SU9516: Biochemical analysis of cdk inhibition and crystal structure in complex with cdk2

Biochemical and Biophysical Research Communications

Volumn 310, Issue 3, 2003, Pages 1026-1031

  Moshinsky, Deborah J ^a,c   Bellamacina, Cornelia R ^a   Boisvert, David C ^b,d   Huang, Ping ^a   Hui, Terence ^a   Jancarik, Jaru ^b   Kim, Sung Hou ^b   Rice, Audie G ^a  

^a SUGEN INC   (United States)

^b UNIVERSITY OF CALIFORNIA   (United States)

^c NOVARTIS INSTITUTES FOR BIOMEDICAL RESEARCH   (United States)

^d BAYER CORPORATION   (United States)

Author keywords

cdk2; Crystal structure; Inhibitor; Kinase; SU9516

Indexed keywords

3 (3H IMIDAZOL 4 YLMETHYLENE) 5 METHOXY 1,3 DIHYDROINDOL 2 ONE; ADENOSINE TRIPHOSPHATE; CYCLIN A; CYCLIN B1; CYCLIN D1; CYCLIN DEPENDENT KINASE 1; CYCLIN DEPENDENT KINASE 2; CYCLIN DEPENDENT KINASE 4; CYCLIN DEPENDENT KINASE INHIBITOR; CYCLIN E; GLUTAMINE; LEUCINE; SU 9516; UNCLASSIFIED DRUG;

ARTICLE; CRYSTAL STRUCTURE; DRUG POTENCY; ENZYME INHIBITION; PRIORITY JOURNAL; X RAY;

EID: 0141868737     PISSN: 0006291X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bbrc.2003.09.114     Document Type: Article

References (33)

1. Morgan D.O. Cyclin-dependent kinases: engines, clocks, and microprocessors. Annu. Rev. Cell Dev. Biol. 13:1997;261-291.
2. Pines J. Cyclin from sea urchins to HeLas: making the human cell cycle. Biochem. Soc. Trans. 24:1996;15-33.
3. Nigg E.A. Cyclin-dependent protein kinases: key regulators of the eukaryotic cell cycle. Bioessays. 17:1995;471-480.
4. N. Olashaw, W.J. Pledger, Paradigms of growth control: relation to cdk activation, Science's Stke [Electronic Resource]: Signal Transduction Knowledge Environment, 2002 (2002) RE7.
5. Sherr C.J., Roberts J.M. Cdk inhibitors: positive and negative regulators of G1-phase progression. Genes Dev. 13:1999;1501-1512.
6. Pines J. Four-dimensional control of the cell cycle. Nat. Cell Biol. 1:1999;E73-E79.
7. Shapiro G.I., Harper J.W. Anticancer drug targets: cell cycle and checkpoint control. J. Clin. Invest. 104:1999;1645-1653.
8. Garrett M.D., Fattaey A. Cdk inhibition and cancer therapy. Curr. Opin. Genet. Dev. 9:1999;104-111.
9. Mettey Y., Gompel M., Thomas V., Garnier M., Leost M., Ceballos-Picot I., Noble M., Endicott J., Vierfond J.M., Meijer L. Aloisines, a new family of cdk/gsk-3 inhibitors. SAR study, crystal structure in complex with cdk2, enzyme selectivity, and cellular effects. J. Med. Chem. 46:2003;222-236.
10. Ortega M.A., Montoya M.E., Zarranz B., Jaso A., Aldana I., Leclerc S., Meijer L., Monge A. Pyrazolo[3,4-b]quinoxalines. A new class of cyclin-dependent kinases inhibitors. Bioorg. Med. Chem. 10:2002;2177-2184.
11. Knockaert M., Greengard P., Meijer L. Pharmacological inhibitors of cyclin-dependent kinases. Trends Pharmacol. Sci. 23:2002;417-425.
12. Fischer P.M. Recent advances and new directions in the discovery and development of cyclin-dependent kinase inhibitors. Curr. Opin. Drug Disc. Dev. 4:2001;623-634.
13. Sielecki T.M., Boylan J.F., Benfield P.A., Trainor G.L. Cyclin-dependent kinase inhibitors: useful targets in cell cycle regulation. J. Med. Chem. 43:2000;1-18.
14. Zhai S., Senderowicz A.M., Sausville E.A., Figg W.D. Flavopiridol, a novel cyclin-dependent kinase inhibitor, in clinical development. Ann. Pharmacother. 36:2002;905-911.
15. Senderowicz A.M. The cell cycle as a target for cancer therapy: basic and clinical findings with the small molecule inhibitors flavopiridol and UCN-01. Oncologist. 7(Suppl. 3):2002;12-19.
16. Mohammadi M., McMahon G., Sun L., Tang C., Hirth P., Yeh B.K., Hubbard S.R., Schlessinger J. Structures of the tyrosine kinase domain of fibroblast growth factor receptor in complex with inhibitors. Science. 276:1997;955-960.
17. Sun L., Tran N., Tang F., App H., Hirth P., McMahon G., Tang C. Synthesis and biological evaluations of 3-substituted indolin-2-ones: a novel class of tyrosine kinase inhibitors that exhibit selectivity toward particular receptor tyrosine kinases. J. Med. Chem. 41:1998;2588-2603.
18. Sun L., Tran N., Liang C., Tang F., Rice A., Schreck R., Waltz K., Shawver L.K., McMahon G., Tang C. Design, synthesis, and evaluations of substituted 3-[(3- or 4-carboxyethylpyrrol-2-yl)methylidenyl]indolin-2-ones as inhibitors of VEGF, FGF, and PDGF receptor tyrosine kinases. J. Med. Chem. 42:1999;5120-5130.
19. Sepp-Lorenzino L., Thomas K.A. Antiangiogenic agents targeting vascular endothelial growth factor and its receptors in clinical development. Expert Opin. Invest. Drugs. 11:2002;1447-1465.
20. McMahon G. VEGF receptor signaling in tumor angiogenesis. Oncologist. 5:2000;3-10.
21. Mendel D.B., Laird A.D., Smolich B.D., Blake R.A., Liang C., Hannah A.L., Shaheen R.M., Ellis L.M., Weitman S., Shawver L.K., Cherrington J.M. Development of SU5416, a selective small molecule inhibitor of VEGF receptor tyrosine kinase activity, as an anti-angiogenesis agent. Anti-Cancer Drug Des. 15:2000;29-41.
22. Toogood P.L. Cyclin-dependent kinase inhibitors for treating cancer. Med. Res. Rev. 21:2001;487-498.
23. Lane M.E., Yu B., Rice A., Lipson K.E., Liang C., Sun L., Tang C., McMahon G., Pestell R.G., Wadler S. A novel cdk2-selective inhibitor, SU9516, induces apoptosis in colon carcinoma cells. Cancer Res. 61:2001;6170-6177.
24. Rosenblatt J., De Bondt H., Jancarik J., Morgan D.O., Kim S.H. Purification and crystallization of human cyclin-dependent kinase 2. J. Mol. Biol. 230:1993;1317-1319.
25. Gray N.S., Wodicka L., Thunnissen A.M., Norman T.C., Kwon S., Espinoza F.H., Morgan D.O., Barnes G., LeClerc S., Meijer L., Kim S.H., Lockhart D.J., Schultz P.G. Exploiting chemical libraries, structure, and genomics in the search for kinase inhibitors. Science. 281:1998;533-538.
26. Lawrie A.M., Noble M.E., Tunnah P., Brown N.R., Johnson L.N., Endicott J.A. Protein kinase inhibition by staurosporine revealed in details of the molecular interaction with cdk2. Nat. Struct. Biol. 4:1997;796-801.
27. Davis S.T., Benson B.G., Bramson H.N., Chapman D.E., Dickerson S.H., Dold K.M., Eberwein D.J., Edelstein M., Frye S.V., Gampe R.T. Jr., Griffin R.J., Harris P.A., Hassell A.M., Holmes W.D., Hunter R.N., Knick V.B., Lackey K., Lovejoy B., Luzzio M.J., Murray D., Parker P., Rocque W.J., Shewchuk L., Veal J.M., Walker D.H., Kuyper L.F. Prevention of chemotherapy-induced alopecia in rats by cdk inhibitors. Science. 291:2001;134-137.
28. De Bondt H.L., Rosenblatt J., Jancarik J., Jones H.D., Morgan D.O., Kim S.H. Crystal structure of cyclin-dependent kinase 2. Nature. 363:1993;595-602.
29. Jeffrey P.D., Russo A.A., Polyak K., Gibbs E., Hurwitz J., Massague J., Pavletich N.P. Mechanism of cdk activation revealed by the structure of a cyclinA-cdk2 complex. [comment]. Nature. 376:1995;313-320.
30. Davies T.G., Pratt D.J., Endicott J.A., Johnson L.N., Noble M.E. Structure-based design of cyclin-dependent kinase inhibitors. Pharmacol. Ther. 93:2002;125-133.
31. Bramson H.N., Corona J., Davis S.T., Dickerson S.H., Edelstein M., Frye S.V., Gampe R.T. Jr., Harris P.A., Hassell A., Holmes W.D., Hunter R.N., Lackey K.E., Lovejoy B., Luzzio M.J., Montana V., Rocque W.J., Rusnak D., Shewchuk L., Veal J.M., Walker D.H., Kuyper L.F. Oxindole-based inhibitors of cyclin-dependent kinase 2 (cdk2): design, synthesis, enzymatic activities, and X-ray crystallographic analysis. J. Med. Chem. 44:2001;4339-4358.
32. Sausville E.A. Complexities in the development of cyclin-dependent kinase inhibitor drugs. Trends Mol. Med. 8:2002;S32-S37.
33. Ikuta M., Kamata K., Fukasawa K., Honma T., Machida T., Hirai H., Suzuki-Takahashi I., Hayama T., Nishimura S. Crystallographic approach to identification of cyclin-dependent kinase 4 (cdk4)-specific inhibitors by using cdk4 mimic cdk2 protein. J. Biol. Chem. 276:2001;27548-27554.