Cell-permeable bicyclic peptide inhibitors against intracellular proteins

Journal of the American Chemical Society

Volumn 136, Issue 28, 2014, Pages 9830-9833

  Lian, Wenlong ^a   Jiang, Bisheng ^a   Qian, Ziqing ^a   Pei, Dehua ^a  

^a OHIO STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACIDS; CELL MEMBRANES; CYTOLOGY;

CELL-PENETRATING PEPTIDE; CELL-PERMEABLE; CYCLIC PEPTIDES; INTRACELLULAR PROTEINS; PEPTIDE INHIBITORS; PROTEIN-TYROSINE PHOSPHATASE 1B; RESEARCH TOOLS; THERAPEUTIC AGENTS;

PEPTIDES;

CELL PROTEIN; CYCLOPEPTIDE; PEPTIDYLPROLYL ISOMERASE PIN1; PROTEIN TYROSINE PHOSPHATASE 1B; BICYCLO COMPOUND; CELL PENETRATING PEPTIDE; ENZYME INHIBITOR; PEPTIDYLPROLYL ISOMERASE;

ANIMAL CELL; ARTICLE; CELL MEMBRANE; CELL MEMBRANE PERMEABILITY; CELLS; NONHUMAN; PROTEIN DEGRADATION; ANTAGONISTS AND INHIBITORS; CHEMISTRY; HUMAN; STRUCTURE ACTIVITY RELATION; SYNTHESIS; TUMOR CELL LINE;

BICYCLO COMPOUNDS; CELL LINE, TUMOR; CELL MEMBRANE PERMEABILITY; CELL-PENETRATING PEPTIDES; ENZYME INHIBITORS; HUMANS; PEPTIDES, CYCLIC; PEPTIDYLPROLYL ISOMERASE; PROTEIN TYROSINE PHOSPHATASE, NON-RECEPTOR TYPE 1; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 84904430241     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja503710n     Document Type: Article

References (45)

1. Pomilio, A. B.; Battista, M. E.; Vitale, A. A. Curr. Org. Chem. 2006, 10, 2075
2. Meutermans, W. D. F.; Golding, S. W.; Bourne, G. T.; Miranda, L. P.; Dooley, M. J.; Alewood, P. F.; Smythe, M. L. J. Am. Chem. Soc. 1999, 121, 9790
3. Schafmeister, C. E.; Po, J.; Verdine, G. L. J. Am. Chem. Soc. 2000, 122, 5891
4. Sun, Y.; Lu, G.; Tam, J. P. Org. Lett. 2001, 3, 1681
5. Kohli, R. M.; Walsh, C. T.; Burkart, M. D. Nature 2002, 418, 658
6. Qin, C.; Bu, X.; Zhong, X.; Ng, N. L. J.; Guo, Z. J. Comb. Chem. 2004, 6, 398
7. Turner, R. A.; Oliver, A. G.; Lokey, R. S. Org. Lett. 2007, 9, 5011
8. Hili, R.; Rai, V.; Yudin, A. K. J. Am. Chem. Soc. 2010, 132, 2889
9. Lee, J.; McIntosh, J.; Hathaway, B. J.; Schmidt, E. W. J. Am. Chem. Soc. 2009, 131, 2122
10. Frost, J. R.; Vitali, F.; Jacob, N. T.; Brown, M. D.; Fasan, R. ChemBioChem 2013, 14, 147
11. Eichler, J.; Lucka, A. W.; Pinilla, C.; Houghten, R. A. Mol. Diversity 1996, 1, 233
12. Giebel, L. B.; Cass, R. T.; Milligan, D. L.; Young, D. C.; Arze, R.; Johnson, C. R. Biochemistry 1995, 34, 15430
13. Scott, C. P.; Abel-Santos, E.; Wall, M.; Wahnon, D. C.; Benkovic, S. J. Proc. Natl. Acad. Sci. U.S.A. 1999, 96, 13638
14. Millward, S. W.; Takahashi, T. T.; Roberts, R. W. J. Am. Chem. Soc. 2005, 127, 14142
15. Sako, Y.; Morimoto, J.; Murakami, H.; Suga, H. J. Am. Chem. Soc. 2008, 130, 7232
16. Li, S.; Marthandan, N.; Bowerman, D.; Garner, H. R.; Kodadek, T. Chem. Commun. 2005, 581
17. Joo, S. H.; Xiao, Q.; Ling, Y.; Gopishetty, B.; Pei, D. J. Am. Chem. Soc. 2006, 128, 13000
18. Heinis, C.; Rutherford, T.; Freund, S.; Winter, G. Nat. Chem. Biol. 2009, 5, 502
19. Tse, B. N.; Snyder, T. M.; Shen, Y.; Liu, D. R. J. Am. Chem. Soc. 2008, 130, 15611
20. Leduc, A.-M.; Trent, J. O.; Wittliff, J. L.; Bramlett, K. S.; Briggs, S. L.; Chirgadze, N. Y.; Wang, Y.; Burris, T. P.; Spatola, A. F. Proc. Natl. Acad. Sci. U.S.A. 2003, 100, 11273
21. Millward, S. W.; Fiacco, S.; Austin, R. J.; Roberts, R. W. ACS Chem. Biol. 2007, 2, 625
22. Tavassoli, A.; Lu, Q.; Gam, J.; Pan, H.; Benkovic, S. J.; Cohen, S. N. ACS Chem. Biol. 2008, 3, 757
23. Wu, X.; Upadhyaya, P.; Villalona-Calero, M. A.; Briesewitz, R.; Pei, D. Med. Chem. Commun. 2013, 4, 378
24. Birts, C. N.; Nijjar, S. K.; Mardle, C. A.; Hoakwie, F.; Duriez, P. J.; Blaydes, J. P.; Tavassoli, A. Chem. Sci. 2013, 4, 3046
25. Kawakami, T.; Ishizawa, T.; Fujino, T.; Reid, P. C.; Suga, H.; Murakami, H. ACS Chem. Biol. 2013, 8, 1205
26. Lian, W.; Upadhyaya, P.; Rhodes, C. A.; Liu, Y.; Pei, D. J. Am. Chem. Soc. 2013, 135, 11990
27. Rezai, T.; Bock, J. E.; Zhou, M. V.; Kalyanaraman, C.; Lokey, R. S.; Jacobson, M. P. J. Am. Chem. Soc. 2006, 128, 14073
28. Chatterjee, J.; Gilon, C.; Hoffman, A.; Kessler, H. Acc. Chem. Res. 2008, 41, 1331
29. 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
30. Elchelby, M.; Payette, P.; Michaliszyn, E.; Cromlish, W.; Collins, S.; Loy, A. L.; Normandin, D.; Cheng, A.; Himms-Hagen, J.; Chan, C. C.; Ramanchandran, C.; Gresser, M. J.; Tremblay, M. L.; Kennedy, B. P. Science 1999, 283, 1544
31. Zabolotny, J. M.; Bence-Hanulec, K. K.; Stricker-Krongrad, A.; Haj, F.; Wang, Y.; Minokoshi, Y.; Kim, Y. B.; Elmquist, J. K.; Tartaglia, L. A.; Kahn, B. B.; Neel, B. G. Dev. Cell 2002, 2, 489
32. He, R.; Zeng, L.-F.; He, Y.; Zhang, Z.-Y. In New Therapeutic Strategies for Type 2 Diabetes: Small Molecule Approaches; Jones, R. M., Ed.; RSC Publishing: Cambridge, U.K., 2012; pp 142 ff.
33. Burke, T. R., Jr.; Kole, H. K.; Roller, P. P. Biochem. Biophys. Res. Commun. 1994, 204, 129
34. Qian, Z.; Liu, T.; Liu, Y.-Y.; Briesewitz, R.; Barrios, A. M.; Jhiang, S. M.; Pei, D. ACS Chem. Biol. 2013, 8, 423
35. Liu, R.; Marik, J.; Lam, K. S. J. Am. Chem. Soc. 2002, 124, 7678
36. Chen, X.; Tan, P. H.; Zhang, Y.; Pei, D. J. Comb. Chem. 2009, 11, 604
37. Thakkar, A.; Wavreille, A.-S.; Pei, D. Anal. Chem. 2006, 78, 5935
38. Ren, L.; Chen, X.; Luechapanichkul, R.; Selner, N. G.; Meyer, T. M.; Wavreille, A.-S.; Chan, R.; Iorio, C.; Zhou, X.; Neel, B. G.; Pei, D. Biochemistry 2011, 50, 2339
39. Xie, L.; Lee, S.-Y.; Andersen, J. N.; Waters, S.; Shen, K.; Guo, X.-L.; Moller, N. P. H.; Olefsky, J. M.; Lawrence, D. S.; Zhang, Z.-Y. Biochemistry 2003, 42, 12792
40. Lessard, L.; Stuible, M.; Tremblay, M. L. Biochim. Biophys. Acta 2010, 1804, 613
41. Lu, K. P.; Zhou, X. Z. Nat. Rev. Mol. Cell Biol. 2007, 8, 904
42. More, J. D.; Potter, A. Bioorg. Med. Chem. Lett. 2013, 23, 4283
43. Liu, T.; Liu, Y.; Kao, H.-Y.; Pei, D. J. Med. Chem. 2010, 53, 2494
44. Reineke, E. L.; Lam, M.; Liu, O.; Liu, Y.; Stanya, K. J.; Chang, K. S.; Means, A. R.; Kao, H. Y. Mol. Cell. Biol. 2008, 28, 997
45. Qian, Z.; LaRochelle, J. R.; Jiang, B.; Lian, W.; Hard, R. L.; Selner, N. G.; Luechapanichkul, R.; Barrios, A. M.; Pei, D. Biochemistry 2014, 53, 4034-4046