The formation of a covalent complex between a dipeptide ligand and the SRC SH2 domain

Bioorganic and Medicinal Chemistry Letters

Volumn 8, Issue 10, 1998, Pages 1189-1194

  Alligood, Krystal J ^a   Charifson, Paul S ^a   Crosby, Renae ^a   Consler, Thomas G ^a   Feldman, Paul L ^a   Gampe Jr , Robert T ^a   Gilmer, Tona M ^a   Jordan, Steven R ^a   Milstead, Mark W ^a   Mohr, Christopher ^a   Peel, Michael R ^a   Rocque, Warren ^a   Rodriguez, Marc ^a   Rusnak, David W ^a   Shewchuk, Lisa M ^a   Sternbach, Daniel D ^a  

^a GLAXOSMITHKLINE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

DIPEPTIDE DERIVATIVE;

ARTICLE; CANCER; COVALENT BOND; DRUG STRUCTURE; DRUG SYNTHESIS; HYDROGEN BOND; MOLECULAR INTERACTION; X RAY CRYSTALLOGRAPHY;

ALDEHYDES; AMINO ACID SEQUENCE; BINDING SITES; CRYSTALLOGRAPHY, X-RAY; CYSTEINE; DIPEPTIDES; HYDROGEN BONDING; LIGANDS; MAGNETIC RESONANCE SPECTROSCOPY; MODELS, MOLECULAR; PHOSPHOTYROSINE; PROTEIN CONFORMATION; PROTEINS; SRC HOMOLOGY DOMAINS;

EID: 17544396544     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0960-894X(98)00195-4     Document Type: Article

References (36)

1. 1. Ottenhof-Kalff, A. E.; Rijksen, G.; van Beurden, A. C. M.; Hennipman, M. P.; Michels, A. A.; Staal, G. E. J. Cancer Res. 1992, 49, 4773.
2. 2. Mazurenko, N. N.; Kogan, E. A.; Zborovskaya, I. B.; Kisseljov, F. L. Eur. J. Cancer 1992, 28, 372.
3. 3. Weber, T. K.; Steele, G.; Summerhayes, I. C. J. Clin. Inves. 1992, 90, 815.
4. 4. Fumagalli, S.; Totty, N. F.; Hsuan, J. J.; Courtneidge, S. A. Nature 1994, 368, 871. Pillay, I.; Nakano, H.; Sharma, S. V. Cell Growth Differ. 1996, 7, 1487.
5. 4. Fumagalli, S.; Totty, N. F.; Hsuan, J. J.; Courtneidge, S. A. Nature 1994, 368, 871. Pillay, I.; Nakano, H.; Sharma, S. V. Cell Growth Differ. 1996, 7, 1487.
6. 5. Dikic, I.; Tokiwa, G.; Lev, S.; Courtneidge, S. A.; Schlessinger, J. Nature 1996, 383, 547.
7. 6. Tanake, S.; Amling, M.; Neff, L.; Peyman, A.; Uhlmann, E.; Levy, J. B.; Baron, R. Nature 1996, 383, 528.
8. 7. Pawson, T. Curr. Opin. Struc. Biol. 1992, 2, 432. Margolis, B. Cell Growth Differ. 1992, 3, 73. Pawson, T.; Gish, G. D. Cell 1992, 71, 359.
9. 7. Pawson, T. Curr. Opin. Struc. Biol. 1992, 2, 432. Margolis, B. Cell Growth Differ. 1992, 3, 73. Pawson, T.; Gish, G. D. Cell 1992, 71, 359.
10. 7. Pawson, T. Curr. Opin. Struc. Biol. 1992, 2, 432. Margolis, B. Cell Growth Differ. 1992, 3, 73. Pawson, T.; Gish, G. D. Cell 1992, 71, 359.
11. 8. Luttrell, D. K.; Lee, A.; Lansing, T. J.; Crosby, R. M.; Jung, K. D.; Willard, D.; Luther, M.; Rodriguez, M.; Berman, J.; Gilmer, T. M. Proc. Nat. Acad. Sci. U.S.A. 1994, 91, 83.
12. 9. Mori, S.; Ronnstrand, L.; Yokote, K.; Engstrom, A.; Courtneidge, S. A.; Claesson-Welsh, L.; Heldin, C. -H. EMBO 1993, 12, 2257.
13. 10. Muthuswamy, S. K.; Segel, P. M.; Dankort, D. L.; Webster, M. A.; Muller, W. J. Mol. Cell. Biol. 1994, 14, 735.
14. 11. Cobb, B. S.; Schaller, M. D.; Leu, T. H.; Parsons, J. T. Mol. Cell. Biol. 1994, 14, 147.
15. 12 Levitski, A. Anti-Cancer drug design 1996, 11, 175. Saltiel, A. R.; Sawyer, T. K. Chem. Biol. 1996, 3, 887.
16. 12 Levitski, A. Anti-Cancer drug design 1996, 11, 175. Saltiel, A. R.; Sawyer, T. K. Chem. Biol. 1996, 3, 887.
17. 13. Songyang, Z.; Shoelson, S. E.; Chaudhuri, M.; Gish, G.; Pawson, T.; Haser, W. G.; King, F.; Roberts, T.; Ratnofsky, S.; Lechleider, R. J.; Neel, B. G.; Birge, R. B.; Fajardo, J. E.; Chao, M. M.; Hanafusa, H.; Schaffhausen, B.; Cantley, L. C. Cell 1993, 72, 767.
18. 14. Xu, R. X.; Word, M.; Davis, D.; Rink, M.J.; Willard, D. H.; Gampe, R. T. Biochemistry 1995, 34, 2107.
19. 15. Gilmer, T. M.; 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.
20. 16. Waksman, G.; Shoelson, S. E.; Pant, N.; Cowburn, D.; Kuriyan, J. Cell 1993, 72, 779.
21. 17) Rodriguez, M.; Crosby, R.; Alligood, K.; Gilmer, T. M.; Berman, J. Lett. Pep. Sci. 1995, 2, 1. Plummer, M. S.; Lunney, E. A.; Para, K. S.; Prasad, J. V. N. V.; Shahripour, A.; Singh, J.; Stankovic, C. J.; Humblet, C.; Fergus, J. H.; Marks, J. S.; Sawyer, T. K. Drug Design and Discovery 1996, 13, 75.
22. 17) Rodriguez, M.; Crosby, R.; Alligood, K.; Gilmer, T. M.; Berman, J. Lett. Pep. Sci. 1995, 2, 1. Plummer, M. S.; Lunney, E. A.; Para, K. S.; Prasad, J. V. N. V.; Shahripour, A.; Singh, J.; Stankovic, C. J.; Humblet, C.; Fergus, J. H.; Marks, J. S.; Sawyer, T. K. Drug Design and Discovery 1996, 13, 75.
23. Plummer, M. S.; Lunney, E. A.; Para, K. S.; Shahripour, A.; Stankovic, C. J.; Humblet, C.; Fergus, J. H.; Marks, J. S.; Herrera, R.; Hubbell, S.; Saltiel, A.; Sawyer, T. K. Bioorg. Med. Chem. 1997, 5, 41.
24. 18. Boerner, R. J.; Consler, T. G.; Gampe, R. T. Jr.; Weigl, D.; Willard, D. H.; Davis, D. G.; Edison, A. M.; Loganzo, F. Jr.; Kassel, D. B.; Xu, R. X.; Patel, I. R.; Robbins, J. S.; Lansing, T.; Gilmer, T. M.; Luther, M. A.; Knight, W. B. Biochemistry 1995, 34, 15351.
25. 19. SH2 domain sequences published to date indicate that a cysteine residue in the 188 position is unique to src.
26. 20) Rich, D. H. In Comprehensive Medicinal Chemistry; Hansch, C.; Sammes, P. G.; Taylor, J. B., Eds.; Pergamon: Oxford, 1990; pp 431-433. Krantz, A. In Advances in Medicinal Chemistry; Maryanoff, B. E.; Maryanoff, C. A., Eds.; JAI: Greenwich, 1992; vol. 1, pp 235-261.
27. 20) Rich, D. H. In Comprehensive Medicinal Chemistry; Hansch, C.; Sammes, P. G.; Taylor, J. B., Eds.; Pergamon: Oxford, 1990; pp 431-433. Krantz, A. In Advances in Medicinal Chemistry; Maryanoff, B. E.; Maryanoff, C. A., Eds.; JAI: Greenwich, 1992; vol. 1, pp 235-261.
28. 21. Woo, J. T.; Sigeizumi, S.; Yamaguchi, K.; Sugimoto, K.; Kobori, T.; Tsuji, T.; Kondo, K. Bioorg. Med. Chem. Lett. 1995, 5, 1501.
29. 22. Stille, J. K. Angew. Chem., Int. Ed. Engl. 1986, 25, 508.
30. 50 (AcY*EEIE). For details of the ELISA see ref 15.
31. 25. Charifson, P. S.; Shewchuk, L. M.; Rocque, W.; Hummel, C. W.; Jordan, S. R.; Mohr, C.; Pacofsky, G. J.; Peel, M. R.; Rodriguez, M.; Sternbach, D. D.; Consler, T. G. Biochemistry 1997, 36, 6283.
32. 26. Brunger, A. T. Acta Crytallogr. 1990, A46, 46.
33. 15N) was described in ref 14.
34. 4 shows the aldehyde masked as an acetal.
35. 29. The problems of phosphatase lability and cell permeability have been investigated by a number of workers. See for example: Burke, T. R.; Smyth, M. S.; Otaka, A.; Nomizu, M.; Roller, P. P.; Wolf, G.; Case, R.; Shoelson, S. E. Biochemistry, 1994, 33, 6490-6494.
36. 30. Following the completion of this study, Jagoe and co-workers reported that a series of catechols inhibited the binding of src family SH2 domains to high affinity ligands. The proposed mechanism involves initial oxidation of the catechol to an o-quinone which may then react with a thiol group such as that found at Cys-188 of the src SH2 domain. Jagoe, C. T.; Kreifels, S. E.; Li, J. Bioorg. Med. Chem. Lett. 1997, 7, 113.