Structural insights into the design of nonpeptidic isothiazolidinone- containing inhibitors of protein-tyrosine phosphatase 1B

Journal of Biological Chemistry

Volumn 281, Issue 49, 2006, Pages 38013-38021

  Ala, Paul J ^a,b   Gonneville, Lucie ^a   Hillman, Milton ^a   Becker Pasha, Mary ^a   Yue, Eddy W ^a   Douty, Brent ^a   Wayland, Brian ^a   Polam, Padmaja ^a   Crawley, Matthew L ^a   McLaughlin, Erin ^a   Sparks, Richard B ^a   Glass, Brian ^a   Takvorian, Amy ^a   Combs, Andrew P ^a   Burn, Timothy C ^a   Hollis, Gregory F ^a   Wynn, Richard ^a  

^a Experimental Station   (United States)

^b DUPONT COMPANY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMIDES; BENZIMIDAZOLE; PHOSPHATASE; VAN DER WAALS INTERACTIONS;

AMINO ACIDS; CRYSTAL STRUCTURE; ENZYME INHIBITION; HYDROGEN BONDS; MECHANICAL PERMEABILITY; PROTEINS; VAN DER WAALS FORCES;

ENZYME KINETICS;

ASPARTIC ACID; BENZIMIDAZOLE; ISOTHIAZOLIDINONE PHOSPHATE; PHENYLALANINE; PROTEIN TYROSINE PHOSPHATASE 1B; PROTEIN TYROSINE PHOSPHATASE 1B INHIBITOR; SULFONAMIDE; THIAZOLIDINE DERIVATIVE; UNCLASSIFIED DRUG;

AMINO TERMINAL SEQUENCE; ARTICLE; CARBOXY TERMINAL SEQUENCE; CARBOXYLATION; CRYSTAL STRUCTURE; DRUG CONFORMATION; DRUG DESIGN; DRUG MECHANISM; DRUG PROTEIN BINDING; DRUG STRUCTURE; ENZYME ACTIVE SITE; HYDROGEN BOND; PRIORITY JOURNAL; PROTEIN INTERACTION; STRUCTURE ACTIVITY RELATION; STRUCTURE ANALYSIS;

CATALYTIC DOMAIN; CRYSTALLOGRAPHY, X-RAY; DRUG DESIGN; ELECTROSTATICS; ENZYME INHIBITORS; HUMANS; HYDROGEN BONDING; MODELS, MOLECULAR; PROTEIN CONFORMATION; PROTEIN-TYROSINE-PHOSPHATASE; RECOMBINANT PROTEINS; STRUCTURE-ACTIVITY RELATIONSHIP; THIAZOLES;

EID: 33845993617     PISSN: 00219258     EISSN: 1083351X     Source Type: Journal    
DOI: 10.1074/jbc.M607913200     Document Type: Article

References (29)

1. Kenner, K. A., Anyanwu, E., Olefsky, J. M., and Kusari, J. (1996) J. Biol. Chem. 271, 19810-19816
2. Saltiel, A. R., and Kahn, R. (2001) Nature 414, 799-806
3. Byon, J. C., Kusari, A. B., and Kusari, J. (1998) Mol. Cell. Biochem. 182, 101-108
4. Elchebly, M., Payette, P., Michaliszyn, E., Cromlish, W., Collins, S., Loy, A. L., Normandin, D., Cheng, A., Himms-Hagen, J., Chan, C.-C., Ramachandran, C., Gresser, M. J., Tremblay, M. L., and Kennedy, B. P. (1999) Science 283, 1544-1548
5. Klaman, L. D., Boss, O., Peroni, O. D., Kim, J. K., Martino, J. L., Zabolotny, J. M., Moghal, N., Lubkin, M., Kim, Y.-B., Sharpe, A. H., Stricker-Krongrad, A., Shulman, G. I., Neel, B. G., and Kahn, B. B. (2000) Mol. Cell. Biol. 20, 5479-5489
6. Zinker, B. A., Rondinone, C. M., Trevillyan, J. M., Gum, R. J., Clampit, J. E., Waring, J. F., Xie, N., Wilcox, D., Jacobson, P., Frost, L., Kroeger, P. E., Reilly, R. M., Koterski, S., Opgenorth, T. J., Ulrich, R. G., Crosby, S., Butler, M., Murray, S. F., McKay, R. A., Bhanot, S., Monia, B. P., and Jirousek, M. R. (2002) Proc. Natl. Acad. Sci. U. S. A. 99, 11357-11362
7. Johnson, T. O., Ermolieff, J., and Jirousek, M. R. (2002) Nat. Rev. Drug Disc. 1, 696-709
8. Blaskovich, M. A., and Kim, H.-O. (2002) Expert Opin. Ther. Pat. 12, 871-905
9. Liu, G. (2003) Curr. Med. Chem. 10, 1407-1421
10. Taylor, S. D., and Hill, B. (2004) Expert Opin. Investig. Drugs 13, 199-214
11. Pei, Z., Liu, G., Lubben, T. H., and Szczepankiewicz, B. G. (2004) Curr. Pharm. Des. 10, 3481-3504
12. Costantino, L., and Barlocco, D. (2004) Curr. Med. Chem. 11, 2725-2747
13. Bialy, L., and Waldmann, H. (2005) Angew. Chem. Int. Ed. Engl. 44, 3814-3839
14. Combs, A. P., Yue, E. W., Bower, M., Ala, P. J., Wayland, B., Douty, B., Takvorian, A., Polam, P., Wasserman, Z., Zhu, W., Crawley, M., Pruitt, J., Sparks, R., Glass, B., Modi, D., McLaughlin, E., Bostrom, L., Li, M., Galya, L., Blom, K., Hillman, M., Gonneville, L., Reid, B., Wei, M., Becker-Pasha, M., Klabe, R., Huber, R., Li, Y., Hollis, G., Burn, T. C., Wynn, R., Liu, P., and Metcalf, B. (2005) J. Med. Chem. 48, 6544-6548
15. Ala, P. J., Gonneville, L., Hillman, M. C., Becker-Pasha, M., Wei, M., Reid, B. G., Klabe, R., Yue, E. W., Wayland, B., Douty, B., Combs, A. P., Polam, P., Wasserman, Z., Bower, M., Burn, T. C., Hollis, G. F., and Wynn, R. (August 17, 2006) J. Biol. Chem. 10.1074/jbc.M606873200
16. Combs, A. P., Zhu, W., Crawley, M. L., Glass, B., Polam, P., Sparks, R. B., Modi, D., Takvorian, A., McLaughlin, E., Yue, E. W., Wasserman, Z., Bower, M., Wei, M., Rupar, M., Ala, P. J., Reid, B. M., Ellis, D., Gonneville, L., Emm, T., Taylor, N., Yeleswaram, S., Li, Y., Wynn, R., Burn, T. C., Hollis, G., Liu, P. C., and Metcalf, B. (2006) J. Med. Chem. 49, 3774-3789
17. Szczepankiewicz, B. G., Liu, G., Hajduk, P. J., Abad-Zapatero, C., Pei, Z., Xin, Z., Lubben, T. H., Trevillyan, J. M., Stashko, M. A., Ballaron, S. J., Liang, H., Huang, F., Hutchins, C. W., Fesik, S. W., and Jirousek, M. R. (2003) J. Am. Chem. Soc. 125, 4087-4096
18. Berman, H. M., Westbrook, J., Feng, Z., Gilliland, G., Bhat, T. N., Weissig, H., Shindyalov, I. N., and Bourne P. E. (2000) Nucleic Acids Res. 28, 235-242
19. Barford, D., Flint, A. J., and Tonks, N. K. (1994) Science 263, 1397-1404
20. Salmeen, A., Andersen, J. N., Myers, M. P., Tonks, N. K., and Barford, D. (2000) Mol. Cell 6, 1401-1412
21. Jia, Z., Barford, D., Flint, A. J., and Tonks, N. K. (1995) Science 268, 1754-1758
22. Andersen, J. N., Mortensen, O. H., Peters, G. H., Drake, P. G., Iversen, L. F., Olsen, O. H., Jansen, P. G., Andersen, H. S., Tonks, N. K., and Møller, N. P. (2001) Mol. Cell. Biol. 21, 7117-7136
23. Iversen, L. F., Andersen, H. S., Branner, S., Mortensen, S. B., Peters, G. H., Norris, K., Olsen, O. H., Jeppesen, C. B., Lundt, B. F., Ripka, W., Møller, K. B., and Møller, N. P. H. (2000) J. Biol. Chem. 275, 10300-10307
24. Yao, Z.-J., Ye, B., Wu, X.-W., Wang, S., Wu, L., Zhang, Z.-Y., and Burke, T. R., Jr. (1998) Bioorg. Med. Chem. 6, 1799-1810
25. Chen, L., Wu, L., Otaka, A., Smyth, M. S., Roller, P. P., Burke, T. R., Jr., Hertog, J. D., and Zhang, Z.-Y. (1995) Biochem. Biophys. Res. Commun. 216, 976-984
26. Liu, G., Xin, Z., Liang, H., Abad-Zapatero, C., Hajduk, P. J., Janowick, D. A., Szczepankiewicz, B. G., Pei, Z., Hutchins, C. W., Ballaron, S. J., Stashko, M. A., Lubben, T. H., Berg, C. E., Rondinone, C. M., Trevillyan, J. M., and Jirousek, M. R. (2003) J. Med. Chem. 46, 3437-3440
27. Dufresne, C., Roy, P., Wang, Z., Asante-Appiah, E., Cromlish, W., Boie, Y., Forghani, F., Desmarais, S., Wang, Q., Skorey, K., Waddleton, D., Ramachandran, C., Kennedy, B. P., Xu, L., Gordon, R., Chan, C. C., and Leblanc, Y. (2004) Bioorg. Med. Chem. Lett. 14, 1039-1042
28. Burke, T. R., Jr., Yao, Z. J., Zhao, H., Milne, G. W. A., Wu, L., Zhang, Z. Y., and Voigt, J. H. (1998) Tetrahedron 54, 9981-9994
29. Hansen, T. K., Iversen, L. F., Lau, J., Petersen, A. K., Olsen, O. H., Moller, K. B., Mortensen, S. B., Billestrup, N., Ge, Y., Newman, M., Holsworth, D., Lund, I. K., Andersen, B., Peters, G., Andersen, H. S., and Moller, N. P. (2002) in Potent Nonpeptide Protein-tyrosine Phosphatase Inhibitors, 223rd ACS National Meeting, Orlando, FL, April 7-11, 2002, ACS Publications, Washington, D. C.