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NESACS

February 2002 Vol. LXXX, No. 6

MonthlyMeetingWillie E. May speaks about NIST programs in chemicalmetrology

Book Review“The Thirteenth Element”by John Emsley

SummerScholarReportModeling of Blood-Brain Barrier Permeability for Drugs

Board ofDirectorsNotes of the Meeting of November 8, 2001

2 The Nucleus February 2002

Eastern Analytical Symposium

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The Nucleus February 2002 3

The Nucleus is distributed to the members of the Northeastern Section of the American Chemical Society, to the secretaries of the Local Sections, and to editors of all local A.C.S. Section publications.Forms close for advertising on the 1st of the month of the preceding issue. Text must be received by theeditor six weeks before the date of issue.Editor: Arno Heyn, 21 Alexander Rd., Newton, MA 02461,

Tel: 617-969-5712, FAX: 617-527-2032; e-mail: [email protected] Editor: Myron S. Simon, 20 Somerset Rd., W. Newton, MA 02465, Tel: 617-332-5273Board of Publications: Patrick M. Gordon (Chair), Frank R. Gorga, Marietta H. Schwartz, E. Joseph

Billo (Consultant)Business Manager: Karen Piper, 19 Mill Rd., Harvard, MA 01451,

Tel: 978-456-8622Advertising Manager: Vincent J. Gale, P.O. Box 1150, Marshfield, MA 02050,

Tel: 781-837-0424; FAX: 781-837-8792Contributing Editors: Mukund Chorghade, Patricia Hamm, Features; Edward Atkinson, History of

Chemistry; Maryann Solstad, Health; Dennis Sardella, Book Reviews; Marietta H.Schwartz, Software Reviews; E. Joseph Billo, Puzzles.

Calendar Coordinator: Donald O. Rickter, e-mail: [email protected]: E. Joseph Billo, Donald O. Rickter, M.S. SimonWebpage: Webmaster: Frank R. Gorga, [email protected]

Asst. Webmasters:Terry Brush, [email protected] Heinselman, [email protected]

Copyright 2002, Northeastern Section of the American Chemical Society, Inc.

ContentsNESACS Committee Chairs for 2002_______________________4

Monthly Meeting _______________________________________5Joint Meeting with YCC and NOBCChE. Willie E. May from the National Instituteof Standards and Technology speaks on its programs in chemical metrology

NOBCChE ____________________________________________7The National Organization for the Professional Advancement of Black Chemistsand Chemical Engineers

Book Review __________________________________________7“The Thirteenth Element” by John Emsley, reviewed by Dennis Sardella

Board of Directors _____________________________________9Notes of the Meeting of November 8, 2001

Summer Scholar Report ________________________________11“Modeling of Blood-Brain Barrier Permeability for Drug and Drug-Like Compounds” by Kimberly Rose and Lowell H. Hall

Applications Invited ___________________________________16James F. Norris and T.W. Richards Undergraduate SummerResearch Scholarships for 2002

Puzzle Column _______________________________________17

Cover: Dr. Willie E. May (NIST)

Deadlines: April 2002 issue: February 21, 2002May 2002 issue: March 14, 2002

The Northeastern Section of the AmericanChemical Society, Inc.Office: Marilou Cashman, 23 Cottage St.,Natick, MA 01760. 1-800-872-2054 (Voice or FAX) or 508-653-6329. e-mail: [email protected] Section business may be conducted via the business office above.NESACS Homepage:http://www.NESACS.orgFrank R. Gorga, WebmasterWashington, D.C. ACS Hotline:1-800-227-5558Officers 2002Chair:Morton Z. HoffmanChemistry Department, Boston UniversityBoston, MA 02215-2507; 617-353-2494 [email protected]:John L. Neumeyer1 Holiday Rd.Wayland, MA 01778; 617-855-3388 [email protected] Past Chair:Timothy B. FrigoAdvanced Magnetics, Inc.61 Mooney St., Cambridge, MA 02138617-497-2070x3007 [email protected]:Michael SingerSigma RBI1 Strathmore Rd.Natick, MA [email protected]:James PiperSimmons College, 300 The FenwayBoston, MA 02115,617-521-2722 [email protected]:Anthony RosnerArchivist:Myron Simon20 Somerset Rd.Newton, MA 02465; [email protected]:Michael E. Strem, Joseph A. Lima,Esther A.H. HopkinsCouncilors: Alternate Councilors:Term Ends 12/31/2002 Term Ends 12/31/2002Mary T. Burgess Michael J. DubeMichaeline F. Chen Jean Fuller-StanleyDoris I. Lewis Patrick M. GordonJulia H. Miwa John L. NeumeyerTerm Ends 12/31/2003 Term Ends 12/31/2003Catherine E. Costello Wallace J. GleekmanWilliam Klemperer Arno H.A. HeynDorothy J. Phillips Howard R. MayneBarbara G. Wood Alfred ViolaTerm Ends 12/31/2004 Term Ends 12/31/2004Thomas R. Gilbert Timothy B. FrigoPatricia H. Hamm Morton Z. HoffmanMichael J. Hearn Truman S. LightArlene W. Light Donald O. Rickter

All Chairs of standingCommittees, the editor of THE NUCLEUS, and the Trustees of SectionFunds are members of theBoard of Directors. AnyCouncilor of the American Chemical Societyresiding within the section area is an ex officiomember of the Board of Directors.

DirectionsFrom the West: Take the Mass. Turn-pike (I-90) to Exit 18. Exit left, followsigns to Cambridge. At the second setof lights turn right into Storrow Drive.Exit at the Kenmore Square Exit. Fol-low * below.From the South or North: Take Rte.I-93 to Boston. Exit into Storrow Driveat Exit 26. Continue on Storrow Driveto the Kenmore Exit. Follow * below.

*From the Kenmore Exit off Storrow Drive:At the first set of lights turn right into BeaconStreet. In Kenmore Square stay in the center laneand take the center road, which is Beacon St. TheHoliday Inn is about 0.6 Mi. on the right at St.Paul St. Enter the driveway into the garage at thein-town end of the building. Bring parking ticketto dinner desk for validation. Parking at meterson Beacon Street may also be available, shouldthe garage be full (no meter charge after 6:00pm).By Public Transportation: Take (or change atPark St. to) the Green Line, “C” train. Exit at theSt. Paul St. stop (3rd. stop after K enmore) acrossfrom the Holiday Inn ◆◆


Corporate PatronsAlfa Aesar, a Johnson Matthey Com-

panyHoechst Marion Roussel Co.Pharm-Eco Laboratories, Inc.Physical Sciences, Inc.Polaroid CorporationStrem Chemicals, Inc.Corporate SponsorsAerodyne Research, Inc.AstraZeneca R&DBorregaard Synthesis, Inc.Bristol-Myers SquibbCambridge Isotope LabsConsulting Resources CorporationDike, Bronstein, Roberts &

Cushman, LLPHoughton Chemical Corp.JEOL, USA, Inc.MassTrace, Inc.New England BiolabsOrganix, Inc.Pfizer, Inc.Research Biochemicals Int’lZymark Corporation

YCC CareerEventFebruary 14, 2002,3:30-5:30 pm Holiday Inn, Brookline, MA 1200 Beacon St.

Younger Chemists are invited to attendthis Career Clinic to learn about possi-ble careers in chemistry. The FREEevent will be held before the monthlymeeting of the Northeastern Section,ACS. Contact Marilou Cashman [email protected] or at 800-872-2054 if you wish to stay for dinner andthe evening lecture. For students thedinner price is only $ 8.00!

3:30-4:00 Résumé Writing. Dr.Mukund Chorghade,Geltex Pharmaceuticals

4:00-4:20 Industry. Mark Behnke,Genetics Institute/Wyeth-Ayerst Research

4:20-4:40 Patent Law. Dr. JesseFecker, Hamilton, Brook,Smith & Reynolds

4:40-5:00 Industry. Dr. AngelesDios, Geltex Pharmaceuti-cals

5:00-5:20 Academia. Prof. CherylSchnitzer, Stonehill Col-lege ◆◆

CommitteeChairs for2002Awards Michael DubeBrauner Award Doris LewisBd. of Publications Patrick GordonBudget James PiperBusiness Liaison Michael StremChem. Health & Safety Mary Ann SolstadChemical Education Ruth TannerConstitution and Bylaws Catherine CostelloContinuing Education Alfred ViolaEducation Task Force James GolenEsselen Award Judith KoobGovernment Relations Michael HearnLocal Arrangements Mary BurgessMedicinal Chemistry Ernie GromanMembership Michaeline ChenNational Chemistry Week Sara IacobucciNational Meeting Morton HoffmanNominationg Tim FrigoNorris Award Patricia SamuelProfessional Services Patricia HammProgramming John NeumeyerProject SEED Patricia MabroukPublic Relations Mukund ChorghadePublic Service James GolenRichards Medal Patricia MabroukSenior Chemists Charles BardsleySpeakers’ Bureau Susan Chiri-ButaSummerthing Wallace GleekmanWebmaster Frank GorgaYounger Chemists Amy Tapper ◆◆

BiographyWillie E. May received the B.S.degree in chemistry from KnoxvilleCollege, Knoxville, TN in 1968 and aPh.D. in analytical chemistry from theUniversity of Maryland at CollegePark, MD in 1977. He was employedat the Oak Ridge Gaseous DiffusionPlant from 1968-1971. He joined theNational Bureau of Standards, as aResearch Chemist, in 1971. Hebecame Group Leader for LiquidChromatography, Organic AnalyticalResearch Division 1976 and becameChief of the Division in 1983. In 1994,

Dr. May became Chief of the Analyti-cal Chemistry Division (a combinationof the Organic Analytical and Inor-ganic Analytical Chemistry Divisions).

The Analytical Chemistry Divi-sion is one of five Divisions in theChemical Science and TechnologyLaboratory, National Institute of Stan-dards and Technology. Dr. May isresponsible for policy development,planning, priority setting, fiscal alloca-tion, staffing, and management of theday-to-day operations of the Division’sapproximately 100 scientists, techni-cians and administrative/ clerical sup-port staff. The Division has an annualbudget of about $15M of which about

$6M supports programs of other Fed-eral and State Government Agenciesand/or American Industry on a costreimbursable basis.

The Division serves as theNation’s reference laboratory forchemical measurements and standards.The core competencies reside in fiveGroups: Spectrochemical Methods,Organic Analytical Methods, GasMetrology and Classical Methods,Molecular Spectrometry and Microflu-idic Methods, and Nuclear AnalyticalMethods.

Dr. May’s personal research activ-ities were focussed in the area of traceorganic analytical chemistry, with spe-cial emphasis on the development ofliquid chromatographic methods forthe determination of individual organicspecies in complex mixtures (i.e.,extracts of environmental, food, andclinical samples) and the developmentof liquid chromatographic methods forthe determination of physico-chemicalproperties such as aqueous solubilities,octanol/water partition coefficients,and vapor pressures of organic com-pounds. This work is described inmore than 100 peer-reviewed publica-tions. He has presented more than 150invited lectures during his 30-year pro-fessional career at U.S. industrial sites,Colleges/Universities and TechnicalMeetings throughout the world.

Dr. May has several leadershipresponsibilities in addition to those atNIST. Currently he is Chair, OrganicAnalysis Working Group, ConsultativeCommittee on the Quantity of Mater-ial, International Committee forWeights and Measures; Chair, Techni-cal Committee, North AmericanMetrology Cooperation; and Chair,Chemical Metrology Working Group,Interamerican System for Metrology.In the past he has served as Presidentand Executive Board Member for theInternational Society for PolycyclicAromatic Compounds; Chair, PhysicalSciences Panel, Ford Foundation Pre-doctoral Fellowship Evaluation Board;Chair, Chemistry Panel, Texas HigherEducation Coordinating Board; Chair,Chemical Metrology Subpanel, Insti-tute for National Measurement Stan-


Monthly MeetingThe 831st Meeting of the Northeastern Section of the AmericanChemical Society, held jointly with the Younger ChemistsCommittee and the National Organization for the ProfessionalAdvancement of Black Chemists and EngineersThursday, February 14, 2002 at the Holiday Inn,1200 Beacon St., Brookline, MA5:30 pm Social Hour; a table of Career Services Literature and Aids will be

available 6:30 pm Dinner7:45 pm Evening Meeting, Dr. Morton Z. Hoffman, Chair, presiding

Dr. Willie E. May, Analytical Chemistry Division, Chemical Scienceand Technology Laboratory, National Institute of Standards and Tech-nology: NIST Program in Chemical Metrology and its Impact on U.S.Industrial Competitiveness, Trade, and Quality of Life

In honor of the day, you are invited to bring your special Valentine to the dinneras guest of the Section.Dinner reservations should be made no later than noon, February 7, 2002.Please call or f ax Marilou Cashman at (800) 872-2054 or e-mail [email protected]. Reservations not cancelled at least 24 hours inadvance must be paid. Members, $25.00; Non-members, $28.00; Retirees,$15.00; Students, $ 8.00. THE PUBLIC IS INVITED.Anyone who needs special services or transportation, please call MarilouCashman a few days in advance so that suitable arrangements can be made.Free Parking in the underground Hotel garage, enter from westbound BeaconSt. Obtain voucher at dinner desk.Next Meeting: Richards Medal Award to Prof. Stephen J. Lippard (M.I.T.)“Three Avenues in Bioinorganic Chemistry: Cisplatin, Methane Monoxygenase,and Metalloneurochemistry

continued on page 6

From its very inception, the UnitedStates established the authority of Con-gress to “… fix the standard of weightsand measures…” (Constitution of theUnited States, Article 1, § 8). Thenational importance of measurementscience and measurement standards inthe U.S. and a commitment to a strongFederal role was again recognized inthe early 20th century with the estab-lishment of the National Bureau ofStandards (NBS) in 1901.

This well-defined role for NBSwas re-articulated and expanded whenthe Bureau was renamed the NationalInstitute of Standards and Technology(NIST) in the Omnibus Trade andCompetitiveness Act of 1988. NISTwas asked to:

“… augment its unique abilityto enhance the competitivenessof American industry whilemaintaining its traditional func-

tion as lead national laboratoryfor providing the measurement,calibrations, and quality assur-ance techniques which underpinU.S. commerce, technologicalprogress, improved product reli-ability and manufacturingprocesses and public safety;”

Although physical quantities suchas length, mass, temperature, time, etc.are the first to come to mind when onethinks about NIST and measurementstandards, chemical measurementresearch and standards have been amajor activity since the establishmentof NBS. Because the analytical chem-istry function at NIST has a differentobjective than similarly named func-tions in industry or academia, it is car-ried out at NIST in a some whatdifferent manner.

This talk will describe ho wNIST’s research and service programsin Analytical Chemistry are structuredto provide the reference base andunderpinning for chemical measure-ments made throughout the U.S. andon a de facto basis – through much ofworld. Examples will be given regard-ing the economic and social impact ofresearch and measurement serviceactivities in the areas of:

• Healthcare• Food and Nutrition• the Environment• Forensics• Pricing and Trade of Commodities• Advanced Materials Characteriza-

tion ◆◆

AbstractNIST Program in Chemical Metrology and its Impact on U.S.Industrial Competitiveness, Trade and Quality of Life


Have you looked at the NESACS

website?WWW.NESACS.org

dards, Canadian National ResearchCouncil; and Chair, Committee onMinority Affairs, American ChemicalSociety.

Honors and Awards presented toDr. May include: Department of Com-merce Bronze, Silver and GoldMedals; National Institute of Stan-dards and Technology Equal Employ-ment Opportunity Award (1982 and1993); Arthur S. Flemming Award forOutstanding Individual Performancein the Federal Government before theage of 40; Presidential Award forSenior Executive Service to the Fed-eral Government; the NOBCChEPercy L. Julian Award for OutstandingResearch in Organic Analytical Chem-istry; and the 2001 Distinguished Ser-vice in the Advancement of AnalyticalChemistry Award given by the Analyt-ical Division of the American Chemi-cal Society.

Dr. May is married (Jeannie Tram-ble) and the proud father of JeannieceMichele and Eric Jermaine May. ◆◆

BiographyContinued from page 5

“The Thirteenth Element”, by JohnEmsley, traces the history of phospho-rus from its discovery to its importancein the present day. The book is billedas the first biography of an element,although I would almost be tempted todescribe it as something between aportrait and a police “rap sheet”.

The story begins in the latter partof the seventeenth century with anaccount of the discovery of elementalphosphorus by the alchemist HennigBrandt. Seeking the philosopher’sstone, the legendary substance reputedto be able to convert base metals intogold, Brandt pyrolyzed the residue oflarge volumes of urine, obtaining thefirst impure sample of the element.Fascinated by its luminescence, Brandtspent several years vainly attempting touse it to transmute elements. Eventu-ally, he settled into a less dramatic,albeit somewhat more lucrative, careeras a supplier of phosphorus to others,who took the element “on the road” asa scientific curiosity, performingdemonstrations at the courts of Euro-pean princes, and for groups of scien-tists willing to pay for the privilege ofwitnessing its eerie glow and ability tocombust spontaneously. During thetwilight period when alchemy wasgradually transforming into chemistry,the unique behavior of phosphorusbrought it to the attention of seriousscientists, who seem to have expectedit to have almost magical powers. Thestory of Robert Boyle’s fascinationwith phosphorus is intriguing and illus-trative of the times, encompassingextensive scientific study of its proper-ties, attempts to use it to transmutebase metals into gold, and what canonly be described as the type of anticsthat would get a freshman chemistrystudent thrown out of lab.

“His [Boyle’s] favorite trick wasto dip his finger in the liquid phospho-rus and draw lines on linen or on thehands of guests, both men and women,noting how a little phosphorus went along way, and that those hands hetouched could then touch others andpass the luminosity on.”

By the time Boyle got around tophosphorus, however, it was already onthe medical map, a subject taken up byEmsley in chapter 3. Paracelsus’ con-viction that all disease had a chemicalbasis had prepared the ground for theuse of chemicals as medications, andthe seemingly magical properties ofelemental phosphorus naturally led toits use as a tincture to treat a wide vari-ety of conditions. Oddly, despite thetwin impediments of its ineffectivenessand its toxicity, its use persisted eveninto the very early twentieth century,and one wonders what collateral dam-age its prescription might ha veentailed. (One rather amusing side-light: a nineteenth century sourcerefers delicately to its ability to pro-duce “venereal excitation”, conjuringup a picture of phosphorus as a kind ofpotential Victorian Viagra.)

By far, though, the most wide-spread use of phosphorus was in theproduction of lucifers and strike-any-where matches, and Emsley devotesseveral chapters to the development,growth, and social impact of the matchindustry, including the dreadful plagueof “phossy jaw” that afflicted its work-ers. This material is really social his-tory, and provided me with moreinformation about the match industrythan I really wanted to know.

The catalog of grim stories contin-ues in the next chapter, with an accountin gory detail (in both the literal and


NOBCChEThe National Organization forthe Professional Advancementof Black Chemists andChemical Engineers (Pronounced “No be shay”,www.nobcche.org)

NOBCChE, which was established in1975, is committed to the discovery,transmittal, and application of knowl-edge in the fields of science and engi-neering. The mission of NOBCChEtherefore is to build an eminent com-munity of scientists and engineers byincreasing the number of minorities inthese fields. NOBCChE will achieveits mission through diverse programsdesigned to foster professional devel-opment and encourage students to pur-sue careers in science and technicalfields. To this end, NOBCChE willestablish educational partnerships withschool districts, municipalities, busi-nesses, industries, other institutionsand organizations in the public andprivate sectors.

Awards are presented to recognizeachievements by outstanding minorityscientists, engineers and science teach-ers who have made significant contri-butions in their fields. These are veryprestigious awards and are judgedcarefully by peers as well as by theAwards Committee.

The Organization’s first nationalmeeting was held in March 1974 inNew Orleans and has continued to be astrong program throughout the years.The national meeting provides a rareopportunity for Afro-Americanchemists and chemical engineers todiscuss issues of significance to theircareers, to present technical papers, toformulate priorities and topics forfuture Meetings.Dorothy J. Phillips ◆◆

Book ReviewThe Thirteenth Element: The Sordid Tale of Murder,Fire and Phosphorus,by John Emsley (John Wiley & Sons, 2000) 327 pp.,ISBN 0.471 39455-6; $24.95 (hardcover)Reviewed by Dennis J. Sardella Department of Chemistry Boston College, Chestnut Hill, MA. 02467

Ucontinued on page 9


metaphorical senses) of the develop-ment of phosphorus incendiary bombsin the war. Here again, the chapter readmuch longer than it was. Was a day-by-day account of the firebombing ofHamburg really necessary?

Succeeding chapters recount theuse of phosphorus in nerve gases andinsecticides, and as a readily available,cheap, and apparently common poison(in the latter instance, in perhaps some-what more detail than was warranted).Quite a few murder cases were outlined,most of which seemed rather repetitivewithout affording much new insight.

Chapter 10 affords a brief respite,with the story of the growth of thephosphorus industry, but is quicklysucceeded by a survey in chapter 11 ofenvironmental disasters involvingphosphorus.

Chapter 12 finally brings somewelcome relief from the rather longand dreary tale of illness, death anddestruction by introducing phosphorus’ubiquitous role in the biosphere, princi-pally in the forms of adenosine diphos-phate and adenosine triphosphate.Justus Von Liebig’s research in agricul-tural chemistry led him to formulatethe Law of the Minimum, essentiallyan application of the limiting reagentprinciple, a theme continued as Emsleyoutlines the positive role of phospho-rus, and I found myself wishing thisportion of the book were longer.

In the book’s final chapter, Emsleyveers toward the border of the gothic,focusing on the topic of spontaneoushuman combustion, a subject that Ihave hitherto tended to associate morewith supermarket tabloid headlines andhorror films than with serious science.Nonetheless, he recounts se veralinstances throughout history (includingsome supposed eyewitness reports) inwhich humans have allegedly sponta-neously burst into flame and been vir-tually entirely consumed.

Seeing possible significance in thecommon observation that flames seemoften to initially erupt from the chestcavity, Emsley hypothesizes that oneconceivable mechanism might be the

generation of the p yrophoric gasdiphosphine (P2H4) in the stomach orintestines and its subsequent contactwith oxygen, either internally, orthrough body openings. Since it isunclear whether there is any evidencefor the metabolic production of diphos-phine, this hypothesis, while interest-ing and perhaps entertaining, seemsspeculative at best.

The book underwent a namechange at some point on its trans-atlantic journey, from “The ShockingHistory of Phosphorus”, a title bothless mysterious than “The ThirteenthElement”, and more subtle than itssubtitle “The Sordid Tale of Murder,Fire and Phosphorus.” In fact, Ems-ley’s Acknowledgements and his Intro-duction still refer to it by the Britishtitle, a small slip that should have beencaught for the sake of consistency.

Like all of Emsley’s books, The“Thirteenth Element” is entertainingand informative, although since thechemistry of phosphorus is relativelylimited, there is little in the way ofvariety that Emsley is able to offer, andhe thus places much more emphasis onthe misuses of phosphorus, Mr. Hyde

after all, being rather more interestingthan Dr. Jekyll. However, I amreminded of having once heard some-one comment of “Paradise Lost” thatMilton did such a masterful job ofdepicting the evil persona of Satan,that God rather paled by comparison,and while it is entertaining and inform-ative, I am a bit concerned that thelong litany of perfidy and harm in “TheThirteenth Element” might only servemore to reinforce a non-scientist ’s pre-conceptions about chemicals than tocreate a positive impression of theirimportance. ◆◆

New MembersInvitation to attend a meetingYou are cordially invited to attend oneof our upcoming Section meetings asguest of the Section at the Social hourand dinner preceding the meeting.

Please call Marilou Cashman at800-872-2054, 508-653-6329, or:[email protected] by noon of thefirst Thursday of the month, letting herknow that you are a new member. ◆◆

Book ReviewContinued from page 7


ACS NewsNIST Designated as a NationalHistoric Landmark

Celebrating the National Institute ofStandards and Technology’s 100thanniversary, the American ChemicalSociety designated NIST as a NationalHistoric Chemical Landmark onDecember 5. NIST formerly theNational Bureau of Standards, wasfounded in 1901 to develop measure-ments and standards that strengthen theeconomy and improve quality of life.Throughout its history, the Institute hasbeen a reliable source of assistance toindustry, science, and government.NIST laboratories and other programsprovide critical measurements, tech-nology support, and start-up fundingthat benefit factories, communicationnetworks, laboratories, educationalorganizations and other aspects of thenew economy.

“Few Americans appreciate all themany ways the National Institute ofStandards and Technology hasmade our lives richer, easier, andsafer-from preserving nationaltreasures such as the Declaration ofIndependence, to developing airtraffic control systems that enablepilots to land planes in poor visibil-ity, to setting national standards forradiation doses used in medicaldiagnosis and cancer therapy,”

stated ACS Board Chair Nina E.McClelland during the ceremony atNIST’s campus in Gaithersburg, Mary-land.

ACS established its landmarksprogram to honor and preserve mile-stones in the history of chemistry andto heighten public awareness of the keyrole chemistry plays in our daily li ves.More than 35 places, discoveries anddevices have achieved landmark statussince the program’s inception in 1992.

To learn more about NIST’s chem-ical landmark designation go tohttp://www.chemistry.org/landmarks.From the December 2001 ACS “Capi-tol Connection.” ◆◆

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IntroductionA significant challenge in contemporary drug-design isproper targeting of the molecule to the appropriate tissues.One particularly crucial area is penetration of the blood-brain barrier (BB). Whether a molecule has the potential topenetrate the BB arises from non-covalent interactions, dueto the structural and electronic features of the molecule.Small polar molecules and lipophilic drugs are known tocross the barrier. Larger polar molecules and lipid-insolubleorganic molecules, including plasma proteins, do not pene-trate well. The partitioning of a compound across the BB ismeasured experimentally as the ratio of the concentration ofthe compound in the brain to that in the blood:BB =[brain]/[blood].

Given the cost of time and fiscal resources to accuratelymeasure blood-brain barrier partitioning, the ability tomodel this property accurately is valued. Use of such a

model as a predictive scheme should be rapid, reliable, easy-to-use, and lend itself to interpretation of the structural fea-tures that influence BB partitioning.

A hypothesized relation exists between local hydropho-bicity, molecular size, lipophilicity and molecular flexibility1

to BB partitioning, but no mathematical relationship hasbeen given. Attempts to delineate the relationship haveresulted in models based on various 3D methods. In thispresent investigation, only topological structure descriptorsare employed to create the mathematical model that relatesstructure to BB penetration. The topological method appliedto the BB partitioning data leads to a model that is statisti-cally equivalent or somewhat better than models reported inthe literature2,3 Further, the method based on topologicalstructure representation is considerably less time-consumingand less expensive to apply. Finally, interpretation of signifi-cant structural features is obtained by analysis of each of thestructure descriptors in the model.

Topological methods have been explored for the last 20years4-6, resulting in a variety of structurally descriptiveindices (electrotopological state indices4, molecular connec-tivity chi indices, and kappa shape indices). These topologi-cal indices are relevant for describing facets of structure thatinfluence non-covalent intermolecular interactions. Theseinteractions are largely due to the distribution of the elec-trons on the surface of the molecule. This distribution comesfrom the physical arrangements of atoms (connectivity and

Summer ScholarReportModeling of Blood-Brain Barrier Permeabilityfor Drug and Drug-Like CompoundsKimberly Rose# and Lowell H. Hall*

Department of Chemistry, Eastern Nazarene College Quincy, MA

# 2001 Norris/Richards Summer Scholar∗ e-mail: [email protected] continued on page 12


shape) but is most elegantly described by the electrotopolog-ical indices, because these indices encode both the elec-tronic and topological character molecule.

In the electrotopological approach to structure represen-tation (E-State), basic structure information is developed foreach atom (such as >N-, =O, -Cl) and each hydride group(such as -CH3, -NH2, -OH) in the molecule. The E-Stateindex for an atom in a molecule, S(i), is composed of anintrinsic state, Ii, derived from a measure of valence stateelectronegativity and a measure of the local topology, plusthe sum of perturbations, ∆Iij, from other atoms. The E-Statevalue for atom i in a molecule is computed as follows: S(i) =Ii + Σj ∆Iij (sum over all other atoms j).

Through the E-state formalism, a value is created foreach atom that describes the electron accessibility at a par-ticular atom site in the molecule due to the electronic andtopological nature of the entire molecule4. The E-State valueS(i) is computed for each atom in the molecule and is calledthe atom-level E-State value. Variations of this definitioninclude the atom-type E-state, a sum of the E-states for eachtype of atom in a molecule, and hydrogen E-states5. Due tothe heterogeneity of the BB data set, only atom-type E-Stateand hydrogen E-states are used along with chi and kappaindices.

In this investigation, we developed a model for blood-

brain barrier partitioning and demonstrated its validity byprediction of external test sets. The whole data set consistsof 106 observations on neutral compounds ranging fromCH4 and benzene to acetylsalicylic acid and caffeine to vera-

Summer ScholarContinued from page 11

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Figure 1 N-methylpropylamide with the calculated E-state valuesencoding electron accessibility for each atom.-Oxygen has the highest value, as expected for an atom with thegreatest electronegativity. This accessibility is due both to thetopology of the molecule and electron distribution of two lonepairs and a pi bond within the carbonyl group arrangement.-From similar reasoning, the carbonyl carbon has the lowestvalue. This is due to its sheltered location within the moleculeand the presence of two nearby electronegative groups (O and N). -The two methyl groups on the end of the atoms both ha ve lowvalues due to low electronegativity. However, the values for thegroups are different due to the differing environments. The lowervalue occurs on the methyl next to the electronegative nitrogen.


pamil and indomethacin. The logBB values range over threeand one half orders of magnitude of BB from -2.15 to +l.44;the molecular weight ranges from 16.0 to 613.8.MethodsData Entry. While a variety of blood-brain barrier partition-ing data obtained through various protocols is available, welimited the data to in vivo measurements obtained from rats.The data and molecular structures were taken from elevensources 2,3. The resulting data set contains 106 compoundswith the corresponding BB values. These BB values wereconverted to the logarithm basis. Compounds were enteredas structure drawings with ChemDraw7 and structure datasaved as MDL mol files. All structure indices used in thisinvestigation were computed from Molconn-Z, ver 3.50 8.

For QSAR analysis, we selected atom-type E-State andhydrogen E-State indices, along with molecular connectivitychi and difference chi indices, and with kappa shape indices.Statistical Analysis. The data matrix was submitted for sta-tistical analysis using the SAS system9. The RSQUAREselection method in proc REG was used to examine everyQSAR equation from one to five variables, listing the top 10most statistically significant. The most important variables,because they appear the most often, are E-State indices thatemphasizes hydrogen bond donating ability, HST(HBd),along with certain non-polar structure features, HST(arom),and skeletal architecture, in the difference chi index, d2χv.

At this point in the model de velopment, we introducedsquares of the prominent variables to simulate a possiblenon-linear relation between structure and logBB. Significantimprovement was obtained in the regressions. Only thesquares of the HST(arom) and d2χv variables were statisti-cally significant. Based on these preliminary investigations,three structure descriptors were selected for further model-ing and validation: HST(HBd), [HST(arom)]2, and [d2χv]2.Development of Final Model. Based on the preliminaryanalysis and on validation studies, the three selected struc-ture descriptors were considered good choices for this dataset. To create a final model that could be used for predictionof compounds not in the current data set, we established amodel for the whole set of 106 compounds and carefullyexamined the residuals. In order to optimize predicti ve abil-ity, we decided to remove observations with large residuals,that is, residuals greater than 2.5 standard deviations. Wefound four observations with residuals greater than ±1.2 anddeleted them. The q2 value, based on the leave-one-out(LOO) method, improved from 0.52 to 0.62 upon removalof the four observations. The final model is shown in equa-tion l.Validation Studies. Four standard approaches to validationof the model were adopted for this data set: creation of anexternal validation test set (20% of data set), cross-valida-tion by the leave-group-out method10, prediction of anentirely different (+/-) data set, and extension of the modelto a large database of drug and drug-like compounds. Theresults of these validation studies supported the predictiveability of the model.

Results and DiscussionThe QSAR ModelThe model based on three variables yielded statistical infor-mation as follows: eq. 1logBB = -0.202(±0.026) HST(HBd) + 0.00627(±0.00095)

[HST(arom)]2 -0.105(±0.016) [d2χv]2- 0.425(±0.069)r2 = 0.66, s = 0.45, F = 62.4, n =102, q2 = 0.62, spress= 0.48 Quantities in parentheses are the standard deviations of thecoefficients. The statistical quantities q2 (= r2

press) and spressare based on the leave-one-out (LOO) method. A plot of thecalculated logBB versus observed logBB values (Fig. 2)revealed a linear trend. An examination of the plot of residu-als versus observed logBB revealed no trends and appears tobe randomly distributed.

The statistical criteria for selection of the QSAR modelfor the logBB data are based on the follo wing: r2 and q2 forthe final model (n=102); the mean absolute error (MAE) forthe test set (n = 20); and the MAE for the cross-v alidation

(five-fold cross-validation). The MAE value was consideredthe most important statistic because an equation should notbe considered a QSAR model unless it has demonstratedpredictive value.Interpretation of the Model. The three-variable model (eq.l) adequately represents the logBB data for both training andtest sets. Each of the variables is a descriptor of an aspect ofmolecular structure and will be discussed to indicate thespecific structure information encoded. Let us consider threerepresentative molecules from the data set in Table 1.

The HST(HBd) term describes the hydrogen-bonddonor ability of a molecule. The hydrogen E-state values of

continued on page 14

Fig. 2

all electron-donating groups (-OH, -NH2, and-NH-) are combined. Molecules withstronger hydrogen-bond donor abilities havehigh values for the HST(HBd) index. Beingrather hydrophilic, such molecules normallydo not penetrate the BB well. For example,note that salicylic acid has a large HST(HBd)value and it does not penetrate, as would beexpected for a topical therapeutic agent.

The [HST(arom)]2 term describes thehydrogen E-state of all aromatic hydrogens.These hydrogens are related to a measure ofthe non-polar aromaticity and lipophilicity ofa molecule. The more aromaticity a com-pound has, the higher its [HST(arom)]2.Lipophilic compounds tend to cross the BB,as seen in the example of promazine, an antipsychotic CNSdrug.

The third term, [d2χv]2, is a measure of the skeletalbranching and general polarity within the molecule. Thisindex provides more fine-tuned structure information aboutthe nonpolar aromatic groups and electronegative groups.Molecules with less branching tend to penetrate the barriermore easily. Caffeine is only marginally penetrating due toits branching and polarity.

In summary, the model given as eq. 1 indicates that

blood-barrier penetration is favored for compounds witharomatic CH groups, less skeletal branching, and no hydro-gen bond donor groups. The model permits the direct esti-mation of logBB for organic structures and blends togetherthe structure information of the three structure descriptors ineq. l.

At the conclusion of this analysis, a 3-variable model isproduced to describe the relationship between molecularstructures and blood-brain barrier partitioning. This model isfound to successfully predict a molecule’s BB penetrationbehavior and provides easily interpretable results. These


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Table 1- Representative molecules from the 106 compound data set. Thesecompounds were chosen as examples of well-predicted molecules thateither easily penetrate the BB (promazine), do not penetrate (salicylic acid),or marginally penetrate (caffeine).


results are obtained quickly (4,000-5,000 compounds/minute) and in acost-effective manner. In addition, theexcellent outcome was obtained inde-pendent of information from 3D geom-etry based considerations.Note: During the research project,models were also developed for toxic-ity of chlorophenols to various organ-isms and for fish toxicity of anilines,alkyl-and chlorophenols, and nitro-andhalo-aromatics.Acknowledgements: K. Roseacknowledges the support of theNortheastern Section, ACS, through aNorris/Richards Summer ResearchFellowship. The author also wishes toexpress her thanks for the support andadvice by Prof. Lowell H. Hall.References1 Crivori,P.; Cruciani,G.; Carrupt,P.; Testa,

B. Predicting Blood-Brain Barrier Perme-ation from Three-Dimensional MolecularStructure, J. Med. Chem. 2000, 43, 2204-2216.

2 Luco,J. Prediction of the Blood-Brain Dis-ribution of a Large Set of Drugs fromStructurally Derived Descriptors UsingPartial Least-Squares (PLS) Modeling. J.Chem. Inf. Comput. Sci. 1999, 39, 396-404.

3 Keserü, G.; Molnár, L. High-ThroughputPrediction of Blood-Brain Partitioning: AThermodynamic Approach, J. Chem. Inf.Comput. Sci. 2001, 41, 120-128, andsources within.

4 Kier, L.B.; Hall, L.H. Molecular StructureDescription: The Electrotopological State,Academic Press, San Diego, CA, 1999

5 Hall, L.H.; Kier, L.B. Electrotopologicalstate indices for atom types: A novel com-bination of electronic, topological andvalence state information, J. Chem. Inf.Comput. Sci. 1995, 35, 1039-1045.

6 Hall, L.H.; Kier, L.B. Molecular Connec-tivity Chi Indices for Database Analysisand Structure-Property Modeling, in Topo-logical Indices and Related Descriptors inQSAR and QSPR, Devillers, James; Bala-ban, Alexandru T., Eds., Gordon andBreach, Reading, UK, 307-360, 1999

7 ChemDraw, ver 4.5, CambridgeSoft, Cam-bridge, MA.

8 Molconn-Z, ver 3.50, available from: HallAssociates Consulting, Quincy, MA; Edu-Soft, LC, Ashland, VA; SciVision, Inc.,Burlington, MA.

9 SAS, ver 8.0, SAS Institute, Cary, NC 2751310 Maw, H.H.; Hall, L.H. E-State Modeling

of Corticosteroids Binding Affinity Valida-tion of Model For Small Data Set, J.Chem. Inf. Comput. Sci. 2001, 41, 1248-1254 ◆◆

Board ofDirectorsNotes of Meeting of November8, 2001NOTE: Board Meetings are held on themonthly meeting day at 4:30 p.m. Sec-tion members are invited to attend.Officers’ Reports:Chair: (Holiday Lecture), BassamShakhashiri was awarded an HonoraryLifetime Membership in the Northeast-ern Section.The Division of Chemical Techniciansis seeking new members and asks forthe support of Local Sections in thiseffort.Chair-Elect: M. Hoffman stated that amini-grant proposal has been submit-ted to the ACS Office of Diversity forsupport of the February 2002 jointmeeting of NESACS and YCC withNOBCChE.Treasurer: J. Piper, via written report,presented the status of the NESACScash flow for October 2001. the BoardAPPROVED the report.Standing Committees:Bd. Of Publications: P. Gordonreported that the Committee hadapproved a 2002 budget request.

He stated that the Bd. of Pubs.requested that M. Schwartz remain onthe committee as the appointee for2002, and that P. Gordon assume thechair of the Board of Publications.

Editor: A. Heyn stated that theDecember 2001 issue will be 20 pages.Membership: M. Chen reported thatletters of welcome were sent to 450new members in September. 5 newmembers attended the October SectionMeeting. Three new membersexpected for tonight’s meeting.Nominating: Nominees for the Nomi-nating Committee to be elected by theBoard were presented by Tim Frigo.The Board elected M. Hearn and J.Billo as the Board representatives onthe Committee.Chemistry Education: M. Hoffmanreported for R. Tanner that the Under-graduate Day was a big success andwas very well attended.

Applications for the YCC visit to Ger-many in March 2002 are due byDecember 31, 2001. An ACS mini-grant has been awarded by the ACS toNEACS for supporting Connections toChemistryR. Tanner stated that this program wasoversubscribed: 150 High SchoolTeachers applied for 110 places. Only six applications ha ve beenreceived for Grants-in-aid for attendingthe Orlando meeting. The BU Under-graduate Day had 125 participantsfrom 16 colleges and universities.Constitution and Bylaws: C. Costellostated that the C&B changes whichhad been approved at the OctoberBoard meeting have been submitted tothe ACS C&B Committee for a prelim-inary review. Esselen Award: J. Koob submitted awritten report, stating that the processhas moved into the selection stagefrom the four nominations which havebeen received. Selection of an awardeewill be made in early January. TheCommittee is seeking ways to reducethe cost of the award event which wentover budget last year.Other Committees:Continuing Education: A. Viola washappy to report that the fall ShortCourse produced a positive balance ofabout $5,000. For 2002, because ofBoston being the site of the F all meet-ing, a short course will be impractical.Government Affairs: M. Hearnreported that a new initiative is beingplanned for the spring of 2002, includ-ing outreach to new Congressmenfrom Massachusetts.Natl. Chemistry Week: S. Iacobuccireported that the Science Museum w asvery happy about the good response tothe November 3 program and thecooperation by members of NESACSwith the arrangements. Four schoolssent volunteers. The Forsyth event onNovember 6 also w as very wellattended. This has been the biggestNESACS NCW program to date.Younger Chemists: A. Tapper statedthat the group is looking for people toassume leadership positions.New Business: M. Hoffman expressedhis thanks for condolences sent him onthe death of his mother. ◆◆


Applications InvitedThe James Flack Norris and Theodore William Richards Undergraduate SummerResearch Scholarships

The Northeastern Section of the American Chemical Society(NESACS) established the James Flack Norris andTheodore William Richards Undergraduate Summer Schol-arships to honor the memories of Professors Norris andRichards by promoting research interactions between under-graduate students and faculty.

Research awards of $3250 will be given for the summerof 2002. The student stipend is $2750 for a minimum com-mitment of ten weeks of full-time research work. Theremaining $500 of the award can be spent on supplies,travel, and other items relevant to the student project.

Institutions whose student/faculty team receives a Nor-ris/Richards Undergraduate Summer Research Scholarshipare expected to contribute toward the support of the facultymembers and to waive any student fees for summerresearch. Academic credit may be granted to the students atthe discretion of the institutions.

Award winners are required to submit a report (~5-7double-spaced pages including figures, tables, and bibliog-

raphy) of their summer projects to the NESA CS EducationCommittee by November 8, 2002 for publication in TheNucleus. They are also required to participate in the North-east Student Chemistry Research Conference (NSCRC) inApril 2003.

Eligibility: Applications will be accepted from student/f ac-ulty teams at colleges and universities within the Northeast-ern Section. The undergraduate student must be achemistry, biochemistry, chemical engineering, or molecularbiology major in good standing, and have completed at leasttwo full years of college-level chemistry by summer, 2002.

Application: Application forms are available on theNESACS web site at http://www.nesacs.org. Completedapplications are to be submitted no later than March 22,2002 to the Chair of the Selection Committee:

Professor Edwin Jahngen,University of Massachusetts LowellChemistry Department, Room 520265 Riverside Street, Olney HallLowell, MA 01854-5047

Notification: Applicants will be notified of the results by e-mail on April 26, 2002. Written confirmation will follow.◆◆

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iomycetes 43. Central Europe river44. O-rings, such as for gasoline tanks 46. Take into police custody48. Afternoons/evenings 49. Heap51. Violin family member54. Ratio that needs careful adjustment to

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For additional information, call:Am. Assoc. Clinical Chemists - (617) 732-6987,pager 11161Boston College - (617) 552-2605Boston University - (617) 353-4277Brandeis University - (781) 736-2500Dartmouth College - (603) 646-2501Harvard University - (617) 495-4198Mass. Inst. Technology - (617) 253-1803Northeastern University - (617) 373-2822Tufts Univ. - (617) 627-2634 UMass Boston - (617) 287-6130UMass Dartmouth - (508) 999-8232UMass Lowell - (978) 934-3675 Univ. of New Hampshire - (603) 862-1550Worcester Polytechnic Institute - (508) 831-5250Check the NESACS Homepage for lateadditions:http://www.NESACS.org

Note also the MIT Chemistry DepartmentWebpage calendar: http://web.mit.edu/chemistry/www/temp/seminars/pchemseminars.htmland the Harvard Chemistry web site for updates:http://www-chem.harvard.edu/events/Physical_Seminars.html(which includes the Harvard/MIT joint seminars)

February 4Prof. George Whitesides (Harvard Univ.)“Unconventional Nanofabrication. Using soft-lithographic tools to make patternednanostructures”Boston Univ., 590 Commonwealth Ave., ScienceCenter Auditorium, SCI 107, 4:00 pm

February 6Dr. Chris Chang (Nocera Group)TBA [Inorganic Chemistry Seminar]MIT, Room 6-120, 4 pm

February 7Prof. Paul Alivisato (UC Berkeley)Harvard Univ., MB-23 Pfizer Lecture Hall, 4:15pm

February 11Prof. Mike Maroney (Univ. of Massachusetts)“Structure and Function in Metallobiochemistry:A Nickel Tour.”Boston Univ., 590 Commonwealth Ave., ScienceCenter Auditorium, SCI 107, 4:00 pm

February 12Prof. Marisa Kozlowski (Univ. of Pennsylvania)TBABoston College, Merkert Chemistry Center,Room 130, 2609 Beacon St.4:00 pmProf. Andrew Marcus (Univ. of Oregon)TBA [Physical Chemistry Seminar] MIT, Rm. 2-105, 4 pmProf. Andrei Tokmakoff (Mass. Institute ofTechnology)“Molecular Structure and Dynamics in SolutionObserved Through Two-Dimensional InfraredSpectroscopy”Tufts Univ., Pearson Chem. Building, 62 TalbotAve., Medford,Room 106, 4:30 pm

February 13Prof. Tom Tullius (Boston Univ.)TBABoston College, Merkert Chemistry Center,Room 130, 2609 Beacon St.4:00 pmProf. Jeffrey S. Moore (Univ. of Illinois)TBA [Karl Pfister Lectures in OrganicChemistry]MIT, Room 6-120, 4 pm

February 14Prof. Hagan Baley (Texas A&M Univ., Dept.Medical Biochem. & Genetics)Harvard Univ., MB-23 Pfizer Lecture Hall,4:15 pmProf. Jeffrey S. Moore (Univ. of Illinois)TBA [Karl Pfister Lectures in OrganicChemistry]MIT, Room 6-120, 4 pmProf. George Kebalka (Univ. of Tenn, Knoxville) “Organic Synthesis Using OrganometallicReagents in the Absence of Organic Solvents :Green Chemistry”Northeastern Univ., 129 Hurtig Hall, 4:00 pm

February 18Prof. Michael Gelb (Univ. of Washington)“Interfacial Enzymology and Cell Biology of theMammalian Phospholipase A2 Family”MIT, Room 6-120, 4 pm

February 19Prof. Martin Gruebele (Univ. of Illinois)TBA [Physical Chemistry Seminar] MIT, Rm. 2-105, 4 pm

Prof. Seiichi Matsuda (Rice Univ.)“Tinkering with Terpene Biosynthesis”Tufts Univ., Pearson Chem. Building, 62 TalbotAve., Medford,Room 106, 4:30 pm

February 20Prof. Guillermo Bazan (Univ. of California)TBA [Harvard/MIT Inorganic ChemistrySeminar @ MIT]MIT, Room 6-120, 4 pm

February 21Prof. David Bruns (Univ. of Virginia)“Evidence-Based Laboratory Medicine”American Association for Clinical Chemistry,DoubleTree Guest Suites Hotel, Waltham at 128;Social, 6 pm; dinner, 7 pm; lecture, 8pmDr. Mukund Chorghade (GeltexPharmaceuticals, Inc.)“Progress of a Drug from Conception toCommercialization”Tufts Univ., Chemistry Seminar Hosted by theACS Sudent Affiliate Chapter at Tufts,Pearson Chem. Building, room 106, 4:30 pm

February 25Prof. Wes Sundquist (Univ. of Utah)Boston Univ., 590 Commonwealth Ave., ScienceCenter Auditorium, SCI 107, 4:00 pm

February 26Prof. Tom Wandless (Stanford Univ.)TBABoston College, Merkert Chemistry Center,Room 130, 2609 Beacon St.4:00 pmProf. Steve Bradforth (Univ. of SouthernCalifornia)“The Mechanisms for Electron Photoejection inLiquid Water”MIT, Rm. 2-105, 4 pmProf. John T. Groves (Princeton Univ.)TBATufts Univ., Pearson Chem. Building, 62 TalbotAve., Medford,Room 106, 4:30 pmProf. John MacDonald (Worcester PolytechnicInstitute)“Supramolecular Synthesis of Organic andOrganometallic Crystalline Materials”Univ. of New Hampshire, Durham, IddlesAuditorium L103,11:00 am

February 28Prof. Jonathan L. Sessler (Univ. of Texas)TBA [Seminar in Organic Chemistry]MIT, Room 6-120, 4 pm

Notices for the NucleusCalendar should be sent to:Dr. Donald O. Rickter, 88 Hemlock St.,Arlington, MA 02474-2157e-mail: [email protected]

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