Small molecule peptidomimetics containing a novel phosphotyrosine bioisostere inhibit protein tyrosine phosphatase 1b and augment insulin action

Biochemistry

Volumn 40, Issue 19, 2001, Pages 5642-5654

  Bleasdale, John E ^a   Ogg, Derek ^b   Palazuk, Barbara J ^a   Jacob, Cynthia S ^a   Swanson, Michael L ^a   Wang, Xin Yuan ^a   Thompson, David P ^a   Conradi, Robert A ^a   Mathews, W Rodney ^a   Laborde, Alice L ^a   Stuchly, Christopher W ^a   Heijbel, Anna ^b   Bergdahl, Katrin ^b   Bannow, Carol A ^a   Smith, Clark W ^a   Svensson, Carina ^b   Liljebris, Charlotta ^a   Schostarez, Heinrich J ^a   May, Paul D ^a   Stevens, F Craig ^a   Larsen, Scott D ^a   more..

^a PFIZER INC   (United States)

^b Pharmacia Corporation   (Sweden)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSIS; DISEASE CONTROL; DRUG PRODUCTS; ENZYME INHIBITION; INSULIN; METABOLISM; ORGANIC ACIDS; POLYPEPTIDES;

DEPHOSPHORYLATION; PEPTIDOMETICS;

ENZYMES;

ANTIDIABETIC AGENT; CHOLECYSTOKININ DERIVATIVE; INSULIN; PHOSPHOTYROSINE; PROTEIN TYROSINE PHOSPHATASE;

ANIMAL CELL; ARTICLE; DEPHOSPHORYLATION; DRUG PROTEIN BINDING; INSULIN METABOLISM; INSULIN RESISTANCE; MOUSE; NON INSULIN DEPENDENT DIABETES MELLITUS; NONHUMAN; PRIORITY JOURNAL; SIGNAL TRANSDUCTION;

3T3 CELLS; AMINO ACID SEQUENCE; ANIMALS; BINDING, COMPETITIVE; CACO-2 CELLS; CHO CELLS; CRICETINAE; CRYSTALLOGRAPHY, X-RAY; DRUG SYNERGISM; ENZYME INHIBITORS; FEMALE; HUMANS; INSULIN; ISOMERISM; MICE; MOLECULAR MIMICRY; MOLECULAR SEQUENCE DATA; PEPTIDES; PHOSPHOTYROSINE; PROTEIN BINDING; PROTEIN-TYROSINE-PHOSPHATASE; RATS; SINCALIDE; SOLUTIONS; XENOPUS LAEVIS;

ANIMALIA;

EID: 0035873420     PISSN: 00062960     EISSN: None     Source Type: Journal    
DOI: 10.1021/bi002865v     Document Type: Article

References (58)

1. Kruszynska, Y. T., and Olefsky, J. M. (1996) J. Invest. Med. 44, 413-28.
2. Seely, B. L., Staubs, P. A., Reichart, D. R., Berhanu, P., Milarski, K. L., Saltiel, A. R., Kusari, J., and Olefsky, J. M. (1996) Diabetes 45, 1379-85.
3. Wang, X. Y., Bergdahl, K., Heijbel, A., Liljebris, C., and Bleasdale, J. E. (2001) Mol. Cell. Endocrinol. 173, 109-19.
4. Bandyopadhyay, D., Kusari, A., Kenner, K. A., Liu, F., Chernoff, J., Gustafson, T. A., and Kusari, J. (1997) J. Biol. Chem. 272, 1639-45.
5. Ramachandran, C., Aebersold, R., Tonks, N. K., and Pot, D. A. (1992) Biochemistry 31, 4232-8.
6. Ahmad, F., Li, P. M., Meyerovitch, J., and Goldstein, B. J. (1995) J. Biol. Chem. 270, 20503-8.
7. Kenner, K. A., Anyanwu, E., Olefsky, J. M., and Kusari, J. (1996) J. Biol. Chem. 271, 19810-6.
8. Ahmad, F., Azevedo, J. L., Cortright, R., Dohm, G. L., and Goldstein, B. J. (1997) J. Clin. Invest. 100, 449-58.
9. Ahmad, F., Considine, R. V., Bauer, T. L., Ohannesian, J. P., Marco, C. C., and Goldstein, B. J. (1997) Metab. Clin. Exp. 46, 1140-5.
10. Chen, H., Cong, L. N., Li, Y., Yao, Z. J., Wu, L., Zhang, Z. Y., Burke, T. R., Jr., and Quon, M. J. (1999) Biochemistry 38, 384-9.
11. Maegawa, H., Ide, R., Haseguwa, M., Ugi, S., Egawa, K., Iwanishi, M., Kikkawa, R., Shigeta, Y., and Kashiwagi, A. (1995) J. Biol. Chem. 270, 7724-30.
12. 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, 1544-8.
13. Burke, T. R., Jr., and Zhang, Z. Y. (1998) Biopolymers 47, 225-41.
14. Wrobel, J., Sredy, J., Moxham, C., Dietrich, A., Li, Z., Sawicki, D. R., Seestaller, L., Wu, L., Katz, A., Sullivan, D., Tio, C., and Zhang, Z. Y. (1999) J. Med. Chem. 42, 3199-202.
15. Malamas, M. S., Sredy, J., Moxham, C., Katz, A., Xu, W. X., McDevitt, R., Adebayo, F. O., Sawicki, D. R., Seestaller, L., Sullivan, D., and Taylor, J. R. (2000) J. Med. Chem. 43, 1293-310.
16. Iversen, L. F., Andersen, H. S., Branner, S., Mortensen, S. B., Peters, G. H., Norris, K., Olsen, O. H., Jeppesen, C. B., Lundi, B. F., Ripka, W., Moller, K. B., and Moller, N. P. H. (2000) J. Biol. Chem. 275, 10300-7.
17. Gao, Y., Wu, L., Luo, J. H., Guo, R., Yang, D., Zhang, Z. Y., and Burke, T. R. (2000) Bioorg. Med. Chem. Lett. 10, 923-7.
18. Burke, T. R., Yao, Z. J., Zhao, H., Milne, G. W. A., Wu, L., Zhang, Z. Y., and Voigt, J. H. (1998) Tetrahedron 54, 9981-94.
19. Yu, L., McGill, A., Ramirez., J., Wang, P. G., and Zhang, P. G. (1995) Bioorg. Med. Chem. Lett. 5, 1003-6.
20. Ham, S. W., Park, J. G., Lee, S. J., and Yoo, J. S. (1999) Bioorg. Med. Chem. Lett. 9, 185-6.
21. Larsen, S. D., May, P. D., Bleasdale, J. E., Liljebris, C. L., Schostarez, H. J., and Barf, T. (1998) PCT Int. Appl. WO 99/11606. 19990311.
22. Guan, K. L., and Dixon, J. E. (1991) J. Biol. Chem. 266, 17026-30.
23. Baykov, A. A., Evtushenko, O. A., and Avaeva, S. M. (1988) Anal. Biochem. 171, 266-70.
24. Sizer, K. M., Smith, C. L., Jacob, C. S., Swanson, M. L., and Bleasdale, J. E. (1994) Mol. Cell. Endocrinol. 102, 119-29.
25. Koivisto, U. M., Martinez-Valdez, H., Bilan, P. J., Burdett, E., Ramlal, T., and Klip, A. (1991) J. Biol. Chem. 266, 2615-21.
26. Tsai, T. D., Shuck, M. E., Thompson, D. P., Bienkowski, M. J., and Lee, K. S. (1995) Am. J. Physiol. 268, C1173-8.
27. Songyang, Z., Carraway, K. L., Eck, M. J., Harrison, S. C., Feldman, R. A., Mohammadi, M., Schlessinger, J., Hubbard, S. R., Smith, D. P., Eng, C., Lorenzo, M. J., Ponder, B. A. J., Mayer, B. J., and Cantley, L. C. (1995) Nature 373, 536-9.
28. Jia, Z. C., Barford, D., Flint, A. J., and Tonks, N. K. (1995) Science 268, , 1754-8.
29. Otwinoski, Z., and Minor, W. (1997) Methods Enzymol. 277, 307-26.
30. Collaborative Computational Project, Number 4 (1994) Acta Crystallogr. D50, 750.
31. Brunger, A. (1993) X-PLOR, version 3.1, Yale University Press, New Haven, CT.
32. Murshudov, G. V., Vagin, A. A., and Dodson, E. J. (1997) Acta Crystallogr. D53, 240-55.
33. Jones, T. A., Zou, J. Y., Cowan, S. W., and Kjeldgaard, M. (1991) Acta Crystallogr. A47, 110-9.
34. Lamzin, V. S., and Wison, K. S. (1997) Methods Enzymol. 277, 269-305.
35. Larsen, S. D., et al. (2001) J. Med. Chem. (manuscript submitted for publication).
36. Zhang, Z. Y., Wang, Y. A., and Dixon, J. E. (1994) Proc. Natl. Acad. Sci U.S.A. 91, 1624-7.
37. Lee, S. R., Kwon, K. S., Kim, S. R., and Rhee, S. G. (1998) J. Biol. Chem. 273, 15366-72.
38. Niculescu, R., Bradford, H. N., Colman, R. W., and Kalf, G. F. (1995) Chem.-Biol. Interact. 98, 211-22.
39. Zhang, Z.-Y., Maclean, D., McNamara, D. J., Sawyer, T. K., and Dixon, J. E. (1994) Biochemistry 33, 2285-90.
40. Desmarais, S., Jia, Z. C., and Ramachandran, C. (1998) Arch. Biochem. Biophys. 352, 225-31.
41. Glover, N. R., and Tracey, A. S. (1999) J. Am. Chem. Soc. 121, 3579-89.
42. Kole, H. K., Ye, B., Akamatsu, M., Ford, H., Yan, X., Barford, D., Roller, P. P., and Burke, T. R. (1995) Biochem. Biophys. Res. Commun. 209, 817-22.
43. Tonks, N. K., Cicirelli, M. F., Diltz, C. D., Krebs, E. G., and Fischer, E. H. (1990) Mol. Cell. Biol. 10, 458-63.
44. Bundgaard, H. (1991) in A Textbook for Drug Design and Development (Krogsgaard-Larsen, P., and Bundgaard, H., Eds.) pp 111-91, Harwood Academic Publishers, Chur, Switzerland.
45. Sarmiento, M., Puius, Y. A., Vetter, S. F., Keng, Y.-F., Wu, L., Zhao, Y., Lawrence, D. S., Almo, S. C., and Zhang, Z.-Y. (2000) Biochemistry 39, 8171-9.
46. Groves, M. R., Yao, Z.-J., Roller, P. P., Burke, T. T., Jr., and Barford, D. (1998) Biochemistry 37, 17773-83.
47. Flocco, M. M., and Mowbray, S. L. (1995) J. Mol. Biol. 254, 96-105.
48. Worm, D., Vinten, J., and Beck-Nielsen, H. (1999) Diabetologia 42, 1146-7.
49. Goldstein, B. J., Ahmad, F., Ding, W., Li, P. M., and Zhang, W. R. (1998) Mol. Cell. Biochem. 182, 91-9.
50. Wallace, A. C., Laskowski, R. A., and Thornton, J. M. (1995) Protein Eng. 8, 127-34.
51. Vetter, S. W., Keng, Y. F., Lawrence, D. S., and Zhang, Z. Y. (2000) J. Biol. Chem. 275, 2265-8.
52. Glover, N. R., and Tracey, A. S. (1999) Biochem. Cell Biol. 77, 469-86.
53. Peters, G. H., Frimurer, T. M., Andersen, J. N., and Olsen, O. H. (2000) Biophys. J. 78, 2191-200.
54. Sarmiento, M., Zhao, Y., Gordon, S. J., and Zhang, Z.-Y. (1998) J. Biol. Chem. 273, 26368-74.
55. Puius, Y. A., Zhao, Y., Sullivan, M., Lawrence, D. S., Almo, S. C., and Zhang, Z.-Y. (1997) Proc. Natl. Acad. Sci. U.S.A. 94, 13420-5.
56. Taing, M., Keng, Y.-F., Shen, K., Wu, L., Lawrence, D. S., and Zhang, Z.-Y. (1999) Biochemistry 38, 3793-803.
57. Venable, C. L., Frevert, E. U., Kim, Y.-B., Fischer, B. M., Kamatkar, S., Neel, B. G., and Kahn, B. B. (2000) J. Biol. Chem. 275, 18318-26.
58. Goldstein, B. J., Bittner-Kowalczyk, A., While, M. F., and Harbeck, M. (2000) J. Biol. Chem. 275, 4283-9.