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Ny Sin Cv 2016 Ucsf Prepared: June 1, 2016 University of California, San Francisco CURRICULUM VITAE Name: Ny Sin Position: Adjunct Instructor, Step 2 Neurology School of Medicine Address: University of California, San Francisco Email: [email protected] EDUCATION 1985 - 1989 Holy Cross College, Worcester, B.A. Chemistry Prof. Ronald M. MA Jarret 1989 - 1996 Syracuse University, Syracuse, Ph.D. Organic Prof. James N.Y Chemistry Kallmerten PRINCIPAL POSITIONS HELD 1996 - 1998 Yale University, New Haven, Postdoctoral Department of Molecular, CT Fellow Cellular, and Developmental Biology 1998 - 2002 Bristol-Myers Squibb Research Discovery Chemistry Research and Development, Investigator II Wallingford, CT 2002 - 2007 Bristol-Myers Squibb Senior Research Discovery Chemistry Research and Development, Investigator I Wallingford, CT 2007 - 2015 Bristol-Myers Squibb Senior Research Discovery Chemistry Research and Development, Investigator II Wallingford, CT 2016 - present University of California, San Associate Institute for Neurodegenerative Francisco, CA Adjunct Diseases Professor HONORS AND AWARDS 1996 Sessel Anonymous Postdoctoral Fellow (1996-1998) Yale University MEMBERSHIPS 1990 - present Member of the American Chemical Society (ACS) 1990 - present Member ACS Organic Division 1998 - present Member ACS Medicinal Chemistry Division 1998 - present Member New Haven Local Section INVITED PRESENTATIONS - NATIONAL 2005 230th ACS National Meeting and Exposition Poster 2008 236th ACS National Meeting and Exposition Poster 2009 238th ACS National Meeting and Exposition Poater 2010 240th ACS National Meeting and Exposition Poster RESEARCH AND CREATIVE ACTIVITIES SUMMARY Key Accomplishments: -Designed the HIV-1 maturation inhibitor clinical candidate, BMS-955176, which is currently in Phase 2b clinical trials. Co-inventor on granted US patent claiming BMS-955176. -Co-inventor on granted US patents claiming two clinical candidates, BMS-605339 and asunaprevir (BMS-650032) in the HCV NS3 protease inhibitor program. SunvepraTM (asunaprevir) was approved in Japan on July 2014 as a combination treatment with DaklinzaTM (daclatasvir) for chronic hepatitis C infection. -Designed and synthesized BMS-433771, a pre-clinical candidate that inhibits respiratory syncytial virus (RSV) fusion protein. -Co-inventor on granted US patent 6831099. Proteolix, Inc. (co-founded by Professor Craig Crews) licensed this patent from Yale University to initiate its medicinal chemistry program, leading to the discovery of Carfilzomib/KyprolisTM, a second generation proteosome inhibitor approved by FDA in 2012 to treat multiple myeloma. KyprolisTM achieved $331 million and $512 million in sales in 2014 and 2015, respectively. -Co-inventor on 20 granted US patents and an author/co-author of 22 peer-reviewed journal articles. Skills: • Medicinal chemist with strong synthetic organic chemistry skill • Experience in multi-step organic synthesis design, execution and optimization • Experience with small molecule, natural product and peptide analogs synthesis • Experience with immobilization of natural products onto solid support. Successfully added fluorescent tag or biotinylated numerous natural products to use as molecular probes for enzymatic activity studies and to isolate their binding proteins • Knowledge of standard analytical and preparative chemistry techniques including NMR, LC-MS, HPLC, GC, TLC, and flash chromatography • Demonstrated strong ability to creatively solve complex problems in medicinal chemistry projects • Ability to interact effectively and directly within a multi-disciplinary team PEER REVIEWED PUBLICATIONS 1. Jarret, R. M.; Sin, N.; Ramsey, T.; Saunders, M. The use of IR spectroscopy to monitor the conversion of matrix-isolated phenylacetyl chloride to phenylacetyl cation, without decarbonylation to benzyl cation. J. Phys. Org. Chem. 1989, 2(1), 51-56. 2. Jarret, R. M.; Sin, N. Molecular mechanics as an organic chemistry laboratory exercise. J. Chem. Educ. 1990, 67(2), 153-5. 3. Matulewicz, M. C.; Cerezo, A. S.; Jarret, R. M.; Sin, N. High resolution 13C-NMR spectroscopy of 'mixed linkage' xylands. Int. J. Biol. Macromol. 1992, 14, 29-32. 4. Sin, N.; Kallmerten, J. Diastereoselective [2,3] Wittig rearrangement of carbohydrate- derived tertiary allylic ethers. 2. Synthesis of an advanced rapamycin intermediate from D- glucose. Tetrahedron Lett. 1993, 34(5), 753-6. 5. Sin, N.; Kallmerten, J. Synthesis of (2S,3S,8S,9S)-adda from D-glucose. Tetrahedron Lett. 1996, 37(32), 5645-5648. 6. Jarret, R. M.; Sin, N.; Dintzner, M. Deuterium isotope effects on 13C NMR chemical shifts of amides. Microchem. J. 1997, 56(1), 19-21. 7. Sin, N.; Meng, L.; Wang, M. Q. W.; Wen, J. J.; Bornmann, W. G.; Crews, C. M. The anti- angiogenic agent fumagillin covalently binds and inhibits the methionine aminopeptidase, MetAP-2. Proc. Natl. Acad. Sci. U.S.A. 1997, 94(12), 6099-6103. 8. Meng, L.; Sin, N.; Crews, C. M. The Antiproliferative agent didemnin B uncompetitively inhibits palmitoyl protein thioesterase. Biochemistry 1998, 37(29), 10488-10492. 9. Sin, N.; Meng, L.; Auth, H.; Crews, C. M. Eponemycin analogs: syntheses and use as probes of angiogenesis. Bioorg. Med. Chem. 1998, 6(8), 1209-1217. 10. Meng, L.; Kwok, B. H. B.; Sin, N.; Crews, C. M. Eponemycin exerts its antitumor effect through the inhibition of proteasome function. Cancer Res.1999, 59(12), 2798-2801. 11. Sin, N.; Kim, K. B.; Elofsson, M.; Meng, L.; Auth, H.; Kwok, B. H. B.; Crews, C. M. Total synthesis of the potent proteasome inhibitor epoxomicin: a useful tool for understanding proteasome biology. Bioorg. Med. Chem. Lett. 1999, 9(15), 2283-2288. 12. Meng, L.; Mohan, R.; K., Benjamin H. B.; Elofsson, M.; Sin, N.; Crews, C. M. Epoxomicin, a potent and selective proteasome inhibitor, exhibits in vivo anti-inflammatory activity. Proc. Natl. Acad. Sci. U.S.A. 1999, 96(18), 10403-10408. 13. Kim, K. B.; Myung, J.; Sin, N.; Crews, C. M. Proteasome inhibition by the natural products epoxomicin and dihydroeponemycin: insights into specificity and potency. Bioorg. Med. Chem. Lett. 1999, 9(23), 3335-3340. 14. Cianci, C.; Yu, K. -L.; Combrink, K.; Sin, N.; Pearce, B.; Wang, A.; Civiello, R.; Voss, S.; Luo, G.; Kadow, K.; Genovesi, E. V.; Venables, B.; Gulgeze, H.; Trehan, A.; James, J.; Lamb, L.; Medina, I.; Roach, J.; Yang, Z.; Zadjura, L.; Colonno, R.; Clark, J.; Meanwell, N.; Krystal, M. Orally active fusion inhibitor of respiratory syncytial virus. Antimicrob. Agents. Chemother. 2004, 48(2), 413-422. 15. Cianci, C.; Genovesi, E. V.; Lamb, L.; Medina, I.; Yang, Z.; Zadjura, L.; Yang, H.; D'Arienzo, C.; Sin, N.; Yu, K. -L.; Combrink, K.; Li, Z.; Colonno, R.; Meanwell, N.; Clark, J.; Krystal, M. Oral efficacy of a respiratory syncytial virus inhibitor in rodent models of infection. Antimicrob. Agents. Chemother. 2004, 48(7), 2448-2454. 16. Yu, K. -L.; Sin, N.; Civiello, R. L.; Wang, X. A.; Combrink, K. D.; Gulgeze, H. B.; Venables, B. L.; Wright, J. J. K.; Dalterio, R. A.; Zadjura, L.; Marino, A.; Dando, S.; D’Arienzo, C.; Kadow, K. F.; Cianci, C. W.; Li, Z.; Clarke, J.; Genovesi, E. V.; Medina, I.; Lamb, L.; Colonno, R. J.; Yang, Z.; Krystal, M.; Meanwell, N. A. Respiratory syncytial virus fusion inhibitors. Part 4: Optimization for oral bioavailability. Bioorg. Med. Chem. Lett. 2007, 17(4), 895-901 17. Sin, N.; Venables, B. L.; Combrink, K. D.; Gulgeze, H. B.; Yu, K. -L.; Civiello, R. L.; Thuring, J.; Wang, X. A.; Yang, Z.; Zadjura, L.; Marino, A.; Kadow, K. F.; Cianci, C. W.; Clarke, J.; Genovesi, E. V.; Medina, I.; Lamb, L.; Krystal, M.; Meanwell, N. A. Respiratory syncytial virus fusion inhibitors. Part 7: Structure-activity relationships associated with a series of isatin oximes that demonstrate antiviral activity in vivo. Bioorg. Med. Chem. Lett. 2009, 19(16), 4857-4862. 18. Sin, N; Venables, B. L.; Liu, X.; Huang, S.; Gao, Q.; Ng, A.; Dalterio, R.; Rajamani, R.; Meanwell, N. A. The alkylation of isatin-derived oximes: Spectroscopic and X-ray crystallographic structural characterization of oxime and nitrone products. J. Heterocyclic Chem. 2009, 46(3), 432-442. 19. Liu, X.; Huang, X. S.; Sin, N.; Venables, B. L.; Roongta, V. 15N chemical shifts of a series of isatin oxime ethers and their corresponding nitrone isomers. Magn. Reson. Chem. 2010, 48(11), 873-876. 20. Scola, P. M.; Wang, A.; Good, A. C; Sun, L.; Combrink, K. D.; Campbell, J. A.; Chen, J.; Tu, Y.; Sin, N.; Venables, B. L.; Sit, S. -Y.; Chen, Y.; Cocuzza, A.; Bilder, D. M.; D’Andrea, S.; Zheng, B.; Hewawasam, P.; Ding, M.; Thuring, J.; Hernandez, D.; Yu, F.; Falk, P.; Zhai, G.; Sheaffer, A. K.; Chen, C.; Lee, M. S.; Barry, D.; Knipe, J. O.; Han, Y. H.; Jenkins, S.; Gesenberg, C.; Sinz, M. W.; Santone, K. S.; Zvyaga, T.; Rajamani, R.; Klei, H. E.; Colonno, R. J.; Grasela, D. M.; Hughes, E.; Chien, C.; Adams, S.; Levesque, P. C.; Li, D.; Zhu, J.; Meanwell, N. A.; McPhee, F. Discovery and early clinical evaluation of BMS-605339, a potent and orally efficacious tripeptidic acylsulfonamide NS3 protease inhibitor for the treatment of hepatitis C virus infection. J. Med. Chem. 2014, 57(5), 1708-1729. 21. Scola, P. M.; Sun, L.; Wang, A.; Chen, J.; Sin, N.; Venables, B. L.; Sit, S. -Y.; Chen, Y.; Cocuzza, A.; Bilder, D. M.; D'Andrea, S.; Zheng, B.; Hewawasam, P.; Tu, Y.; Friborg, J.; Falk, P.; Hernandez, D.; Levine, S.; Chen, C.; Yu, F.; Sheaffer, A. K.; Zhai, G.; Barry, D.; Knipe, J. O.; Han, Y. H.; Schartman, R.; Donoso, M.; Mosure, K.; Sinz, M. W.; Zvyaga, T.; Good, A.C.; Rajamani, R.; Kish, K.; Tredup, J.; Klei, H. E.; Gao, Q.; Mueller, L.; Colonno, R. J.; Grasela, D. M.; Adams, S. P.; Loy, J.; Levesque, P. C.; Sun, H.; Shi, H.; Sun, L.; Warner, W.; Li, D.; Zhu, J.; Meanwell, N. A.; McPhee, F. The discovery of asunaprevir (BMS-650032), an orally efficacious NS3 protease inhibitor for the treatment of hepatitis C virus infection. J. Med. Chem. 2014, 57(5), 1730-1752. 22. Swidorski, J. J.; Liu, Z.; Sit, S. –Y.; Chen, J.; Chen, Y.; Sin, N.; Venables, B. L.; Parker, D.
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