Investigations of linker structure on the potency of a series of bidentate protein tyrosine phosphatase inhibitors

Bioorganic and Medicinal Chemistry

Volumn 13, Issue 8, 2005, Pages 2981-2991

  Xie, Jian ^a   Seto, Christopher T ^a  

^a BROWN UNIVERSITY   (United States)

Author keywords

Divalent inhibitor; Linker; Phosphatase; Ketocarboxylic acid

Indexed keywords

PROTEIN TYROSINE KINASE; PROTEIN TYROSINE KINASE INHIBITOR; PROTEIN TYROSINE PHOSPHATASE;

ARTICLE; CELL FUNCTION; CHEMICAL BOND; CONTROLLED STUDY; CORRELATION ANALYSIS; IC 50; NONHUMAN; PHOSPHORYLATION; PURIFICATION; YERSINIA;

EID: 15244355146     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2005.02.001     Document Type: Article

References (34)

1. Z.Y. Zhang Acc. Chem. Res. 36 2003 385
2. M.A. Blaskovich, and H.O. Kim Exp. Opin. Ther. Pat. 12 2002 871
3. M. Elchebly, P. Payette, E. Michaliszyn, W. Cromlish, S. Collins, A.L. Loy, D. Normandin, A. Cheng, J. Himms-Hagen, C.-C. Chan, C. Ramachandran, M.J. Gresser, M.L. Tremblay, and B.P. Kennedy Science 283 1999 1544
4. L.D. Klaman, O. Boss, O.D. Peroni, J.K. Kim, J.L. Martino, J.M. Zabolotny, N. Moghal, M. Lubkin, Y.-B. Kim, A.H. Sharpe, A. Stricker-Krongrad, G.I. Shulman, B.G. Neel, and B.B. Kahn Mol. Cell. Biol. 20 2000 5479
5. K.E. YouTen, E.S. Muise, A. Itie, E. Michaliszyn, J. Wagner, S. Jothy, W.S. Lapp, and M.L. Tremblay J. Exp. Med. 186 1997 683
6. Ibarra-Sanchez, M.; Tremblay, M.; Simoncic, P. Patent WO 00/36111
7. R.Q.J. Schaapveld, H.T.G. Schepens, G.W. Robinson, J. Attema, F.T.J.J. Oerlemans, J.A.M. Fransen, M. Streuli, B. Wieringa, L. Hennighausen, and W.J.A.J. Hendriks Dev. Biol. 188 1997 134
8. T.T. Yeo, T. Yang, S.M. Massa, J.S. Zhang, J. Honkaniemi, L.L. Butcher, and F.M. Longo J. Neurosci. Res. 47 1997 348
9. J.M. Ren, P.M. Li, W.R. Zhang, L.J. Sweet, G. Cline, G.I. Shulman, J.N. Livingston, and B.J. Goldstein Diabetes 47 1998 493
10. Muller, T.; Ullrich, A. Patent WO 00/61180
11. M.L. Thomas, and E.J. Brown Immunol. Today 20 1999 406
12. C. Kung, J.T. Pingel, M. Heikinheimo, T. Klemola, K. Varkila, L.I. Yoo, K. Vuopala, M. Poyhonen, M. Uhari, M. Rogers, S.H. Speck, T. Chatila, and M.L. Thomas Nat. Med. 6 2000 343
13. R.A. Urbanek, S.J. Suchard, G.B. Steelman, K.S. Knappenberger, L.A. Sygowski, C.A. Veale, and M.J. Chapdelaine J. Med. Chem. 44 2001 1777
14. A.I. Lazarovits, S. Poppema, Z. Zhang, M. Khandaker, C.E. LeFeuvre, S.K. Singhal, B.M. Garcia, N. Ogasa, A.M. Jevnikar, M.J. White, G. Singh, C.R. Stiller, and R.Z. Zhong Nature 380 1996 717
15. J.B. Bliska, K.L. Guan, J.E. Dixon, and S. Falkow Proc. Natl. Acad. Sci. U.S.A. 88 1991 1187
16. C. Leung, J. Grzyb, J. Lee, N. Meyer, G. Hum, C.G. Jia, S.F. Liu, and S.D. Taylor Bioorg. Med. Chem. 10 2002 2309
17. S.D. Larsen, F.C. Stevens, T.J. Lindberg, P.M. Bodnar, T.J. O'Sullivan, H.J. Schostarez, B.J. Palazuk, and J.E. Bleasdale Bioorg. Med. Chem. Lett. 13 2003 971
18. J. Xie, A.B. Comeau, and C.T. Seto Org. Lett. 6 2004 83
19. Y.T. Chen, M.B. Onaran, C.J. Doss, and C.T. Seto Bioorg. Med. Chem. Lett. 11 2001 1935
20. Y.T. Chen, and C.T. Seto J. Med. Chem. 45 2002 3946
21. Y.T. Chen, J. Xie, and C.T. Seto J. Org. Chem. 68 2003 4123
22. Y.T. Chen, and C.T. Seto Bioorg. Med. Chem. 12 2004 3289
23. Z.Y. Zhang, Y. Wang, L. Wu, E.B. Fauman, J.A. Stuckey, H.L. Schubert, M.A. Saper, and J.E. Dixon Biochemistry 33 1994 15266
24. Y.A. Puius, Y. Zhao, M. Sullivan, D.S. Lawrence, S.C. Almo, and Z.Y. Zhang Proc. Natl. Acad. Sci. U.S.A. 94 1997 13420
25. B.G. Szczepankiewicz, G. Liu, P.J. Hajduk, C. Abad-Zapatero, Z.H. Pei, Z.L. Xin, T.H. Lubben, J.M. Trevillyan, M.A. Stashko, S.J. Ballaron, H. Liang, F. Huang, C.W. Hutchins, S.W. Fesik, and M.R. Jirousek J. Am. Chem. Soc. 125 2003 4087
26. M. Taing, Y.F. Keng, K. Shen, L. Wu, D.S. Lawrence, and Z.Y. Zhang Biochemistry 38 1999 3793
27. K. Shen, Y.F. Keng, L. Wu, X.L. Guo, D.S. Lawrence, and Z.Y. Zhang J. Biol. Chem. 276 2001 47311
28. Z.C. Jia, Q.L. Ye, A.N. Dinaut, Q.P. Wang, D. Waddleton, P. Payette, C. Ramachandran, B. Kennedy, G. Hum, and S.D. Taylor J. Med. Chem. 44 2001 4584
29. X.L. Guo, S. Kui, F. Wang, D.S. Lawrence, and Z.Y. Zhang J. Biol. Chem. 277 2002 41014
30. J.P. Sun, A.A. Fedorov, S.Y. Lee, X.L. Guo, K. Shen, D.S. Lawrence, S.C. Almo, and Z.Y. Zhang J. Biol. Chem. 278 2003 12406
31. E. Asante-Appiah, S. Patel, C. Dufresne, P. Roy, Q.P. Wang, V. Patel, R.W. Friesen, C. Ramachandran, J.W. Becker, Y. Leblanc, B.P. Kennedy, and G. Scapin Biochemistry 41 2002 9043
32. Ethyl bromoacetate was used to introduce the carboxylic acid functionality for coupling with diamines. However, due to the instability of α-ketoacid tert-butyl ester under basic conditions, selective deprotection of the ethyl ester in the presence of the tert-butyl ester was not successful
33. Eickhoff, D.; Degenhardt, C.; Mciver, J. Patent WO 00/18733
34. S. Galic, M. Klingler-Hoffmann, M.T. Fodero-Tavoletti, M.A. Puryer, T.C. Meng, N.K. Tonks, and T. Tiganis Mol. Cell. Biol. 23 2003 2096