Screening bicyclic peptide libraries for protein-protein interaction inhibitors: Discovery of a tumor necrosis factor-α Antagonist

Journal of the American Chemical Society

Volumn 135, Issue 32, 2013, Pages 11990-11995

  Lian, Wenlong ^a   Upadhyaya, Punit ^a   Rhodes, Curran A ^a   Liu, Yusen ^b   Pei, Dehua ^a  

^a OHIO STATE UNIVERSITY   (United States)

^b THE OHIO STATE UNIVERSITY COLLEGE OF MEDICINE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

COMBINATORIAL LIBRARY; GENERAL SOLUTIONS; PEPTIDE LIBRARY; PROTEIN SURFACE; PROTEIN-PROTEIN INTERACTIONS; RECEPTOR INTERACTION; SMALL MOLECULES; TUMOR NECROSIS FACTORS;

CELL DEATH; DIAGNOSIS; GLYCOPROTEINS; LIBRARIES; MACROPHAGES; MOLECULES; PEPTIDES;

SCAFFOLDS (BIOLOGY);

ANTICACHEXIN C1; TUMOR NECROSIS FACTOR ALPHA; TUMOR NECROSIS FACTOR ALPHA INHIBITOR; TUMOR NECROSIS FACTOR ALPHA RECEPTOR; UNCLASSIFIED DRUG;

AMINO ACID SEQUENCE; ARTICLE; BINDING AFFINITY; BINDING SITE; CELL DEATH; COMBINATORIAL LIBRARY; COMPLEMENTARITY DETERMINING REGION; CYCLIZATION; DRUG SCREENING; DRUG TARGETING; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; INHIBITION KINETICS; PEPTIDE LIBRARY; PROTEIN BINDING; PROTEIN PROTEIN INTERACTION; SEQUENCE ANALYSIS;

AMINO ACID SEQUENCE; ANIMALS; BICYCLO COMPOUNDS; CELL DEATH; CELL LINE; DRUG DISCOVERY; FIBROBLASTS; MICE; MOLECULAR SEQUENCE DATA; PEPTIDE LIBRARY; PEPTIDES; PROTEIN INTERACTION MAPS; RECEPTORS, TUMOR NECROSIS FACTOR, TYPE I; TUMOR NECROSIS FACTOR-ALPHA;

EID: 84882282136     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja405106u     Document Type: Article

References (57)

1. Wells, J.; McClendon, C. Nature 2007, 450, 1001-1009
2. Yin, H.; Hamilton, A. D. Angew. Chem., Int. Ed. 2005, 44, 4130-4163
3. Garner, A. L.; Janda, K. D. Curr. Top. Med. Chem. 2011, 11, 258-280
4. Morelli, X.; Bourgeas, R.; Roche, P. Curr. Opin. Chem. Biol. 2011, 15, 475-481
5. Ockey, D. A.; Gadek, T. R. Expert Opin. Ther. Pat. 2002, 12, 393-400
6. Loregian, A.; Palu, G. J. Cell. Physiol. 2005, 204, 750-762
7. Tanaka, T.; Rabbitts, T. H. Cell Cycle 2008, 7, 1569-1574
8. Koide, A.; Bailey, C. W.; Huang, X.; Koide, S. J. Mol. Biol. 1998, 284, 1141-1151
9. Beste, G.; Schmidt, F. S.; Stibora, T.; Skerra, A. Proc. Natl. Acad. Sci. U.S.A. 1999, 96, 1898-1903
10. Rutledge, S. E.; Volkman, H. M.; Schepartz, A. J. Am. Chem. Soc. 2003, 125, 14336-14347
11. Steiner, D.; Forrer, P.; Plückthun, A. J. Mol. Biol. 2008, 382, 1211-1227
12. Leduc, A. M.; Trent, J. O.; Wittliff, J. L.; Bramlett, K. S.; Briggs, S. L.; Chirgadza, N. Y.; Wang, Y.; Burris, T. P.; Spatola, A. F. Proc. Natl. Acad. Sci. U.S.A. 2003, 100, 11273-11278
13. Fasan, R.; Dias, R. L. A.; Moehle, K.; Zerbe, O.; Vrijbloed, J. W.; Obrecht, D.; Robinson, J. A. Angew. Chem., Int. Ed. 2004, 43, 2109-2112
14. Millward, S. W.; Fiacco, S.; Austin, R. J.; Roberts, R. W. ACS Chem. Biol. 2007, 2, 625-634
15. Tavassoli, A.; Lu, Q.; Gam, J.; Pan, H.; Benkovic, S. J.; Cohen, S. N. ACS Chem. Biol. 2008, 3, 757-764
16. Ardi, V. C.; Alexander, L. D.; Johnson, V. A.; McAlpine, S. R. ACS Chem. Biol. 2011, 6, 1357-1366
17. Yamagishi, Y.; Shoji, I.; Miyagowa, S.; Kawakami, T.; Katoh, T.; Goto, Y. Chem. Biol. 2011, 18, 1562-1570
18. Dewan, V.; Liu, T.; Chem, K.; Qian, Z.; Xiao, Y.; Kleiman, L.; Mahasenan, K. V.; Li, C.; Matsuo, H.; Pei, D.; Musier-Forsyth, K. ACS Chem. Biol. 2012, 7, 761-769
19. Wu, X.; Upadhyaya, P.; Villalona-Calero, M. A.; Briesewitz, R.; Pei, D. MedChemComm 2013, 4, 378-382
20. Zhou, H.; Liu, L.; Huang, J.; Bernard, D.; Karatas, H.; Navarro, A.; Lei, M.; Wang, S. J. Med. Chem. 2013, 56, 1113-1123
21. Terrett, N. MedChemComm 2013, 4, 474-475
22. Rezai, T.; Yu, B.; Millhauser, G. L.; Jacobson, M. P.; Lokey, R. S. J. Am. Chem. Soc. 2006, 128, 2510-2511
23. White, T. R.; Renzelman, C. M.; Rand, A. C.; Rezai, T.; McEwen, C. M.; Gelev, V. M.; Turner, R. A.; Linington, R. G.; Leung, S. S. F.; Kalgutkar, A. S.; Bauman, J. N.; Zhang, Y. Z.; Liras, S.; Price, D. A.; Mathiowetz, A. M.; Jacobson, M. P.; Lokey, R. S. Nat. Chem. Biol. 2011, 7, 810-817
24. Chatterjee, J.; Gilon, C.; Hoffman, A.; Kessler, H. Acc. Chem. Res. 2008, 41, 1331-1342
25. Qian, Z.; Liu, T.; Liu, Y.-Y.; Briesewitz, R.; Barrios, A. M.; Jhiang, S. M.; Pei, D. ACS Chem. Biol. 2013, 8, 423-431
26. Sun, Y.; Lu, G.; Tam, J. P. Org. Lett. 2001, 3, 1681-1684
27. Virta, P.; Lonnberg, H. J. J. Org. Chem. 2003, 68, 8534
28. Heinis, C.; Rutherford, T.; Freund, S.; Winter, G. Nat. Chem. Biol. 2009, 5, 502-507
29. Chen, S.; Morales-Sanfrutos, J.; Angelini, A.; Cutting, B.; Heinis, C. ChemBioChem 2012, 13, 1032-1038
30. Sako, Y.; Morimoto, J.; Murakami, H.; Suga, H. J. Am. Chem. Soc. 2008, 130, 7232-7234
31. Timmerman, P.; Barderas, R.; Desmet, J.; Altschuh, D.; Shochat, S.; Hollestelle, M. J.; Höppener, J. W. M.; Monasterio, A.; Casal, J. L.; Meloen, R. H. J. Biol. Chem. 2009, 284, 34126-34134
32. Lee, J. H.; Kim, H.-S.; Lim, H.-S. Org. Lett. 2011, 13, 5012-5015
33. Vollrath, S. B. L.; Brase, S.; Kirshenbaum, K. Chem. Sci. 2012, 3, 2716-2731
34. Chen, G.; Goeddel, D. V. Science 2002, 296, 1634-1635
35. Kawakami, M.; Cerami, A. J. Exp. Med. 1981, 154, 631-639
36. Beutler, B.; Mahoney, J.; Le Trang, N.; Pekala, P.; Cerami, A. J. Exp. Med. 1985, 161, 984-995
37. Esposito, E.; Cuzzocrea, S. Curr. Med. Chem. 2009, 16, 3152-3167
38. Alzani, R.; Corti, A.; Grazioli, L.; Cozzi, E.; Ghezzi, P.; Marcucci, F. J. Biol. Chem. 1993, 268, 12526-12529
39. He, M. M.; Smith, A. S.; Oslob, J. D.; Flangan, W. M.; Braisted, A. C.; Whitty, A.; Cancilla, M. T.; Wang, J.; Lugovskoy, A. A.; Yoburn, J. C.; Fung, A. D.; Farrington, G.; Eldredge, J. K.; Day, E. S.; Cruz, L. A.; Cachero, T. G.; Miller, S. K.; Friedman, J E.; Choong, I C.; Cunningham, B. C. Science 2005, 310, 1022-1025
40. Chan, D. S.; lee, H.; Yang, F.; Che, C.; Wong, C. C. L.; Abagyan, R.; Leung, C.; Ma, D. Angew. Chem., Int. Ed. 2010, 49, 2860-2864
41. Choi, H.; Lee, Y.; Park, H.; Oh, D.-S. Bioorg. Med. Chem. Lett. 2010, 20, 6195-6198
42. Buller, F.; Zhang, Y.; Scheuermann, J.; Schafer, J.; Buhlmann, P.; Neri, D. Chem. Biol. 2009, 16, 1075-1086
43. Leung, C. H.; Chan, D. S.; Kwan, M. H.; Cheng, Z.; Wong, C. Y.; Zhu, G. Y.; Fong, W. F.; Ma, D. L. ChemMedChem 2011, 6, 765-768
44. Joo, S. H.; Xiao, Q.; Ling, Y.; Gopishetty, B.; Pei, D. J. Am. Chem. Soc. 2006, 128, 13000-13009
45. Liu, R.; Marik, J.; Lam, K. S. J. Am. Chem. Soc. 2002, 124, 7678-7680
46. Lam, K. S.; Salmon, S. E.; Hersh, E. M.; Hruby, V. J.; Kazmierski, W. M.; Knapp, R. J. Nature 1991, 354, 82-84
47. Houghten, R. A.; Pinilla, C.; Blondelle, S. E.; Appel, J. R.; Dooley, C. T.; Cuervo, J. H. Nature 1991, 354, 84-86
48. Furka, A.; Sebestyen, F.; Asgedom, M.; Dibo, G. Int. J. Pept. Protein Res. 1991, 37, 487-493
49. Yin, J.; Straight, P. D.; McLoughlin, S. M.; Zhou, Z.; Lin, A. J.; Golan, D. E.; Kelleher, N. L.; Kolter, R.; Walsh, C. T. Proc. Natl. Acad. Sci. U.S.A. 2005, 102, 15815-15820
50. Kodadek, T.; Bachhawat-Sikder, K. Mol. BioSyst. 2006, 2, 25-35
51. Hu, B. H.; Jones, M. R.; Messersmith, P. B. Anal. Chem. 2007, 79, 7275-7285
52. Hintersteiner, M.; Kimmerlin, T.; Kalthoff, F.; Stoeckli, M.; Garavel, G.; Seifert, J.-M.; Meisner, N.-C.; Uhl, V.; Buehler, C.; Weidemann, T.; Auer, M. Chem. Biol. 2009, 16, 724-735
53. Liu, T.; Qian, Z.; Xiao, Q.; Pei, D. ACS Comb. Sci. 2011, 13, 537-546
54. Thakkar, A.; Wavreille, A.-S.; Pei, D. Anal. Chem. 2006, 78, 5935-5939
55. Chen, X.; Tan, P. H.; Zhang, Y.; Pei, D. J. Comb. Chem. 2009, 11, 604-611
56. Martin, T. L.; Mufson, E. J.; Mesulam, M. M. J. Histochem. Cytochem. 1984, 32, 793
57. Khabar, K. S.; Siddiqui, S.; Armstrong, J. A. Immunol. Lett. 1995, 46, 107-110