3 a e central illinois local section undergraduate … · nicotine extraction, quantification, and...

3RD ANNUAL

EAST CENTRAL ILLINOIS LOCAL SECTION

UNDERGRADUATE RESEARCH

CONFERENCE

November 17, 2018

TABLE OF CONTENTS / INSTRUCTIONS

SCHEDULE OF EVENTS 3

INDEX OF PRESENTERS 4

DRIVING AND PARKING MAP 5

ILLINI UNION MAP 6

RESTAURANT MAP 7

POSTER SESSION I: OVERVIEW 8

POSTER SESSION II: OVERVIEW 10

SPEAKER SESSION I: ABSTRACTS* 12

POSTER SESSION I: ABSTRACTS* 16

POSTER SESSION II: ABSTRACTS* 44

SPEAKER SESSION II: ABSTRACTS* 72

COMMITTEE / PAST AWARD RECIPIENTS 76

SUPPORTING GROUP DETAILS 77

2019 URC INFO 78

*found online at eastcentralillinois.sites.acs.org/conference.htm

PRESENTERS – Please have your poster up five minutes before your session is supposed to begin and

take them down promptly before the next session. You are expected to be present at your poster during

the entire 50 minutes. Failure to do so will cause you to be disqualified from any awards.

JUDGES – Please pick up your folders at the registration booth when you sign-in and return them to

the same place when finished.

AWARDS – Awards will be presented during the awards ceremony. If you are unable to attend the

ceremony, you will be contacted through the e-mail you provided should you be chosen for an award.

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SCHEDULE OF EVENTS

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9:30 AM CHECK-IN/REGISTRATION

10:00 AM OPENING REMARKS

SPEAKER SESSION I

Clare Gallagher (Chemical Biology @ Purdue University)Whole Cell Organic Solvent Extraction of Chaperone Protein from E.coli

Benjamin M. Oxley (Inorganic @ Purdue University)Synthesis and Characterization of trans-CoIII(DMC) mono-phenylacetylide and bisphenylacetylide

Yuanheng Wang (Physical @ University of Illinois at Urbana-Champaign)Internal Structure, Band Alignment and Charge Transfer Dynamics of ZnTe/CdSe Core/Shell Quantum Dots

Elizabeth A. Murphy (Materials @ University of Illinois at Urbana-Champaign)Soluble Zwitterionic Poly(sulfobetaine) Destabilizes Proteins

11:00 AM POSTER SESSION I

12:00 PM LUNCH AND NETWORKING BREAKER

1:30 PM POSTER SESSION II

2:30 PM SPEAKER SESSION II

Chrishan Fernando (Biochemistry @ Purdue University)Identifying factors that genetically interact with R-loops to suppress gene expression

Alayna M. Johnson (Materials @ Northwestern University)Engineering Considerations for the Design of Strong and Easily-Recyclable Plastics

Alex Solivais (Analytical @ Indiana University Northwest)Nicotine extraction, quantification, and mechanistic assessment for mass fragmentation

Yuquan Tong (Organic @ University of Illinois at Urbana-Champaign)An Iterative Approach for the Synthesis of Enantio-selective Polyols

3:30 PM AWARDS CEREMONY

Stephen Moore 61

Elizabeth A. Murphy 15

Daniel Olson 26

Selena Oskard 62

Tianhong Ouyang 27

Benjamin M. Oxley 13

Gina Partipilo 28

Lisset Perez 29

Andrea N. Perry 30

Sirikarn Phuangthong 31

Takeru Saito 32

Jack H. Schnieders 63

Alex Solivais 74

Amara Spencer 33

Magdelana Stinnett 64

Alexander L. Tesmer 65

Elizabeth Thayer 66

Zachary W. Thom 34

Huiying Tian 35

M. Roarke Tollar 36

Yuquan Tong 75

Killian L. Tracey 37/67

Vishaal Venkatesh 38

Jose Ignacio Vergara Panzone 39

Steven Vo 40

Brendan J. Wall 41

Yuanheng Wang 14

Matthew Wieskamp 42

Mark F. Will 68

Justin Shing Him Wong 43

Cheyanne Woolwine 54

Ruiwen Xu 69

Jeff Zhang 70

Zhouyang Zhu 71

INDEX OF PRESENTERS

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Zach Bennett 44

Anna Bockman 44

Jacob J. Bulandr 16

Douglas S. Chan 45

Pravin Chandra 46

Sriyankari Chitti 47

Jiachong Chu 17

Chukwunalu Chukwuma 36

Hunter DeHaan 48

Madison Edwards 18

Johanna Ehlbeck 62

Bushra Fatima 49

Mara Fattah 19

Chrishan Fernando 72

Samuel S. Fisher 50

Jack Floreancig 51

Heriberto Flores Jr 20

Lawrence Xi-Bin Fung 52

Clare Gallagher 12

Jake Grabowski 53

Benjamin Grubbs 21

Kassidy Grumbles 44

Jonathan Hicks 54

Ethan Hose 55

Juan Isaiz 22

Marko R. Ivancevic 56

Alayna Johnson 73

Alyssa Lambrecht 23

Luyang Li 57

Kyle Lieberum 24

Eric Liu 25

Claire Lundberg 58

Derric E. Meyer 59

Eric Micheli 60

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DRIVING AND PARKING MAP

Driving Recommendations

Traveling east on I-74 (from Bloomington, IL;Macomb, IL) or south on I-57 (from Evanston, IL;Gary, IN; Palos Hills, IL; Valparaiso, IN). From I-57, take exit 237A for I-74 E. Once on I-74, take exit183 for Lincoln Ave. Turn right at the light and takeLincoln Ave south towards the UIUC campus.

Traveling east on I-72 (from Jacksonville, IL) ornorth on I-57 (from Charleston, IL). From I-57, takeexist 235A for I-72 E. Once on I-72, continue ontoUniversity Ave towards the UIUC campus.

Traveling west on I-74 (from Crawfordsville, IN;Indianapolis, IN; West Lafayette, IN). From I-74,take exit 185 for IL-130. Continue straight as IL-130becomes University Ave at the first stop light.Continue on University Ave towards the UIUCcampus.

Parking Recommendations

Excluding spaces individually marked by ablue sign, parking in UIUC lots is free onSaturdays. Many parking lots exist within afew blocks of the Illini Union (marked in redto the right). Smaller lots closer to the IlliniUnion can fill quickly depending on campusactivities, but larger lots (marked in yellow tothe right) should have plenty of space. For afull map, please visit the link below.

Notes: Metered street parking is typicallycontrolled by the cities of Champaign andUrbana, both of which enforce meters onSaturday. Please read all posted signscarefully as policies may change without ourknowledge.

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http://www.parking.illinois.edu/visitors/campus-maps/campus-parking-map

University Ave

Linco

ln A

ve

Green St

Springfield Ave

Wrigh

t St

Go

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win

Ave

ILLINI UNION MAP

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Green Street

Main Quad

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RESTAURANT MAP

Restaurant RecommendationsThere are many restaurants in the area surrounding the Illini Union (red star above). Some key areasinclude Green St (1), the corner of Goodwin and Oregon (2), and Gregory St (3).

1. There are too many restaurants to name on Green St and the surrounding side streets, especiallyclose to the Illini Union. American, Chinese, Indian, Italian, Korean, Mexican, and Thai, are justsome of the cuisines available.

2. Interested in something more sit-down? The corner of Goodwin and Oregon features both BreadCompany and Timpone’s, common destinations for UIUC chemistry functions.

3. The stretch of Gregory St sandwiched between Oregon and Nevada is dense with options rangingfrom Cajun to sushi, from American diner to Korean.

Vegetarian or vegan? Unfortunately the exclusively vegan restaurant (The Red Herring) is closed onSaturdays. A number of the places along Green St have options, especially the Indian and Thairestaurants.

WCC Lunch PanelIf you registered for the graduate student panel discussion hosted by the UIUC Women ChemistCommittee, lunch will be provided in Room 165 of Noyes Laboratory (the building marked by the W onthe map above).

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W

POSTER SESSION I: OVERVIEW

1. Jacob J. Bulandr (Organic @ Illinois State University)Investigation of Silyloxypyrone-Alkene [5+2] Cycloadditions

2. Jiachong Chu (Chemical Biology @ Purdue University)Identification and Characterization of the New Aurora Kinase A Substrate in Castration Resistant Prostate Cancer

3. Madison Edwards (Analytical @ Purdue University)MRM-Profiling Exploration as a Predictive Tool in Cancer Clinical Trials

4. Mara Fattah (Neurochemistry @ Purdue University)Novel Potassium Channel Blocker 4-AP-3-MeOH Restores Acrolein-Mediated Conduction LossinPeripheral Nervous System Injury

5. Heriberto Flores Jr. (Analytical @ University of Illinois at Urbana-Champaign)Fabrication and Characterization of Nanoelectrodes used in Scanning Electrochemical Microscopy (SECM)

6. Benjamin Grubbs (Analytical @ Wabash College)Using Second Harmonic Generation Microscopy to Image Crystalline Pesticides on Leaf Surfaces

7. Juan Isaiz (Organic @ Moraine Valley Community College)Production of Bioactive Isothiocyanates via Microbial Myrosinase

8. Alyssa Lambrecht (Chemical Biology @ Purdue University)Alkynylnicotinaamide-Based Compounds as ABL1 Inhibitors with Potent Activities against Drug-Resistant CML Harboring ABL1(T315I) Mutant Kinase

9. Kyle Lieberum (Chemical Education @ Illinois State University)Reinforcement of Daily Learning Objectives: The Importance of Connecting the End of a Lesson with Your Objective

10. Eric Liu (Inorganic @ Purdue University)Examining the Effects of Amino and Thiolate Ligands on the Reactivity and Selectivity of Palladium on Carbon in Hydrogenation Reactions

11. Daniel Olson (Organic @ University of Illinois at Urbana-Champaign)Total Synthesis of (+)-Lycoricidine and (+)-Narciclasine

12. Tianhong Ouyang (Materials @ Purdue University)Noncovalently Functionalized 2D Materials Template Solution Assembly of Ultranarrow GoldNanorods Along 1-nm-Wide Rows of Functional Headgroups

13. Gina Partipilo (Chemical Biology @ University of Illinois at Urbana-Champaign)A New Probe for the Point-of-Care Detection of Ovarian Cancer with Isotopically Enriched Designer Substrate

14. Lisset Perez (Inorganic @ Illinois College)Investigation of a Series of Nickel Phosphine Catalysts for "Green" Suzuki-Miyaura Coupling Reactions

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POSTER SESSION I: OVERVIEW

15. Andrea N. Perry (Materials @ University of Illinois at Urbana-Champaign)Porous Silicon Matrix for Novel Fabrication of an Asymmetric, Tunable Microscale Lens to Demonstrate Sub-Diffraction Optics

16. Sirikarn Phuangthong (Inorganic @ Illinois College)Synthesis of Air-stable Ruthenium and Nickel Catalysts

17. Takeru Saito (Organic @ Purdue University)Synthetic Studies Toward the Divergent Total Synthesis of Lycopodium Alkaloids

18. Amara Spencer (Organic @ Indiana University-Purdue University Indianapolis)An Undergraduate Teaching Oriented Approach to Reaction Investigation and Optimization

19. Zachary W. Thom (Organic @ Indiana University-Purdue University Indianapolis)Selective #-Amination of Ethers Using Stable N-Chloroamines and Lithium tert-butoxide

20. Huiying Tian (Analytical @ University of Illinois at Urbana-Champaign)Single Cell Analysis by Hyphenation of CE-ESI-MS and ICC

21. M. Roarke Tollar, Chukwunalu Chukwuma (Organic @ Wabash College)Synthesis and Testing of an Acid Phosphatase Sensor

22. Killian L Tracey (Chemical Education @ Western Illinois University)Evolution of Solid State Synthesis for Implementation in an Education Laboratory

23. Vishaal Venkatesh (Materials @ University of Illinois at Urbana-Champaign)Novel Depolymerization Mechanism of Transient Polymeric Materials

24. Jose Ignacio Vergara Panzone (Organic @ University of Illinois at Urbana-Champaign)Synthesis of Therapeutic Agents for Myotonic Dystrophy Type 1 (DM1)

25. Steven Vo (Biochemistry @ University of Illinois at Urbana-Champaign)The Role of Iron-Sulfur Clusters in YcaO-domain Containing Proteins

26. Brendan J. Wall (Inorganic @ Illinois State University)Synthesis and Characterization of Ruthenium-Based Alzheimer’s Disease Therapeutics

27. Matthew Wieskamp (Chemical Biology @ Western Illinois University)Determination of Transcriptional Changes Induced by an Ovarian Cancer Targeting Peptide

28. Justin Shing Him Wong (Inorganic @ Purdue University)Magnetostructural Coupling in Transition-Metal Based Compounds, TCrX (T = Mn-Ni; X = Al, Si, Ge)

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POSTER SESSION II: OVERVIEW

29. Zach Bennett, Anna Bockman, Kassidy Grumbles (Organic @ Valparaiso University)Streamlining the synthesis of folate mimics

30. Douglas S. Chan (Chemical Biology @ University of Illinois at Urbana-Champaign)Development of Probes for Photoacoustic Imaging of Tissue Hypoxia in Prostate Cancer

31. Pravin Chandra (Materials @ University of Illinois at Urbana-Champaign)Polyaniline-impregnated filters and their possible applications

32. Sriyankari Chitti (Organic @ University of Illinois at Urbana-Champaign)Iterative Synthesis of Csp3 Rich Small Molecules by using Bifunctional Carbenoid-Boronate Building Blocks

33. Hunter DeHaan (Organic @ Indiana University Northwest)Synthetic Optimization of PET-Imaging Ligands: Aza-Thia 14-membered Heteromacrocycles

34. Bushra Fatima (Organic @ Indiana University Northwest)NMR Analysis of Nepatalactone: Quantitation and Stereochemical Assignment

35. Samuel S. Fisher (Inorganic @ Illinois State University)Synthesis and Characterization of Ruthenium-Based Complexes for Alzheimer's Disease Therapy

36. Jack Floreancig (Organic @ Indiana University-Purdue University Indianapolis)Borylation of Aryl Iodides Using a Pd/Cu Dual Catalysis

37. Lawrence Xi-Bin Fung (Materials @ Purdue University)Fourier Transform Infrared Spectroscopy on Corn Protein -Tannic Acid Formulations

38. Jake Grabowski (Organic @ Indiana University-Purdue University Indianapolis)Exploration and Application of Oxidopyrylium-Alkene [5+2] Cycloadditions

39. Jonathan Hicks, Cheyanne Woolwine (Chemical Biology @ Purdue University)Targeting Therapeutics for Accelerated Bone Fracture Repair

40. Ethan Hose (Organic @ Eastern Illinois University)Synthesis and Photochromicity of Various N-Phenyl Cinnamaldehyde Semicarbazones

41. Marko R. Ivancevic (Materials @ Oak Ridge National Laboratory)High Performing Waste Tire Carbon Electrodes for Desalination via Capacitive Deionization

42. Luyang Li (Chemical Biology @ University of Illinois at Urbana-Champaign)Elaboration of a thiol-based probe for HNO

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POSTER SESSION II: OVERVIEW

43. Claire Lundberg (Materials @ University of Illinois at Urbana-Champaign)The Effect of Polymer Backbone on Aqueous Mechanochemistry

44. Derric E. Meyer (Inorganic @ Eastern Illinois University)Halogen Atom Effect on the near-infrared Emission of Porphyrinate Ytterbium (III) Complexes

45. Eric Micheli (Inorganic @ Eastern Illinois University)Synthesis and Spectroscopic Studies of Porphyrinate Ytterbium (III) Complexes

46. Stephen Moore (Analytical @ Indiana University Northwest)Isolation, Method Development, and Quantification of Nepetalactone From Raw Plant Tissue

47. Selena Oskard, Johanna Ehlbeck (Inorganic @ Illinois State University)Small Molecule Metal Ion Chelators for Parkinson's Disease Therapy

48. Jack H Schnieders (Analytical @ University of Illinois at Urbana-Champaign)Chiral Measurements of D-Aspartate in the Pancreas

49. Magdelana Stinnett (Organic @ Indiana University-Purdue University Indianapolis)Development of Aminooxy Reagents for Analysis of Carbonyl-Containing AHAS and ALS Biosynthetic Products

50. Alexander L. Tesmer (Chemical Biology @ Purdue University)Engineering Bioluminescent Sensors of Cyclic AMP to Study Opioid Signaling

51. Elizabeth Thayer (Chemical Biology @ Purdue University)Role of cyclic GMP-AMP Synthase (cGAS) in microglial immune response

52. Killian Lee Tracey (Chemical Engineering @ Western Illinois University)Room Temperature Production of Lithium via Electrodeposition

53. Mark F. Will (Inorganic @ Illinois State University)Ruthenium Complexes for Alzheimer’s Disease Therapy

54. Ruiwen Xu (Chemical Biology @ University of Illinois at Urbana-Champaign)Optimization of Photoacoustic Probes for Nitric Oxide Detection

55. Jeff Zhang (Analytical @ Purdue University)Complete Chemical Analysis of Crude Oil Bound to Kaolinite

56. Zhouyang Zhu (Chemical Biology @ University of Illinois at Urbana-Champaign)Development of Novel Ratiometric Probes for Cancer Stem Cells

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SPEAKER SESSION I: ABSTRACTS

Whole Cell Organic Solvent Extraction of Chaperone Protein from E.coli

Clare Gallagher, Craig Sweet, and David H. Thompson

Purdue University

A 20 amino acid sequence derived from alpha-β crystallin, a protein chaperone found in retinal epithelialtissue, has shown promising results for treatment of age-related macular degeneration. However due toits small size, it has limited therapeutic potential. To combat this issue, a protein inspired by humantropoelastin was attached to the alpha-β crystallin to increase therapeutic efficiency and provide ease inpurification. The crystallin-elastin like polypeptide fusion (CryS96) retained the inherent hydrophobicnature of these elastin-like polypeptides, allowing for CryS96 to be purified by an organic solventextraction procedure. This purification scheme rapidly simplified purification for CryS96 to ~30 minutes.Clarified lysates and later whole cell E.coli containing CryS96 were extracted using varying organicsolvent blends to identify which worked best. Once an optimal combination was found, the removal ofthe organic solvent was required. A back extraction using ethyl acetate and water was performed torapidly removal excess organic solvent. The entire extraction process was evaluated with SDS-PAGE totest for protein purity and relative yields. Retention of chaperone activity is paramount, thus, ADHassays were performed to test if chaperone activity was retained after organic extraction. The results fromthe assay indicate the CryS96 was able to limit aggregation of ADH, providing evidence chaperoneactivity was retained after organic extraction purification.

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Synthesis and Characterization of trans-CoIII(DMC) mono-phenylacetylide and bisphenylacetylide

Benjamin M. Oxley, Brandon Mash, Matthias Zeller, Susannah Banziger, and Tong Ren

Purdue University

Reported herein are the complete synthesis and characterization of new mono- and bis-phenylacetylidesbased on CoIII(DMC), where DMC is 5,12-dimethyl-1,4,8,11tetraazacyclotetradecane. Preparation of trans-[CoIII(DMC)(C2Ph)Cl]Cl was achieved under weak base conditions. Synthesis of trans-[CoIII(DMC)(C2Ph)2]OTf was also achieved under weak base conditions through in situ formation of atrans-[CoIII(DMC)(C2Ph)OTf]OTf intermediate followed by the addition of Et3N and phenylacetylene.Cyclic voltammetry studies revealed both complexes displayed three irreversible Co-based couples.Single-crystal X-ray diffraction studies revealed that both trans-[CoIII(DMC)(C2Ph)Cl]Cl and trans-[CoIII(DMC)(C2Ph)2]OTf adopt a pseudo-octahedral symmetry in which the Cl—Co—C angles of theformer and C—Co—C of the latter range from 177.7 (2) to 178.0 (2)˚ and from 177.67 (9) to 179.67 (9)˚,respectively. In both structures, the CoIII metal center is coordinated in the equatorial plane by four Natoms, in which the N—Co—N angles range from 85.6 (3) to 94.4 (3)˚.

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Internal Structure, Band Alignment and Charge Transfer Dynamics of ZnTe/CdSe Core/Shell Quantum Dots

Yuanheng Wang, Cecilia Gentle, Tyler Haddock, Conner Dykstra, Ryan Cornelius, Andre Al Haddad, Ming-Feng Tu, Gilles Doumy, Anne Marie March, and Renske van der Veen

University of Illinois at Urbana-Champaign

ZnTe/CdSe core/shell quantum dots are a novel material for the next generation of solar cell materials.Ultrafast X-ray absorption spectroscopy (XAS), optical absorption spectroscopy and other techniqueshave been used to investigate the charge transfer dynamics of this nanomaterial. XAS has the advantageof being element-specific, and is sensitive to the local environment around a particular atom. Based onmass spectrometry and extended X-ray absorption fine structure results for all four elements contained inthe material, it was found that a CdTe interface layer was formed between the core and the shell, whichalters the band alignment. Picosecond-resolved transient X-ray absorption near edge structure analysis atthe Zn and Se edges, supported by FEFF simulations, suggests a charge transfer feature, that cannot beexplained by a simple edge shift or laser induced heating effect. Optical transient absorption (OTA)studies are complimentary to the time-resolved XAS experiments, allowing us to correlate electronicinformation from OTA with element specific electronic and local geometric information from time-resolved XAS on the charge separated state, electron and hole trap states and exciton recombinationlifetimes of ZnTe/ CdSe QDs. This contribution will greatly advance knowledge of the charge transferprocess and could ultimately lead to increased efficiency in solar energy conversion devices.

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Soluble Zwitterionic Poly(sulfobetaine) Destabilizes Proteins

Elizabeth A. Murphy, Lydia Kisley, Kali A. Serrano, Caitlin M. Davis, Drishti Guin, Martin Gruebele, and Deborah E. Leckband


Proteins have proven to have tremendous potential in biological pharmaceuticals and drug targets due totheir highly specific and complex set of functions and biocompatibility. In many cases, the key tosuccessfully utilizing proteins for these applications is maintaining conformational stability and desiredfunction. There is widespread interest in the use of water-soluble polymers such as neutral poly(ethyleneglycol) (PEG) and zwitterionic poly(sulfobetaine) (pSB) to stabilize proteins in solution due to theirassumed low binding to proteins. However, differences in PEG and pSB-protein interaction mechanismshave yet to be completely understood. For example: despite the existence of complementary charged andpolar patches on pSB and proteins, why would pSB not interact with proteins? Here it is demonstratedthat poly(zwitterion) chains in solution can actually interact with proteins directly, reduce the thermalstability, and increase the protein folding cooperativity relative to proteins in buffer solutions. pSB wassynthesized using atom transfer radical polymerization and characterized using end group analysis anddynamic light scattering. Polymer-protein interactions were investigated using tryptophan fluorescenceemission spectra and thermal denaturation studies on three structurally-distinct proteins. This researchreveals that pSB is not universally protein-repellent and its efficacy in biotechnology will depend on thespecific protein used.

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POSTER SESSION I: ABSTRACTS

Investigation of Silyloxypyrone-Alkene [5+2] Cycloadditions

Jacob J. Bulandr, John R. Goodell, and T. Andrew Mitchell

Illinois State University

Investigation of intramolecular silyloxypyrone-based [5 + 2] cycloadditions revealed three significantfactors impacting conversion to cycloadduct: 1) the more robust tbutyldiphenylsilyl (i.e. TBDPS) transfergroup was found to be significantly more effective than the conventional t-butyldimethylsilyl (i.e. TBS)group; 2) α,β-unsaturated esters were more reactive than terminal olefins demonstrating trace conversioneven at room temperature; and 3) the proximity of the intramolecular tether to the silyl transfer grouprevealed a critical alignment trend. These investigations provided insight regarding the steric andelectronic parameters of this useful reaction leading to improvements for the intermolecular variants.

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Identification and Characterization of the New Aurora Kinase A Substrate in Castration Resistant Prostate Cancer

Jiachong Chu, Hanan Haymour, and Kavita Shah

Purdue University

The main reason for prostate cancer ranking No.2 in cancer-related death in men is the emergence ofcastration-resistant prostate cancer (CRPC) and the following metastasis and chemoresistance for whichhas no way to cure. Only the early stage prostate tumors can be treated by surgery, radiation, andandrogen-deprivation therapy, which typically failed after 2-3 years. Thus, it is an urgent to identify thespecific molecular target for preventing the emergence of CRPC or castration-resistant tumors or givethese tumors higher sensitivity to chemotherapies. Aurora Kinase A (AURKA) is overexpressed in 96% ofhigh-grade prostate intraepithelial neoplasia and 98% of prostate cancer lesions, including CRPC. Usingan innovative chemical genetic approach, we recently identified many AURKA substrates in CRPC cells.The goal for the project was to clone, express and affinity purify these protein substrates. Using an invitro kinase assay, we show that AURKA directly phosphorylates these substrates. At present, we areworking on identifying the direct phosphorylation sites on these substrates. After cloning 6x-His-taggedProtein X-1, Protein X-2 and Protein X-3, and the corresponding phospho-dead mutants in an E. colivector, we expressed, and affinity purified them with Ni-NTA beads. Then the substrates were examinedin an in vitro kinase assay using recombinant AURKA. These experiments will lead to the identificationof direct Aurora A sites on these substrate proteins.

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MRM-Profiling Exploration as a Predictive Tool in Cancer Clinical Trials

Madison Edwards, Christina Ferreira, Greg Durm, and Graham Cooks

Purdue University

Multiple Reaction Monitoring (MRM)-profiling is an analytical strategy within exploratory metabolomicsand lipidomics by mass spectrometry (MS). We aim to evaluate MRM-profiling as a correlative tool incancer clinical trials to anticipate the suitability of a given treatment for a patient. This approach detectssmall molecules present in the samples guided by functional group screening using precursor (Prec) andneutral loss (NL) scans. The information from Prec and NL is organized into fast and sensitive MRM scanlists that can be used to interrogate a large number of samples for biomarkers of therapeutic outcome.These experiments are typically performed in a triple quadrupole MS with direct sample injectionwithout chromatographic separation. Using MRM-profiling to isolate and analyze fragmentations and toassociate them with their small molecule functional groups is estimated to be 10 times faster than liquidchromatography (LC)- high resolution MS or LC-MS/MS and to generate less data. This project includesblood serum samples (ca. 300), managed by the Big Ten Cancer Research Consortium, from patientstreated for a variety of cancers pre-treated with a standard therapy and then given one of twoimmunotherapy treatments against their pre-treatment analyses and normal controls. We expect thatMRM-profiling will predict specific treatment outcomes in response to a panel of small molecules andmight in the future be a clinically useful assay to support the best treatment.

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Novel Potassium Channel Blocker 4-AP-3-MeOH Restores Acrolein-Mediated Conduction Lossin Peripheral Nervous System Injury

Mara Fattah, Jessica Page, and Riyi Shi

Purdue University

The neurotoxin acrolein is known to cause conduction loss, a key pathology in neurotrauma and disease.Acrolein is a reactive aldehyde whose toxicity is increased by its ability to self perpetuate through lipidperoxidation. Acrolein application results in myelin retraction- the axonal sheath composed of lipids-exposing voltage-gated potassium channels. Exposure leads to the efflux of potassium ions whichdisrupts membrane potential and blocks conduction. Previous studies have shown the use of potassiumchannel blockers (PCBs) to restore axonal conduction, such as 4-aminopyridine-3-methanol (4-AP-3-MeOH); this mechanism has not been evaluated in the PNS. Recent evidence suggests acrolein damagecould affect the PNS. The purpose of this study is to determine if acrolein causes axonal conduction lossin the PNS and can be restored by PCBs. Using rat sciatic nerve, we assessed conduction by recording exvivo compound action potentials (CAP) before and after treatment of 500 uM acrolein. Following acroleinapplication, we observed a significant reduction in CAP amplitude. We also demonstrated 100 uM 4-AP-3MeOH significantly restored axonal conduction after acrolein application. This is the first study todemonstrate the effects of acrolein on PNS axonal conduction and potential restoration by PCB 4-AP-3-MeOH. Our findings are consistent with CNS observations, and could present PCBs as potentialtreatments for conduction restoration following acrolein-mediated PNS neuropathy.

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Fabrication and Characterization of Nanoelectrodes used in Scanning Electrochemical Microscopy (SECM)

Heriberto Flores Jr., Zachary T. Gossage, and Joaquín Rodríguez-López


Scanning Electrochemical Microscopy (SECM) is an electroanalytical tool implemented to acquirelocalized measurements and mapping of electrochemical processes occurring at a surface. Themethodologies based on SECM provide a range of tools for quantitative analysis of materials related toenergy storage and catalysis. SECM is a scanning probe technique which typically utilizes conductiveprobes on the micrometer and nanometer scale submerged in electrolyte solutions. Significantdevelopments in SECM point to the nanometer sized probes as the preferred instrument over themicrometer sized probes. The benefit of smaller electrodes is the improved resolution for studyingnanosized species. However, handling nanoelectrodes is known to be difficult. Tip breakage frequentlyoccurs, and one must execute caution when handling these fragile probes. Here, we focus on differentnanoelectrode fabrication methods and their characterization. Through SECM and other electroanalyticalmethods, we assessed their probe quality for different electroanalytical applications.

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Using Second Harmonic Generation Microscopy to Image Crystalline Pesticides on Leaf Surfaces

Benjamin Grubbs, Brennan Davenport, Wesley Slaughter, Nicholas Etter, and Paul D. Schmitt

Wabash College

Second harmonic generation (SHG) microscopy was used to image agrochemical crystallinity directly onthe surface of corn, soy bean, and wheat grass leaves. Proof of concept experiments were completed thatshow i) the general absence of SHG activity from untreated leaves and ii) the ability to image a variety ofcrystalline active ingredients directly on the leaf surface. Following this initial testing, the crystallizationof active ingredient was imaged in a variety of contexts. First, solutions of pure agrochemical actives weredeposited on leaves, with crystallization followed in real time. Second, these same actives wereformulated as wettable powders (WPs) with biodegradable excipients, whereby SHG imaging revealed asignificant increase in active ingredient crystallization time. Such an increase in crystallization time isconsistent with the desired behavior of extended release formulations, an emerging formulationapproach in the agrochemical industry. Finally, SHG microscopy was used to assess the presence orabsence of crystallinity in a commercial fungicide product.

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Production of Bioactive Isothiocyanates via Microbial Myrosinase

Juan Isaiz, Xiaoji Liu, and Michael J. Miller

Moraine Valley Community College

The focus of the project is on the hydrolysis of glucosinolates (GSLs) into isothiocyanates (ITC) by gutmicrobial myrosinase. For this experiment we have chosen two candidate myrosinases from the gutmicrobe E. coli Nissle 1917 and the soil microbe Citrobacter. The myrosinase from Citrobacter was thepositive control in this experiment. We had the genes from these two candidate myrosinases synthesized(Thermofisher) and cloned into expression plasmids pRSET A. We transformed E. coli BL21(DE3) withthe plasmids. We plated them on LB inoculated with Ampicillin, positive clones were picked and thepresence of the plasmids was checked by DNA electrophoresis. The overexpression of microbialmyrosinases was induced by IPTG. The myrosinases were purified by Ni-NTA column. The hydrolysis ofGSL, sinigrin, was examined by cyclocondensation-HPLC. The hydrolysis of 4- nitrophenyl #-d-glucopyranoside (4NPG) was examined at A405nm. Our results showed that the purified Citrobactermyrosinase had activity in that it hydrolyzed both the GSL and 4NPG. However, the candidate E. coliNissle 1917 did not hydrolyze any of these two substrates. We have first-documented, direct evidencethat a microbial myrosinase can produce detectable ITCs from GSLs. It is possible that the Nisslemyrosinase is still a functioning enzyme, but only capable of hydrolyzing phosphorylated substrate, notGSLs/4NPG.

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Alkynylnicotinaamide-Based Compounds as ABL1 Inhibitors with Potent Activities against Drug-Resistant CML Harboring ABL1(T315I) Mutant Kinase

Alyssa Lambrecht, Elizabeth A. Larocque, N. Naganna, Clement Opoku-Temeng, and Herman O. Sintim

Purdue University

Chronic Myeloid Leukemia makes up about 10% of all leukemia diagnoses. Although the 5-year survivalrate has increased from 6% to 90% in the last 30 years from the introduction of imatinib, there are severalmutated forms of the cancer that are resistant to treatment. Treatments such as Ponatinib can be used totreat CML patients that harbor the T315I mutation, but they have toxic effects on the body. Safertreatments need to be discovered to inhibit the proliferation of these resistant lines by inhibiting theactivity of proteins and mutated proteins. Through research done utilizing cell cultures of CML linesK562 and KCL22 and the resistant line KCL22-IR, several compounds have been found to be effective ininhibiting the proliferation of these cancer cell lines. This research suggests that isoquinoline- ornapthyridine- based compounds could be safer alternatives for treating drug resistant CML.

24


Reinforcement of Daily Learning Objectives: The Importance of Connecting the End of a Lesson with Your Objective

Kyle Lieberum


Writing daily learning objectives for a course and providing them to students is a practice used by somehigh school chemistry teachers. These objectives provide a clear goal for what students should learn thatday in class. Whether enforced by school policy or teacher preference, this technique has been proven toimprove student achievement. However, while the practice of using daily learning objectives has beenstudied, the timing of the usage during class is not clear in the current literature. The focus of this studywas to see whether student achievement or attitudes on learning objectives were impacted by when theobjective is stated during a class period. Three classes of general chemistry high school studentsparticipated in this study. One class received the learning objectives at the beginning of their class, oneclass received them at the beginning and end, and the last had the learning objective written on the boardbut it had used learning objectives sparingly. Student unit test scores were collected prior to and duringthe use of the learning objectives. Two surveys were also distributed before and after the study tomeasure perceptions. This poster presentation will provide the results of the study.

25


Examining the Effects of Amino and Thiolate Ligands on the Reactivity and Selectivity of Palladium on Carbon in Hydrogenation Reactions.

Eric Liu and Christina Li

Purdue University

Heterogeneous catalysts are used widely by chemical and energy industries because they show highreactivity but often suffer from lack of selectivity. On the other hand, ligands are commonly used inhomogeneous catalysts to control the reactivity and selectivity; however, the effects of the ligands on thesteric and electronic properties of heterogeneous catalysts are less understood. We examine the effects offour different ligands: 1-adamantanethiol, 1adamantylamine, 1-dodecanethiol, and 1-dodecylamine, forthe commercial hydrogenation catalyst palladium on carbon. Hydrogenation reactions are used as ascreening tool to see the behavior that the different catalysts exhibit in the presence of unsaturatedfunctional groups. Specifically, we study the hydrogenation of alkynes, carbonyls, nitriles, and nitrofunctional groups as well as the reductive amination between an aldehyde and an amine. Trends acrossthe reactions are observed and are related back to the properties of the different ligands. In thehydrogenation of diphenylacetylene, the catalyst with 4 equivalents of 1-adamantanethiol as the ligandwith respect to palladium shows 73.32% selectivity towards the alkene product whereas the non-ligatedpalladium on carbon goes 100% to alkane. This shows how ligands can affect the selectivity ofheterogeneous catalysts. As ligands effects are understood more thoroughly, more effective catalysts canbe designed for industrial reactions.

26


Total Synthesis of (+)-Lycoricidine and (+)-Narciclasine

Daniel Olson, Tanner Bingham, Lucas Hernandez, and David Sarlah


Two of the more potent congeners of the Amaryllidaceae isocarbostyril alkaloid class of natural products,(+)-lycoricidine and (+)-narciclasine possess sub micromolar cytotoxicity against the NCI’s panel of all 60cancer cell lines as well as a broad therapeutic window. However, preclinical studies of these compoundshave been hindered from further development due to their scarce abundance in nature. Despite theirpotency, their relative insolubility in water provides another issue of low bioavailability. Thus, we soughtto develop a concise and scalable synthesis of (+)lycoricidine and (+)-narciclasine that also allows forsynthetic access to a wide variety of analogues that possess increased bioactivity and bioavailability. Ourapproach employs a dearomative [4+2] photocycloaddition of the arenophile N-methyl-1,2,4-triazolinedione (MTAD) with benzene. The resultant cycloadduct is then subjected to a nickel catalyzedasymmetric dearomative transcarboamination to introduce all the carbons of the natural products in asingle operation. The resulting compound is then subjected to olefin functionalization chemistry followedby a cascade epoxide elimination, lithium halogen exchange, and intramolecular nucleophilic addition,that produces the isocarbostyril core of these natural products and provides access to (+)-lycoricidine and(+)-narciclasine.

27


Noncovalently Functionalized 2D Materials Template Solution Assembly of Ultranarrow Gold Nanorods Along 1-nm-Wide Rows of Functional

Headgroups

Tianhong Ouyang, Ashlin G. Porter, Tyler R. Hayes, Shane R. Russell, and Shelley A. Claridge

Purdue University

For current electronics, fabrication lithographic methods only allow for patterning at the 12 nm scale,whereas next-generation electronics require 5-7 nm metal/oxide patterns. The cell membrane has ahydrophilic-hydrophobic chemical orthogonality built into phospholipids on the 6 nm scale, which isideal for addressing this need. We have discovered that after 2D materials noncovalently functionalizedwith lying down phases of long chain amines are photopolymerized, they can act as templates forassembling gold nanowires. Gold nanowires were templated on monolayers composed of long chainamines such as 4,6-pentacosadiynamine, 10,12pentacosadiynamine and 23:2 diyne phosphoethanolaminewhere tested with diyne PE having overall superior gold nanowires ordering. At the same time,monolayers with different chain architectures result in differences in wire orientation during assembly.These result suggest that noncovalently functionalized 2D materials can be used for templating inorganicnanowires, nanocrystals or nanoparticles in a controllable fashion.

28


A New Probe for the Point-of-Care Detection of Ovarian Cancer with Isotopically Enriched Designer Substrate

Gina Partipilo, Sarah Gardner, Xin Huang, and Jefferson Chan


Ovarian cancer is the greatest cause of gynecological cancer death in the developed world, and isresponsible for approximately 75,700 deaths a year in developing countries. Due to the largely non-specific symptoms; pelvic or abdominal pain, bloating, indigestion, abdominal distention, and painduring intercourse; ovarian carcinomas are diagnosed at a late stage in 80% of patients. Early interventionand early diagnostics are key to increasing survival. The current diagnostic drawbacks have given rise tothe need for a new diagnostic tool with the ability to detect early stage malignancies in order to aid inprompt, targeted intervention. This new point-of-care screening protocol must be non-invasive, selective,and multi-faceted. Herein, we introduce a new class of chemical probe design that caters to a large classof enzymatic activities through the metabolic fragmentation of carbamate linkages to release gaseousproducts. We have utilized the enzyme #-galactosidase as the initial target for our new class of chemicalprobes, as the expression of #-galactosidase is associated with the progression of ovarian cancer. Such atest would detect the gaseous products released from enzymatic cleavage, and would be indicative ofpotential early stage ovarian cancer in women displaying non-descript symptoms or carrying germ linemutations.

29


Investigation of a Series of Nickel Phosphine Catalysts for "Green" Suzuki-Miyaura Coupling Reactions

Lisset Perez, Lindsay Bruce, and Jocelyn Lanorio

Illinois College

A series of nickel phosphine catalysts, NiCl2(PCy3)2, NiCl2(PPh3)2, NiCl2(PTA)2, and NiCl2(DPPE),were synthesized in our group by Phuagthong, and employed in two different "green" Suzuki-Miyauracoupling reactions. Our reaction system comprised of: (1) heterocyclic substrates which are importantpharmaceutical building blocks, (2) a less expensive and air-stable nickel catalyst, and (3) a more benignsolvent, tert-amyl alcohol, as opposed to the typical use of hazardous and easily volatile substance. Theformation of the desired products, 5-(furan-3-yl) pyrimidine and 5-(2-methoxypyridine-3-yl) pyrimidine,were observed and determined to be pure by 1H and 13C NMR spectroscopy. Herein, we report the effectof the phosphine ligands on the catalytic activity of nickel complexes.

30


Porous Silicon Matrix for Novel Fabrication of an Asymmetric, Tunable Microscale Lens to Demonstrate Sub-Diffraction Optics

Andrea N. Perry, Christian Ocier, Jinlong Zhu, Lynford L. Goddard, and Paul V. Braun


Porous silicon (PSi) originally gained popularity due to its photoluminescence in the visible range,however it has since proven attractive as a more versatile optical material due to its tunable properties,namely that its porosity, and therefore refractive index, can be modulated during the course of fabricationvia electrochemical etching by controlling the applied current density. Recently, Zhu and Goddardproposed a novel asymmetrical microstructure, consisting of a supporting stage and spherical cap, for thegeneration of a highly focused, intense beam termed photonic nanojet (PNJ) whose properties can beprecisely controlled by tuning the geometrical dimensions of the microstructure. Such structures couldenable the probing of nanoscale objects located deep within biological cells and the trapping andmanipulation of nanoscale objects, among other applications. However, because of the delicate nature ofthe high aspect ratio microstructure, realization of its fabrication presents a significant challenge. Here,we present a novel fabrication approach in order to realize the complex geometries of such asymmetricalmicrostructures by employing two-photon polymerization lithography to write the geometries within thePSiO2 supporting matrix. Such geometries hold capabilities for focusing light well below the diffractionlimit for conventional optics, and thus pave the way for novel optical applications.

31


Synthesis of Air-stable Ruthenium and Nickel Catalysts

Sirikarn Phuangthong and Jocelyn Lanorio

Illinois College

A series of air-stable nickel and ruthenium phosphine complexes have been synthesized andcharacterized. The phosphine ligands employed include the monodentate triphenylphosphine (PPh3) and1,3,5-triaza-7-phosphaadamantane (PTA), and the bidentate 1,2bis(diphenylphosphino)ethane (dppe).Addition of PTA resulted to more stable complexes both in solution and solid state. Nickel andruthenium complexes containing the PTA ligand exhibit high water-solubility and are potential catalystsin green solvents such as alcohol, water, or ionic liquids.

32


Synthetic Studies Toward the Divergent Total Synthesis of Lycopodium Alkaloids

Takeru Saito, Brandon S. Martin, and Mingji Dai

Purdue University

Background: Lycodine-type lycopodium alkaloids have been frequent synthetic targets due to theirstructural complexity and acetylcholinesterase inhibitory activity. Our synthetic efforts have beentowards the targets shown in Figure 1 and several structurally related compounds.

Synthetic Route: The general synthetic strategy for lycodine-type lycopodium alkaloids involveselaboration of (R)- (+)-pulegone to the enone/benzyl ether intermediate shown. The target alkaloids willbe accessible by a series of further transformations.

Current Work: Disclosed will be the preparation of the benzyl ether intermediate on large scale.Additionally, the preparation of a model substrate for investigation of a Ciamician-Dennstedtrearrangement to be used later in the synthesis will be described.

33


An Undergraduate Teaching Oriented Approach to Reaction Investigation and Optimization

Amara Spencer, Jack Floreancig, Robert Minto, and Sébastien Laulhé

Indiana University-Purdue University Indianapolis

Peer-Lead Team-Learning (PLTL) educational approaches have been shown to increase student’sunderstanding of content presented to them in a lecture setting. Given the expertise our department hasacquired in the incorporation of PLTL to the teaching of organic chemistry, we sought out to utilize thismethod of teaching in the Organic Chemistry II laboratory setting. In particular, we aimed at using aPLTL approach to develop an undergraduate research experience in the model of a CAPSPiE module.Our Peer Lead Undergraduate Research Initiative (PULRI) exposes students to a real research experienceled by peer teaching assistances (PTAs). This approach not only benefits the students taking the lab, butalso represents a unique research and managerial opportunity for the PTAs. The students conduct all thenecessary screens to optimize an organic reaction. Currently students are performing a palladium/copperdual catalysis to form (Pinacolboryl)benzene from bromobenzene. For the past two semesters, we haveperformed qualitative interviews of the students and PTA’s involved in these new research exposuremodules. Both research and educational data will be presented.

34


Selective #-Amination of Ethers Using Stable N-Chloroamines and Lithium tert-butoxide

Zachary W. Thom, Makafui Gasonoo, and Sébastien Laulhé


Hemiaminal ether is a commonly encountered functional group in many pharmaceutical and biologicallyactive products such as mycalamide A, pederin, and psymberin, which have been shown to exhibitcytotoxicity against various human tumor cell lines. A popular approach to generating #-aminated ethersproceeds via hydroamination of enol ethers, which are reactive and acid sensitive functional groups.Performing direct C(sp3)-H amination of ethers represents a more efficient approach and also enableslate-stage functionalization of complex molecules. Methods that access #-aminated ethers through suchC–H activation processes can be divided into three main categories depending on the nature of theaminating agent: i) transition-metal catalyzed nitrene insertions; ii) metal-free organonitrenoid insertionreactions; and iii) radical-based or metal catalyzed cross-coupling reactions of NH-amines. Herein wedescribe a metal-free selective #amination of ethers using stable N-chloroamines as the aminating agent.Our method generates the desired products in good to excellent yields at room temperature without theneed of transition metals or light. Optimized reaction conditions, substrate scope, and early mechanisticdetails will be presented.

35


Single Cell Analysis by Hyphenation of CE-ESI-MS and ICC

Huiying Tian, Marina C. Philip, Elizabeth K. Neumann, Joseph F. Ellis, Stanislav S. Rubakhin, and Jonathan V. Sweedler


Single cell analysis is crucial to understanding fundamental brain function and treatment of braindiseases. The study of single cells provides insight into brain function on a cellular level. One of our goalsof single cell analysis is to characterize differences between cell types. However, selecting specific celltypes to assay can be difficult without using immunocytochemistry (ICC) or transcriptomics. In the caseof ICC, the process of fixing the cells often eliminates the possibility of performing follow-up analysis. Todo multiple analyses by using different analytical techniques, a liquid microjunction extraction (LMJ)probe is utilized to extract samples into two contents: extract content and content remaining on a glassslide. The structural proteins remaining on the slide will be stained using ICC, which is a gold standardway to identify astrocytes and neurons. The extract content will be analyzed in a CapillaryElectrophoresis-Electrospray Ionization Mass Spectrometry (CE-ESI-MS) system to measure cellularmetabolites. The combination of CE-ESIMS and ICC after LMJ extraction is a powerful method to dosingle cell analysis. This method increases analytes coverage and it allows both qualitative andquantitative characterization of single cells by measuring the cellular metabolites and identifying celltypes. Single cell analysis on astrocytes and neurons will improve the understanding of brain on acellular level, and potential treatment of brain diseases.

36


Synthesis and Testing of an Acid Phosphatase Sensor

M. Roarke Tollar, Chukwunalu Chukwuma, and Laura M. Wysocki

Wabash College

Fluorescein and its derivatives are known to have a wide range of applications in biochemicalexperiments, including as enzyme substrates. One attractive target for monitoring acid phosphataseactivity is 2’,7’-difluorofluorescein diphosphate. However, the phosphate groups on Oregon Green areunstable in water, making it unsuitable for experiments involving aqueous environments. This research isfocused on synthesizing a fluorescein-based indicator with hydrolytic stability that will act as acontinuous acid phosphatase sensor in aqueous environments. To realize this goal, we want to usephosphatoxymethyl ether (PME) groups on Oregon Green. In order to test the enzyme activity andaqueous stability of the PME group, we have synthesized a model compound, the masked derivative ofp-nitrophenol. In preliminary testing, we found this novel target has comparable chemical stability andKm values in an acid phosphatase assay to the commonly used p-nitrophenylphosphate (pNPP). Theseresults suggest that the PME group will be a suitable substrate for acid phosphatase for the fluorescentprobe. The bis(PME) derivative of Oregon Green has been synthesized and will be tested after carefulpurification.

37


Evolution of Solid State Synthesis for Implementation in an Education Laboratory

Killian L. Tracey and Brian J. Bellott

Western Illinois University

Solid state chemistry is an important rising field of, with advancements in medicine as aneurismtreatments and technology as liquid crystal display (LCD) screens, undergraduate students should havemore exposure to this area of the science. However, the increased need for solid state chemists is risingfaster than the resources for undergraduate work in it; thus is the reason for the development of aneducational lab for undergraduate studies. Our goal is to develop an efficient synthesis of MxQy (whereM is a transition metal and Q is either S, Se, or Te) combinations to be performed by undergraduatestudents over two 3-hour teaching laboratories. Copper (II) Sulfide is the first solid state process to bedeveloped, as it is known that CuS can be synthesized. Elements are measured out in specific ratios, andfor some trials, flux of potassium bromide and sodium bromide is added to lower the melting point of theelements to increase the vigor for the reaction. Over one week in the furnace, the compound is heatedfrom room temperature to 520 degrees Centigrade and then cooled. The slow cool rate of the furnaceallows for the largest amount of reaction time so the crystals can form as large as possible. Products areanalyzed via SEM-EDS for chemical composition and structure.

38


Novel Depolymerization Mechanism of Transient Polymeric Materials

Vishaal Venkatesh


Kinetically dormant yet thermodynamically unstable transient polymers are capable of controllablydegrading, offering a route to the production of efficient recyclable materials, transient packagingsystems and targeted delivery systems. To this end, we investigate cyclic poly(phthalaldehyde) (cPPA), apolymer that rapidly depolymerizes into o-phthalaldehyde when subjected to thermal, acid, andmechanochemical triggers. Elucidating the mechanistic details of depolymerization is imperative todetermining the scope of cPPA’s applications. Previous results suggested that thermolytic conditionsinduce cPPA depolymerization via a radical chain unzipping and acid catalysed cationic unzippingmechanism. cPPA polymer films doped with TEMPO, a stable radical species, were expected to exhibitinhibited radical chain unzipping, and those doped with DBPDA, a Lewis base were expected to exhibitinhibited cationic unzipping. Thermogravimetric analysis (TGA) and Gel Permeation chromatographyrevealed no radical inhibition via TEMPO. Herein, we report that chain unzipping occurs solely througha cationic pathway triggered by acid or single electron transfer (SET) oxidation. The SET mechanism wasinvestigated via TGA of cPPA polymer films doped with reductants, inhibiting depolymerization, andoxidants, facilitating depolymerization. SET induced depolymerization opens the way to newtransduction pathways for triggered transience such as chemical, photochemical and electrochemicaloxidation.

39


Synthesis of Therapeutic Agents for Myotonic Dystrophy Type 1 (DM1)

J. Ignacio Vergara P., Lauren D. Hagler, and Steven C. Zimmerman


Myotonic dystrophy type 1 (DM1) is a trinucleotide repeat expansion disease (TRED) characterized by aprogressive expansion of a d(CTG) repeated sequence in the dystrophia myotonia protein kinase (DMPK)gene. Following transcription, the expanded r(CUG) can form hairpins with mismatched uridine basesand sequester an alternative splicing regulator, muscleblind like protein (MBNL1), causing hundreds ofpremRNAs to be mis-spliced and symptoms such as myotonia, cardiac defects and insulin resistance. Apotential pathway to treat the disease is to outcompete MBNL1 during the sequestration event bydesigning multivalent ligands capable of binding to the toxic RNA hairpin more strongly than MBNL1.To maximize cell uptake of the therapeutic agent, the precursors to the ligand can be assembled inside thecell using the templating effect of the RNA secondary structure via a [3+2] Huisgen cycloaddition. Thesynthesis of various clickable azide and alkyne ligands are herein described for RNA and DNA targets.

40


The Role of Iron-Sulfur Clusters in YcaO-domain Containing Proteins

Steven Vo


YcaO domain-containing proteins have previously been categorized with a variety of functions: catalysisof amide phosphorylation in ribosomal peptide backbones, assist in RimO dependent methylthiolation,or in azoline, macroamidine, and thioamide formation. They are involved in microcin antibiotic synthesisby forming oxazoles and thiazoles in an ATP-dependent cyclodehydration fashion. Heterocyclessynthesized by YcaO domains are characteristic of the synthesis of ribosomally synthesized andposttranslationally modified peptides (RiPPs), which are natural products that have a large range ofpractical use from preservatives to antibiotics. A RiPP cluster in Lachnospiraceae bacterium C6A11contains a YcaO domain with an uncommon 4Fe-4S cluster. Proteins with Fe-S clusters are involved in:DNA synthesis, O2 processing, gene expression, DNA repair, and free iron level regulation. Theseclusters situate themselves as one electron-transfer groups in redox reactions. The unusual presence of an4Fe-4S cluster in YcaO domain containing proteins may be either crucial to the structural integrity of theprotein, as an essential catalytic domain, or in some cases both. The crystal structure of LahD1 hasfavored the possibility of a structural role based on the inherent positioning in the folded state. Furtherkinetics and co-crystallization results are required to facilitate a stronger conclusion of a structuralcontribution.

41


Synthesis and Characterization of Ruthenium-Based Alzheimer’s Disease Therapeutics

Brendan J. Wall and Michael I. Webb


Amyloid-beta (Aβ) peptide aggregation is a primary characteristic of Alzheimer’s disease (AD), the mostcommon neurodegenerative disorder. Aβ peptide aggregates have been observed to contain the redox-active metals, copper and zinc, which lead to the generation of reactive oxygen species which aredamaging to nearby neural membranes, and is the basis for the development of AD. Given the affinity ofAβ peptide aggregates for metal ions present in the brain, metal-based therapeutics should offer analternative target for Aβ, preventing aggregation and reactive oxygen species. The Ruthenium metalcomplex, imidazolium trans-tetrachloro(dimethylsulfoxide)imidazoleruthenium(III) (NAMI-A) has beenstudied for its effect on binding the Aβ peptide and have proven effects in preventing Aβ aggregation.However, questions regarding the relationship between the ligands around the Ruthenium metal center,and the complex’s activity need to be defined to advance development of Ruthenium-based ADtherapeutics. We have prepared pyridine-based NAMI-A derivatives and have begun to characterize theirinteractions with Aβ. Preliminary data shows that there is association between our derivative complexesand the Aβ peptide, further evaluations of this interaction are ongoing and will be discussed.

42


Determination of Transcriptional Changes Induced by an Ovarian Cancer Targeting Peptide

Matthew Wieskamp, Lindsey Weintraub, James Rudy, Sue Hum-Musser, Richard Musser, and Mette Soendergaard


The fifth leading cause of cancer-related deaths among women is ovarian cancer. While most patientsinitially respond to therapy, the majority relapses with drug resistant malignancy, and ultimatelysuccumbs to the disease. Bacteriophage (phage) display technology was previously used to discover a 15-mer peptide (J18) with specific binding to human ovarian adenocarcinoma (SKOV-3) cells. Based on theovarian cancer binding properties of J18, the cytotoxic properties of the peptide was investigated using an3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) assay. These results showed that J18significantly (p<0.01) decreased SKOV-3 cell viability compared to no peptide (DMSO). Here, thecytotoxic mechanism of J18 was sought elucidated by quantitative polymerase chain reaction (qPCR).Specifically, genes involved in cancer progression (MYC, ELK-1, SMAD4, HSPB1, and TP53), andapoptosis (FADD, CASP3, and CFLAR) as well as housekeeping (SDHA) were chosen for analysis.Results showed that expression of FADD was significantly (Students t-test, p<0.05) decreased, indicatingthat a decrease in expression of FADD may be involved in J18 mediated cytotoxicity. Expression ofCFLAR, HSPB1, MYC, SMAD4, CASP3, ELK1, and TP53 were not significantly different for peptide J18compared to DMSO. These results indicate that the loss of cell viability mediated by peptide J18 is notassociated with changes to the transcriptional levels of these genes.

43


Magnetostructural Coupling in Transition-Metal Based Compounds, TCrX (T = Mn-Ni; X = Al, Si, Ge)

Justin Shing Him Wong, George Agbeworvi, and Corey M Thompson

Purdue University

In recent years, transition-metal based equiatomic TT’X (T and T’ = Transition metals; X = nonmetals)compounds have been a subject of immense interest, due to their large magnetocaloric and exchange biaseffect. In this system, the combinations of late-and-late (TT’X) transition metals have been thoroughlystudied (i.e., Fe(Co)MnSi). In contrast, combinations of early-and-late transition metals have beenunderexplored. Hence, we have synthesized several new compounds with an early transition metal,TCrX (T = Mn-Ni; X = Al, Si, Ge). These novel phases exhibit a variety of crystal structures and magneticbehavior. Herein, we will present on their structural and magnetic properties and make comparisons totheir late-and-late transition metal counterparts.

44

POSTER SESSION II: ABSTRACTS

Streamlining the synthesis of folate mimics

Zach Bennett, Anna Bockman, Kassidy Grumbles, and Jeff Pruet

Valparaiso University

Pterins are a class of nitrogen-heterocycle with wide application in the field of medicinal chemistry. Theimportance of pterin derivatives stems from discovery of numerous biologically relevant pterins, such asfolate and bioterin. Due to this biological relevance, pterins can be viewed as a privileged scaffold, as thediscovery of new pterin analogs gives rise to a vast array of potential drug candidates. 7-carboxymethyl-pterin (7-CMP) is a useful scaffold for the rapid generation of structurally diverse pterins, utilizing aDBU-promoted amidation process. We are currently exploring multiple routes towards 7-CMP to assessthe most efficient method of generating this useful scaffold. Furthermore, we have explored the scopeand limitations of the DBU-amidation.

45


Development of Probes for Photoacoustic Imaging of Tissue Hypoxia in Prostate Cancer

Douglas S. Chan, Hailey J. Knox, Brandon Li, and Jefferson Chan


Hypoxia occurs when tissue oxygen supply to rapidly growing tumors becomes inadequate to supportphysiological processes. This induces a series of changes in gene expression that play a role in tumormetastasis and treatment resistance. In particular, hypoxia has been directly correlated with tumor gradeand clinical stage in prostate cancer. Therefore, identifying hypoxia in prostate tumors can guidetreatment planning and predict patient responses. Previous work in our lab yielded the development ofHypoxia Probe 1 (HyP-1), a hypoxia-responsive small-molecule probe designed for hypoxia detectionusing photoacoustic (PA) imaging. PA imaging uses near-infrared light to induce the production ofultrasound signals, enabling acquisition of high-resolution images in deep tissue. Currently, we arefocused on the development of a prostate cancer targeted hypoxia probe (HyP-PCa), which targets theprostate-specific membrane antigen overexpressed in almost all prostate cancers. The goal of our work isto combine HyP-PCa with modified clinical U.S. systems to enable PA imaging of prostate tumor hypoxiain order to determine tumor grade and clinical stage.

46


Polyaniline-impregnated filters and their possible applications

Pravin Chandra, Xinyue Cui, Kacper Lachowski, and Nikolai M. Kocherginsky


Acid-doped polyaniline is the best-known electroconductive polymer, or ‘synthetic metal,’ with manypractical applications. Traditional methods of synthesis are based on the reaction of aniline withpersulfate in aqueous hydrochloric acid. It is assumed that persulfate radicals lead to polymerization insolution. We have demonstrated that it is also possible to polymerize aniline when its acidic solution fillsthe pores of a nitrocellulose filter, and the solution containing the impregnated filter is then exposed togaseous chlorine. Chlorine enters the solution phase and initiates polymerization by oxidizing anilineinside the membrane. By varying experimental conditions, it is possible to deposit polyaniline in thepores, on both sides of the membrane, or even just on one side. The polymer remains electroconductive,and the reaction with chlorine forms a new type of asymmetric thin material with one surface beingconductive, and the other not. Reaction with chlorine is very fast, and it leads to change in filter colorfrom white to black. Therefore, aniline-impregnated filters may be used as a simple indicator paper todetect presence of chlorine in air. This can be used to detect dangerous leakage of chlorine in chlorinationof potable and swimming pool water, and also to detect usage of chlorine gas as a chemical weapon in bya simple, inexpensive and convenient method.

47


Iterative Synthesis of Csp3 Rich Small Molecules by using Bifunctional Carbenoid-BoronateBuilding Blocks

S. Chitti, D. Koystra, D. J. Blair, and M. D. Burke


The building block based approach - or the iterative assembly of interchangeable parts is increasinglybeing recognized as a highly flexible and efficient method for the construction of small molecules. Forbiopolymers such as polypeptides, oligosaccharides and oligonucleotides, the common linkages betweenbuilding blocks is easy to recognize. This has led to the development of automated platforms which havebroadly enabled both experts and non-experts to explore biopolymer chemical space. If a similar strategycould be applied to small organic molecules the societal impact would be tremendous as it would addressa key bottleneck in the development and discovery of new drugs, fragrances, fertilizers and materials. Abuilding block based analysis of small organic molecules is substantially more challenging as therepeating units are not obvious. However, if C-C bond forming reactions could be rendered sufficientlygeneral, then essentially any C-C bond could be regarded as a common linkage. Toward this objective, weare developing bifunctional building blocks which contain a protected boronate and a masked chiralcarbenoid. Treatment of these carbenoids with a simple Grignard reagent promotes a stereospecificcoupling reaction with an unprotected boronate such that a C-C bond is formed with near-perfectstereocontrol. We are now developing conditions to iterate this procedure and are exploring how thismethod can be applied within the context of total synthesis.

48


Synthetic Optimization of PET-Imaging Ligands: Aza-Thia 14-membered Heteromacrocycles

Hunter DeHaan, Ian Taschner, and Tia Walker

Indiana University Northwest

Technological development of copper radioisotopes has allowed researchers to overcome the limitassociated with morphological imaging and shift to biometabolic imaging, allowing for rapid diseasediagnosis, high-resolution imaging (non-invasive) of the human body, and treatment options for thedisease. Radioisotope, 64Cu, has a suitable decay (half-life Tau1/2 = 12.7 hours, 17.8% (symbol beta)+,0.653 MeV) essential and biocompatible in positron emission tomography (PET) imaging. Cheatingligands such as the cyclam scaffold is a common ligand for 64Cu metal complexation, includingfunctionalized TETA ligands such as the TE2A. Although thermodynamically stable and inert in vitrothese ligands show instability in vivo, with evidence of trans-chelation to superoxide dismutase. Toinvestigate the effects on stability using mixed N,S macrocycles, synthesis and characterization of 1,11-dithia-4,8-diazacyclotetradecane (L1) and 1,4dithia-8,11-diazacyclotetradecane (L2) was performed. Thisproject currently focuses on synthetic optimization strategies for 1,11-dithia-4,8-diazacyclotetradecane(L1) including the discovery of new methods for detosylation to minimize decomposition products andmaximize product yield.

49


NMR Analysis of Nepatalactone: Quantitation and Stereochemical Assignment

Bushra Fatima and Ian Taschner


One natural monoterpene biosynthetically produced within Nepeta cataria (catnip), trans-cisnepetalactone (1), was extracted and subjected to a thermodynamically mediated epimerizationaffording thermodynamically stable cis-trans-nepetalactone (2). The presence of diastereomers (1 and 2)were identified using thin layer chromatography (TLC) doped with silver nitrate. Gas chromatography intandem with mass spectrometry (GCMS) was utilized to analyze the cesium carbonate mediatedepimerization of 1 using a rapid method developed in our lab. The enthalpically stable cis-fused [4.3.0]bicyclic lactone 2 was converted quantitatively (GCMS). Use of 2D-through space cross-relaxation(NOESY) provided stereochemical assessment for 1 and 2. According to the Karplus curve a spin-spininteraction at 90° between the alpha proton and the stereogenic methyl will not provide and coupling. Toovercome this a dynamic NMR NOESY experiment was performed in order to observe through spacecoupling.

50


Synthesis and Characterization of Ruthenium-Based Complexes for Alzheimer's Disease Therapy

Samuel S. Fisher, Samantha E. Huffman, and Michael I. Webb


Alzheimer’s disease is currently an incurable neurodegenerative disorder that is characterized by theaggregation of the peptide amyloid-β (Aβ). Ruthenium-based compounds have been observed tomodulate the aggregation of Aβ, thus preventing toxicity. However, further evaluation is imperative todiscern what properties of the ruthenium-compounds are most significant and effective in preventing Aβtoxicity. The ruthenium complex, imidazolium [trans-tetrachloro(1H-imidazole)(S-dimethylsulfoxide)ruthenate(III)] (NAMI-A), was evaluated for its ability to prevent Aβ aggregation invitro and displayed promising results. By modifying the ligands on the ruthenium center, derivatives ofNAMI-A will be prepared to determine the impact of the ligands on Aβ binding and peptide aggregation.Once synthesized, the metal-based compounds will be studied under biological conditions for theirstability and effectiveness in limiting the toxicity of Aβ. Aggregation was monitored using a ThTfluorescence assay, from which preliminary data suggest that our NAMI-A derivatives inhibit Aβaggregation better than the trans-symmetric complexes. The implications of this study are discussed inrelation to expanding alternative therapeutic strategies for Alzheimer’s disease.

51


Borylation of Aryl Iodides Using a Pd/Cu Dual Catalysis

Jack Floreancig, Amara Spencer, and Sébastien Laulhé


Aryl Boronic esters are important coupling partners in metal-catalyzed cross-coupling reactions as well asa variety of synthetic transformations. Their utility comes from their mild nucleophilicity, high stability,and low toxicity. Traditional ways to synthesize aryl boron reagents requires the use of highly reactivereagents such as n-BuLi or stoichiometric amounts of organometallic species such as Grignard reagents.Catalytic methods using transition-metals such as palladium or copper exist, but these methods oftenlead to competitive homo-coupling byproducts and often require harsh reaction conditions. We surmisedthat in current palladium-catalyzed methodologies the major catalytic hurdle is the activation andtransmellation step of the diboron reagents, while oxidative addition is limiting for copper-catalyzedreactions. Therefore, we proposed that using a combination of palladium and copper in a dual-metalcatalysis approach would better partition the roles of each metal enabling facile oxidative addition bypalladium while generating fast transmetallating copper-boron species. Reaction conditions usingiodobenzene with bis(pinacolato)diboron have been optimized and will be presented alongside withsubstrate scope and proposed catalytic cycle.

52


Fourier Transform Infrared Spectroscopy on Corn Protein -Tannic Acid Formulations

Lawrence Xi-Bin Fung and Gudrun Schmidt

Purdue University

Tannic acid is a plant-based polyphenol composed of condensed gallic acid units. When used as cross-linking agent, tannic acid can provide cohesive strength to polymers such as corn protein. Thisfunctionality is quite useful when designing nontoxic polymer glues and packaging materials. We useformulation and Fourier transform infrared (FTIR) spectroscopy to provide some molecular informationregarding cross-linking reactions that may have taken place during curing of corn protein-tannic acidcompositions. Regions of particular importance are those characteristic for protein, tannic acid andcombinations thereof. We also compare our results to the cross-linking chemistry of catechol.

53


Exploration and Application of Oxidopyrylium-Alkene [5+2] Cycloadditions

Jake Grabowski and T. Andrew Mitchell


Cycloaddition reactions are valuable synthetic tools, providing efficient reaction pathways toward theformation of complex three-dimensional polycyclic structures from planar precursors. Previously, theMitchell research group has reported differing reactivity of various acetoxypyranone substrates in theinvestigation of oxidopyrylium-alkene based [5+2] cycloadditions (Scheme 1). Cycloadditions proceedingvia silyloxypyrones are also efficient routes toward bridged polycyclic ethers, which are commonstructural motifs found in several types of biologically active compounds. Thus, further exploration ofoxidopyrylium-based [5+2] cycloaddition pathways will lead to the synthesis of these classes ofcompounds. Toxicodenane A, one example of a bridged polycyclic ether, provides an opportunity todemonstrate the utility of this powerful reaction. Major disconnections reveal the possibility of anintramolecular oxidopyrylium [5+2] cycloaddition mediated by a silyl-allene tether as an efficient routetoward Toxicodenane A beginning from commercially available dimedone (Scheme 2). While recentadvancements have been made by other groups, we propose a total synthesis of toxicodenane Aimplementing the key oxidopyrylium based [5+2] cycloaddition to construct the bridged-ether core.

54


Targeting Therapeutics for Accelerated Bone Fracture Repair

Jonathan Hicks and Cheyanne Woolwine

Purdue University

Approximately 6.3 million bone fractures occur annually within the US. Compounded by an increasingage demographic, this problem is projected to increase over time, with hip fractures alone having apredicted 160% increase by the year 2040. Our group focuses on the targeted delivery of bone anabolicagents, specifically Parathyroid hormone related protein (PTHRP). PTHRP is a well-researched boneanabolic agent, having shown significant clinical ability. Via modification of the protein, we havesuccessfully increased the bone regrowth rate, while also strengthening its material properties. This iscompleted via the addition of a hydroxyapatite targeting ligand to the drug in question. The targetingmechanism allows the drug to selectively bind to hydroxyapatite, which is only exposed at the fracturesite. By use of this targeting mechanism, the drug can be sustained at much higher concentrations for alonger time than the non-targeted variant of the drug, which is typically excreted within 24 hours. It hasbeen shown in rodent trials, that even in small time-frames, the effects of the targeted drug on bonevolume, as well as density, are significantly higher than the non-targeted drug. This indicates that afracture can be healed in a significantly shorter time while still maintaining mechanical strength. This ispotentially beneficial to elderly patients, for whom 50% will never regain full mobility following a hipfracture, and 25% will die due to related complications.

55


Synthesis and Photochromicity of Various N-Phenyl Cinnamaldehyde Semicarbazones

Ethan Hose and Edward M. Treadwell

Eastern Illinois University

Cinnamaldehyde semicarbazone has previously been found to possess photochromic properties thatchange as the ring is substituted, but no studies have been done when various N-phenyl substituents areadded to the terminal nitrogen. Semicarbazides containing methoxy, phenoxy, and dimethylaminosubstituents were prepared in 18-100% yields in two steps by reacting carbonyldiimidazole (CDI) with asubstituted aniline, and treating the resulting urea with hydrazine monohydrate. After reaction with oneof three cinnamaldehydes, the crude final products were recrystallized from 95% EtOH. 4-Pyridyl, 2-pyridyl, and phenyl semicarbazides failed to yield product, regardless of the cinnamaldehyde that wasused. 1H NMR analysis showed that some of the electron-rich anilines formed dimeric ureas, whichcould be avoided by dilution and shorter reaction times. Also, some cinnamaldehyde semicarbazoneswere formed as mixtures of syn/ anti products, in ratios ranging from 2:1 to 20:1. The final products werevisually inspected for photochromic behavior, and further analyzed by UV-Vis spectroscopy.

56


High Performing Waste Tire Carbon Electrodes for Desalination via Capacitive Deionization

Marko R. Ivancevic, Samuel F. Evans, Zachary D. Hood, Shiba P. Adhikari, Costas Tsouris, Amit K. Naskar, and M. Parans Paranthaman.

Oak Ridge National Laboratory

Oak Ridge National Laboratory scientists developed a method for recovering carbon from waste tires. Weapplied this carbon to a low cost and low energy desalination method called capacitive deionization(CDI). Using the tire carbon as electrode material, we hypothesized creating a desalination process that isboth efficient and economically viable. We chemically treated the carbon and upon analysis obtained aspecific surface area of 952 m2/g with a unique micro/meso pore distribution. We then synthesized anactivated carbon, polyaniline, and polytetrafluoroethylene slurry, and coated it on nickel foam currentcollectors. Polyaniline, when combined with the carbon, coats the carbon and increases capacitance due toits commensurate conducting properties. Furthermore, we used cyclic voltammetry, galvanostatic charge-discharge, and electrochemical impedance spectroscopy to characterize the carbon polyaniline composite.Our analyses yielded a high specific capacitance value of 168.2 F/g. Finally, we used a continuous-flowCDI cell and membrane-assisted CDI (MCDI) cell for desalination testing. We obtained salt uptake valuesof 12.1 and 24.7 mg/g for CDI and MCDI respectively. Through electrode cycling tests, we found theelectrodes maintained over 60% efficiency after 5000 cycles. These are some of the highest salt uptakevalues, and the most robust cycling for CDI using activated carbon to the best of our knowledge.

57


Elaboration of a thiol-based probe for HNO

Luyang Li, Nicholas W. Pino, and Jefferson Chan

Nankai University and University of Illinois at Urbana-Champaign

Nitroxyl (HNO), the one-electron reduced congener of nitric oxide, is difficult to detect due to its highreactivity with biological thiols (k = 106 – 109 M-1 s-1). Our group has developed a thiol-based HNO-responsive trigger that can compete against reactive thiols. However, we have experienced challengeswith deactivation through a disulfide pathway, especially in living cells. To address this problem, effortsin stabilizing the trigger through structural modifications have been made by connecting three functionalfragments together to develop a new probe. These fragments include a pro-fluorescent fragment, anHNO-reactive fragment, and a UV-reactive cap. This design masks the reactive thiol by a UV-sensitivegroup, preventing disulfide formation during cell staining. Additionally, this capping method offersspaciotemporal control over the localization of the active probe. Surprisingly, despite promisingpreliminary results, early generations of this compound have failed to react in the expected manner. Inresponse, further work will go into identifying the source of low reactivity and construction of a moreeffective platform.

58


The Effect of Polymer Backbone on Aqueous Mechanochemistry

Claire Lundberg, Abigail Halmes, Qiong Wu, and Jeffrey Moore


A mechanophore is a molecular moiety that responds to mechanical force with a chemical change.Mechanophores are incorporated into a polymer matrix which effectively transduces force to themechanochemically active bonds. In this study we target water soluble polymers in order to demonstratethe relevance of mechanochemically active materials in biological applications. Previously reportedsystems require organic solvents to dissolve polymer samples. We hypothesize that the incorporation of amaleimide-anthracene (MA) mechanophore into the center of a water soluble polymer results in adecrease in molecular weight after mechanical force is applied by sonication. When MA is activated bysonication in organic solvent, it undergoes a [4+2] retro Diels-Alder reaction. Gel permeationchromatography (GPC) experiments before and after sonication of each polymer are used to determinepolymer molecular weight. We test multiple water soluble polymers to determine which system willperform best under aqueous conditions. These findings will inform the design of biocompatiblemechanoresponsive materials.

59


Halogen Atom Effect on the near-infrared Emission of Porphyrinate Ytterbium (III) Complexes

Derric E. Meyer and Hongshan He


Near-infrared emission from lanthanide complexes is usually realized by a sensitization process, in whichenergy from the excited state of a sensitizer transfers to the excited states of lanthanide ion, which emitsin the NIR region when it relaxes to the ground state. It is of importance for ligands to have a high tripletyield to produce efficient near-infrared emission from lanthanide ions. In this presentation, we willreport synthesis and characterization of three ytterbium (III) complexes of 5, 15-diphenylporphyrinateligands. Two Br and I atoms are introduced into the 5, 15-positions of the porphyrin ring to induce hightriplet yields as well as to suppress the quenching from the nearby C-H vibration. The complexes can beeffectively sensitized by a green light source producing a strong emission at 980 nm. The impact ofhalogenation on the quantum yields and emission lifetimes will be discussed. This work is supported bythe National Science Foundation (Grant #1507871).

60


Synthesis and Spectroscopic Studies of Porphyrinate Ytterbium (III) Complexes

Eric Micheli and Hongshan He


Lanthanide ions including ytterbium(III), neodymium(III) and erbium(III) have great potential in medicaldiagnosis due to their unique emission in the near-infrared region. Emission is usually realized by asensitization process, in which energy from the excited state of a sensitizer transfers to the excited statesof lanthanide ion and emits in the NIR region when it relaxes to the ground state. However, it is quitechallenging to obtain high emission efficiency in lanthanide complexes under long wavelength excitation.Here we report the synthesis, characterization and photophysical properties of porphyrinate ytterbium(III) complexes. The ytterbium (III) is coordinated by a tetraphenyl porphyrinate dianion, a chloride ion,and a 1,10-phenanthroline ligand. The complexes showed characteristic emission at 978 and 1003 nmupon excitation at 545 nm. The emission quantum yields and emission lifetimes will be reported. Theeffect of the substitute on the phenanthroline will be discussed. This work is supported by the NationalScience Foundation (Grant #1507871)

61


Isolation, Method Development, and Quantification of Nepetalactone From Raw Plant Tissue

Stephen Moore and Ian Taschner


Nepetalactone (1 and 2), an iridoid, produced notably by Nepeta cataria (catnip) in a stereoselectivefashion rendering the trans diastereomer 1. Extraction and quantification of 1 within the plant matrix wasperformed using a saturated mixed salt aqueous solution and acetonitrile (QuEChERs). This isolationprotocol provided an extraction efficiency of 94(±5) % of 1 without the presence of epimer 2. Epimer 1was subjected to gas chromatography in tandem with mass spectroscopy (GCMS) to determine a propermethod for separation and detection. During this process, matrix effects within the acetonitrile extractcaused the retention time associated with 1 to vary. Development of a “clean-up” method followingextraction was established using a soliddispersive extraction with PSA/C18, activated carbon, andDowex-50W-X8. All three solids proved to be effective at reducing/eliminating matrix effects, but Dowex-50W-X8 had the highest extraction efficiency (89(±4) %). The extraction/clean-up protocol was thenutilized to determine distribution of 1 throughout the different parts of catnip.

62


Small Molecule Metal Ion Chelators for Parkinson's Disease Therapy

Selena Oskard, Johanna Ehlbeck, and Michael Webb


Parkinson’s disease (PD) is a common neurodegenerative disorder affecting nearly 1 million Americans.Currently, therapeutic options for PD merely treat the symptoms of the disease, while the underlyingcause is not actively targeted. One of the hallmarks of PD are protein deposits comprised primarily of theprotein α-synuclein (α-syn). The combination of the α-syn and the redox-active metals, copper and iron,accelerate the formation of the aggregates known as Lewy bodies and promote a toxic environment. Theprevalence of iron within these Lewy bodies is a promising target for chelation, as the removal of themetal ions from α-syn should promote the disruption of the problematic protein deposits. We arecurrently preparing several new small molecule metal ion chelators using the copper-catalyzedcycloaddition reaction between an azide and an alkyne forming a 1,2,3-triazole. Once synthesized, thecompounds are characterized by Nuclear Magnetic Resonance and Mass Spectrometry. We furtheranalyze the compounds affinity for metals by UV-Visible Spectroscopy. Following this, analysis will bedone to test the ability of the 1,2,3-triazoles to disrupt or prevent α-syn aggregation. Ultimately, thesechelators would be the basis of a therapeutic strategy designed to directly target the key marker of neuraldegeneration in Parkinson’s Disease.

63


Chiral Measurements of D-Aspartate in the Pancreas

Jack H. Schnieders, Amit V. Patel, Cindy Lee, Stanislav S. Rubakhin, and Jonathan V. Sweedler


The islets of Langerhans are small cell clusters in the mammalian pancreas which cooperate to maintainglucose homeostasis. Immunostaining the islets revealed high concentrations of D-aspartate (D-Asp) andglucagon in alpha cells, and of D-alanine (D-Ala) and insulin in beta cells. Beta cells release D-Ala withinsulin in high glucose concentrations, indicating they are co-localized in the same granules. Is D-Aspreleased similarly with glucagon from alpha cells at low glucose concentrations? Characterizing D-aminoacids in the islets will yield information on their potential usage as pancreatic signaling molecules whichmay help develop diabetes therapies. This study is conducted using capillary electrophoresis (CE) withlaser-induced fluorescence (LIF). CE separates compounds based on charge, viscosity and size, and theaspartate enantiomers are resolved by incorporating chiral additives into the buffer. All species arereacted with a fluorogenic tag to allow their relative concentrations to be determined by LIF. The D-Asppeak is identified in the complex electropherograms by standard addition and enzyme treatmentexperiments. Islet samples are limited, necessitating small volume injection, and analyzing D-Asprequires a low detection limit due to their natural low abundance. CE-LIF meets both of theserequirements, making it the ideal choice for the study. Current testing is conducted using an ammoniumbicarbonate buffer that shows good separation of the Asp enantiomers.

64


Development of Aminooxy Reagents for Analysis of Carbonyl-Containing AHAS and ALS Biosynthetic Products

Magdelana Stinnett, Alexander Latta, Michael McLeish, and Sébastien Laulhé


To meet the increasing demand in the world’s food supply, crop production may be maximized usingherbicides. Acetohydroxyacid synthase (AHAS) and acetolactate synthase (ALS) are two enzymescapable of forming (S)-acetolactate, a compound required for valine biosynthesis. Additionally, AHAS canform (S)-acetohydroxybutyrate, a precursor to isoleucine, while ALS cannot. Therefore, selectiveinhibition of AHAS prevents synthesis of isoleucine and valine, systematically leading to plant death.Introduction of an ALS mutant capable of fulfilling the biosynthetic role of AHAS into a plant genomecould yield an herbicide-resistant species analogous to Roundup® resistant crops. Current methods forisolating (S)-acetolactate and (S)-acetohydroxybutyrate from AHAS and ALS require a chemicaldecarboxylation that is time consuming, involves special equipment, leads to loss of product, and fails toretain stereogenic information. Our aim is to create a series of chemoselective derivitization reagents toanalyze (S)-acetolactate and (S)-acetohydroxybutyrate production by our ALS mutant enzymes. Previousliterature demonstrates that an aminooxy moiety will selectively react with carbonyls to yield stableoxime ether compounds. Design features of our two aminooxy-containing reagents include elements tofacilitate analysis by gas chromatography-mass spectrometry (GC-MS) and liquid chromatography-massspectrometry (LC-MS). Synthetic details and reagent design will be presented.

65


Engineering Bioluminescent Sensors of Cyclic AMP to Study Opioid Signaling

Alexander L. Tesmer, Alexander R. French, and Mathew Tantama.

Purdue University

Opioids are small signaling molecules which bind to opioid receptors on the surface of cells. The kappaopioid receptor (KOR) is one of three major types of opioid receptors found in human neurons. When anopioid binds to a KOR, a variety of biochemical signaling pathways are activated inside the cell. Each ofthese pathways are associated with different physiological effects of KOR activation. The production of asmall signaling molecule, cyclic adenosine monophosphate (cAMP), is known to be inhibited during KORactivation of the analgesic (pain-killing) signaling pathway. We have developed a biosensor that operatesusing bioluminescent resonance energy transfer (BRET), and we demonstrate it can be used to quantifycAMP by both fluorescence and luminescence measurements. Specifically, the application of our sensorfor dual-color live-cell microscopy was demonstrated in mammalian cells using fluorescence andbioluminescence microscopy. Further proof-of-principle studies in KOR-expressing mammalian cellsdemonstrates the viability of our sensor for live-cell KOR signaling.

66


Role of cyclic GMP-AMP Synthase (cGAS) in microglial immune response

Elizabeth Thayer, Priya Prakash, and Gaurav Chopra

Purdue University

The cyclic GMP-AMP Synthase (cGAS) protein belongs to an intracellular signaling pathway that sensesgenomic DNA in the cytoplasm and activates inflammatory factors like IFN-#, NO, etc. Recently, it wasshown that microglia, the immune cells in the brain, upregulate cGAS in Neurodegenerative Diseases(NDs). However, the cellular and molecular mechanisms of cGAS in microglial immune response are stillunknown. Therefore, we utilized two cGAS small molecule inhibitors Suramin and Quinacrine in an invitro model of BV2 mouse microglia that are activated by bacterial lipopolysaccharide in culture. Theeffect of cGAS inhibitors on microglial nitric oxide (NO) production was evaluated at various doses withGriess assay. The toxicity of the inhibitors and their effect on cell viability were measured using MTTassay. Interestingly, we found that Suramin increased microglial NO secretion in a dose-dependentmanner from 12.5 to 100 µM. Microglial NO production was not affected by inhibiting cGAS withSuramin at the lower doses of 3.625 and 6.25 µM. On the other hand, Quinacrine increased microglial NOproduction at the same lower doses of 3.625 and 6.25 µM but proved to be toxic to activated BV2microglia at concentrations greater than 12.5 µM. Our data suggests that microglial NO production maybe modulated using cGAS inhibitors at specific doses. Our ongoing work involves investigation of cGASinhibitors on microglial phagocytic function in the context of different NDs.

67


Room Temperature Production of Lithium via Electrodeposition

Killian Lee Tracey, Patricia Ignacio-de Leon, Daniel Arenas, Donghyeon Kang, and John Hryn


Lithium metal is an attractive material for use as an anode in primary and rechargeable batteries due tobeing the lightest and most electropositive metal. Current production methods for lithium involve hightemperature electrolysis of a mixture of molten lithium chloride and potassium chloride. Herein wepresent a room-temperature electrodeposition method and the optimization of process parameters andconditions to produce a layer of lithium metal onto a conductive substrate from an aqueous lithiumsource through a lithium-ion conducting separator. Through control of process parameters, the processcan yield uniform, densely-packed dendrite-free lithium metal nanorods with aspect ratios up to 100(diameter ca. 350 nm and length ca. 35 um), see Figure 1. Room-temperature methods for producinghigh-purity lithium metal eliminate energy-consuming steps in the current manufacturing process, thusreducing the manufacturing cost of the final product. Our lithium metal deposition process providesprecise control over lithium morphology during deposition and growth, which is expected to improvebattery performance as a result of uniform lithium metal dissolution during battery discharge.

68


Ruthenium Complexes for Alzheimer’s Disease Therapy

Mark F. Will and Michael I. Webb


Alzheimer’s Disease (AD) is a neurodegenerative disorder that is estimated to afflict nearly 6 millionAmericans. AD is characterized by Amyloid-beta (Aβ) plaques, which are extracellular deposits of the Aβpeptide that contain copper, zinc, and iron. Metal-based drugs have shown promise in inhibiting thetoxicity of the Aβ peptide. Ruthenium-based (Ru) complexes such as indazolium trans-[tetrachlorobisindazoleruthenate(III)] (KP 1019), imidazolium[trans-tetrachloro(dimethylsulfoxide)imidazoleruthenate(III)(1H-imidazole)(DMSO-S)] (NAMI-A), and (2-aminothiazolium [trans-tetrachlororbis(2-aminothiazole)ruthenate(III)] (PMru 20) have been shown to be strong candidates forAD therapy, however, a higher understanding of the activities of individual Ru complexes must beobtained for further development. To gain a stronger understanding of Ru compounds for AD therapy,we will synthesize derivatives of NAMI-A with pyridines containing differing functional groups.Preliminary data show that the pyridine-based derivatives will bind to Aβ, while evaluation of theirimpact on aggregation is ongoing. The results of this study will produce insight into the importance ofthe ligands around the Ru center and their impact on Aβ binding.

69


Optimization of Photoacoustic Probes for Nitric Oxide Detection

Ruiwen Xu, Christopher J. Reinhardt, and Jefferson Chan


Photoacoustic imaging is a noninvasive technology that utilizes near-infrared light excitation and acousticdetection to enable high-resolution imaging of biological tissues within deep tissue. The utility of thistechnology for the detection of specific biological analytes can help understand the role of analytes withinthe native environment as well as their potential as activatable contrast agents for diagnostic purposes.Particularly, we are interested in nitric oxide (NO) as it plays a key role in regulating physiological andpathological processes. NO is an innately unstable molecule such that it is essential to develop sensitivecompounds for its detection. Therefore, we developed an acoustogenic dye thioAPNO selectively for thedetection of NO in inflammation and cancer. To increase the sensitivity relative to the previousgeneration, we proposed to redshift the wavelength of maximum absorbance so that thioAPNO and itsturnover product are detectable within the range of commercial photoacoustic imaging setups (680-950nm). Herein, we replaced the phenyl substituents associated with the basic aza-BODIPY platform withthienyl rings, which allows the dye to planarize and results in a substantial redshift. Moreover, we aim todevelop targeted analogs for systemic application of the compounds. With the compounds in hand, weaim to apply the thioAPNO series for imaging cancer, inflammatory responses, and other pathologicalstates.

70


Complete Chemical Analysis of Crude Oil Bound to Kaolinite

Jeff Zhang, Jeremy Manheim, Ravikiran Yerabolu, Cliff T. Johnston, and Hilkka I. Kenttämaa

Purdue University

Knowledge on the classes of compounds in crude oil that preferentially bind to kaolinite, a claycommonly found in oil reservoirs, can aid in enhanced oil recovery efforts. In this study, the compositionof crude oil bound to kaolinite (COBK) was compared to the composition of non-bound crude oil (NBCO)in order to identify the molecular species that preferentially bind to kaolinite. Two different crude oilswere each mixed for seven days with kaolinite followed by centrifugation to obtain two COBK andNBCO samples. Each sample was fractionated into three compound classes by using an auto-columnwith hexane, dichloromethane, and isopropyl alcohol eluents. Fourier transform infrared spectroscopyand thermogravimetric analysis of COBK samples demonstrated most of the crude oil was removed fromCOBK samples after fractionation. High-resolution mass spectrometry was utilized to obtain elementalcomposition and structural information for compounds in each fraction obtained for COBK and NBCO.The mass spectra show that the hexane and dichloromethane fractions of both crude oils contain moreheteroatom containing compounds for NBCO than for COBK. Also, the average RDBE values are greaterfor compounds in the hexane fraction of COBK than in the same fraction for NBCO, while the averageRDBE values are smaller for the DCM fraction of COBK than for NBCO. These results provide the firstinsights into the types of molecules in crude oil that prefer to bind to kaolinite.

71


Development of Novel Ratiometric Probes for Cancer Stem Cells

Zhouyang Zhu, Hailey Knox, and Jefferson Chan


Cancer stem cells (CSCs) are self-renewing, multipotent cancer cells that can generate heterogenoustumor bulk, and those that survive treatment are hypothesized to cause tumor relapse and metastasis. Inorder to better understand the biology of CSCs and perhaps develop CSC-targeting therapies, it isimportant to develop tools for in vivo detection and imaging of these cell populations within tumors. Onereliable marker for CSCs is aldehyde dehydrogenase 1A1 (ALDH1A1), which is highly overexpressed inCSCs across many cancer types. AlDeSense, a fluorescent probe previously developed in our lab, isALDH1A1-responsive. It is, however, limited to shallow imaging depths in vivo owing to significantscattering of visible light. Herein, we present a modified AlDeSense design for in vivo detection ofALDH1A1 using deep tissue imaging approaches, which overcomes traditional imaging barriersassociated with depth penetration, resolution, and background interference. With this probe in hand, wewill be able to detect and track SCSs in deep tissue with minimal error associated with heterogeneousprobe distribution and individual variation.

72

SPEAKER SESSION II: ABSTRACTS

Identifying factors that genetically interact with R-loops to suppress gene expression

Chrishan Fernando, Youssef Hegazy, Sara Cloutier, and Elizabeth Tran

Purdue University

Long non-coding RNAs (lncRNAs) were once thought not to have useful functions in organisms butrather to be products of aberrant transcription. However, roles are being found for lncRNAs in beneficialprocesses such as controlling gene expression. In some of these cases, lncRNAs form R-loops in vivo. R-loops are nucleic acid structures consisting of hybridized strands of single stranded DNA (ssDNA) andsingle-stranded RNA as well as the displaced strand of ssDNA. Formation of these R-loops is importantfor gene regulation by the lncRNAs. However, the mechanisms by which this form of regulation occurs ispoorly understood. Thus, there is a need to identify factors that participate in R-loop mediated generepression. To identify such factors, a genetic reporter strain has been constructed in Saccharomycescerevisiae using the PHO84 gene. It is an appropriate gene for the reporter because expression of PHO84is suppressed by the formation of R-loops containing an antisense lncRNA produced downstream ofPHO84. The PHO84 reporter strain is being used to perform direct testing of factors that potentiallyinteract with R-loops to suppress gene expression. A synthetic gene array screen will also be performed inS. cerevisiae to identify genes that promote R-loop formation genome-wide. The effects of these geneswill be studied thoroughly to develop a mechanistic understanding of how they interact with R-loopsand how they suppress gene expression.

73


Engineering Considerations for the Design of Strong and Easily-Recyclable Plastics

Alayna M. Johnson, Jacob S. A. Ishibashi, and Julia A. Kalow

Northwestern University

Commodity plastics are traditionally classified as either thermosets (covalently crosslinked polymerswith strong mechanical properties) or thermoplastics (easily recyclable polymers that lack covalentcrosslinks). Vitrimers have emerged as a new class of materials that boast both the robustness ofthermosets and the recyclability of thermoplastics, affording them wide potential applications in fieldssuch as medicine, electronics, and automotives. However, vitrimers have not yet achieved industrialacceptance because most rely on harmful catalysts, function poorly at low temperature and/or degrade inthe presence of water. This work presents a new vitrimer synthesis method that is water-stable, nontoxic,and catalyst-free: namely, the reversible conjugate addition-elimination of polydimethylsiloxane (PDMS)to a Meldrum’s acid derivative. The resulting vitrimers recycle easily, with no network degradation after10 reprocessing cycles, but lack mechanical strength. Upon addition of commercially-available fillers (e.g.,fumed silica and activated carbon), a significant increase in mechanical strength is observed without lossof recyclability. In particular, the filled networks withstand 56% strain on average while the unfillednetworks break easily at approximately 16% strain. Together, these findings provide an environmentally-benign and industrially-relevant method for vitrimer synthesis and demonstrate the use of fillers as a toolfor control of mechanical properties.

74


Nicotine extraction, quantification, and mechanistic assessment for mass fragmentation

Alex Solivais and Ian Taschner


Nicotine, an entheogenic alkaloid found primarily in the nightshade family, has been used as a stimulantacross centuries and cultures. The concentration of nicotine in tobacco varies from crop to crop, howevertobacco companies standardize the amount of nicotine present in cigarettes via proprietary blendingprocess. Nicotine concentrations range from 10-15 mg per cigarette, dependent on brand and product.Our research group has developed a modified Quick-EasyCheap-Effective-Rugged extraction(QuEChERs) for extraction and quantification of nicotine freebase found in tobacco via GasChromatography-Mass Spectrometry (GCMS). This method utilizes a dispersive solid phase cleanup forremoval of saccharides, acidic organic molecules, lipids, and some pigments present after extraction,which significantly reduces the matrix effects and GC column degradation. Our method was determinedto have an extraction efficiency of 89.5(±5) %. Additionally, the mass spectra associated with nicotine,nicotine-d4, and nicotine-d3 suggest a fragmentation pattern that differs from those reported in literature.The fragmentation pathway we have proposed for parent ions m/z = 162, 165, and 166 to daughter ions atm/z = 133, 136, and 136 proceeds through an elimination followed by an intramolecular SN2Ar affordingpyrrolopyridinium fragments.

75


An Iterative Approach for the Synthesis of Enantio-selective Polyols

Yuquan Tong, Aidan M. Kelly, Albert Lee, Daniel J. Blair, and Martin D. Burke


Small molecules have extensive untapped potential to benefit society, but access to this potential is toooften restricted by limitations inherent to the highly customized strategies. An alternative “building blockapproach” – that is, generalized iterative assembly of interchangeable parts – is an increasingly importantstrategy for the highly efficient and flexible construction of small organic molecules. In this way, a smallsubset of building blocks should allow a wide range of structural diversity to be accessed. Continuouspolyol chains represent important stereochemistry rich motifs within natural products, yet the density offunctionality inherent with this motif often renders them challenging to be prepared. We are seeking todevelop a building block based stereo-controlled method for the synthesis of contiguous polyol chains byusing a reagent-controlled reaction for the diastereoselective allylboration of aldehydes, which we willthen oxidize to furnish a new aldehyde and establish an iterative allylative protocol. As it is wellunderstood that the relative stereochemistry of allylboration is controlled by the geometry of theallylboronate, we expect to achieve high diastereo-control. To control absolute stereochemistry, we willleverage the exquisite facial selectivity imparted by chiral PIDA ligated boronates to block one face of theallylating reagent, thereby controlling the absolute stereochemical outcome of allylations.

COMMITTEE / PAST AWARD RECIPIENTS

2018 ECI-ACS URC CommitteeCo-coordinators: Sarah Bonson and Hailey Knox

Jesselle Alhambra, Thomas Bearrood, Edzna Garcia, Elizabeth Neumann, Raul Sun Han Chang

ECI Outstanding Oral Presentation Awards2017 Alayna Johnson

2017 Travis Lantz

ECI Outstanding Poster Awards2017 Dominic Aiello

2017 Michael Niederbrach

2017 Matthew Clawson

2017 Terry Kim

2017 Eliot Rapoport

2016 Thomas Dieter

2016 Brenton Hull

2016 William Lau

2016 Kang Yong Loh

2016 Nathan Reed

2016 Steven Szymanski

SACNAS Outstanding Poster Awards2017 Amanda Cowfer

2017 Luis Curet

2016 Amanda Cowfer

2016 Christian Ocampo

2016 Andrea Salazar

WCC Outstanding Poster Awards2017 Sarah Ackenhusen

2017 Jonathon Adams

2017 Hannah Frerker

2017 Gina Partipilo

2017 Andrea Perry

2016 Paige Degarmo

2016 Audrey Rex

2016 Julia Zuo

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SUPPORTING GROUP DETAILS

American Chemical Society – The mission of ACS is to advance the broader chemistry enterprise and itspractitioners for the benefit of Earth and its people. This includes advancing science, advocating forchemistry, enabling career development, educating the public, supporting future chemists, andpromoting diversity. For more than 140 years ACS has been improving people’s lives through thetransforming power of chemistry.

East Central Illinois – Local Sections help chemists stay active and involved in their communities byproviding a forum for networking and collaboration and by supporting chemists’ efforts to educate theircommunity about chemistry. The East Central Illinois (ECI) Local Section of the American ChemicalSociety has over 500 members from Effingham to Champaign. The list of institutions that our chapterserves includes the University of Illinois at Urbana-Champaign, Eastern Illinois University, and ParklandCollege. We encourage fellow chemists, other scientists, students, and the interested public to meet us atour public lectures and special events.

UIUC ACS Student Chapter - The ACS Student Chapter (ACS-SC) at the University of Illinois offersmany networking, educational, and professional opportunities. The goal of ACS-SC is to promotepersonal, professional, and scientific development through organized events and individualizedmentoring. The chapter primarily serves as a support group for chemistry and chemical engineeringmajors. Whether it is for a career in industry, pursuit of higher education, or an interest in science, there isa spot for any individual in the organization.

UIUC Women Chemists Committee - The UIUC Women Chemists Committee was founded in the fall of2005 to promote the advancement of women in the chemical sciences. With the support of our localsection and the University of Illinois Department of Chemistry, we have planned professional and socialevents that benefit graduate students, faculty, staff, and undergraduates.

Younger Chemists Committee - YCC advocates for and provides resources to students, early-careerchemists, and professionals in the chemical sciences and related fields. YCC also addresses specific issuesfacing younger chemists within ACS and serves as their voice in ACS. Past events have included industrytours, webinars, networking events, and professional development.

UIUC SACNAS Chapter - Society for the Advancement of Chicano/Hispanic and Native Americans inthe Sciences (SACNAS) is an inclusive society of scientists dedicated to fostering the success of scientistsof diverse backgrounds including those of Hispanic/Chicano and Native American descent. Our missionis to increase the diversity of the scientific community by mentoring and sharing science at all levels ofeducation. We are dedicated to helping underrepresented groups obtain advanced degrees, careers, andpositions of leadership in science in order to increase resources, eliminate barriers, and achieve greaterequality.

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3 a e central illinois local section undergraduate … · nicotine extraction, quantification, and...

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