Darryl L. McDougald

* ******** ***** – Durham, NC 27713 – acqpd0@r.postjobfree.com

Work: 919-***-**** Cell: 919-***-****

Qualifications

Accomplished, multidiscipline Research Scientist with significant research experience in the fields of medicinal, synthetic and analytical chemistry. Background includes design and synthesis of a half dozen phase1 drug candidates of which I am personally responsible for or supervised as a manager. Process development of drug candidates in a GMP facility. Development of numerous analytical techniques designed to develop drug candidates, purify and isolate proteins, analyze unknown samples, develop radiopharmaceuticals and generate SOPs. I am also skilled in the area of nuclear medicine with experience working with numerous radioisotopes both synthetically and biologically. Additionally I am experienced in a host of biological techniques such as cell culture, cell assays, electrophoresis, western blot, flow cytometry and others. I am an enthusiastic teammate with great respect for team dynamics and professional growth.

Skills and Techniques

I am fluent in a number of skills and analytical techniques which include NMR(COSY, NOESY, TOCSY and HSQC), Mass Spec.(LCMS, GCMS, ESI, MALDI, FAB, CI, EI (high and low res.)) atomic absorption analysis, DSC, Raman IR, FTIR, GC, Applied biosystems peptide synthesizer, HPLC(prep and analytical), TLC, ISCO and Biotage automated chromatography systems, Anton Parr and Biotage microwave reactors, flash chromatography, polarimeter, high vacuum distillations, high pressure reactors(Parr), MACS stem cell isolation technologies, Silver staining (gel), protein dialysis protocols, Aldefluor stemcell identification techniques, flow cytometry, SDS PAGE gel electrophoresis, western blot, gamma and beta counter analysis, cellular assays, Bioscan radiomaging scanner, Capentec radio calibrators, Beckman radiodectector(HPLC), preparative TLC, Millipore gel readers and Hazmat training.

I am also proficient in most of the software routinely used in Lab and office settings including MS word, excel, powerpoint, Onenote, lotus notes, spotfire, scifinder, beistien, E-labnotebook, Outlook, chemdraw, isisdraw, ACD software, Labview.

Professional Experience

Sept. 2008-Present Research Scientist Duke Medical Center, Durham, NC 27710

I am presently serving as a research scientist with the Duke Radiology nuclear medicine group. The focus of our research is in translational stem cell resistance. I am currently working on a number of cancer chemotherapy projects as well as small molecule imaging projects. My duties include synthesis of small molecules and the evaluation of the SAR of these molecules as potential chemotherapeutic agents. It includes optimization of the cellular uptake of selected small and large molecules for tumor cell imaging. This work involves synthesis of small and large molecules (small peptides and antibodies) as well as measuring their cellular uptake in tumor cells. In concert with this work my duties include routinely performing cell assays, cell culture, protein identification and isolation via gel electrophoresis, western blot analysis, silver staining techniques and flowcytometry and others. My responsibilities also include labeling selected molecules with radioisotopes (123I, 124I, 125I, 131I and 18F) via radiosynthetic techniques. Ultimately these compounds are evaluated in mice and humans via PET (positron emission topography) imaging for tumor cells evaluation.

I am also responsible for monitoring exposure to chemical and radioactive materials. This includes Bicron analysis of work sites, Ludlum meters for thyroid analysis and measuring fume hood performance via flow meters.

Principle Scientist GlaxoSmithKline Inc., Research Triangle

As a principle scientist at GlaxoSmithKline I was responsible for execution of drug discovery projects. My primary responsibility was the development of medicinal, synthetic and analytical chemistries of a wide variety of chemical templates all of which led to candidate selection. As a scientific principle I was typically the primary\solo lead chemist in developing chemistries around chemical templates of interest with the ultimate goal of passing on the technological advancements to the much larger chemical team. These responsibilities included development of tractable synthetic pathways for general synthetic manipulations, development of appropriate analytical procedures for reliable analysis across project norms, advancement in structure activity relationships designed to push the project towards it candidate selection, vigilant exploration of available literature in order to take advantage of the most recent project related advancement\innovations, generation of detailed status reports with specific attention to timelines, do ability and validation. My responsibilities also included routine oral presentations, supervisions of project teams(1-5 headcount) and evaluation of employee performance. This work also entailed early stage development chemistry specifically with respect to formulation development, sculpting of metabolic profiles and detailed analytical analysis. As a research principle my duties included the championing of novel “target to lead” projects. The projects were intended to validate novel receptor based targets as potential lead optimization projects. As a supervisor\manager I was also the laboratory manager responsible for all laboratory functions (safety, maintenance, purchasing etc.). Selected projects included JNK-1 kinase for diabetes, POP inhibitors project for obesity, SARM agonist for anti-aging, DPP4/7 dual antagonist project for diabetes, AXOR 109 project for diabetes, MCH project for obesity and DPP4 for diabetes.

Senior Scientist GlaxoWellcome, Research Triangle Park, NC

I am served as a senior scientist on the RXR project for diabetes. I was primarily responsible for synthesizing analogs on the various templates, improving the chemical tractability of the series and development of SAR for different series. My work also included following up on hits from HTC (hits to lead). My primary job description was to be the lead chemist on all projects to develop analytical, medicinal and synthetic chemistry across the project teams.

Research Scientist GlaxoWellcome, Research Triangle Park, NC

I am served as a research scientist on the TNF project for rheumatoid arthritis. My responsibilities included design and synthesis of novel reverse hydroximates. I was directly responsible for design and synthesis of three drug development candidates. I provide a large scale chemical support to the project by synthesizing several hundred gram quantities of intermediates and final compounds and I also was the chemical lead for the Aggrecanase project. My primary job description was to be the lead chemist on all projects to develop analytical, medicinal and synthetic chemistry that were specific to current chemistry.

Scientist GlaxoWellcome Research Triangle Park, NC

I am served as a scientist on the Amylin project for type 2 diabetes. My responsibilities included design and synthesis of amylin antagonist. I was directly responsible for design and synthesis of hundreds of novel analogs and templates. I provide a large scale chemical support to the project by synthesizing a number of intermediates. This work also included synthesis of various peptide that ranged from 2-18 amino acids in length via a peptide synthesizer.

Associate Scientist Glaxo Research Triangle Park, NC

I worked as a synthetic chemist chemical development. My responsibilities included working on milligram to kilogram scale as well as working under GLP and GMP guidelines. My responsibilities also required that I matrix with all other development organization to promote project all the way to phase3.

Education

M.S. in Medicinal Chemistry University of North Carolina, Chapel Hill, NC

Research Director: Professor Steven D. Wyrick Dissertation: Synthesis of selective D1

dopamine antagonist

B.A. in Chemistry University of North Carolina, Wilmington, NC

Selected Patents and Publications

G. Vaidyanathan,, B.J. White, D.J. Affleck, X.G. Zhao, P.C. Welsh, D. McDougald, J. Choi, M.R. Zalutsky, SIB-DOTA: A trifunctional prosthetic group potentially amenable for multi-modal labeling that enhances tumor uptake of internalizing monoclonal antibodies, Bioorganic & Medicinal Chemistry, Volume 20, Issue 24, 15 December 2012, Pages 6929–6939

Bennett B. Chin, Anita Hjelemand, Jeremy Rich, Haijing Song, Christopher Lascola, Robert Storms, Roger McLendon4, Robert Reiman, Kim L. Greer, Scott D. Metzler, Darryl McDougald, Diana Dai, Ganesan Vaidyanathan, Synthesis and preliminary evaluation of n.c.a. Iodoquine: A novel radiotracer with High uptake in cells with high ALDH expression, Current Radiopharmaceuticals (2012), 5, 47-58 Language: English, Database: CAPLUS

Vaidyanathan, Ganesan; White, Benjamin; Affleck, Donna J.; McDougald, Darryl; Zalutsky, Michael R. Radioiodinated O6-Benzylguanine derivatives containing an azido function, Nuclear Medicine and Biology (2011), 38(1), 77-92. Language: English, Database: CAPLUS

Vaidyanathan, Ganesan; McDougald, Darryl L.; Linda Grasfeder, Michael R. Zalutsky, and Bennett B. An Alternative and Expedient Synthesis of Radioiodinated

4-Iodophenylalanine, Applied Radiation and Isotopes 69 (2011) 1401–1406.

Vaidyanathan, Ganesan; Song, Haijing; Affleck, Donna; McDougald, Darryl L.; Storms, Robert W.; Zalutsky, Michael R.; Chin, Bennett B.

Targeting aldehyde dehydrogenase: a potential approach for cell labeling. Nuclear Medicine and Biology (2009), 36(8), 919-929. Language: English, Database: CAPLUS

Cadilla, Rodolfo; Larkin, Andrew; McDougald, Darryl Lynn; Randhawa, Amarjit Sab; Ray, John A.; Stetson, Katherine; Stewart, Eugene L.; Turnbull, Philip Stewart; Zhou, Huiquiang. Preparation of indole derivatives as modulators of androgen receptor. PCT Int. Appl. (2008), 369pp. CODEN: PIXXD2 WO 200-***-**** A2 20080410 CAN 148:449452 AN 2008:445054

Haffner, Curt D.; McDougald, Darryl L.; Reister, Steven M.; Thompson, Brian D.; Conlee, Christopher; Fang, Jing; Bass, Jonathan; Lenhard, James M.; Croom, Dallas; Secosky-Chang, Melissa B.; Tomaszek, Thaddeus; McConn, Donavon; Wells-Knecht, Kevin; Johnson, Paul R. 2-Cyano-4-fluoro-1-thiovalylpyrrolidine analogues as potent inhibitors of DPP-IV. Bioorganic & Medicinal Chemistry Letters (2005), 15(23), 5257-5261. CODEN: BMCLE8 ISSN:0960-894X. CAN 144:51883 AN 2005:1144496 CAPLUS

Lambert, Millard H.; Blackburn, R. Kevin; Seaton, Theresa D.; Kassel, Daniel B.; Kinder, Daniel S.; Leesnitzer, M. Anthony; Bickett, D. Mark; Warner, Janet R.; Andersen, Marc W.; Badiang, Jennifer G.; Cowan, David J.; Gaul, Michael D.; Petrov, Kimberly G.; Rabinowitz, Michael H.; Wiethe, Robert W.; Becherer, J. David; McDougald, Darryl L.; Musso, David L.; Andrews, Robert C.; Moss, Marcia L. Substrate specificity and novel selective inhibitors of TNF- converting enzyme (TACE) from two-dimensional substrate mapping. Combinatorial Chemistry and High Throughput Screening (2005), 8(4), 327-339. CODEN: CCHSFU ISSN:1386-2073. CAN 144:102782 AN 2005:452261 CAPLUS

Haffner, Curt D.; Lenhard, James M.; Miller, Aaron B.; McDougald, Darryl L.; Dwornik, Kate; Ittoop, Olivia R.; Gampe, Robert T., Jr.; Xu, H. Eric; Blanchard, Steve; Montana, Valerie G.; Consler, Tom G.; Bledsoe, Randy K.; Ayscue, Andrea; Croom, Dallas. Structure-Based Design of Potent Retinoid X Receptor Agonists. Journal of Medicinal Chemistry (2004), 47(8), 2010-2029. CODEN: JMCMAR ISSN:0022-2623. CAN 140:303476 AN 2004:202648 CAPLUS

Tippin, Timothy K.; Hamilton, Geraldine; Moore, Linda; Beaudet, Elizabeth J.; Jolley, Summer; Brodie, Thomas A.; Andrews, Robert C.; Becherer, J. David; McDougald, Darryl L.; Gaul, Michael D.; Hoivik, Debie J.; Mellon-Kusibab, Kathy; Lehmann, Jurgen; Kliewer, Steven; Novick, Steven; Laethem, Ron; Zhao, Zhiyang; LeCluyse, Edward L. CYP3A induction by N-hydroxyformamide tumor necrosis factor- converting enzyme/matrix metalloproteinase inhibitors: Use of a pregnane X receptor activation assay and primary hepatocyte culture for assessing induction potential in humans. Drug Metabolism and Disposition (2003), 31(7), 870-877. CODEN: DMDSAI ISSN:0090-9556. CAN 140:12429 AN 2003:512699 CAPLUS

Haffner, Curt Dale; Kaldor, Istvan; McDougald, Darryl Lynn; Miller, Aaron Bayne. Preparation of retinoid analogs that have selectivity as RXR agonists. PCT Int. Appl. (2003), 82 pp. CODEN: PIXXD2 WO 200-***-**** A2 20030403 CAN 138:287846 AN 2003:261825 CAPLUS

Haffner, Curt Dale; McDougald, Darryl Lynn; Lenhard, James Martin. Preparation of fluoropyrrolidinecarbonitrile derivatives as dipeptidyl peptidase inhibitors. PCT Int. Appl. (2003), 133 pp. CODEN: PIXXD2 WO 200-***-**** A2 20030109 CAN 138:90072 AN 2003:22868 CAPLUS

Haffner, Curt Dale; McDougald, Darryl Lynn; Randhawa, Amarjit Sab; Reister, Steven Michael; Lenhard, James Martin. Preparation of fluoropyrrolidinecarbonitrile derivatives as dipeptidyl peptidase inhibitors. PCT Int. Appl. (2003), 186 pp. CODEN: PIXXD2 WO 200-***-**** A2 20030109 CAN 138:90071 AN 2003:22848 CAPLUS

Haffner, Curt Dale; McDougald, Darryl Lynn; Randhawa, Amarjit Sab; Reister, Steven Michael; Deaton, David N.; Lenhard, James Martin. Preparation of pyrrolidine- or thiazolidinecarbonitrile derivatives as dipeptidyl peptidase inhibitors. PCT Int. Appl. (2003), 48 pp. CODEN: PIXXD2 WO 200-***-**** A2 20030109 CAN 138:73532 AN 2003:22847 CAPLUS

Rabinowitz, Michael H.; Andrews, Robert C.; Becherer, J. David; Bickett, D. Mark; Bubacz, Dulce G.; Conway, James G.; Cowan, David J.; Gaul, Micheal; Glennon, Kimberly; Lambert, Millard H.; Leesnitzer, M. Anthony; McDougald, Darryl L.; Moss, Marcia L.; Musso, David L.; Rizzolio, Michele C. Design of Selective and Soluble Inhibitors of Tumor Necrosis Factor- Converting Enzyme (TACE). Journal of Medicinal Chemistry (2001), 44(24), 4252-4267. CODEN: JMCMAR ISSN:0022-2623. CAN 136:79266 AN 2001:752302 CAPLUS

Conway, James G.; Andrews, Robert C.; Beaudet, Beth; Bickett, D. Mark; Boncek, Virginia; Brodie, Thomas A.; Clark, Richard L.; Crumrine, R. Christian; Leenitzer, Michael A.; McDougald, Darryl L.; Han, Bajin; Hedeen, Kevin; Lin, Peiyuan; Milla, Marcos; Moss, Marcia; Pink, Heather; Rabinowitz, Michael H.; Tippin, Timothy; Scates, Phillip W.; Selph, Jeffrey; Stimpson, Stephen A.; Warner, Janet; Becherer, J. David. Inhibition of tumor necrosis factor- (TNF- ) production and arthritis in the rat by GW3333, a dual inhibitor of TNF- -converting enzyme and matrix metalloproteinases. Journal of Pharmacology and Experimental Therapeutics (2001), 298(3), 900-908. CODEN: JPETAB ISSN:0022-3565. CAN 135:352507 AN 2001:616531

Musso, D. L.; Andersen, M. W.; Andrews, R. C.; Austin, R.; Beaudet, E. J.; Becherer, J. D.; Bubacz, D. G.; Bickett, D. M.; Chan, J. H.; Conway, J. G.; Cowan, D. J.; Gaul, M. D.; Glennon, K. C.; Hedeen, K. M.; Lambert, M. H.; Leesnitzer, M. A.; McDougald, D. L.; Mitchell, J. L.; Moss, M. L.; Rabinowitz, M. H.; Rizzolio, M. C.; Schaller, L. T.; Stanford, J. B.; Tippin, T.; Warner, J. R.; Whitesell, L. G.; Wiethe, R. W. N-Hydroxyformamide peptidomimetics as TACE/Matrix metalloprotease inhibitors: oral activity via P1' isobutyl substitution. Bioorganic & Medicinal Chemistry Letters (2001), 11(16), 2147-2151. CODEN: BMCLE8 ISSN:0960-894X. CAN 135:358135 AN 2001:612029

Moss, M. L.; Becherer, J. D.; Conway, J. G.; Warner, J. R.; Bickett, D. M.; Leesnitzer, M. A.; Seaton, T. M.; Mitchell, J. L.; McConnell, R. T.; Tippin, T. K.; Whitesell, L. G.; Rizzolio, M. C.; Hedeen, K. M.; Beaudet, E. J.; Andersen, M.; Lambert, M. H.; Austin, R.; Stanford, J. B.; Bubacz, D. G.; Chan, J. H.; Schaller, L. T.; Gaul, M. D.; Cowan, D. J.; Boncek, V. M.; Rabinowitz, M. H.; Musso, D. L.; McDougald, D. L.; Kaldor, I.; Glennon, K.; Wiethe, R. W.; Guo, Y.; Andrews, R. C. Screening and design of tumor necrosis factor- converting enzyme inhibitors. Cytokine Inhibitors (2001), 163-176. CODEN: 69BACA CAN 135:162023 AN 2001:214187

Andrews, Robert Carl; Anderson, Marc W.; Stanford, Jennifer Badaing; Bubacz, Dulce Garrido; Chan, Joseph H.; Cowan, David J.; Gaul, Michael D.; McDougald, Darryl Lynn; Musso, David Lee; Rabinowitz, Michael H.; Wiethe, Robert W. Preparation of N-formyl-N-hydroxypeptide analogs as metalloprotease inhibitors. Brit. UK Pat. Appl. (2000), 127 pp. CODEN: BAXXDU GB 2348198 A 20000927 CAN 134:42444 AN 2001:12831

Andrews, Robert Carl; Andersen, Marc Werner; Stanford, Jennifer Badiang; Babacz, Dulce Garrido; Chan, Joseph Howing; Cowan, David John; Gaul, Michael David; Mcdougald, Darryl Lynn; Musso, David Lee; Rabinowitz, Michael Howard; Wiethe, Robert William. Preparation of peptidyl formamide compounds as therapeutic agents. PCT Int. Appl. (2000), 115 pp. CODEN: PIXXD2 WO 200******* A1 20000309 CAN 132:208133 AN 2000:161247

Andrews, Robert Carl; Andersen, Marc Werner; Stanford, Jennifer Badiang; Bubacz, Dulce Garrido; Chan, Joseph Howing; Cowan, David John; Gaul, Michael David; Mcdougald, Darryl Lynn; Musso, David Lee; Rabinowitz, Michael Howard; Wiethe, Robert William. Preparation of peptidyl formamide compounds as therapeutic agents. PCT Int. Appl. (2000), 171 pp. CODEN: PIXXD2 WO 200******* A1 20000309 CAN 132:208132 AN 2000:161126

Andrews, Robert Carl; Andersen, Marc Werner; Stanford, Jennifer Badiang; Bubacz, Dulcie Garrido; Chan, Joseph Howing; Cowan, David John; Gaul, Michael David; McDougald, Darryl Lynn; Musso, David Lee; Rabinowitz, Michael Howard; Wiethe, Robert William. Preparation of peptidyl reverse hydroxamate derivatives as metalloprotease inhibitors. PCT Int. Appl. (1998), 164 pp. CODEN: PIXXD2 WO 9838179 A1 19980903 CAN 129:216923 AN 1998:608610

Fang, Francis G.; Bankston, Donald D.; Huie, Edward M.; Johnson, M. Ross; Kang, Kyung-Chol; LeHoullier, Craig S.; Lewis, George C.; Lovelace, Thomas C.; Lowery, Melissa W.; McDougald, Darryl L.; Meerholz, Clive A.; Partridge, John J.; Sharp, Matthew J.; Xie, Shiping. Convergent catalytic asymmetric synthesis of camptothecin analog GI147211C. Tetrahedron (1997), 53(32), 109**-*****. CODEN: TETRAB ISSN:0040-4020. CAN 127:262890 AN 1997:553117

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