he adds.

To print the single-crystal films, Hasegawa and his team first patterned the SiO2 surface with small hydro-philic areas of a particular shape. Then, they rapidly deposited on those surface patches droplets of N,N-dimethylformamide, which does not dissolve, and thus is an antisolvent of, the benzothiophene molecule.

Finally, they added droplets of the molecule dissolved in dichlorobenzene. As both solvent and antisolvent evaporate, the benzothiophene molecules grow into a single-crystal film. Compared with single-solvent ink-jet

printing, this dual-solvent approach pro-duces more uniformly thick films.

The researchers tested the method by incorporating a printed benzothiophene-containing film into a field-effect transistor, an electronic circuit compo-nent that acts as a voltage-controlled switch. The device performed as well as, if not better than, other transistors made with organic semiconducting single-crystal films.

The next steps for the team, Hasegawa says, are to enable the ink-jet technique to print electrical metal wires and then print an entire electronic circuit. —LAUREN WOLF

ELECTRONICS: Ink-jet method makes ordered semiconducting layers

PRINTING SINGLE-CRYSTAL FILMS

During printing (from top), antisolvent (A) is deposited on a patterned surface, followed by a solution of semiconducting organic molecules (B). The molecules form a single-crystal film that solidifies as the liquids evaporate.

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NEWS OF THE WEEK

Had DuPont followed its own safety recommendations, it might have avoided a series of accidents at its Belle, W.Va., plant in 2010 that caused the deathof one worker, the Chemical Safety & Hazard Investigation Board (CSB) con-cluded in a preliminary report, released on July 7 at a news conference in Wash-ington, D.C.

The death was caused by a braided pipe that burst, spraying a worker with phosgene ( C&EN, Feb. 1, 2010, page 8 ). DuPont records show that the pipe had not been maintained properly and that

the company was aware of the safety is-sue and was considering upgrading to a safer pipe material and improving other phosgene safety measures. But the firm never made the changes, CSB found.

“These kinds of findings would cause us great concern at any chemical plant, but particularly at DuPont, with its his-torically strong work and safety culture,” CSB member John Bresland said at the news conference. “I would hope that Du-Pont officials are examining the safety culture company-wide.”

DuPont says it has completed its own

investigation of the accidents and is fully cooperating with CSB as well as state and federal agencies. The company also says it has implemented many of the recommendations of the CSB report for the Belle facility. These include perform-ing an intensive safety operations review, improving the hose maintenance system, strengthening its process hazards review system, and initiating a new alarm man-agement system.

CSB will accept public comments on its draft report through Aug. 22. —DAVID HANSON

INVESTIGATION Safety board report on 2010 accidents says DuPont was lax on safety action

TO HELP SHIFT its business away from the vola-tile active pharmaceutical ingredient (API) area, Lonza plans to acquire Arch Chemicals in a $1.4

billion cash deal. Although it will still have a leading position in custom manufacturing, the Swiss company will benefit from a new 15% share of the $10 billion-per-year antimicrobial market.

The deal offers a “unique opportunity” and “marks the next step of Lonza building a world-class life science company,” Lonza CEO Stefan Borgas said in a confer-ence call with analysts. The combined company will have about $4.3 billion in annual sales, with 43% in mi-crobial control products, 35% in custom API manufac-turing, and 22% in life sciences and nutrition products.

Custom manufacturing, especially for biologics, currently accounts for more than half of Lonza’s sales, whereas microbial control is about 14% of sales. Acquir-ing Arch will help strengthen and balance Lonza’s port-folio in many ways, Borgas said, and Lonza can improve Arch’s profitability. He also expects that Lonza’s cus-tom manufacturing business will continue to grow.

Despite Borgas’ assurances, investment analysts question the attractiveness of buying a less profitable, cyclical, and mature business at what some call a hefty price. Lonza’s dramatic shift away from pharmaceutical ingredients is “an effort to rebalance the business to-ward industrial end markets to reduce the risk attached to the declining opportunities within recombinant pro-duction technology,” Citigroup Global Markets analyst Dominik Frauendienst told clients.

About 86% of Arch’s $1.4 billion in annual sales falls into four microbial control areas: water products, wood protection, industrial biocides, and personal care. Lonza will support Arch’s decision to find a buyer for its perfor-mance products business, which had sales of $186 million in 2010.

Arch has 23 primary manufactur-ing and research facilities around the world and employs about 3,000 people. Lonza operates six antimicrobials pro-duction locations with a workforce of 550. The acquisition will expand Lon-za’s business in China, India, Brazil, and South Africa, which are among the fastest-growing markets for microbial control.

Because the companies’ products are complementary, Lonza notes, anti trust issues should be avoided and sales in the firms’ respective markets have the potential to expand. In fact, Lonza expects to generate $40 mil-lion in new sales within three years by leveraging the technical capabilities, applications expertise, and extended reach of the two businesses. New formulations should emerge quickly by combining al-ready approved microbial agents, and the company’s larger scale will enable it to invest in R&D for new products, Borgas explained.

Lonza expects $50 million in annual cost savings, largely by eliminating redundant administrative func-tions. Taking advantage of the strong Swiss franc, it will finance the purchase entirely through debt. After buying Arch stock—at a 37% premium to the firm’s recent share price—and getting regulatory approvals, Lonza hopes to close the deal later this year. —ANN THAYER

LONZA TO BUY ARCH CHEMICALS

SPECIALTIES: Acquisition will make the Swiss company a leader in the microbial control market

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Arch Chemicals supplies biocides for use in antibacterial soaps.

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NEWS OF THE WEEK

FUTURE FEDERAL assessments of chemicals’ health hazards will be shorter and clearer and will present the scientific rationale behind them,

the Environmental Protection Agency announced last week.

The changes affect EPA’s database of chemical toxic-ity information. Called the Integrated Risk Information System (IRIS), it contains the agency’s scientific judg-ments on the safe daily dose of more than 540 chemi-cals. Environmental and health regulators in the U.S. and around the world rely on IRIS as they decide on the degree of cleanup that polluters must undertake at a contaminated site or how much to limit human expo-sure to a chemical.

EPA’s assessments, which take years or even decades to complete, have come under attack from industry. For instance, chemical manufacturers have complained about the lack of information on how the agency chooses

to include or exclude scientific studies in assessments.Now, that situation is changing.“People will be able to understand the basis of our

calls, the basis of our determinations,” says Paul T. An-astas, head of EPA’s Office of Research & Development.

“EPA will evaluate and describe the strengths and weaknesses of critical studies in a more uniform way,” according to an agency statement. “EPA will also indi-cate which criteria were most influential in evaluating the weight of the scientific evidence supporting its choice of toxicity values.”

IRIS documents will always be scientifically and tech-nically complex, Anastas says. But future assessments will convey information more clearly in part through greater use of graphs and tables of data.

The changes will be phased in over time and will most heavily affect chemical assessments that are now in their beginning stages, Anastas says.

“We’re pleased to see EPA recognizes the need to reform IRIS,” says Scott Jensen, spokesman for the American Chemistry Council, a trade association of chemical manufacturers.

EPA’s move implements recommendations for im-proving IRIS that the National Research Council tucked into its recent report criticizing the agency’s assess-ment of formaldehyde (C&EN, April 18, page 10). The NRC panel said EPA needed to improve accessibility to and transparency of its assessments. —CHERYL HOGUE

TRANSPARENCY: EPA chemical assessments to become more concise,

describe scientific decisions

BETTER HAZARD INFORMATION

Anastas

EP

A

TOUGHER RULES are needed to improve the safety of U.S. nuclear power facilities and to better protect the public from the type of di-

saster that occurred this spring at Japan’s Fukushima Daiichi nuclear energy plant, says a preliminary re-port released by the Nuclear Regulatory Commission (NRC) on July 12.

Nonetheless, the report recognizes that nuclear plants can be operated safely and declares that “a sequence of events like the Fukushima accident is unlikely to occur in the U.S.” However, it adds that a U.S. nuclear power “accident involving core damage and uncontrolled release of radioactivity to the envi-ronment, even one without significant health conse-quences, is inherently unacceptable.”

A “patchwork” of existing regulations developed over the decades should be replaced with a “logical, system-atic, and coherent regulatory framework” to further bol-ster reactor safety in the U.S., according to the report,

which was prepared by a task force of nuclear power experts. NRC ordered the panel’s 90-day review of the safety and level of emergency preparedness of the 104 U.S. nuclear reactors after Japan’s March 11 earthquake and tsunami triggered an ongoing nuclear crisis.

Plant operators in the U.S., the report continues, should reevaluate and upgrade, if necessary, protec-tions against earthquakes and floods; secure backup power and instrumentation to monitor and cool spent-fuel pools after a natural disaster; and ensure that emergency plans address prolonged station blackouts and events involving multiple reactors at a single site.

Rep. Edward J. Markey of Massachusetts, the top Democrat on the House Natural Resources Commit-tee and a longtime critic of the nuclear power industry, urged NRC to move quickly to adopt the task force’s recommendations. “America’s nuclear fleet remains vulnerable to a similar disaster,” he says.

But Sen. James M. Inhofe (R-Okla.), the Environ-ment & Public Works Committee’s ranking member, cautions against sudden, sweeping regulatory revi-sions. “Changes in our system may be necessary,” he says, but “a nuclear accident in Japan should not au-tomatically be viewed as an indictment of U.S. institu-tional structures and nuclear safety requirements.”

The short-term review will be followed by a more in-depth analysis by the task force. That report is due in January 2012. —GLENN HESS

REVIEW: U.S. nuclear plants need stronger safeguards for

catastrophic events, panel says

SPOTLIGHT ON NUCLEAR POWER

Nuclear power plants need to reevaluate their earthquake and flood risks, says a panel studying Japan’s reactor crisis.

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NEWS OF THE WEEK

Keeping the public safe in an age of global pharmaceutical sourcing requires improved safety testing standards, great-er industry oversight of contract manu-facturers and suppliers, and expanded enforcement authority for FDA backed by stronger penalties and clearer account-ability, says a new report from the Pew Charitable Trusts .

The study, released last week on Capi-tol Hill, looks at risks posed to consumers by the increasingly global nature of the pharmaceutical supply chain. It focuses

on the challenges of quality manage-ment, barriers to FDA oversight, and the potential for crime in drug distribution.

The report also includes a raft of poli-cy recommendations.

Titled “After Heparin: Protecting Con-sumers from the Risks of Substandard and Counterfeit Drugs,” Pew’s report presents case histories of drug adultera-tion, including the heparin recall of 2008, and statistics illustrating a steep rise in the number of overseas pharmaceuti-cal suppliers to the U.S. According to

Pew, 80% of active ingredients and bulk chemicals used in drugs in the U.S. are currently imported.

Tougher regulations and more strin-gent oversight on the part of manufactur-ers are required “to remove the competi-tive advantage of noncompliance, which currently exists for companies able to flout the law beyond FDA’s reach,” said Deborah Autor, compliance director at FDA’s Center for Drug Evaluation & Research, in her remarks to the forum. —RICK MULLIN

PHARMACEUTICALS Report recommends measures to mitigate risk in a global supply chain

ISRAELI CHEMISTS have demonstrated a new con-cept in electrochemistry: a circuit in which the two electrodes—one doped with an organic

dye—are made of the same metal. The work could lead to new types of electrode materials for use in batteries and fuel cells.

Electrochemical cells are classically prepared with a pair of electrodes made of different metals to establish a potential difference and drive a current, such as in Alessandro Volta’s origi-nal copper/zinc battery built in 1800. But David Avnir and Ofer Sinai of Hebrew University of Jerusalem have pulled off the feat of using the same metal for both electrodes: one made of pure silver and the other made of silver infused with the diazo compound Congo red (Chem. Mater., DOI: 10.1021/cm2000655 ).

Avnir’s group previously developed a method to dope metals with a few weight percent of small organic mole-cules, polymers, organometallic catalysts, and enzymes to make new catalyst materials (C&EN, Dec. 22, 2008, page 13). They create the composites, designated as organics@metals, by reducing metal ions in a solution containing the dopant. As the metal is reduced, nano-crystallites form and then aggregate into a porous mate-rial that preserves many of the pure metal’s properties.

In analyzing a Congo red@silver electrode, Avnir and Sinai found that the composite’s electrode poten-

tial is different enough from that of a similarly pre-pared pure silver electrode to create a simple electro-chemical cell. The researchers inserted the fabricated electrodes into a lemon, which served as the electrolyte solution, a tactic commonly used by schoolchildren to build circuits for science fair projects.

By connecting the electrodes through an external circuit, they established enough current flow to power a light-emitting diode; when they used two pure silver

electrodes, the LED didn’t light up. Avnir and Sinai showed that the potential difference origi-nates from the different rates of reactions taking place at the elec-

trodes, rather than by different types of reactions.

“This is a really elegant piece of work—bona fide sci-ence that has an artistic side,” says catalyst materials scientist Gadi Rothenberg of the University of Amster-dam. The research is an eye-opener, Rothenberg ob-serves, and not just for using a lemon to help “see the light.”

The experiment’s great value, he notes, is in demonstrating a conceptual change in the way electrode materials are made, which is “essential for helping bring about step changes in technology.”

Besides developing new types of batteries based on one doped and one un-doped electrode or two differently doped electrodes, the technology could be used to improve metal corrosion resistance in industrial applications, Avnir points out. It also could allow cheaper metals such as iron to replace platinum electrodes in water-splitting applications in fuel cells for electric cars, he says. —STEVE RITTER

MATERIALS CHEMISTRY: Electrochemical cell based on

same-metal electrodes is a first

SILVER SOLOS IN LEMON CIRCUIT

One doped and one undoped silver electrode stuck in a lemon have enough potential difference to trigger the external circuit and light up a red LED.

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COVER STORY

THE EXPLOSION of BP’s Deepwater Ho-rizon oil rig caused 4.9 million barrels of oil to be dumped into the Gulf of Mexico. Of that total, an estimated 17% was recovered and close to 8% was skimmed or burned off. More than one-third is believed to have evaporated, dissolved, or dispersed naturally, and about 16% was dispersed chemically. The fate of the remaining oil—roughly 1 million bbl—is uncertain.

Within two weeks of the April 20, 2010, disaster, the National Oceanic & Atmo-spheric Administration began closing federal waters to fishing. By June 2, the clo-sures reached a peak when 88,522 sq miles, or 37% of the Gulf, were declared off-limits. After the wellhead was sealed in mid-July, NOAA began to reopen large areas. With the reopening on April 19, 2011, of the last

1,041-sq-mile sector immediately around the wellhead, the entire Gulf was open to fishing a year after the spill.

The closings had a massive impact on the Gulf Coast seafood industry. Gulf fish-ermen harvest some 1.3 billion lb per year of fish, crabs, oysters, and shrimp—about 20% of U.S. commercial seafood produc-tion. Oiled areas were closed to prevent contaminated seafood from reaching the market, and fishing was allowed only after all sampled seafood tested clean.

Putting a testing process in place took a concerted effort. NOAA, in cooperation with the Food & Drug Administration , the Environmental Protection Agency, and state authorities, agreed on a reopening protocol that included analytical testing for contaminants. Of greatest concern

were potentially toxic and carcinogenic polycyclic aromatic hydrocarbons (PAHs) and the chemicals in the dispersants. Sur-veillance testing is ongoing.

“We’re very confident that the steps that we have put in place to ensure the safety of seafood have worked,” says Donald W. Kraemer, acting deputy director of FDA’s Center for Food Safety & Applied Nutri-tion, in a video posted on the agency’s website. “We had an extensive program of sampling at that time and since then, and the results have consistently been 100 to 1,000 times below our levels of concern.”

Balancing consumer protection with the seafood industry’s desire to get back in business required analytical methods that could provide answers quickly with-out compromising accuracy, reliability, or safety. Multiple FDA, NOAA, and state labs worked to refine testing procedures, cre-ate new ones, and put them into practice.

TESTING GULF SEAFOODAfter the oil spill, ANALYTICAL PROTOCOLS to assess contaminants in seafood

found few problems, but the public and some scientists are not reassured ANN M. THAYER, C&EN HOUSTON

MORE ONLINESee a comparison of risk assessment parameters for different oil spills at C&EN Online, cenm.ag/gulf.

SNIFF TEST Steven Wilson, chief quality officer for NOAA’s Seafood Inspection Program, demonstrates sensory analysis of a sample of shrimp.

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Although the tests themselves are consid-ered adequate, environmental groups and academic researchers have raised concerns about the government’s overall approach to risk assessment.

Experience from previous spills gave regulators an understanding of which PAHs to test for and how long it takes animals to clear oil from their systems, ac-cording to Kraemer. Oysters, for example, are the first to pick up contaminants, and they hold on to them the longest. Finfish, or non-shellfish, metabolize PAHs much faster and have a low potential to accumu-late them in their tissue and transfer them up the food chain, according to NOAA. Shrimp and crabs fall in between.

ON THE BASIS of such knowledge, levels of concern (LOCs) for contaminants in sea-food were set in the reopening protocol by using what Kraemer has called “very con-servative estimates” for people’s seafood consumption and exposure duration. LOCs fell into the range of hundreds of parts per million for chemicals that FDA viewed as not potentially carcinogenic to as low as parts per billion for more harmful ones.

All seafood samples underwent initial sensory screens, or sniff-and-taste tests, which are common in food inspection. Specially trained at NOAA’s National Sea-food Inspection Laboratory in Pascagoula, Miss., inspectors can detect unusual odors and flavors at down to about the 10-ppm level. If samples failed, the associated fishing areas were kept closed. Sea-food samples that passed were then subject to chemi-cal analysis.

Because of previous oil spills, chemical screening methods already existed for seafood. The accepted NOAA method for PAH detection uses gas chroma-tography along with mass spectrometry. However, the method requires extensive sample cleanup. To handle the large amounts of sea-food that would need to be tested, FDA wanted a sim-pler approach with higher sample throughput.

By late July 2010, FDA scientists and collaborators had adapted known extrac-tion and liquid chromatog-

raphy-fluorescence detection (LC/FD) methods. In the adapted method, PAHs are extracted from pulverized seafood through a modified QuEChERS (quick, easy, cheap, effective, rugged, and safe) sample prep de-veloped for monitoring pesticide residues in food. The extracts are filtered but don’t require further cleanup for LC/FD analysis. Testing times were reduced from about a week to two days.

The method can be used to screen for 13 target PAHs, as well as common alkylated homologs and metabolites. It was validated for fish, oysters, shrimp, and crabs. Samples found positive for a target PAH were re-quired to undergo confirmatory testing us-ing the GC/MS method.

Testing for trace dispersants didn’t emerge until later. According to FDA and NOAA, their own and independent studies had shown that because the dispersants are metabolized and excreted, they “do not accumulate in seafood, and therefore there is no public health concern.” EPA also re-ported that mixtures of dispersant and oil were no more toxic than the oil alone.

Ultimately, the extent and unique use of the dispersants—about 1.8 million gal worth, about half of which was applied deep underwater instead of only on the surface—called for greater caution. To ensure consumer confidence in the safety of Gulf seafood, FDA and NOAA added dis-persant testing to the reopening protocol.

But a chemical test had to be developed, and sensory assessors trained.

The agencies decided to test for dioctyl sodium sulfosuccinate (DOSS), a major dispersant component that has low volatil-ity and the potential to persist in the envi-ronment. DOSS is used in pharmaceuticals and in food at levels of up to 10 ppm. FDA calculated LOCs at 100 ppm for finfish and 500 ppm for shrimp, oysters, and crabs.

BY LATE OCTOBER 2010, when just 4% of the Gulf was still closed, FDA’s Forensic Chemistry Center in Cincinnati and NOAA’s Northwest Fisheries Science Cen-ter in Seattle announced that they had a test method for DOSS. The procedure drew upon and complemented the PAH method, relying on QuEChERS for sample extrac-tion, followed by LC and tandem mass spectrometry (LC/MS/MS) analysis.

With the method in place, 1,735 samples, including about half of the original number collected and new samples coming in, were analyzed for DOSS. “Pretty much as we had predicted, there almost never were any detectable findings of the dispersant in the fish flesh,” Kraemer said. FDA and NOAA reported that all samples passed sensory testing and that LC/MS/MS showed no de-tectable residues in 99% of samples. For the 1% that tested positive, DOSS levels were less than one-thousandth of the LOCs.

Although speed was desirable, sensitivity was key. The DOSS method can detect dispersant at a level that is one two-thou-sandth of the lowest LOC, according to the agencies. When it comes to PAH test-ing, LC/FD is cheaper and faster than GC/MS, but there are trade-offs in terms of exactly what compounds can be identified. Both meth-ods, however, are sensitive enough to detect well below the LOCs and provide reli-able estimates of PAH levels, according to scientists who developed and used the techniques.

EPA had classified seven of the target PAHs as prob-able human carcinogens. And FDA set the LOC for benzo[a]pyrene, one of the most widely occurring and potent of them, at 35 ppb. The LC/FD method’s

UPPER LIMITS Levels of concern set for polycyclic

aromatic hydrocarbons in Gulf seafood

LEVELS OF CONCERN (PPM)

CHEMICALa SHRIMP/CRABS OYSTERS FINFISH

NON-CANCER CAUSINGb

Naphthalene 123 133 32.7

Fluorene 246 267 65.3

Anthracene & phenanthrene 1,846 2,000 490

Pyrene 185 200 49.0

Fluoranthene 246 267 65.3

CANCER POTENTIALb,c

Chrysene 132 143 35.0

Benzo[k]fl uoranthene 13.2 14.3 3.5

Benzo[b]fl uoranthene 1.32 1.43 0.35

Benzo[a]anthracene 1.32 1.43 0.35

Indeno[1,2,3-cd]pyrene 1.32 1.43 0.35

Dibenzo[a,h]anthracene 0.132 0.143 0.035

Benzo[a]pyrene 0.132 0.143 0.035

a Includes alkylated homologs; C1, C2, C3, C4 naphthalenes; C1, C2, C3 fluorenes; and com-bined C1, C2, C3, C4 anthracenes/phenanthrenes. b Target compounds and cancer potential based on Agency for Toxic Substances & Disease Registry. c Based on a 1-in-100,000 increase in lifetime upper-bound cancer risk adjusted for exposures expected to last five years. For samples containing any of the last seven compounds, the sum of the individual ratios of the detected levels to the levels of concern cannot exceed 1. SOURCE: Food & Drug Administration

14WWW.CEN-ONLINE.ORG JULY 18, 2011

COVER STORY

detection limit is down to the single-digit-ppb range for most PAHs, according to the scientists who developed it. In contrast, the GC/MS method can be about 10 times more sensitive.

WHILE FDA AND NOAA labs across the country handled testing of seafood from federal waters, state labs followed the same protocols for their coastal waters. As a contract lab, Eurofins Central Analytical Laboratories, located in Metairie, La., con-ducted testing for Louisiana, according to the lab’s director, John M. Reuther.

Eurofins always used a GC/MS method, Reuther says. “The GC/MS method is sim-ply overall more specific, more sensitive, and more selective toward running those compounds,” he says. “The LC method is good for a qualitative reporting of hydro-carbons and serves the purpose of saying there are no hydrocarbons of concern, but if we ever find anything that indicates any-thing close to a positive it will have to be confirmed by the GC/MS method anyway.”

Although the LC/FD method supported quickly reopening Gulf waters, testing now that the oil has dissipated addresses prob-lems of perception about the quality of fish coming out of the Gulf, Reuther explains. “The most important thing to do is demon-strate, by the most sensitive and selective methods we can find, that the product is either good or not good,” he says. Eurofins conducts testing for PAHs, DOSS, and met-als for Gulf Wild, one of many programs that have emerged in the region to rebuild

consumer confidence in seafood safety.Indeed, although all samples have come

up clean, a perception problem still exists. According to an October 2010 Institute of

Medicine report, many observers, includ-ing members of Congress, nongovernmen-tal organizations, scientists, fishermen, seafood processors, and chefs, have had

INSTRUMENTATION

Firms Help Meet Demand For Equipment

The Deepwater Horizon oil spill is on re-cord for many things, including prompt-ing one of the most intensive and public seafood safety programs ever.

Less public was the participation of instrumentation companies, which sup-plied the gas and liquid chromatography, mass spectrometry, and detection tech-nologies used by federal and state re-searchers for safety testing. Instrument suppliers, as well as academic labs, also validated testing procedures and offered new approaches for sample prep and the analysis of polycyclic aromatic hydrocar-bons (PAHs) and dispersants.

“The only right thing to do was to re-spond in a timely fashion and, with our experts, partner and collaborate with others to try to solve these problems,” says Mike McGettigan, vice president of marketing for PerkinElmer ’s analytical sciences and lab services business.

Vendors provided a range of analyti-cal techniques for tackling the unprece-dented need for testing. “When this spill happened, we thought that we surely

should be able to find something in our arsenal that would be of interest to the researchers,” says Alex Mutin, strategic marketing manager at Shimadzu Sci-entific Instruments . The company was among those that offered streamlined ordering and special discounts for labs working on the spill.

Shimadzu and Agilent Technologies separately worked with the Mississippi State Chemical Laboratory . Located on the Mississippi State University cam-pus, the lab is home to the Office of the State Chemist and provides analytical services for many state departments. “When the spill happened, there weren’t methods available right away that are fast and accurate,” Mutin says. “We pro-vided our equipment on a consignment basis so that the lab could immediately start work on developing new methods.”

Oil can be identified relatively eas-ily in water by simple techniques, but the chemicals of real concern may be unknown, Mutin points out. Researchers from the Mississippi lab and Shimadzu

15WWW.CEN-ONLINE.ORG JULY 18, 2011

concerns about the adequacy of the federal testing protocol. Some mistrust the risk assessment methods used to establish safe levels for contaminants.

In May, University of Alabama, Bir-mingham, environmental health sciences professor Julia M. Gohlke and colleagues, along with Timothy Fitzgerald of the Envi-ronmental Defense Fund , published a re-view paper in Environmental Health Perspec-tives (DOI: 10.1289/ehp.1103507 ). In it they analyzed the risk assessment process and compared it with those for previous spills.

The assumptions used to set LOCs have been inconsistent across spills, Gohlke and coworkers found. In the case of shrimp and oysters, the recent Gulf LOCs are higher than those set for shellfish in previous in-cidents. And in comparison with the 1989 Exxon Valdez spill, FDA chose a higher body weight and cancer risk level, and shorter exposure time to calculate contaminant levels from the Gulf spill.

The LOCs set by FDA are “grossly inad-equate,” says Miriam Rotkin-Ellman, a sci-entist with the Natural Resources Defense Council , an environmental group. “When

we look at the multiple ways in which FDA underestimated risk, these LOCs are or-ders of magnitude too high.” Last summer, NRDC and two dozen Gulf Coast groups called on NOAA and FDA to strengthen the protocol. NRDC hasn’t yet determined whether the detected levels of contami-nants would fall below the even more strin-gent limits it would like to see, she says.

NRDC CONTENDS that FDA greatly underestimated seafood consumption in calculating LOCs. FDA used figures from national surveys for the top 10% of con-sumers; an NRDC survey found consump-tion rates in the Gulf region to be up to 10 times higher. Yet on the basis of actual con-tamination levels, FDA says, people would have to eat several pounds of fish or oysters or several tens of pounds of shrimp every day for there to be any concern.

By using a heavier body weight than that used for previous spills, FDA also didn’t ac-count for the potential impact on groups including women and children, Rotkin-Ell-man explains. “If you are concerned about lower levels for vulnerable populations, it

raises some valid questions about the appro-priate analytical method.”

Gohlke suggests that using plausible risk parameters for different groups to create a range of LOCs, as presented in the review article, would have been a satisfactory solu-tion. Even with the more conservative LOC estimates, the detected PAH levels would have been deemed safe, she says. In general, PAHs measured in Gulf seafood are “at or below levels reported after previous spills,” according to Gohlke and her coworkers.

Beyond the high LOCs, NRDC takes particular issue with FDA’s failure to cat-egorize naphthalene as a cancer risk. This occurred, Rotkin-Ellman says, “despite the fact that the National Toxicology Program has listed naphthalene as likely to be a car-cinogen, and it is considered by the state of California to cause cancer.”

When it comes to specific PAHs such as naphthalene, most Gulf data show levels not only below LOCs but even below detection limits, Gohlke says. This is encouraging, but “you can’t do any kind of time-series analy-sis because you don’t have any data to work with on the individual PAHs,” she adds.

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used sophisticated GC/MS equipment to look for potentially harmful metabo-lites and to fingerprint different types of oil to identify contamination sources. Shimadzu would like to continue such collaboration, he says. “It is a very broad field, and I think it will take years until we really understand what we should be looking for and how to measure it.”

Mississippi researchers and Agilent collaborated on improving existing GC/MS methods for analyzing PAHs. In July 2010, they came up with an approach

that allowed for processing 24 seafood samples in two-and-a-half to three days—half the typical times. The technique also required just one chemist to conduct sample prep and one for analysis.

Agilent worked closely with the Food & Drug Administration to develop, in less than 30 days, a rapid LC/fluorescence detection method that became the meth-od of choice for the agency’s Gulf reopen-ing protocol. FDA then placed orders for more than 40 such systems to be distrib-uted among its regional labs and state labs in the Food Emergency Response Network, he says. Agilent also worked with FDA’s Forensic Chemistry Center in Cincinnati on dispersant testing.

Although the spill prompted quick ac-tion to address seafood safety, company managers see a longer-term opportunity to provide instrumentation and applications assistance to regulators, state agencies, food processors, and other labs. “There have been other effects from the oil above and beyond what happened to the sea-food,” says Simon Senior, PerkinElmer’s environmental and industrial market seg-ment director. “The longer-term impacts from both the oil and dispersants are still to be assessed.”

SPEEDY SERVICE Agilent engineers installed GC/MS/MS equipment at the Mississippi State Chemical Lab in July 2010.

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Knowing the total amount of PAHs would be helpful in making comparisons and determining whether levels are ris-ing or falling, but such analysis is stymied by the fact that FDA reported totals and NOAA didn’t. Gohlke warns, however, that total PAH numbers shouldn’t be used to make any kind of health claims.

The target PAHs were chosen because of the available information on their health impacts, and those selected haven’t changed much from earlier spills. “A lot of research has been done on PAHs, and there are obviously more PAHs than those currently used in the risk assessment,” she says. “Whether we should be adding more PAHs to that battery is definitely under dis-cussion.” NRDC also encourages expanded testing for other petroleum hydrocarbons.

CONCERNS HAVE also been raised that FDA and NOAA did not appear to be inter-ested in testing for metals. Just recently, FDA posted levels of metals for seafood samples collected between October 2010 and May 2011. “Testing showed that the levels of arsenic, cadmium, lead, and mer-

cury were consistent with the background levels found in seafood not impacted by the oil spill and do not present a public health concern,” the agency states.

Although FDA offered no explanation for the metals testing, posting of the results did come after requests and recommendations made by NRDC, the Institute of Medicine, and Gohlke and coworkers. Critics had complained of a lack of transparency on the part of regulators. Both Rotkin-Ellman and Gohlke say the situation has gotten better.

“We have seen some improvements in the level of disclosure,” Rotkin-Ellman says. “In response to a lot of community pressure, FDA has gotten better about putting data up on its website and is doing it faster.” FDA’s explanations of its data and plans for con-tinued monitoring are less clear, she adds. NOAA also posts data on its website.

After other oil spills, increased PAH levels have been detected in fish and shell-fish up to several years out, according to Gohlke. She and other researchers hope for long-term monitoring programs for PAHs, DOSS, and metals, especially in light of po-tential recontamination from uncaptured

oil and unknowns concerning the environ-mental fate of dispersants.

For now, it appears that regulators will continue monitoring for at least a few months more. FDA’s ongoing surveillance program involves testing seafood at pro-cessing locations rather than from identi-fied areas in the Gulf. The agency’s risk-based program targets oysters, crabs, and shrimp because they retain contaminants longer than finfish do.

NOAA conducts some dockside testing and also goes back to previously contami-nated areas to collect seafood for testing. In November 2010, it closed more than 4,000 sq miles that had been opened off the Louisiana coast after a fisherman brought up tar balls in his nets. Sensory and chemical tests showed that the seafood was clean, and the area was reopened again.

In March 2011, NOAA said it would con-tinue testing through the summer. Reports indicate that FDA will conduct its testing until October 2012. And since late 2010, Gulf state agencies have been using tens of mil-lions of dollars paid by BP for three years of seafood testing and marketing campaigns. ◾

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17WWW.CEN-ONLINE.ORG JULY 18, 2011

CHANGING FORTUNES FOR CELLULOSIC FUEL MAKERS

As one developer of cellulosic biofuels gets funded, two others face dif-ficulties. Natural gas firm Chesapeake Energy has paid $155 million for a 50% stake in Sundrop Fuels. Sundrop uses high temperatures to gasify cellulosic feedstock into synthesis gas, which is catalytically converted to gasoline through a process developed by ExxonMobil. Colorado-based Sundrop plans to have a 40 million-gal-per-year plant operating by late 2013. Cellulosic fuels firm Choren, meanwhile, has declared insolvency in the midst of efforts to commission its own gasification demonstration plant in Freiberg, Germany. The firm encountered financing difficulties before the plant could begin production. And Range Fuels shut down its facility in Soperton, Ga., earlier this year after producing a small volume of ethanol. The company, which was expected to be a large producer of etha-nol via cellulose gasification, has not provided a timeline for restart. Partly as a result of the shutdown, EPA forecasts that no more than 12.9 million gal of cellulosic biofuel will be produced in the U.S. next year, down 97% from the 500 million gal it had projected in February 2010. — MMB

M&G PICKS TEXAS FOR NEW PLANTS

Italian chemical firm Mossi & Ghisolfi has picked Corpus Christi, Texas, for the site of its largest ever investment, a complex that will make polyethylene terephthal-ate (PET) and purified terephthalic acid (PTA). It will take about 30 months to com-plete the facility, which will have capacity to make 1 million metric tons of PET and 1.2 million metric tons of PTA per year. M&G officials say they chose the location among other U.S. Gulf Coast candidates because of the business-friendly climate

and access to nearby port, chemical, and oil-refining infra-structure, which will provide easy access to raw materials such as p -xylene and ethylene glycol. — AHT

Keyuan says it will appeal the decision while working with a new auditor to produce audited statements. KPMG , the original auditor, reported this spring that Keyuan had improperly recorded certain sales and cash transactions. Keyuan denies the assess-ment, has initiated an investigation, and is hiring a new auditor, GHP Horwath. — JFT

AVANTOR AND SACHEM FORM ETCHANTS PACT

Avantor Performance Materials , formerly Mallinckrodt Baker, has entered a joint development agreement with Sachem to provide etching chemicals to the semicon-

LANXESS BUYS TIRE RELEASE AGENTS

Lanxess ’ Rhein Chemie unit has acquired Wacker Chemie’s tire release agents busi-ness, which had less than $10 million in 2010 sales. The agents, most of which are silicone-based dispersions, ensure easy release of tires from molding equipment. Lanxess says the market for the release agents is growing at about 5% annually. Wacker will continue to supply Lanxess with raw materials. Earlier this year, Lanxess bought two rubber chemical lines from Solutia ’s Flexsys division and acquired Darmex, an Argentinian maker of tire re-lease agents and curing bladders. — MSR NASDAQ DELISTS

CHINESE COMPANY

The NASDAQ stock exchange has ordered the delisting of Keyuan Petrochemicals , a commodity chemical producer based in Ningbo, on China’s eastern coast. The delisting, according to a Keyuan statement, is the result of a failure to provide audited financial statements on a timely basis.

SOLVAY AND AVANTIUM JOIN FOR POLYMERS

Solvay and high-throughput-screening firm Avantium have entered a multiyear collabo-ration to develop nylon engineering poly-mers based on Avantium’s YXY platform for furanic chemicals derived from sugar. Avan-tium has found a route to furan dicarboxylic acid, which it reacts with ethylene glycol to make polyethylene furanoate, a polyester that boasts six times the oxygen barrier properties of PET. Solvay and Avantium aim to create new polyamides that can compete on both price and performance. — AHT

BUSINESS CONCENTRATES

PET is used to make the ubiquitous plastic water bottle.

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ductor industry. The firms will focus on surface preparation and removal chemis-tries for thin-film wafer stacks, combining Avantor’s experience in photoresist and residue removal with Sachem’s expertise in bulk etchants and surface preparation. The partners’ first product is SLCT 128, a surface treatment that both cleans and etches. — MM

ITT TO ACQUIRE WATER MONITORING FIRM YSI

ITT Corp . will buy the privately held in-strumentation firm YSI. Based in Yellow Springs, Ohio, 63-year-old YSI develops sensors, instruments, and software for en-vironmental water monitoring. It had sales of $101 million last year and employs 390 people at 22 locations around the world. ITT has been acquiring companies to build its ITT Analytics business in the market for portable, lab, and on-line analytical instru-ments used in environmental, medical, and food applications. — AMT

BASF WINS APPROVAL FOR BIOFUNGICIDE

Brazil has registered the biological fun-gicide Serenade for apples, onions, and strawberries, according to BASF . Licensed by BASF from the biopesticides company AgraQuest , Serenade will be used with traditional fungicides during the criti-

18WWW.CEN-ONLINE.ORG JULY 18, 2011

BUSINESS CONCENTRATES

RESEARCH COMPANIES JOIN WITH NONPROFITS

The Innovative Vector Control Consor-tium has signed an agreement with the contract research firm Scynexis to find compounds suitable for development into new active ingredients for insecticides. Scynexis will screen its chemical library for activity against adult mosquitoes and create methods for screening other librar-ies from organizations around the world. Meanwhile, the Michael J. Fox Founda-tion for Parkinson’s Research has signed a pact with BioFocus related to Parkin-son’s disease treatments. BioFocus will perform fragment-based screening and assay development and will run hit-finding programs. — MM

BMS BUYS STAKE IN INNATE IMMUNOTHERAPY

Bristol-Myers Squibb is shelling out $35 million up front and up to $430 million in milestones for access to IPH2102, a monoclonal antibody being developed by Innate Pharma . IPH2102 taps into a cancer patient’s own immune system by block-ing the interaction between killer-cell immunoglobulin-like receptors and their ligands. Blocking the receptors activates natural killer cells that in turn destroy tu-mor cells. The drug is now in Phase I cancer trials. France-based Innate will continue to develop it through a Phase II trial for acute myeloid leukemia . — LJ KRATON, FORMOSA SET

STYRENICS VENTURE

Kraton Performance Polymers is planning a 50-50 joint venture with Formosa Petro-chemical that will build a 30,000-metric-ton-per-year hydrogenated styrenic block copolymer (HSBC) plant at Formosa’s Mailiao, Taiwan, petrochemical complex. Formosa will provide feedstock and utili-ties for the new plant, which will use Kra-ton’s polymerization technology. The two plan to open the new unit in the second half of 2013 at a cost of $165 million to $200 million. Last year, Kraton said it was evalu-ating four sites in Asia for an HSBC expan-sion (C&EN, Dec. 13, 2010, page 20). — MSR

GILEAD OPENS ACCESS TO HIV TREATMENTS

Gilead Sciences has expanded access to its HIV medicines through agreements with the Medicines Patent Pool Founda-tion (MPPF), a nonprofit supported by UNITAID and the Indian drug firms Het-ero Drugs, Matrix Laboratories, Ranbaxy Laboratories, and Strides Arcolab. Both MPPF and the companies gain the right to produce for the developing world three drugs in late-stage clinical trials: elvite-gravir, an integrase inhibitor; cobicistat, an antiretroviral boosting agent; and the Quad, which combines four Gilead HIV medicines in a once-daily pill. In 2006, Gil-

BUSINESS ROUNDUP

MACDERMID plans to raise up to $200 million in an initial public offering of stock. The firm, which supplies chemicals for electroplating, hydraulic control, printed circuit board fabrication, and oth-er applications, had sales of $694 million last year. It went private in 2007.

LS9 has extended its research collaboration with Chevron to produce hydrocarbon products from sugar feedstocks via fermentation by engi-

neered microbes. Sepa-rately, LS9 has partnered with MAN Latin America , a Brazil-based manufac-turing company, to test its renewable diesel in sta-tionary engines and fleet vehicles.

PRAXAIR has signed a multiyear contract to sup-ply high-purity hydrogen to Hemlock Semiconduc-tor ’s polysilicon plant, now under construction in Clarksville, Tenn. Sepa-rately, Praxair’s White Martins unit has signed a 15-year agreement to sup-ply nitrogen and oxygen to Braskem ’s polyvinyl chlo-

ride expansion in Alagoas, Brazil.

ELEVANCE Renewable Sciences and Clariant will cooperate in the field of renewable additives for plastics. The firms say they are combining Clari-ant’s market knowledge and formulation develop-ment capabilities with Elevance’s renewable products and process technology.

VALEANT Pharmaceuti-cals has agreed to acquire Dermik, a Sanofi subsid-iary that markets derma-tology products including

BenzaClin acne treatment and the facial injectable Sculptra. Valeant will pay Sanofi about $425 million for the business, which had sales last year of ap-proximately $240 million.

CARBOGEN AMCIS has named Mark C. Griffiths as CEO. Griffiths has been overseeing the construc-tion of high-potency drug manufacturing facilities in China and India by Dish-man Pharmaceuticals & Chemicals , the India-based parent of Carbogen.

HIKMA Pharmaceuti-cals, a London-based

drugmaker, has acquired a “significant” minority interest in China’s Hubei Haosun Pharmaceutical for $5.0 million. Haosun operates a plant in China’s Hubei province that spe-cializes in active pharma-ceutical ingredients for oncology.

MERRIMACK Pharma-ceuticals plans to raise up to $172.5 million in an ini-tial public offering. The an-tibody drug company says funds raised from the IPO will support further devel-opment of its lead cancer drug candidates as well as early-phase projects.

Strawberries in Brazil can now be treated with Serenade biofungicide.

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cal pre- and postharvest periods, BASF says. Serenade contains a patented strain of the bacterium Bacillus subtilis . — MM

AMGEN LICENSES MICROMET TECHNOLOGY

Amgen will pay Micromet $14 million up front to apply the Rockville, Md.-based biotech firm’s BiTE antibody technology against three solid-tumor targets. Amgen has the right to develop BiTE antibodies against two of the targets. It will cover all the program’s R&D costs, which the companies say could run up to $35 million. Micromet ’s BiTE antibodies bind T cells to tumor cells, prompting cell death as well as the prolifera-tion of more T cells at the tumor site. — LJ

ead allowed several manufacturers to make generic versions of the HIV drugs Viread and Truvada. — LJ

19WWW.CEN-ONLINE.ORG JULY 18, 2011

ALGAE-GROWING cleantech firms are enjoying a burst of attention, triggered by Solazyme ’s successful initial public offer-ing (IPO) of stock in May. The firm, which raised $227 million from investors, first turned heads in 2008 when it brought a car running on algae-based biodiesel to the Sundance Film Festival. But it’s not fuel that fueled the IPO. Instead, investors and analysts were sold on skin cream and other products made from “tailored oils.”

Solazyme is not the only algae firm to shift its near-term focus away from the fuel market. For companies such as Cellana , Algenol , and Sapphire Energy looking to profit from the fast-growing green goo, the number of possible target markets and products has grown like a giant algal bloom. Algae will likely appear in personal care, animal feed, nutrition, and chemical products before reaching the gas station.

Experts agree that nonfuel markets can be profitable for Solazyme and other algae firms, but they warn that investors will be impatient to access the multi-billion-dollar fuel market. That may set the industry up for failure, because it will be many years—if

ever—before algae can be cost-competitive with petroleum.

“It’s very clear there are many challeng-es. They are real and are often preventing or slowing these companies from reaching the oil or fuel markets,” observes Andrew Soare, a clean technology analyst with Lux Research . “Now that they are scaling up and seeing that the algae grows too fast or too slow, that it takes too much land or wa-ter, or that it’s harder than expected to get big investments, they have to turn to other markets.”

Solazyme’s technology sets it apart from other algae firms, Soare contends. “Be-cause it is using algae to ferment sugars in a dark tank, the company doesn’t need mas-sive infrastructure for massive growth.” Lux classifies Solazyme with fermentation biology companies—ones that don’t use algae—and expects it to be the first algae producer to reach commercial scale.

Now that the firm is public, investors can mull over its production costs and plans for rolling out products. Accord-ing to Solazyme’s S-1 filing with the Securities & Exchange Commis-sion, its lead algae strain for fuels and chemicals could make a crude oil for under $3.44 per gal at commercial scale using sugarcane feedstock.

In the near term, ac-cording to Goldman Sachs equities analyst Mark Wienkes, it is the strength of Solazyme’s partnerships for prod-ucts other than fuels that makes the firm a buy. “We view credible strategic partnerships as

a key progress indicator, particularly for companies like Solazyme that plan to scale up through bolt-on additions at existing mills,” he wrote in a report to investors.

Solazyme has inked a joint venture with grain miller Roquette for algal flour and other nutritional products and has a joint development agreement with Bunge to produce chemicals in Brazil. It also has two agreements with likely customers: Unilever for soap and cleaning product ingredients and Dow Chemical for microal-gae-based oils used in dielectric insulating fluids.

Right now, Solazyme is booking revenue from sales of skin care products contain-ing what it calls alguronic acid. Its Algenist brand antiaging moisturizer sells for $90 for a tiny 2-oz jar. But the high-end per-sonal care market is relatively small and requires expensive marketing.

OVER THE NEXT three to five years, Wienkes says, Solazyme will reach profit-ability by selling tailored oleochemicals—similar to those derived today from palm kernel or linseed oils. He estimates the potential market size to be $7 billion a year for food-related products and $36 billion a year for industrial markets currently served by oleochemicals and petrochemicals.

ALGAE PLANS BLOOMFrom PERSONAL CARE TO FISH FOOD, algae firms

look for ways to make profits quicklyMELODY M. BOMGARDNER, C&EN NORTHEAST NEWS BUREAU

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“Everything we are doing is aimed to being competitive at fuel prices without subsidy.”

BUSINESS

ISLAND HOME Cellana’s algae may be used as feed for Hawaii’s fish farms.

20WWW.CEN-ONLINE.ORG JULY 18, 2011

Hawaii-based Cellana also wants to extract fuel from algae someday, but first the company is developing a product from whole algae: feed for animals, including farm-raised fish. “It’s a very exciting op-portunity; fish eat algae in the open ocean as the main source of protein in the wild,” says Martin Sabarsky, the firm’s chief ex-ecutive officer. The company is conduct-ing fish feeding trials with a $5.5 million grant from the Departments of Energy and Agriculture.

Like Solazyme, Cellana is also pursuing nutraceuticals and personal care ingredi-ents, in its case by deconstructing its native strains of algae and selling off every piece. The company cultures its selected strains in photobioreactors and then puts them in open ponds, where they multiply and are harvested in two to five days. In addition to oil, Sabarsky points out, algae contain be-tween 20 and 50% sugars and high-quality proteins. “We want to generate value from each element of the biomass.”

The full plan, Sabarsky says, is to pro-duce fuels, feeds, and higher value specialty lipids in a biorefinery. “As long as you can economically produce products at a small-er scale and make it modular, then you can scale it larger when there is more capital available,” he explains. “Think of it like a wind farm. You don’t build just one huge windmill.”

SOME ALGAE companies still see fuel as their main target market. Algenol is unusu-al among algae firms in that its algae gener-ate ethanol rather than oil. The company’s hybrid strains grow in flexible plastic pho-tobioreactors, where they live in seawater treated with nutrients and dine on piped-in CO2. The ethanol they excrete evaporates into the headspace of the reactor along with water and is collected. The mixture is distilled to pure ethanol.

But even with this straightforward production model, there is room for di-versification into higher margin products. “Algenol has decided that it is going to em-bark on a green chemistry program, and it will have specific targeted molecules—not more than three or four,” explains CEO Paul Woods, who notes that Algenol has a partnership with Dow. “We have made a fundamental decision with our partners

bankrolling green chemistry, but we’re still unanimously decided that ethanol will be our main product.”

Woods says the chemicals program will go beyond the two-carbon chemicals that can be made directly from ethanol. For example, he reports that his firm has genetically modified algae that can excrete propylene.

Bypassing oil, Lux’s Soare points out, Algenol’s technology circumvents two costly production steps. “Getting from the algae-water mixture to dewatered algae is a rather expensive part of the process. When combined with extracting the oil, that makes for two expensive steps right next to each other.”

Algal oil firm Sapphire Energy also as-serts that fuel is its main product. Sapphire is working on wet extraction techniques to bring down the costs of what it calls green crude oil. The firm uses synthetic biology to create high-production strains of algae and then grows them in open ponds. Its business model is to sell the oil to refiners that would make the end products. “Every-thing we are doing is aimed to being com-petitive at fuel prices without subsidy,” insists Cynthia J. Warner, the company’s president.

“But that doesn’t mean we can’t make high-margin products,” she quickly adds.

“Early on we will not be flooding any fuel markets.” Refiners are currently facing a shortage of high-quality sweet crude. Using Sapphire’s renewable crude would let them fully utilize their capacity to make high-value “middle” streams such as jet fuel and building blocks for chemicals and plastics, according to Warner.

THE QUALITY of Sapphire’s crude makes it ideal for airline diesel and the military. “They are a direct market for us,” Warner says. Soare agrees that such customers could be a good fit, at least temporarily. “Jet fuel is a much different market than other transport fuels. It has centralized buyers willing to pay more and who would work through joint development agreements.” Still, algae firms need to get to cost parity with petroleum to survive in the market long term, he says.

Warner agrees. “This is really important because we don’t want to aim off the target. It could be a trap—you can paint yourself into a corner if you are reliant on those high margins.”

Another nonfuel business opportunity is recycling waste CO2. Industrial gas firm Linde has teamed with Algenol and Sap-phire on processes for CO2 delivery. And Cellana is already working with Hawai-ian Electric and Maui Electric to pipe in emis sions.

The diverse directions algae firms are taking to commercialization should not be seen as a sign that algal fuels are an iffy proposition, Algenol’s Woods ar-gues. “From a layperson’s point of view it looks massively disorganized, but it isn’t. Specific companies have aligned with dif-ferent companies which have different needs.” For example, Algenol’s years-long partnership with Dow has naturally guided it toward making building-block chemicals.

One possible outcome of exploring interim markets is that algae firms won’t move beyond them to reach the scale and low cost necessary to sell meaningful amounts of fuel. “I think the companies themselves are okay with staying in the higher value nonfuel market if they are making a profit on those products,” Soare suggests. However, most firms have inves-tors who flocked to algae because of the opportunities in fuel, and they still want to be in that market. “There is no one answer,” Soare says, “but algae compa-nies will feel some conflict among those forces.” ◾

SMOOTH MOVE Solazyme’s current sales revenues come from high-end skin treatments.

“We want to generate value from each element of the biomass.”

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BIOTECHNOLOGY-BASED cosmetic in-gredients are doing today what synthetic ingredients have done in years past: They are bringing novelty and excitement to the personal care market. Although they are coming on strong, some formulators and consumers are leery of the technology and the ethical issues they can raise.

Traditional cosmetic ingredients such as aloe and essential oils have long been de-rived from plants. To create the new breed of biotech products, suppliers are using cell culture techniques to create, in sterile fermentation reactors, ingredients that oth-erwise would have to be grown, harvested, and extracted. They are also harnessing enzymes, yeasts, and microbes to produce ingredients.

Advances in genetics have not just af-fected pharmaceutical and agricultural research, notes Meyer R. Rosen, president of Interactive Consulting, but have also made possible new cosmetic ingredients and brought about a greater understanding of how such ingredients affect the skin. That understanding is also “a key to making new, safe products that really work,” he says, giv-ing consumers formulations that cover their blemishes and enhance their appearance.

Kline & Co. , which tracks the personal care market, says European cosmetic

companies, which include many of the world’s most innovative formulators, consumed $97 million in biotechnology-derived active ingredients in 2010, up from $69 million in 2007. The firm says demand for such ingredients is growing 13% annually, versus less than 10% annu-ally for other active ingredients.

Many consumers and formulators have enthusiastically embraced cosmetics that include biotech-derived ingredients. In 2009, for example, cosmetics giant L’Oréal introduced Lancôme Génifique, a skin care line with ingredients such as BioLysat, a preparation of the bacteria Bifidobacterium that the company claims can “boost the ac-tivity of genes whose expression dwindles with age.” Earlier this year, the firm said it had sold more than 3 million units of the antiaging serum since its launch.

But not all formulators are ready to em-brace gene-stimulating ingredients. E. Tim McGraw, director of the corporate innova-tion team at consumer products firm Kim-berly-Clark , worries that such ingredients could invite scrutiny from regulators such as the Food & Drug Administration. But he is intrigued by their potential in cosmetics.

Companies that are incorporating bio-tech-derived ingredients in their personal care products are making efforts to back

up performance claims with research using ge-netic arrays, tools that are often associated with drug research. For example, Alain Deguercy, marketing director of the France-

based testing lab BioAlternatives , has used an Affymetrix array to analyze the genetic response of cells to cosmetic ingredients for L’Oréal and others.

An analysis of cell response can help cosmetic formulators substantiate claims, Deguercy says. He adds that a number of cosmetic formulators have their own ar-rays and that his firm has helped verify their findings.

Makers of biotechnology ingredients for cosmetics tell C&EN they also test to be sure their products are safe and effective. A number of them are exploiting techniques from pharmaceutical and agricultural biotechnology to make active ingredients extracted from plant tissue cultured in the lab. The tissues, often referred to as plant stem cells or meristem cells, are a source of extracts from plants that would otherwise be grown on plantations or gathered from the wild.

Ingredients derived from plant stem cells have advantages over their field-grown counterparts, according to Roberto dal Toso, founder and R&D manager of cos-metic ingredient maker Istituto di Ricerche Biotecnologiche (IRB) in Italy. For example, field-grown plants can be contaminated with pesticides and heavy metals, he ex-plained during a seminar on biotechnology at the HBA Global Expo in New York City last month.

FIELD-GROWN PLANTS often vary in quality too, dal Toso said. The active in-gredients they contain can vary because of weather, and crop failures can also limit the availability of plant ingredients. Certain plants are rare because of the conditions under which they grow, and it is often im-possible to gather enough of them without compromising their survival, he pointed out.

In contrast, only a small number of plants are required to develop a plant cell line in a culture, dal Toso said. Plant cell cultivators such as IRB can incubate the cells under ideal conditions and then ob-tain active ingredients through standard extraction and purification techniques.

Scientists have cultured plant stem cells

SUPER NATURAL COSMETIC POTIONS

Advances in biotechnology enable a new generation of PLANT-DERIVED INGREDIENTS

MARC S. REISCH, C&EN NORTHEAST NEWS BUREAU

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for more than 70 years, notes Vince Gruber, director of research at Arch Personal Care Products . To establish a cell line, scientists slice off plant stem cells, usually from the growing tip of a plant, and place them in a petri dish under sterile conditions with a growth medium, he explains. Over two to three weeks, a mass of cells forms. The next step is to place the cells in a shak-er flask where they again multiply.

Finally, Gruber says, the cells are placed in a bioreactor where they con-tinue to grow. Arch’s plant cell biore-actors can hold 450 L, though others in the industry typically use reactors twice that size. Arch only recently started to produce plant stem cells.

Cells grown in the reactors are subjected to “stresses” such as ozone, ultraviolet light, and growth regula-tors to encourage them to express the active ingredients cosmetic makers seek. The stresses can yield known active ingredients or produce entirely new ones that ingredient firms can study and develop for customers. In the end, the result is a consistent biomass yield, Gruber says. “You do not have crop failures, and you grow what you need when you need it.”

What cosmetic ingredient makers are do-ing now with plant tissue culture picks up on the success drugmakers have had in obtain-ing rare ingredients from plants, says Jon Anderson, president of cosmetic ingredient distributor Actives International . Phyton Biotech , for instance, perfected a technique to produce precursors to paclitaxel, the ac-tive ingredient in Bristol-Myers Squibb ’s on-

cology drug Taxol, from plant cell cultures instead of from the rare and slow-growing Pacific yew tree.

The lesson, notes Anderson, who is a medicinal chemist, is that biotechnology can help overcome shortages of pharma-ceutical as well as cosmetic ingredient ma-terials. For instance, squalane, a skin mois-turizer, can be derived from shark or olive oil. The industry tends to shy away from animal-derived squalane, and the olive-oil-derived material is resource intensive.

Using sugar fermentation, companies such as Amyris can produce 2 metric tons of

squalane from sugarcane grown on 1 hectare of land, Anderson says. Olives grown on the same size plot will yield only 50 kg of squalane. Anderson’s com-pany distributes squalane from a partnership be-tween Amyris and French cosmetic ingredient maker Soliance .

Surinder P. Chahal, vice president of research at U.K.-based ingredient maker Croda , says his firm has used biocatalytic techniques to make peptides from plant materials for 40 years, and often with less waste than from plants themselves.

For cosmetic use, Croda recently intro-duced fermentation products including Venuceance, a skin antioxidant, and O.D.A. White, a skin lightener, through its Sederma unit. The firm also opened a fermentation facility in Widnes, Cheshire, England, to produce these new products and others, Chahal says. The facility includes glass-lined tanks designed for marine cell fermentation.

Consumers should have little concern over the use of biotechnology, he argues. “Biotech products such as wine and beer are a part of everyday life,” he says. Consumers use fructose, a sugar produced via the bioen-zymatic conversion of cornstarch, and they also have no problems with laundry deter-gents that incorporate enzymes.

And as Chahal sees it, the market for biotech-produced cosmetic ingredients is growing fast. “People need to understand that biotechnology is the way forwardfor sustainability.” ◾

LIFELINE SKIN CARE

Biotech Firm Adds Human Cell Extracts To Cosmetics Taking biotechnology in the service of beauty one step further, Lifeline Skin Care has developed a nonembry-onic stem cell extract that it says reduces skin wrinkles, improves tone, and aids elas-ticity. In November 2010, the firm incorporated the extract into its own skin care line and offered it for sale on the Inter-net. The Defensive Day Mois-ture Serum and the Recovery

Night Moisture Serum cost $160 and $190, respectively, for a 45-day supply. Through March, the firm had serum sales of $1 million, says Presi-dent Ruslan Semechkin.

Associating stem cells with cosmetic ingredients “risks trivializing” the field of stem cell research, says Mary Dev-ereaux, a bioethicist at the University of California, San Diego . Semechkin admits

that International Stem Cell Corp. (ISCO), Lifeline’s parent, developed the skin care line to bring in new revenues. But the profits go to furthering the start-up firm’s main thrust: developing parthenogenic stem cell lines to cure diseas-es. And because the egg cells are not fertilized, they avoid complications associated with the destruction of human em-bryos, Semechkin argues.

Devereaux, who has worked with ISCO as a consultant, wonders whether the firm has obtained consent to use the cells for cosmetic purposes

from women who have do-nated the eggs. Semechkin tells C&EN that although the women who donate eggs do so to advance treatment of human diseases, they are also informed about the cosmetic use. “We are transparent with them,” he says.

Despite her skepticism, Devereaux says, “You can take the high road and re-strict stem cells to medical research, but that’s not to say a scientist wouldn’t want to take advantage of a cosmetics breakthrough.” She adds, “If it works, I’d try it.”

STIRRED UP Sugarcane-fed yeast brew up farnesene, a raw material for cosmetic moisturizer squalane, in 200,000-L fermenters.

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THIS YEAR marks the 40th anniversary of President Richard Nixon’s signing of the National Cancer Act into law, officially launching the nation’s war on can-cer. Some scientists, and certainly many cancer pa-tients, find the landmark bittersweet—although the act stimulated oncology research and many impor-tant new treatments, we are still far from a cure. At the American Society of Clinical Oncology ’s (ASCO) annual meeting, held recently in Chicago, there was much reflection on what is wrong—and right—about how the war is being waged and what needs to happen in the clinic to turn cancer into a disease that people live with rather than die from.

One message from researchers and clinicians at the ASCO meeting is that it’s a mistake to think prog-ress has not been made just because a cure hasn’t been found. “We ought to think about how cancer was conceived at that time,” Harold E. Varmus, director of the National Cancer Institute, told reporters at the meeting. “The notion was that cancer was a disease that we could win against or lose against.” But in recent years, it has become clear that cancer is not, as Varmus said, “a single enemy,” but rather an array of diseases that are still in the process of being understood.

Even after the human genome was cracked, some 30 years after the cancer act went into effect, there was still a belief that the new-found ability to capture single genetic mutations would lead to cures.

“There was an assumption that if one could isolate a target and use the modern tools of molecular biology—cloning, sequencing, overexpressing, and producing the protein; making a crystal; and designing drugs that inhibited that protein—you’d have a series of fantastic drugs,” said William N. Hait, head of oncology at Johnson & Johnson . “It’s just not that simple.” Rather, Hait observed, scien-tists have come to understand that more than 200 different tumor types exist, each with its own subtypes.

And despite high expectations for biomarkers and companion diagnostics, much of the information about the genetic mutations driving a person’s cancer—not to mention mechanistic informa-tion about a drug—is still gleaned after a potential treatment has entered clinical studies.

At ASCO, researchers said they have learned that designing better, more informative clinical trials is essential to combating cancer. “There’s no way we can model the human disease in the lab perfectly,” said Julian Adams, president of R&D at I nfinity Pharma-ceuticals , a Cambridge, Mass.-based biotech firm. “We will have lab-oratory findings that translate to the clinic, and then clinical findings that have to go back to the lab and sort of redesign the experiments.”

Indeed, a slew of sessions at the cancer conference highlighted data from innovative clinical trials aimed at gathering more information about a how a drug works earlier in the development process.

For example, Aposotalia M. Tsimberidou, associate

professor at the University of Texas M.D. Ander-son Cancer Center in Houston, presented results from a large Phase I study showing that matching a patient’s tumor type to a targeted therapy is a good way of getting better results.

Some 1,144 patients with inoperable or metastatic cancer were given a panel of tests for certain genetic aberrations. Depending on the results, they were given a therapy that blocked one of a handful of kinases. Tsimberidou reported that 27% of the 175 patients with one genetic aberration responded to targeted therapy, compared with a response rate of just 5% in the 116 patients who were treated without molecular matching.

Tsimberidou stressed that the results are prelimi-nary. And because the trial was not randomized, more studies are needed to confirm the effect of matching therapies to genetic aber-rations. Nonetheless, “this still represents a substantial improve-ment in the way we could do drug development,” said University of Chicago Medical Center oncologist Richard L. Schilsky. Phase I trials, typically focused on showing drugs are safe, could also provide scientists with “a better sense of what their activity is” much earlier on in the development process.

IN AN EXAMPLE from the ASCO meeting of how biotech firms are digging deeper into data to find the right patients for their compounds, Infinity discussed plans to conduct an information-rich Phase II trial for its Hsp90 inhibitor IPI-504. The study will be different from any the firm has done before, Adams said. The goal is to pick up on signals seen in a small Phase I trial suggesting the compound is effective in three types of lung cancer patients: those with squamous cell disease, those who are heavy smokers, and those carrying the normal KRas gene.

The next trial, which will look at the benefits of adding IPI-504 to the chemotherapy docetaxel, will be adaptive, meaning the company will pause midtrial, look at which patients are responding best, and adjust accordingly. To understand the genetic profile of the people its drug might work in, Infinity is mandating that archi-val tumor tissue be made available to study certain mutations. “It makes it harder to recruit patients,” but more and more lung cancer doctors are collecting archival tissue now that there are tests for a variety of mutations, Adams said.

Although the cost of running this kind of Phase II trial is high, it pays off later on, Adams pointed out. Phase III studies can conceivably be conducted in smaller patient groups and produce a more impressive response rate than in larger, less focused studies. “It’s just better medicine,” he said.

LISA M. JARVIS, C&EN NORTHEAST NEWS BUREAU

Decades after the National Cancer Act, scientists are turning to information-rich, EARLY-STAGE STUDIES to advance oncology

The Long War On Cancer

Views expressed on this page are those of the author and not necessarily those of ACS.

“There’s no way we can model the human disease in the lab perfectly.”

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GOVERNMENT & POLICY CONCENTRATES

UTILITY STOPS CARBON CAPTURE PROJECT

A major electricity company, American Electric Power (AEP), has halted one of the most successful programs to develop a commercial-scale coal-fired power plant that utilizes carbon dioxide capture and storage (CCS) technology. The company blames the uncertain state of U.S. climate policy and the weak economy. “We are placing the project on hold until economic and policy conditions create a viable path forward,” Michael G. Morris, AEP chairman and chief executive officer, said in a statement. In 2009, the Department of Energy chose AEP to receive up to $334 million through the Clean Coal Power Initiative to partly pay for a CCS system at a coal-powered plant in West Virginia. AEP has terminated that agreement. The system was to capture approximately 1.5 million metric tons of CO2 per year and inject it underground for permanent storage. The project was to be done in four phases, but AEP has informed DOE that it will complete only the first phase, which includes front-end engineering and design, analysis of the environmental impact, and development of detailed Phase II and Phase III schedules. —RRM

EPA FOCUSES ON EXPOSURE TO 14 GLYCOL ETHERS

EPA is acting on its concerns about toxic-ity of and potential increase in consumers’ exposure to 14 ethylene glycol ethers. Last week, the agency proposed a new rule re-quiring that chemical manufacturers notify EPA in advance about any intended new uses of these compounds, which EPA calls glymes, in consumer products. Stephen Ow-ens, EPA assistant administrator for chemi-cal safety and pollution prevention, says, “We need to take a closer look at the poten-tial health effects that additional exposure to these chemicals could have.” Currently, several types of glymes are found in con-sumer printing inks, paints and paint strip-pers, coatings, adhesives, lithium batteries, and brake fluids. Some of these chemicals are linked to developmental and health ef-fects. EPA is concerned about the toxicity of all 14 glymes because of similarities in their molecular structures, physical and chemical properties, and widespread uses. More in-formation on the proposed rule is available at www.epa.gov/oppt/existingchemicals/pubs/glymes.html . —CH

DEFENSE GIVES GRANTS FOR LAB EQUIPMENT

The Department of Defense has made 165 awards totaling $37.8 million to 83 universi-ties to buy research instrumentation. The awards average $230,000 but go as high as $900,000. Made under the Defense University Research Instrumentation Program , the awards are designed to let scientists buy instruments they might not be able to purchase under other research contracts and grants. “Providing awards for much-needed equipment helps U.S. universities provide the world-class re-search and related education that attracts future DOD researchers and engineers,” said Zachary Lemnios, assistant secretary of defense for research and engineering, in a statement. The research areas receiving the awards include surface chemistry and physics; neuroscience; fluid dynamics and propulsion; and ocean, environmental, and biological science and engineering. All of the awards are subject to completion of ne-gotiations between DOD research offices and the academic institutions. —DJH

BILL WOULD REQUIRE ANALYSIS OF AIR RULES

A House committee last week approved a bill that would require Cabinet-level of-ficials to analyze the effects of eight Clean Air Act regulations on employment and the economy. The Republican-backed measure, H.R. 2401, targets EPA’s greenhouse gas emission controls for refineries and utili-ties, a rule aimed at reducing power plant pollution that blows across state lines, and a regulation that clamps down on toxic releases from industrial boilers, including those at chemical manufacturing sites. In addition, the bill includes a rule, not yet finalized by EPA, that would limit mercury emissions from coal-fired power plants. The House Energy & Commerce Com-mittee adopted the legislation 33-13. The legislation would establish a panel with representatives from the Departments of Agriculture, Commerce, Energy, Labor, and Treasury, as well as EPA, the President’s Council of Economic Advisers, the Small Business Administration, the U.S. Inter-national Trade Commission, the Federal Energy Regulatory Commission, and the White House’s regulatory gatekeeper. The

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bill now moves to the House floor, where it is expected to pass. The measure faces dim prospects in the Senate. —CH

FILING FEE REDUCED FOR RAIL COMPLAINTS

The Surface Transportation Board (STB) says it is reducing the fee it charges ship-pers to file a railroad rate or unreasonable practice complaint from $20,000 to $350.

The action has long been sought by chemi-cal companies and other freight rail ship-pers, who have argued that the previous fee made it difficult to challenge railroad industry pricing and practices. “Charging a small business more than $20,000 to bring a complaint is not right,” says STB Chair-man Daniel R. Elliott III, who expressed concern that some meritorious cases may not have been filed with the agency because of high filing fees. “STB should be commended for its effort in lowering filing fees and encouraging previously unrepre-

sented shippers to tell their stories before the commission,” says Glenn English, chairman of Consumers United for Rail Eq-uity, a coalition of railroad shippers. Coali-tion members include the American Chem-istry Council, which represents more than 140 U.S. chemical manufacturers. —GH

25WWW.CEN-ONLINE.ORG JULY 18, 2011

TO REDUCE EXTENSIVE animal testing and speed up safety evaluations, the En-vironmental Protection Agency ’s Office of Pesticide Programs (OPP) is moving slowly but surely to incorporate data from high-throughput-screening assays into its risk assessments. Toward that goal, OPP is considering an integrated approach to pes-ticide testing and assessment. Several EPA officials presented details of the approach at a meeting of EPA’s pesticide scientific advisory panel in late May.

OPP’s integrated approach would combine existing toxicity and exposure information with refined exposure models, computational toxicology models, and high-throughput in vitro assays to narrow down the number of chemicals that need to undergo further testing, says John R. Fowle III, deputy director of OPP’s Health Effects Division. It would also involve developing hazard-based hypotheses about the poten-tial toxicity and fate of a chemical on the basis of its physical-chemical properties.

“The approach allows us to incorporate various tools and types of information, and evolve as the science evolves,” Fowle says. “Our long-term solution is not generating more information faster, but it is really to identify what specific data for which chemicals, which exposures, and which

populations are essential to assess risk,” he stresses.

OPP has also been working closely with EPA’s Office of Research & Development (ORD) to identify key research needs to achieve its vision. Through its new pro-gram—Chemical Safety for Sustainability Research—ORD will work with OPP to address data gaps related to computational toxicology, endocrine disrupters, nano-materials, pesticides, and next-generation human health risk assessment.

“The expectation is that the research coming out of this program is going to provide some broad-reaching, game-changing results on how chemicals are tested, assessed, and managed,” says Elaine Z. Francis, national program director for pesticides and toxics research at ORD. The goal is to provide improved approaches to safety assessments and advanced tools that could help all EPA offices and centers make more-informed decisions, she says, includ-ing what chemicals need to be screened for

endocrine disruption.EPA drew up the first

list of chemicals to be screened for endocrine disruption largely on the basis of exposure and multiple pathways of exposure. The agency selected the second list

largely on the basis of drinking water and pesticide reregistration review priorities. “For the third list, we hope to use the infor-mation from high-throughput assays, quan-titative structure-activity relationships, and exposure information,” Francis says.

EPA could also use high-throughput methods to help prioritize which of the 80,000 chemicals in commerce, most of which have only limited toxicity data, should undergo further testing, particu-larly with respect to reproductive and de-velopmental toxicity.

OPP is keen to adopt new approaches to evaluating risks because it currently requires manufacturers to submit more toxicity data than any other EPA office. Pesticide producers have to conduct ani-mal toxicity studies for numerous possible adverse outcomes, and consequently, EPA receives more data on pesticides than it can use in risk assessments.

“WE ARE FEELING that today’s paradigm of ‘let’s test for everything we can think of and add that on to what we thought of in the 1990s will eventually create a some-what unsustainable process,” OPP Director Steven Bradbury says.

EPA is also finding that “the science is increasingly complex and changing,” Fowle says. “We have nanomaterials coming on board with some novel properties. We are also dealing with chemicals that disrupt hormones.”

The current testing practice “is very time-consuming and resource intensive in terms of both dollars and animal usage,” Fowle points out. It costs the pesticide in-dustry at least $6 million to register a new active ingredient, and it costs EPA an ad-ditional $1.25 million or more and 15 to 36 months to review all those data, he says.

High-throughput assays could save EPA

MODERNIZING TOXICITY TESTS

EPA inches toward high-throughput IN VITRO ASSAYS to reduce cost, time of chemical safety assessments

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terms of both dollars and animal usage.”

FAST SCREENING EPA hopes to use high-throughput methods to decide which chemicals need more testing.

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money and time. For example, EPA’s Tox-Cast program, which aims to predict the toxicity of thousands of chemicals through high-throughput, cell-based assays and computational methods, has screened more than 300 chemicals, mostly pesti-cides, by using about 500 assays over two years at a cost of $6 million, Francis notes. In contrast, it took more than 30 years and $2 billion to obtain the same information with traditional toxicity tests, she says.

Catherine Willett, associate director for regulatory testing for the activist group Peo-ple for the Ethical Treatment of Animals, estimates that 7,000 animals are needed for each registered pesticide. Using cell-based high-throughput assays would significantly reduce that number. But to get there, EPA should develop “a plan with defined goals and targeted completion dates,” she says.

One of the biggest challenges with im-plementing high-throughput methods has been linking cellular and molecular changes that can be monitored with in vitro assays to typical risk assessment end points such as survival, growth, reproductive impair-ment, and disease progression, says Daniel

Villeneuve, an aquatic toxicologist at ORD.“It’s not enough to say we are seeing an

effect; we need to know how that translates into something that we’ve traditionally considered for risk assessment,” Ville-neuve notes. A key step to making that link, he says, is identifying so-called adverse-outcome pathways, which define how an initiating event—a chemical agent interact-ing with a target cell—and a series of sub-sequent events lead to an adverse health effect. No one knows exactly how many adverse-outcome pathways exist, but some scientists predict that there are hundreds.

GENES, PROTEINS, and metabolites are involved in the events leading to adverse outcomes, and how they interact with one another is important, Villeneuve says. By using the high-throughput-enabled “omics” technologies—such as transcriptomics, proteomics, and metabolomics—research-ers can identify the pathways and predict where chemicals are likely to cause pertur-bations that can lead to adverse outcomes.

Identifying toxicity pathways and fo-cusing on systems biology will be critical

“to come up with a more intelligent way of figuring out what data to ask for,” notes Bradbury. Unfortunately, it could take 15 to 20 years to identify all relevant pathways, he warns. However, EPA is optimistic that technological advances, such as improved cell analysis, will eventually lead to rapid identification of the pathways.

Another problem EPA’s pesticides office faces is using data from human-cell-based assays to assess risks on wildlife. Every registered pesticide must meet a human health standard and an ecological stan-dard, Bradbury emphasizes. “Some of the challenges on the ecological front are even more daunting,” he says, in terms of the number of species and different routes of exposure that need to be considered.

The lack of animal cell lines for use with high-throughput assays has Villeneuve and other EPA researchers concerned. In the short term, “we are going to use more animals and more resources,” Villeneuve predicts. But eventually, he says, EPA should be able to predict both ecological risks and human health risks with limited use of animals. ◾

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American Chemical Society www.ProEd.acs.org

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27WWW.CEN-ONLINE.ORG JULY 18, 2011

DNA CAGES SLIP INTO CELLSNanoscientists have fashioned DNA into all man-ner of interesting shapes, from cubes to smiley faces. But a practical use for such structures has remained elusive—until now. A team led by Andrew J. Turberfield of Oxford University reports that tetrahedral cages of DNA can penetrate live mammalian cells, suggest-ing they could be used to deliver drugs and imaging agents (ACS Nano, DOI: 10.1021/nn2005574 ). Turberfield’s team found that fluorescently labeled DNA tetrahedra assembled from four 63-nu-cleotide chains (shown) can slip into human embryonic kidney cells with or without the help of a transfection agent. After pen-etrating the cells, the DNA cages remain largely intact in the cytoplasm for at least 48 hours, experiments show. “These results represent an important first step as proof of concept in efforts to use DNA cages to deliver cargoes and to control their activities within cells,” the researchers note. —BH

TISSUE MORPHING ON PATTERNED SURFACES

Model surfaces presenting gradient ar-rays of ligands have been used for the first time to study tissue shape morphing and directed tissue migration (J. Am. Chem. Soc., DOI: 10.1021/ja204893w ). The study details a strategy for preparing biologically active and chemically selective substrates for investigating various cellular processes including adhesion, migration, and differen-tiation. Wei Luo and Muhammad N. Yousaf of the University of North Carolina, Chapel Hill, used microcontact printing to form a pattern of hydrophobic regions on gold to which they attached fibroblast cells. In the other regions, they deposited hydroqui-none-capped molecules, which, after photo- and electrochemical treatments, were func-tionalized via oxyamine linkages with RGD, a tripeptide that promotes cell migration and adhesion. By controlling the size, shape, and concentration gradient of the RGD regions with patterned photomasks, the team caused cells and tissues to migrate to the RGD regions and form new patterns. In addition, they measured the rate of directed tissue morphing and its dependence on the slope and direction of the gradient. —MJ

MECHANISM REPORTED FOR ELIMINYLATION

Eliminylation, a type of posttranslational protein modification discovered recently, most likely proceeds via a carbanion in-termediate, according to Hua Guo and coworkers at the University of New Mexico

and New York University (J. Am. Chem. Soc., DOI: 10.1021/ja204378q ). Some bacteria use this modification to disrupt signaling in host cells, which usually involves reversible phosphorylation and dephos-phorylation. In eliminylation, bacterial phosphothreonine

lyase enzymes catalyze the irreversible removal of a phosphate group from phos-

TARGETING HOUSEKEEPING TO

TAME TUMORS

Targeting the cell housekeeping processes that cancer mutations hijack might be as effective at killing tumor cells as targeting the cancer-causing mutations themselves, a study suggests (Nature, DOI: 10.1038/nature10167 ). The cancer-fighting drug Gleevec targets a specific mutation, or onco-gene, and effectively treats cancer patients who have the mutation. But Gleevec and similar genetically matched drugs help only a small percentage of patients. So some sci-entists are targeting normal cell processes that get co-opted by oncogenes in hopes of achieving Gleevec-like results. Stuart L. Sch reiber of the Broad Institute and Harvard University, Anna Mandinova and Sam W. Lee of Massachusetts General Hospital , and coworkers have found a molecule that selectively kills cancer cells and tumors in

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Each colored portion of this DNA tetrahedron traces the phosphate backbone in a single strand of DNA.

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mice by blocking a housekeeping process: the ability to quench reactive oxygen spe-cies (ROS). That process is crucial for the survival of cancer cells, but not normal cells. The compound, piperlongumine, comes from the Indian long pepper plant. The team now plans to determine the specific cancer-causing mutations that make cancer cells reliant on ROS quenching, and thus vulner-able to piperlongumine, Schreiber says. Mandinova and Lee have started a company called Canthera Therapeutics to exploit the ROS strategy for cancer treatment. —CD

phorylated threonine. Unlike phosphatase enzymes, which reversibly catalyze a phos-phoryl transfer reaction, the lyases catalyze breakage of a C–O bond and formation of a C=C double bond via β-elimination, which could proceed by any of three mechanisms. Using computational methods, Guo and coworkers find that the most likely mecha-nism is one in which a lysine residue initi-ates the reaction by abstracting a proton to form an enolate carbanion intermediate, which is stabilized by an oxyanion hole in the enzyme. Then, a histidine in the enzyme protonates the phosphate leaving group, which is eliminated to generate a double bond. —CHA

ONE-POT PROTEIN SYNTHESIS

Chemists aiming to design drugs that target vascular endothelial growth factor (VEGF), a protein responsible for blood vessel growth in tumors, could now have a ready synthetic supply of it for their screen-ing tests, thanks to a study (Angew. Chem. Int. Ed., DOI: 10.1002/anie.201103237). Researchers Kalyaneswar Mandal and Stephen B. H. Kent of the University of Chicago have devised a way of producing in one reaction vessel a 204-residue portion of the VEGF protein that is biologically active. “This is the largest protein molecule pre-

28WWW.CEN-ONLINE.ORG JULY 18, 2011

SCIENCE & TECHNOLOGY CONCENTRATES

DETECTING CRUDE OIL IN WATER

A mass spectrometry method could im-prove the way oil-processing facilities detect seawater contaminated with low levels of oil (Anal. Chem., DOI: 10.1021/ac2008042 ). Many national governments regulate the oil concentration of water discharged from these facilities. Stephen Taylor , of the University of Liverpool, in England, and his colleagues sought to improve on the accuracy and sensitivity provided by conventional oil measurement techniques such as ultraviolet fluorescence and infrared spectroscopy by using mem-brane inlet mass spectrometry (MIMS), which can distinguish various types of oil. Rarely used for field testing, MIMS relies on a membrane to block water and other polar molecules from entering the mass spectrometer, while allowing hydrophobic compounds such as oil to pass through for detection. At an oil-processing facility

in Scotland, the researchers measured concentrations of crude oil as low as 15 mg/L, which is half the discharge limit in the U.K. They also could differenti-ate between two types of crude oil, API 35 and API 36, based on hydrocarbon composition. Taylor plans

to couple a portable MIMS instrument with existing oil-in-water monitors to complement their ability to measure oil concentrations quickly. —JNC

COCRYSTAL ENGINEERING SORTS OUT LADDERANES

A cocrystallization strategy commonly used in protein chemistry has been redirected to help elucidate the structures of a pair of complex ladderane isomers, possibly the first application of the technique to the structural characterization of small organic molecules (Proc. Natl. Acad. Sci. USA, DOI: 10.1073/pnas.1104352108 ). Ladderanes are rod-shaped molecules that contain a core set of fused cyclobutane rings. They are used as building blocks in optoelectronics

TAMING A METATHESIS CATALYST

By adding a bipyridine or a phenanthro-line ligand to molybdenum metathesis catalysts, chemists in Germany have trans-formed the sensitive reagents into air-stable precatalysts that can be stored in an open flask for weeks (Angew. Chem. Int. Ed., DOI: 10.1002/anie.201102012 ). Johannes Heppekausen and Alois Fürstner of the

Max Planck Institute for Coal Research note that tetracoordinate molybdenum alkylidenes are “amongst the most power-ful alkene metathesis catalysts known to date.” But because of their sensitivity to air and moisture, the compounds can be tough to work with. Heppekausen and Fürstner discovered that they could transform molybdenum alkylidenes into stable solid precatalysts by reacting them with either 2,2'-bipyridine or 1,10-phenanthroline in toluene at room temperature. To liberate the active catalyst, the chemists simply mix the precatalyst with zinc chloride in toluene at 100 °C. The resulting bipyridine•ZnCl2 or phenanthroline•ZnCl2 precipitate has no effect on the catalyst and need not be filtered. “Our new method combines the

convenience of handling of a crystalline and bench-stable precatalyst with the benefits of a well-defined active species of proven versatility,” the researchers write. —BH

and recently were discovered to be a struc-tural motif in lipid natural products. Leon-ard R. MacGillivray and coworkers of the University of Iowa had prepared a pyridyl-terminated ladderane, but they were unable to pin down the structures of the molecule’s cis-trans isomers by the standard approach of multidimensional NMR. Although the researchers managed to obtain the X-ray crystal structure of one isomer, which is achiral, the other isomer, which is chiral, refused to cooperate, forming only an amor-phous material. But adding 3,5-dinitroben-zoic acid, which forms hydrogen bonds with the ladderane’s pyridyl groups (shown), led to single crystals for the X-ray analysis. “We expect our work will spur others to fol-low similar cocrystallization strategies in synthetic organic chemistry,” MacGillivray says. —SR

pared by one-pot native chemical ligation,” the researchers write. To generate the trun-cated protein, which is a homodimer made of two 102-residue polypeptide chains joined by two disulfide bonds, Mandal and Kent started with three peptide segments and added them together sequentially. The segments covalently bind through the reaction of terminal cysteine groups and thioesters, eventually forming one of the 102-residue monomer chains. These chains then fold, forming three intrachain disul-fide bonds each, and dimerize to yield the biologically active VEGF. What’s signifi-cant about the synthesis, Kent says, is the formation of a total of eight disulfide bonds at near-quantitative yield. —LKW

N

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ZnCl2, toluene

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COCRYSTAL RESCUE This chiral ladderane is naturally an amorphous solid, but addition of a carboxylic acid leads to hydrogen-bonded cocrystals that allow X-ray analysis.

29WWW.CEN-ONLINE.ORG JULY 18, 2011

SCIENCE & TECHNOLOGY

DUTCH ARTIST Madeleine Berkhemer began making sculptures from stockings in 1997, using up to 1,000 pairs of pantyhose to make each of her taut, ethereal pieces. Initially, she didn’t worry about the dura-bility of the nylon- and spandex-based leg-wear in her art.

Then Berkhemer visited a museum showing a work by the French-Ameri-can artist Louise Bourgeois, who also used stockings in her sculptures from the 1940s and onward. The stockings in Bourgeois’ art had lost their elastic-ity and were sagging. “That’s when I got concerned,” Berkhemer says. “I thought, ‘Maybe this will happen with my sculptures.’ ”

Berkhemer contacted Thea van Oosten, a conservation scientist at the Cultural Heritage Agency of the Netherlands . Van Oosten specializes in plastic artifacts and is an expert on polyurethane, the ingredient in span-dex that makes stockings stretchy. The two women have started work-ing together to find a way to prevent Berkhemer’s art from sagging in the decades to come.

Like Berkhemer, many artists are inspired to use plastics without being aware of their limited lifetime. Unfor-tunately, “plastic objects are among the most vulnerable found in muse-ums and galleries,” says Matija Strlič , a chemist at the Centre for Sustain-able Heritage at University College London .

Environmentalists worry about the long lifetimes of plastic packaging in city landfills and the pristine waters of the deep ocean. But museum conser-vators are racing against time to save plastic objects in their collections, whose several-decades-long lifetimes don’t compete with the multiple-mil-lennia-long stability of ancient bronze or stone artifacts, explains Yvonne R. Shashoua , a conservation scientist

at the National Museum of Denmark , in Copenhagen.

Almost all plastics darken with time, as harsh light conditions transform their polymeric ingredients into yellow, orange, or brown molecules. Furthermore, light and temperature fluctuations combine with oxygen and water in the air to break

apart the polymers that make up the plastic. The deg-radation products tend to leach, join-ing an exodus of plastic additives included in recipes to make the material

malleable or to protect it from ultraviolet light or heat. As essential components exit the plastic pieces, artwork begins to crack and crumble—just as a plastic bottle does when left in the sun.

Adding insult to injury, the degradation of some types of plastic isn’t a problem for just the plastic artifact itself. Sometimes the breakdown molecules float over to nearby artifacts, inciting corrosion, stain-ing, or degradation. Researchers and con-servators are figuring out how to diagnose the damage happening to plastic art and artifacts before it is even visible, and they are developing strategies to help these valuable objects last longer.

SINCE THE INVENTION of plastics in the late 1800s, artists and designers have been using them to make everything from high-fashion hair combs and intricate sculptures to moon-mission spacesuits. But “the num-ber of plastics used by artists increased dra-matically in the 1960s,” Shashoua explains, during that era’s love affair with all things plastic and the corresponding increased availability of polymers. Yet it took until the 1990s before the museum world got over what conservators refer to as “plastics deni-

al syndrome”—denying that plastics in a museum’s collection have short lifetimes and degrade—and woke up to the fact that many pieces of plastic-containing art were in grave danger of being lost, van Oosten says.

Four kinds of plastics are particu-larly vulnerable to degradation, she explains. Two of these problematic plastics were among the first devel-oped: cellulose acetate and cellulose nitrate. The third is polyvinyl chlo-ride, one of the top five plastics pro-duced in the world. The fourth is poly-urethane foam, whose many pores increase the material’s surface area and thus exposure to oxygen, light, and water in air—all of which make the plastic susceptible to crumbling.

There’s no one-size-fits-all remedy to deal with plastics in a museum collection—each type of plastic has its own particular chemical quirks that need to be accommodated, van Oosten says. For example, she has found that a spray-on light stabilizer called Tinuvin can protect polyure-thane artwork from light damage and extend its life by decades. The down-side is that it can turn some artwork’s matte look to glossy, which is a deal

PRESERVING PLASTIC ART

Chemistry of polymer-based creations presents UNIQUE PROBLEMS for conservators

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PANTYHOSE HEAVEN Dutch artist Berkhemer made this stocking sculpture, called “Milly’s Chandelier” (2009), from nylon- and spandex-based pantyhose, which have a lifetime of 10 to 15 years.

30WWW.CEN-ONLINE.ORG JULY 18, 2011

SCIENCE & TECHNOLOGY

breaker for many artists and curators, van Oosten adds.

That polyurethane actually has a life-extension option is an exception to the rule in plastics conservation, however. “Once a plastic is made,” Shashoua says, “it’s very difficult to get an antiaging additive into it,” primarily because most plastics are not very porous.

Instead, conservators extend the lives of plastic objects by monitoring and modify-ing the environment around them. This is particularly true of cellulose acetate and cellulose nitrate objects. A famous replacement for ivory and tortoise shell in jewelry of the late 1800s and early 1900s, these plastics were also used in early movie and photographic film. Exposure to light, heat, and air breaks down the polymers so that they release nitric acid and acetic acid. If these acids aren’t removed from the environment around the plastics, they will catalyze further degradation of the cel-lulose acetate and cellulose nitrate.

FURTHERMORE, the acidic off-gassing is so harmful to other artifacts in museum collections—it can destroy metals and tex-tiles—that some conservators refer to cel-lulose acetate and cellulose nitrate as malig-nant plastics. In fashion display cases that present cotton clothing together with these plastic accessories, Shashoua explains, con-servators can find acid-corroded cloth and metal clasps.

Since the mid-1990s, the main weapon against these acids has been adsor-bents—activated carbon for nitric acid and zeolites for acetic acid—which conservators typically place near plastic artifacts to trap the acids.

But little research on the adsorbents’ efficacy has been done since about 2000, mostly “because there aren’t very many scientists working on plastics in museums,” Shashoua says. “We put adsorbents into the storage box because it’s convenient, and usually we see that it improves the situation, but it could be that the cardboard box that we put it in with the adsorbent is actually the important factor that is taking out the acid. We just don’t know.” Shashoua is plan-ning to spend the next year looking at the efficacy of adsorbents and searching the medical, fuel production, and food industry

literature for alternative ways to sequester these acids.

In sharp contrast to objects made with cellulose acetate and cellulose nitrate, which are pre-served by separating them from leachates to prevent further breakdown, objects made from polyvinyl chloride are protected by keeping them sealed in with their leachates. That’s because one of the biggest problems with PVC museum ob-jects—which can include dolls, sculptures, and furniture—is that its plasticizer, typi-

cally di(2-ethyl-hexyl) phthalate, easily migrates out. And we’re not talking just a bit. Some PVC objects “weep plasticizer,” Shashoua says, leaving the plastic brittle and vulner-

able to cracking. But if the plastic artifact is sequestered from the outside atmosphere, then the partial pressure of the exiting plasticizer in the enclosed air counteracts further migration.

Besides destabilizing the structure of PVC museum objects, loss of the plasti-cizer leaves the objects’ surfaces wet and sticky, making them attractive to dust and grime. In the case of the white Apollo

moon-mission space suits, plas-ticizer leaching out of the PVC life-support tubing has crystal-lized on the surface of the plas-tic and stained the nearby white nylon textiles an orangey color, says Lisa Young, a space suit conservator at the Smithsonian National Air & Space Museum in Washington, D.C. Young and

other conservators have had to quaran-tine the PVC from the spacesuits to avoid further unpleasant discolorations of the culturally important suits.

And it’s not just plasticizer that leaches out of PVC. Stearic acid, which is com-monly used in many plastics as a lubricant to keep the object from sticking to its mold, also tends to migrate out and harden, coat-ing the surface of objects with a white pow-dery substance.

When conservators want to clean PVC and other artifacts from these leaching con-stituents, they have to be extremely careful what chemical cleaners they use to remove dust, grime, and any leaking additives. Or-ganic solvents are generally considered a really bad idea, mostly because they tend to dissolve or crack plastics. Use of acetone on polystyrene, for example, turns the trans-parent plastic an opaque white.

Yet water and soap don’t always dis-solve problematic dirt that conservators want to remove. “The process of clean-

Di(2-ethylhexyl) phthalate

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Unfortunately, “plastic objects are among the most vulnerable found

in museums and galleries.”

31WWW.CEN-ONLINE.ORG JULY 18, 2011

ing doesn’t just involve dissolving the dirt—it involves moving it off the surface with a mechanical agent,” Shashoua says. “For example, just rinsing Tupperware with soap and water doesn’t remove the red stain of tomato paste. You also need a scourer or a sponge. In museums, the scourer is going to cause more damage than the water.” Conservators formerly used cotton cloths to clean plastic objects, but increasingly they are trying out new microfibers such as polyester or polypro-pylene or the use of ultrasound to remove dirt via sound waves.

ALTHOUGH CELLULOSE acetate, cel-lulose nitrate, PVC, and polyurethane are the most problematic plastics, museum ob-jects made from polyester and polypropyl-ene are also beginning to show problems, Shashoua says.

Because any conservation or cleaning strategy is specific to a plastic type, muse-um staff need to know an object’s precise plastic makeup. But few plastic art objects come with a chemical ingredient list, and not all museums have laboratories with the tools—primarily infrared and other spectroscopic equipment—to help ana-lyze them. Conservators some-times have to rely on their sense of smell to guide their plastic diagnosis, Shashoua says. Leach-ing phthalate plasticizers give PVC the smell of a new car, she explains, while cellulose acetate smells like vinegar, and polyester has the odor of raspberry jam, cinnamon, and burning rubber.

Strlič thinks it might be pos-sible to replace the human nose with portable devices such as those developed by the military to detect trace amounts of toxic gases. His team is hoping that antiterrorism technology—from portable mass spectrometers to tiny lab-on-a-chip devices—can be tweaked to analyze the smells of plastics in museums.

Strlič has also recently built another tool that conservators can use to identify the type of plastic in a museum object without harming the piece. The tool marries near-infrared spectroscopy with a digital camera to produce two-dimensional chemical maps from which conservators can identify the chemical makeup of many plastic arti-facts. The device can also follow the onset of plasticizer migration before the object

shows external signs of leaching and breakdown (Anal. Chem., DOI: 10.1021/ac200986p ).

As museum staff around the world increasingly realize that plas-tics in their collection are vulnerable, a growing amount of work is being done to find solutions to a problem that is unlikely to go away. For example, conserva-tors from the Smithsonian Institution mu-seums and galleries in the U.S. are trying to create a plastics working group to research and share solutions to plastic degradation problems. In Denmark, museum curators, conservators, the plastics industry, and artists are also starting to work together to fight plastic art degradation under a pro-gram called Plastics Research & Innova-tion for Museums & Industry .

Although researchers are making prog-ress on the protection of plastic pieces,

many artists are still unaware of the ma-terials’ short life even as it becomes easier for them to mix plastics in their ateliers. “There are a lot of ready-to-make plastics available,” van Oosten says. It’s as easy as “putting two cans of liquid material together so polymerization takes place in a mold.” The problem with these do-it-yourself techniques is that the artists don’t realize they need to add the light and heat stabilizers that are often present in indus-

trially produced plastics. “We are seeing problems with art objects made only 10 to 15 years ago,” she notes.

ART SCHOOLS are not filling the educa-tion gap. For example, a recent study of art schools in Europe found that only one—in Munich—gives any training about the inherent instability of plastics, Shashoua says. “Often art schools feel they shouldn’t inhibit the creative skills of artists by say-ing to them at the beginning: ‘If you use

this sort of plastic it will last for 10 years and if you use this other sort of plastic it’s only going to last for three years.’ But the fact is, many museums and art galleries are concerned with the stability of the objects they buy. That means some artists might never get their work in art galleries or museums,” she says.

It’s a dilemma. “As an artist, I shouldn’t be too concerned” about the lifetime of materials—“it stops your creativity,” Berkhemer says. But she thinks more scientific information can also be “a big in-spiration.” Stronger, more durable plastics in the stockings would “allow me to make new forms,” she says.

As some artists begin to consider the chemistry of their supplies and as conser-vation scientists come up with better strat-egies to protect plastic art and artifacts, museum visitors may be able to enjoy these polymeric art forms for centuries to come. Eventually, van Oosten speculates, muse-um visitors may also start to appreciate the look of aged plastic, just as they find aged stone and bronze appealing. It’s probably just a matter of time. ◾

FASHION FAUX PAS Acids floating from cellulose nitrate and cellulose acetate fashion combs can destroy nearby textiles or corrode metal artifacts.

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DEVIL INSIDE A new noninvasive technology makes it possible to identify the nylon (blue) and cellulose acetate (red) makeup of a plastic statue (left).

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32WWW.CEN-ONLINE.ORG JULY 18, 2011

FROM OUTSIDE, the High Explosives Ap-plications Facility at Lawrence Livermore National Laboratory (LLNL) looks like just another office or laboratory building. Inside, however, some of the nation’s most dangerous chemistry is performed.

HEAF, as the facility is known, is the National Nuclear Security Administra-tion ’s designated Center of Excellence for High Explosives Research & Development. Scientists use the facility to synthesize, formulate, and characterize explosive materials. Those tasks play a critical role in nuclear stockpile stewardship by providing a means to understand how components of nuclear weapons age and perform over time. Researchers at HEAF also develop safer explosives to replace older com-pounds, both for the nuclear stockpile and conventional weapons. And the facility’s energetic materials expertise is further brought to bear in counterterrorism ac-tivities, such as explosives detection and mitigation and modeling the effects of im-provised explosive devices.

HEAF and the scientists who use it are part of LLNL’s Energetic Materials Center (EMC), which is directed by Jon L. Maienschein . The beauty of the center, Maienschein says, is that it brings all parts

of explosives research under one roof, including work by experimental chemists, physicists, materials scientists, and engi-neers, along with explosives technicians, machinists, electricians, instrumentation specialists, and modelers. Histori-cally, functions were more isolated. “Particularly, you’d put the people making materials far apart because they’re making dangerous stuff, and you’d put the people blowing stuff up far away because they’re dangerous just to think about,” he says. “Here, we’re all in this one building.”

The integrated approach improves cooperation and communication—for example, someone planning an experiment to test a particular explosive formulation works closely with a modeler to ensure the setup includes the diagnostics and moni-toring necessary to feed back into further computational work. And simultaneous work on nuclear, conventional, and impro-vised weapons means that staff are more likely to see connections between differ-ent projects that better inform their work overall, Maienschein says.

Generally, an energetic material is a combination of an oxidizer and a fuel.

Sometimes the oxidizer and fuel are different compounds, as in common rocket propellants, which incorporate am-

monium perchlorate as the oxidizer and a separate polymer binder that both solidifies the formulation and serves as the fuel. In other cases, the oxidizer and fuel are synthesized together into one molecule. In the classic trinitrotoluene (TNT), for example, the oxygens of the nitro groups are the oxidizers and the car-bons serve as the fuel.

“Low” explosives deflagrate, which means that they propagate energy rela-tively slowly by burning, with one part of a material heating the next. Common ex-amples include gunpowder and fireworks. “High” explosives are those compounds that detonate through a shock front that propagates at 5 to 10 km per second. High explosives include peroxides, azides, TNT, and other compounds.

The explosive properties of compounds can be tuned through their molecular structure, crystal structure, and crystal size; by formulating them into mixtures with various binders or other additives; or even by providing physical constraints. For example, the high explosive octahydro-

1,3,5,7-tetranitro-1,3,5,7-tetra-zocine (commonly known as HMX, for a variety of phrases

including “Her Majesty’s eXplosive”) has two crystal forms, a “chair” β form and a “boat” δ form. HMX crystallizes in the β form at room temperature and transitions from

β to δ at around 165 °C. In an explosion, “the δ phase is often more violent than the β phase,” EMC chemist Elizabeth A. Glascoe says. The volume of HMX also ex-pands with the transition, so depending on how explosives makers want the material to behave, they can either physically con-strain the material to keep it in β or give it room to expand into δ.

WHEN WORKING hands-on with explo-sives, safety is a paramount concern, and safety features are obvious in the warren of hallways of the HEAF laboratories. To start, hallway floors are painted with a white path in the middle. If an explosive

EXAMINING EXPLOSIVESHigh Explosives Applications Facility researchers

tackle science for NATIONAL SECURITYJYLLIAN KEMSLEY, C&EN WEST COAST NEWS BUREAU

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COUNTDOWN LLNL personnel set up flash X-ray equipment at HEAF’s 10-kg firing tank.

SCIENCE & TECHNOLOGY

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33WWW.CEN-ONLINE.ORG JULY 18, 2011

“It’s a fine line to walk between having something be stable and ‘handleable,’ and also have the necessary explosive energy.”

detonates next to a concrete wall, it will send a shock wave through the concrete and blow off the far side, Maienschein ex-plains. People carry-ing samples through the hall must stay on the white path, so that if something happens, it won’t affect an adja-cent lab.

Lab entrances are also color-coded: blue for no explo-sives, green for up to 100 g, orange for 1 kg, and yellow for 10 kg. Labs designed for larger amounts have thicker walls and mazelike entrance halls meant to al-low a pressure wave from an explosion to dissipate before it gets out of the room. Whiteboards state how many people can enter a lab and are used to keep track of who’s there. The cor-ridor rated for 10 kg has a system of warn-ing lights to ensure that multiple people don’t enter at the same time and exceed the limit.

Overall, the building is engineered such that an accidental explosion in one labora-tory doesn’t affect anything or anyone else-where—and no one outside the building knows that anything happened.

To experiment with amounts of ex-plosives from 10 to 90 kg, scientists go to LLNL’s Site 300 , located 15 miles to the southeast; for more than 90 kg, they turn to the Big Explosives Experimental Facil-ity in Nevada.

HEAF staff members are also vigilant about what they do and how they do it. HEAF includes synthesis and formulation labs as well as machine shops and test-ing facilities to explore the properties of explosive compounds and formulations. Work such as mixing explosive crystals with a binder, pressing that mixture into

a pellet, and machin-ing the pellet into a specific geometry—slow cutting and turning rates are key, Maienschein says—is done by operating equipment remotely, from behind a blast shield.

HEAF also pioneered the use of femtosecond laser machining for small parts and particularly sensitive explosives. “The pulses are so short that bonds don’t pick up reso-nance and there’s no heating,” so the material just ablates harmlessly into gas, engineer Jerry Ben-terou says.

In the two de-cades since HEAF was built, no one working at the facil-ity has suffered a significant injury, Maienschein says. “One guy wrenched his knee going down the stairs, and one person got her fin-gers pinched in the tailgate of a truck at the loading dock. We work hard on safety, and we’ve done a

good job,” but staff must stay vigilant, he adds.

A major challenge now for researchers at HEAF is work on improvised explosives that might be used by terrorists. Terrorists “want something easy to make and hard to detect,” Maienschein says. “They don’t care about safety, and they don’t care about stability. We have to work hard on our safety to make sure that for our purposes we handle the materials appropriately.”

To understand all explosives’ thermal and mechanical properties and how they age, scientists perform a battery of tests.

Some tests are mechanical, such as the “drop hammer” test to measure impact sensitivity or a friction sensitivity assay that involves placing a sample on a ceram-ic plate and rubbing it with a peg. Other ways to characterize materials include combustion calorimetry, checks of spark or heat sensitivity, and burn rate measure-ments, which correlate to the violence of an explosion and provide important infor-mation for simulations. Such tests inform both basic material handling and weapons safety, HEAF firing operations manager Brian Cracchiola says. The heat sensitiv-ity of torpedo components, for example, determines whether ship personnel, when faced with a fire in the missle bay, should attempt to fight the flames, flood the bay, or jettison the torpedoes.

HEAF ALSO HAS X-ray and other imaging systems to track crystal sizes and defects, voids between crystals and binder mate-rial, and cracks in pressed pellets, all of which can change with age and affect how an explosive will behave. HEAF’s X-ray capability further plays a role in home-land security—the lab prepares and scans “homemade” explosives to look for signa-tures that can be used by baggage scanners to detect devices, engineer Dan Schneberk says. Scientists have developed materials that mimic those signatures for the Trans-portation Security Administration to use for training personnel.

HEAF has several firing chambers for explosion tests, including two for up to 1 kg of material and one for up to 10 kg. Ex-periments in the tanks are typically heav-ily monitored and analyzed. Wires and sensors embedded in an explosive mate-rial track temperature, pressure, strain, and explosion propagation. If a material is encased in something like a copper tube, how that tube deforms or blows apart also yields information on an explosive’s properties. Sensors track the velocity of flying pieces, and high-speed cameras can record the whole performance.

A new flash X-ray system, called Hydra, allows scientists to peer into a material as it detonates in a firing chamber, to see things such as what happens to a detona-tion shock front when it hits a void in the material. People had assumed—and mod-

FREE FALL The “drop hammer” apparatus drops a weight from as high as 177 cm (nearly 6 feet)to test an explosive’s impact sensitivity.

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eled—that large voids in explosive for-mulations affect the detonation front. “It turns out that once the detonation is es-tablished, it doesn’t care about the voids,” says John D. Molitoris , a physicist and the EMC group leader for dynamic experi-ments. Deflagrations, however, are greatly affected by voids, which can change the symmetry of how a material burns and the degree of violence.

A separate gun tank also enables re-searchers to do “insult” tests to see what would happen when a bullet or some other projectile hits an explosive or other material. “If you want to know what hap-pens to the fuselage of a B-52 bomber if an AK-47 shoots at it, we can do that,” firing operations manager Cracchiola says. Also, if someone has an idea for how to disable roadside bombs by shooting at them, HEAF can test the approach.

IN ADDITION TO characterizing exist-ing explosives, work at HEAF includes synthesis of new explosives that are safer than compounds currently used in weap-ons. Although no explosive compounds are thermodynamically stable, some are more so than others—but with that stability can come a trade-off in power.

Triaminotrinitrobenzene (TATB), for example, is very insensitive to impact and fric-tion—it has a crystal structure in which the rings line up in paral-lel, so layers slide across each other to easily dissipate friction energy. HMX, on the other hand, is harder to handle than TATB—HMX is more heat sensitive and has a herringbone-like crystal structure, so friction can tear up the molecules and set off an explosion. But HMX is also a more powerful explosive than TATB.

“It’s a fine line to walk between having something be stable and ‘handleable,’ and also have the necessary explosive energy,” Maienschein says. LLNL is aiming to split the differ-ence between TATB and HMX with 2,6-diamino-3,5-dinitropyrazine-1-oxide (called LLM-105, for Lawrence Livermore Molecule-105). Compared with other high explosives, LLM-105 has middle-of-the-road energy output and sensitivity, making it relatively easy to handle and unlikely to detonate acciden-tally, but still has enough power to kick off a plutonium charge in a nuclear weapon.

First made nearly 15 years ago, LLM-105 is slowly making its way up the develop-ment chain. LLNL has made nearly 200 molecules to date, and LLM-105 is one of a handful that may see actual use in weap-ons, physicist Thomas Lorenz says. For the nuclear complex, which has stringent re-quirements for safety, long-term stability, toxicity, and high energy density, “you get one explosive every generation,” Lorenz says.

One difficulty with LLM-105 has been synthesis scale-up, says Philip F. Pagoria , EMC group leader for explosive synthesis. Along with standard considerations for taking a synthesis to manufacturing scales, such as cost of materials and waste-stream disposal, there’s the fact that synthetic in-termediates themselves may be explosive. The original LLM-105 synthesis had two issues, Pagoria says: a costly and difficult-to-source starting material plus two ex-plosive intermediates. Pagoria’s group has now streamlined the preparation to make 2,6-diaminopyrazine-1- oxide, which is then nitrated to yield LLM-105.

Other projects at HEAF dive into the fundamental chemistry and physics behind what happens in a detonation, with an

eye toward what makes a particu-lar compound more or less safe to

handle. “When we try to make new molecules, we can’t predict whether one will be a safe one and one will be

a bad one,” chemist Laurence E. Fried says. “We’d like to be able to do that.”

Studies of TATB, for example, show that the detonation process makes nitrogen-containing heterocycles, slowing down final decomposition, whereas nitrometh-ane detonation makes smaller molecules. One indication of safety may be whether detonation products are complicated and can slow down reaction kinetics, Fried says. EMC researchers have also found that some materials under detonation conditions act more like molten salts than

solids, with hydrogen atoms moving and reacting faster than heavier carbon or oxygen.

The integrated approach that EMC and HEAF take for unraveling these

problems is key to their success, Maien-schein says, and goes back to lab founder Ernest O. Lawrence. “The Lawrence hall-mark was integrated teams,” Maienschein says. With the triple mission of stockpile stewardship, better and safer weapons, and counterterrorism, there’s probably no more powerful approach. ◾

SCIENCE & TECHNOLOGY

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Learn more online at

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35WWW.CEN-ONLINE.ORG JULY 18, 2011

BOOKS

IT IS IMPOSSIBLE to be a chemical sci-entist or engineer these days without an acute awareness of the challenges that face this world when it comes to energy. One of the major themes of the 2011 Inter-national Year of Chemistry (IYC) is energy and sustainability.

All the IYC events that I have at-tended—the United Nations Educational, Scientific & Cultural Organization IYC opening and the official IYC events in the U.S., South Africa, Israel, the Philippines, Jordan, and Brazil—have expressed the urgency of our growing energy needs and climate-change challenges, and more pointedly, the responsibilities (as well as capabilities) of chemical scientists to ad-dress these challenges. The severe weather experienced in the middle and southern sec-tions of the U.S. recently and the terrible drought and wildfires we are experiencing in my hometown of Albuquer-que—whether connected with global climate change or not—add a per-sonal anxiety to the urgency of the energy problem.

In light of all this, how refreshing it is to read a logical, nonpolitical plan to ad-dress the energy challenges before us. In “A Cubic Mile of Oil: Realities and Options for Averting the Looming Global Energy Crisis,” authors Hewitt D. Crane, Edwin M. Kinderman, and Ripudaman Malhotra lay out the challenges, opportunities, and complex realities of energy technologies. They are, respectively, one of the founders of the independent think tank SRI Inter-national, an R&D management expert, and an organic chemist. The authors say they wrote the book to inform readers about the technological and economic issues of ener-

gy so that rational, useful policy decisions can be made, understanding that develop-ing new energy technologies to replace fos-sil fuels will take many decades.

The book assumes that we will need sustainable, low-carbon energy sources to dominate our global energy use by the year 2050 and explains the options and challenges in each source of energy from fossil fuels (oil, coal, natural gas, tar sands, etc.) to nuclear energy to many renewables (solar, wind, tidal, etc.). The authors be-lieve we need to make policy choices now to make sure that we have energy options in the future. However, the book does not discuss specific policies nor does it debate global warming. It focuses on energy tech-nology, its challenges, and its possibilities.

All studies of global energy require the dis-cussion of large, almost incompre-hensible, units of energy. To make the concept more intuitive, the authors refer to a cubic mile of oil (CMO),

which roughly equates to the world’s an-nual consumption of crude oil. The world’s total annual energy consumption from all sources is 3.0 CMO, and by 2050, they write, the world will need between 6 and 9 CMO of energy per year to provide for hu-man needs. Although a CMO (which equals 153 quadrillion Btu) may be a more visual unit of energy, I had trouble imagining it. Even when I climbed the Sandia Mountain foothills next to my house in Albuquerque

and looked at the mountain peak rising just about a mile above the plains, a cubic mile of oil still seemed unimaginable.

But the book nonetheless succeeds on many levels. The preface was my favorite part. As a former energy researcher, I have been frustrated by the promotion of energy technology ideas that I know will have little or no impact on the gigantic nature of the global energy problem. The authors make clear that they understand the enormity of the energy problem and thus consider only technologies and solutions that have a pos-sibility of working.

The realistic and helpful nature of their suggestions for energy technologies echoes a highly acclaimed National Acad-emies study, “America’s Energy Future:

TAKING THE MEASURE OF ENERGY OPTIONS

With a STIFF DOSE OF REALISM, book explores the complexity and enormity of global energy challenges

REVIEWED BY NANCY B. JACKSON

Finding a book that leaves the reader with a sense that there are reasonable options for our energy future is both rare and valuable.

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GUSHER The world uses a cubic mile of oil (CMO) each year; by 2050, that figure will inevitably increase.A CUBIC MILE OF OIL:

Realities and Options for Averting the Looming Global Energy Crisis,by Hewitt D. Crane, Edwin M. Kinderman, and Ripudaman Malhotra, Oxford University Press, 2011, 328 pages, $29.95 hardcover (ISBN 978-0-19-532554-6)

36WWW.CEN-ONLINE.ORG JULY 18, 2011

Technology and Transformation,” pub-lished in 2009. Although the authors of “A Cubic Mile of Oil” had no input into the National Academies study, the discussion of energy technologies in their book serves to explain the policy recommendations of the committee. What’s more, the correla-tion between the book and the National Academies study suggests that a meeting of the minds does exist among experts regarding the potential of various energy technologies.

THE AUTHORS go on to explain that they wrote the book to assist others in accurately evaluating potential energy technology schemes. Having seen too many energy technologies proposed and funded that are neither thermodynamically efficient nor a realistic possibility for one reason or another, I find their goal to be worth more than a cubic mile of oil. That is, they succeed in accurately explaining the complexity and enormity of global energy challenges and the requirements for developing realistic energy technology alternatives. “A Cubic Mile of Oil” is an ex-cellent book for anyone who wants to learn enough about energy technology to be able to take the next step and make energy policy decisions.

The book has many useful graphics that effectively display its subject matter. These are a valuable resource for anyone interested in understanding or commu-nicating energy options to other people. Although the book is for lay readers, it has enough technical depth and insight to also be of value to more knowledgeable readers.

That the authors do not advocate for any particular policy direction or specific energy technology is a rare and refreshing characteristic for a book of this type. They avoid scare tactics and threats of disaster. Their plain, technical analysis of energy options leaves the reader unusually opti-mistic about how we can address the ener-gy challenges that will face us in the next 40 years. Finding a book that explains the true hard facts about energy is unusual enough; finding one that leaves the reader with a sense that there are reasonable options for our energy future is both rare and valuable.

NANCY B. JACKSON is a manager at Sandia National Laboratories and the 2011 ACS president.

37WWW.CEN-ONLINE.ORG JULY 18, 2011

OBITUARIES

PEOPLE

Daniel E. Gawiak, 60, research associate in technical services at Baxter Healthcare in Cherry Hill, N.J., died on Nov. 24, 2010.

Born in New York City, Gawiak earned a B.A. in chemistry from Queens College in 1973. He did some graduate work at New York University and Yeshiva University.

Gawiak began his career in 1973 as a junior scientist at the Boyce Thompson In-stitute, in Yonkers, N.Y. In 1976, he briefly worked as a research chemist at Naarden-UOP Fragrances in Long Island City, N.Y. Later that year, he joined Sun Chemical in Carlstadt, N.J., as a research chemist. He returned to the company, now known as Naarden International, as a develop-ment chemist in 1979. From 1982 to 1988, Gawiak worked in Bronx, N.Y., at Hexagon Laboratories, where he became manager of development.

After serving as assistant general man-ager at Rexar Pharmacal in Valley Stream, N.Y., Gawiak was hired by Ganes Chemi-cals in Pennsville, N.J., in 1989, where he was promoted to production manager. A decade later, he joined Wyeth at its Cherry Hill site, which was subsequently pur-chased by Baxter.

Gawiak’s hobbies included music, car-

M. Joan Callanan, 85, a chemist who worked at government agencies for many years, died on April 25 in Washington, D.C., from cardiopulmonary failure.

Born in Washington, D.C., Callanan ob-tained a B.S. in chemistry from Trinity Col-lege, in Washington, in 1948. She received a master’s degree in chemistry from Catholic University in 1950.

She began her career at the National Institutes of Health, doing laboratory re-search on the physicochemical properties of proteins and nucleic acids. Callanan then worked for the National Academy of Scienc-es, writing proposals and grants from 1958 to 1961. From there she moved to the Na-tional Science Foundation, where she wrote and reviewed proposals for projects intend-ed to increase the public’s understanding of science and to provide opportunities for women in science. She retired in 1983.

Callanan became an ACS member in 1950, and she was a fellow of the American Association for the Advancement of Sci-ence. In addition to science, her interests included art, classical music, and traveling.

She is survived by her cousins, Dennis J. Toole and Reilly Ann Toole. —SLR

Gerald J. (Jerry) Keeler, 51, a professor at the University of Michigan, Ann Arbor, who was an expert on measuring and modeling

mercury in the atmo-sphere, died on April 12 after a long battle with cancer.

A native of Burnt Hills, N.Y., he gradu-ated from Boston Col-lege in 1982 with a B.S. in physics and a B.A. in math. He earned

an M.S. in 1983 and a Ph.D. in 1987, both in atmospheric sciences, from the University of Michigan. Keeler was a research associate at the Harvard School of Public Health from 1987 to 1990 and a visiting scientist at the Massachusetts Institute of Technology Nu-clear Reactor Laboratory from 1987 to 1991.

He joined Michigan’s environmental health sciences faculty in 1990, and he be-came a full professor in 2003. He also held appointments in the atmospheric, oceanic, and space sciences department and the geological sciences department.

Keeler founded and directed the univer-sity’s Air Quality Laboratory. He advised state and federal agencies, participated in NATO and United Nations Environment Programme activities, chaired a technical review committee for the Mercury Report to Congress, and testified in 2001 before the House science committee. He became an ACS member in 1993.

Keeler is survived by Joanne, his wife of 27 years, and children, Ryan, Kevin, and Meghan. —SLR

G. N. Russell Smart, 89, professor emeri-tus of chemistry at Muhlenberg College, died on May 3 in Salisbury Township, Pa., of congestive heart failure.

Born in Montreal, he graduated from McGill University in 1942, receiving a B.S. with first honors in chemistry. In 1945, he received a Ph.D. in organic chemistry from McGill, where he conducted research with R. V. V. Nicholls on nitramine explo-sives. He continued conducting explosives research with George F. Wright during postdoctoral study at the University of To-ronto. Smart then worked on organosilanes with Henry Gilman at Iowa State College of Agricultural & Mechanic Arts, in Ames.

In 1947, Smart began a 40-year career teaching organic chemistry at Muhlenberg. He became head of the chemistry depart-ment in 1961 and retired in 1987. Smart was an active researcher in stereochemistry and stereoisomerism.

In 1954, he became a founding direc-tor of the Tuition Exchange, a nonprofit agency that provides college education subsidies to children of college employees. He served as executive director from 1979 to 1994. Smart was a member of First Pres-byterian Church in Allentown, Pa. He was an emeritus ACS member, joining in 1947.

Smart’s wife of 57 years, Margaret, died in 2003. He is survived by a daughter,Megan Skinner; sons, David and Derek; and sister, Barbara Davidson. —SLR

Jane Jones Mackey, 86, a chemical engi-neer, died in Cartersville, Ga., on April 25.

The Nashville native earned a bachelor’s in chemistry in 1944 at Vanderbilt Univer-sity. The following year, Mackey received a bachelor’s in chemical engineering, thereby becoming the first female graduate of Vanderbilt’s School of Engineering.

She joined the Tennessee Valley Author-ity in fertilizer testing and development and was TVA’s first woman engineer. After marrying coworker James S. Mackey in

ing for tropical fish, gardening, and grow-ing orchids. He served on the board of the Delaware Orchid Society and participated in church and civic affairs. He became an ACS member in 1974.

Gawiak is survived by his wife, Victoria; his sister, Diane Oates; and two neph-ews. —SLR

1956, nepotism rules forced her out. But she returned to TVA to serve as editor of a soils and fertilizer abstract journal when those rules were rescinded in 1976. She retired in 1992.

Mackey joined ACS in 1979. She was ac-tive in the society’s Wilson Dam Section and served as the section’s chair in the 1980s. Mackey was also a member of the Sherlock Holmes Club and of Wood Av-enue Church of Christ.

She was preceded in death by her hus-band. Survivors include her son, James, and grandsons, Alexander and Harold. —SLR

Obituary notices of no more than 300 words may be sent to Susan J. Ainsworth at s_ainsworth@acs.org and should include an educational and professional history.

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Please mail your resume indicating Requisition Code 1101151 to Dr. Michael Kannisto, Director, Talent Ac-quisition, BASF Corporation, 100 Campus Drive, Flo-rham Park, NJ 07932. BASF Corporation has a strong commitment to diversity and welcomes applications from all individuals. EOE M/F/D/V.

THE DEPARTMENT OF CHEMISTRY AT NSYSU has faculty positions open starting from February 2012. Outstanding applicants with teaching and research interests in inorganic and analytical chemistry are encouraged to apply. The appointments will be at the rank of Assistant Professor, but established senior applicants will be considered as well. A complete ap-plication should include a curriculum vitae, a summary of research plans, two or more research proposals, a brief statement of teaching interests, and three or more letters of recommendation. Electronic submis-sions are encouraged and should be sent to Profes-sor Wei-Lung Tseng at tsengwl@mail.nsysu.edu.tw or mailed to the Search Committee, Department of Chemistry, National Sun Yat-sen University, 70 Lien-Hai Road, Kaohsiung 80424, Taiwan. Review of applications begins on September 15, 2011, and will continue until the positions are filled.

TEMPORARY FACULTY POSITIONDARTMOUTH COLLEGE

Applications are invited for a temporary faculty posi-tion in General Chemistry for the winter term (Janu-ary–March) of 2012 at Dartmouth College. We seek an experienced teacher with an established record of out-standing teaching. Applicants should submit a curricu-lum vitae, a statement of their teaching background, and arrange for two letters of recommendation to be sent on their behalf. All inquiries and applications will be treated confidentially. Application materials should be sent to Chair, Temporary Faculty Search Commit-tee, Department of Chemistry, 6128 Burke Labora-tory, Dartmouth College, Hanover, NH 03755-3564. The Committee will begin to consider completed appli-cations as they are received and will continue to review applications until the position is filled. With an even dis-tribution of male and female students and over a quar-ter of the undergraduate student population members of minority groups, Dartmouth is committed to diversity and encourages applications from women and minori-ties. Dartmouth College is an Equal Opportunity and Affirmative Action Employer.

ACADEMIC POSITIONS

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newscripts

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CC&&EENN MMOOOBBILLEE.

AUGUST

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This fall, James Pickett , an adjunct chemistry professor at Blackburn College, in Carlinville, Ill., will be

putting his chemistry students to work producing biodiesel that the school can use to power small machinery, such as tractors and lawn mowers.

The idea grew out of Pickett’s contem-porary chemistry course, which o� ers a unit on RENEWABLE FUELS. Rather than having his students do routine chemistry labs, Pickett thought it would be more interesting to have them produce biodiesel for the school. “The college has a sustainability program, and this seemed to be a natural fi t,” Pickett says.

To make the biodiesel, the students will take used cooking oil from the school cafeteria as a starting material and combine it with an alco-hol and a strong base. Pickett anticipates that each semester his class can produce up to 45 gal of fuel for Blackburn.

He acknowledges that the project will hardly put a dent in the school’s fuel budget. But what’s more important, he says, is that the stu-dents will see chemistry in the context of their everyday lives—and they will be helping their community.

Walk into the chemistry building at

Emory University, and the fi rst thing you’ll probably notice is a mo-bile. Not a mobile device, but one of those free-fl oating, asymmetrical objects dangling from the ceiling. Before you know it, you’re surrounded by mobiles, thanks to chemis-try professor Albert Padwa , who has been collecting these WHIMSICAL CREATIONS since the 1970s.

Padwa usually picks up a mobile when-ever he travels to a conference, and in recent years, he has supplemented his collection with mobiles he creates himself. Padwa draws inspiration from Alexander Calder , the famous American sculptor who is credited with inventing the dangling art pieces.

When the mobiles began fi lling his home,

STUDENTS MAKE BIODIESEL, PADWA’S MOBILE CREATIONS

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Padwa brought some of them to work. “I started giving away some of the mobiles I had created to my colleagues in the chemis-try department,” he says. “Almost every-one has a mobile now.” Padwa notes that roughly 80 of his mobiles adorn the various o� ces and corners of the chemistry depart-ment; 40 of them are in his o� ce alone.

He gives mobiles as gifts to celebrate special occasions. For example, he’ll give one to a professor who has just received tenure. During the holiday season, Padwa sends out greeting cards to friends and former

students, and on each card is a� xed a photo of a mobile. His enthusiasm for this art form has been infectious; some of his colleagues have created

their own mobiles. Padwa says someone even gave him a mobile

decorated with dangling amino acid structures that is now a dominant fi xture in his o� ce.

Although Padwa’s mobiles do not have an obvious chemistry con-nection, he claims that the ceiling hangers have been inspired by chemistry. “There is so much science that is inherently con-nected with the nature of complex molecules in three-dimensional space,” he says. “How I regard mobiles is that they fl oat in 3-D. Mobiles possess oddball shapes, which are all in balance, and there is a lot of symbolism between 3-D mobiles and complex molecular struc-

tures. That’s why it ignites my imagination and enthusiasm, and that’s why I build them, much as I assemble complex natural products in our laboratory.”

Padwa hopes that his passion for col-lecting and creating mobiles will become part of his legacy at Emory: “They may not remember me for my science 25 years from now, but there will be enough mobiles in the chemistry building that everybody will remember me.”

Lab experiment: Turning cafeteria cooking oil into biodiesel.Mobile man: Padwa’s office doubles as an art exhibit.

LINDA WANG wrote this week’s column. Please send comments and suggestions to newscripts@acs.org.

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