Electrophilic fragment-based design of reversible covalent kinase inhibitors

Journal of the American Chemical Society

Volumn 135, Issue 14, 2013, Pages 5298-5301

  Miller, Rand M ^b   Paavilainen, Ville O ^a   Krishnan, Shyam ^a   Serafimova, Iana M ^b   Taunton, Jack ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

^b UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

COCRYSTAL STRUCTURE; INDAZOLE; KINASE DOMAINS; KINASE INHIBITORS; LIGAND DESIGN; NANOMOLAR CONCENTRATION; NON-CATALYTIC;

AMINO ACIDS; LIGANDS; TRANSCRIPTION FACTORS;

ENZYMES;

CYCLIC AMP RESPONSIVE ELEMENT BINDING PROTEIN; CYSTEINE; INDAZOLE DERIVATIVE; PHOSPHOTRANSFERASE INHIBITOR; THIOL DERIVATIVE;

ARTICLE; CARBOXY TERMINAL SEQUENCE; CONCENTRATION (PARAMETERS); COVALENT BOND; CRYSTAL STRUCTURE; ELECTROPHILICITY; HIGH THROUGHPUT SCREENING; HYDROGEN BOND; HYDROPHOBICITY; MOLECULAR WEIGHT; PROTEIN DOMAIN; PROTEIN PHOSPHORYLATION; STRUCTURE ACTIVITY RELATION;

ACRYLAMIDE; CYSTEINE; DOSE-RESPONSE RELATIONSHIP, DRUG; HUMANS; LIGANDS; MODELS, MOLECULAR; MOLECULAR STRUCTURE; PROTEIN KINASE INHIBITORS; RIBOSOMAL PROTEIN S6 KINASES, 90-KDA; STRUCTURE-ACTIVITY RELATIONSHIP; SULFHYDRYL COMPOUNDS;

EID: 84876016325     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja401221b     Document Type: Article

References (24)

1. Erlanson, D. A.; McDowell, R. S.; O'Brien, T. J. Med. Chem. 2004, 47, 3363-3482
2. Howard, S.; Berdini, V.; Boulstridge, J. A.; Carr, M. G.; Cross, D. M.; Curry, J.; Devine, L. A.; Early, T. R.; Fazal, L.; Gill, A. L.; Heathcote, M.; Maman, S.; Matthews, J. E.; McMenamin, R. L.; Navarro, E. F.; O'Brien, M. A.; O'Reilly, M.; Rees, D. C.; Reule, M.; Tisi, D.; Williams, G.; Vinković, M.; Wyatt, P. G. J. Med. Chem. 2009, 52, 379-388
3. Bamborough, P.; Brown, M. J.; Christopher, J. A.; Chung, C.; Mellor, G. W. J. Med. Chem. 2011, 54, 5131-5143
4. Hann, M. M.; Leach, A. R.; Harper, G. J. Chem. Inf. Comput. Sci. 2001, 41, 856-864
5. Potashman, M. H.; Duggan, M. E. J. Med. Chem. 2009, 52, 1231-1246
6. Fry, D. W.; Bridges, A. J.; Denny, W. A.; Doherty, A.; Greis, K. D.; Hicks, J. L.; Hook, K. E.; Keller, P. R.; Leopold, W. R.; Loo, J. A.; McNamara, D. J.; Nelson, J. M.; Sherwood, V.; Smaill, J. B.; Trump-Kallmeyer, S.; Dobrusin, E. M. Proc. Natl. Acad. Sci. U.S.A. 1998, 95, 12022-12027
7. Hagel, M.; Niu, D.; St. Martin, T.; Sheets, M. P.; Qiao, L.; Bernard, H.; Karp, R. M.; Zhu, Z.; Labenski, M. T.; Chaturvedi, P.; Nacht, M.; Westlin, W. F.; Petter, R. C.; Singh, J. Nat. Chem. Biol. 2011, 7, 22-24
8. Zhang, J.; Yang, P. L.; Gray, N. S. Nat. Rev. Cancer 2009, 9, 28-39
9. Leproult, E.; Barluenga, S.; Moras, D.; Wurtz, J. M.; Winssinger, N. J. Med. Chem. 2011, 54, 1347-1355
10. Serafimova, I. M.; Pufall, M. A.; Krishnan, S.; Duda, K.; Cohen, M. S.; Maglathlin, R. L.; McFarland, J. M.; Miller, R. M.; Frödin, M.; Taunton, J. Nat. Chem. Biol. 2012, 8, 471-476
11. Deak, M.; Clifton, A. D.; Lucocq, J. M.; Alessi, D. R. EMBO J. 1998, 17, 4426-4441
12. McCoy, C. E.; Campbell, D. G.; Deak, M.; Bloomberg, G. B.; Arthur, J. S. C. Biochem. J. 2005, 387, 507-517
13. Wiggin, G. R.; Soloaga, A.; Foster, J. M.; Murray-Tait, V.; Cohen, P.; Arthur, J. S. C. Mol. Cell. Biol. 2002, 22, 2871-2881
14. Odgerel, T.; Kikuchi, J.; Wada, T.; Shimizu, R.; Kano, Y.; Furukawa, Y. Leukemia 2010, 24, 1087-1090
15. Pérez-Cadahía, B.; Drobic, B.; Espino, P. S.; He, S.; Mandal, S.; Healy, S.; Davie, J. R. J. Biol. Chem. 2010, 286, 42-49
16. van der Heide, L. P.; van Dinther, M.; Moustakas, A.; ten Dijke, P. J. Biol. Chem. 2011, 286, 5003-5011
17. Naqvi, S.; Macdonald, A.; McCoy, C. E.; Darragh, J.; Reith, A. D.; Arthur, J. S. C. Biochem. J. 2012, 441, 347-357
18. Zhu, G.; Gandhi, V. B.; Gong, J.; Thomas, S.; Woods, K. W.; Song, X.; Li, T.; Diebold, R. B.; Luo, Y.; Liu, X.; Guan, R.; Klinghofer, V.; Johnson, E. F.; Bouska, J.; Olson, A.; Marsh, K.; Stoll, V. S.; Mamo, M.; Polakowski, J.; Campbell, T. J.; Martin, R. L.; Gintant, G. A.; Penning, T. D.; Li, Q.; Rosenberg, S. H.; Giranda, V. L. J. Med. Chem. 2007, 50, 2990-3003
19. McTigue, M.; Murray, B. W.; Chen, J. H.; Deng, -L; Solowiej, J.; Kania, R. S. Proc. Natl. Acad. Sci. U.S.A. 2012, 109, 18281-18269
20. Patel, R. Y.; Doerksen, R. J. J. Proteome Res. 2010, 9, 4433-4442
21. Guimarães, C. R. W.; Rai, B. K.; Munchof, M. J.; Liu, S.; Wang, J.; Bhattacharya, S. K.; Buckbinder, L. J. Chem. Inf. Model. 2011, 51, 1199-1204
22. Weerapana, E.; Wang, C.; Simon, G. M.; Richter, F.; Khare, S.; Dillon, M. B. D.; Bachovchin, D. A.; Mowen, K.; Baker, D.; Cravatt, B. F. Nature 2010, 468, 790-795
23. Nonoo, R. H.; Armstrong, A.; Mann, D. J. ChemMedChem. 2012, 7, 2082-2086
24. Erlanson, D. A.; Braisted, A. C.; Raphael, D. R.; Randal, M.; Stroud, R. M.; Gordon, E. M.; Wells, J. A. Proc. Natl. Acad. Sci. U.S.A. 2000, 97, 9367-9372