Bivalent inhibitors of protein tyrosine kinases

Journal of the American Chemical Society

Volumn 121, Issue 2, 1999, Pages 280-283

  Profit, Adam A ^a   Lee, Tae Ryong ^a   Lawrence, David S ^a  

^a ALBERT EINSTEIN COLLEGE OF MEDICINE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ENZYME INHIBITOR; PROTEIN TYROSINE KINASE;

ARTICLE; BINDING AFFINITY; ENZYME BINDING; ENZYME INHIBITION; SYNTHESIS;

EID: 0040111705     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja983515n     Document Type: Article

References (28)

1. Ottenholf-Kalf, A. E.; Rijkesen, G.; Van Beurden, E. A.; Staal, G. E. Cancer Res. 1992, 52, 4773-4778.
2. Hajjar, D. P.; Pomerants, H. B. FASEB J. 1992, 6, 2933-2941.
3. Elder, J. E.; Fisher, G. J.; Lindquist, P. B.; Voorthees, J. J.; Coffey, R. J. Science 1989, 243, 811-814.
4. Libby, P.; Schwartz, D.; Borgie, E.; Tanaka, H. A. Circulation 1992, 86, 47-52.
5. Young, S. W.; Poole, R. C.; Hudson, A. T.; Halestrap, A. P.; Denton, R. M., Tavaré, J. M. FEBS Lett. 1993, 316, 278-282.
6. Traut, T. W. Mol. Cell. Biochem. 1994, 140, 1-22.
7. Lawrence, D. S.; Niu, J. Pharmacol. Ther. 1998, 77, 81-114.
8. Cole, P. A.; Grace, M. R.; Phillips, R. S.; Burn, P.; Walsh, C. T. J. Biol. Chem. 1995, 270, 22105-22108.
9. Pawson, T.; Gish, G. D. Cell 1992, 71, 359-362.
10. Pawson, T. Adv. Cancer Res. 1994, 64, 87-110.
11. Pawson, T. Nature 1995, 373, 573-580.
12. Gilmer, T.; Rodriguez, M.; Jordan, S.; Crosby, R.; Alligood, K.; Green, M.; Kimery, M.; Wagner, C.; Kinder, D.; Charifson, P.; Hassell, A. M.; Willard, D.; Luther, M.; Rusnak, D.; Sternbach, D. D.; Mehrotra, M.; Peel, M.; Shampine, L.; Davis, R.; Robbins, J.; Patel, I. R.; Kassel, D.; Burkhart, W.; Moyer, M.; Bradshaw, T.; Berman, J. J. Biol. Chem. 1994, 269, 31711-31719.
13. Xu, R. X.; Word, M. J.; Davis, D. G.; Rink, M. J.; Willard, D. H.; Gampe, R. T. Biochemistry 1995, 34, 2107-2121.
14. Niu, J.; Lawrence, D. S. J. Biol. Chem. 1997, 272, 1493-1499.
15. Xu, W.; Harrison, S. C.; Eck, M. J. Nature 1997, 385, 595-602.
16. Sicheri, F.; Moarefi, I.; Kuriyan, J. Nature 1997, 385, 602-9.
17. Moarefi, I.; LaFevre-Bernt, M.; Sicheri, F.; Huse, M.; Lee, C. H.; Kuriyan, J.; Miller, W. T. Nature 1997, 385, 650-3.
18. Bjorge, J. D.; Bellagamba, C.; Cheng, H.-C.; Tanaka, A.; Wang, J. H.; Fujita, D. J. J. Biol. Chem. 1995, 270, 24222-24228.
19. Lee, T. R.; Lawrence, D. S., unpublished results.
20. While this work was in progress, Miller and his colleagues described model substrates, employing an approach analogous to that described herein, to investigate processive phosphorylation by Src family kinases [Pellicena, P.; Stowell, K. R.; Miller, W. T. J. Biol. Chem. 1998, 273, 15325-15328]. The most potent substrates exhibited a-10-fold reduction in Michaelis constant, results comparable to those obtained with the bivalent substrate 9 versus that of a previously described substrate lacking the SH2-targeting motif [Lee, T. R.; Niu, J.; Lawrence, D. S. J. Biol. Chem. 1995, 270, 5375- 5380].
21. While this work was in progress, Miller and his colleagues described model substrates, employing an approach analogous to that described herein, to investigate processive phosphorylation by Src family kinases [Pellicena, P.; Stowell, K. R.; Miller, W. T. J. Biol. Chem. 1998, 273, 15325-15328]. The most potent substrates exhibited a-10-fold reduction in Michaelis constant, results comparable to those obtained with the bivalent substrate 9 versus that of a previously described substrate lacking the SH2-targeting motif [Lee, T. R.; Niu, J.; Lawrence, D. S. J. Biol. Chem. 1995, 270, 5375-5380].
22. Yuan, C. J.; Jakes, S.; Elliot, S.; Graves, D. J. J. Biol. Chem. 1990, 265, 16205-16209.
23. Fry, D. W.; McMichael, A.; Singh, J.; Dobrusin, E. M.; McNamara, D. J. Peptides 1994, 15, 951-957.
24. Niu, J.; Lawrence, D. S. J. Am. Chem. Soc. 1997, 119, 3844-3845.
25. Alfaro-Lopez, J.; Yuan, W.; Phan, B. C.; Kamath, J.; Lou, Q.; Lam, K. S.; Hruby, V. J. J. Med. Chem. 1998, 41, 2252-2260.
26. Cowburn, D.; Zheng, J.; Xu, Q.; Barany, G. J. Biol. Chem. 1995, 270, 26738-26741.
27. Pluskey, S.; Wandless, T. J.; Walsh, C. T.; Shoelson, S. E. J. Biol. Chem. 1995, 270, 2897-2900.
28. Eck, M. J.; Pluskey, S.; Trub, T.; Harrison, S. C.; Shoelson, S. E. Nature 1996, 379, 277-280.