Structure-based design of COX-2 selectivity into flurbiprofen

Bioorganic and Medicinal Chemistry Letters

Volumn 9, Issue 3, 1999, Pages 307-312

  Bayly, Christopher I ^a   Black, W Cameron ^a   Léger, Serge ^a   Ouimet, Nathalie ^a   Ouellet, Marc ^a   Percival, M David ^a  

^a MERCK FROSST CENTRE FOR THERAPEUTIC RESEARCH   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOOXYGENASE 2; CYCLOOXYGENASE 2 INHIBITOR; FLURBIPROFEN; ISOENZYME;

ARTICLE; BINDING KINETICS; COMPUTER MODEL; CRYSTAL STRUCTURE; DRUG BINDING; DRUG DESIGN; DRUG SELECTIVITY; DRUG STRUCTURE; ENZYME ACTIVE SITE; ENZYME BINDING; ENZYME STRUCTURE;

BINDING SITES; CRYSTALLOGRAPHY, X-RAY; CYCLOOXYGENASE 2; CYCLOOXYGENASE 2 INHIBITORS; CYCLOOXYGENASE INHIBITORS; DRUG DESIGN; FLURBIPROFEN; HUMANS; ISOENZYMES; MEMBRANE PROTEINS; MOLECULAR STRUCTURE; PROSTAGLANDIN-ENDOPEROXIDE SYNTHASES;

EID: 0033535150     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0960-894X(98)00717-3     Document Type: Article

References (16)

1. Vane, J. R.; Botting, R. M. Inflamm. Res. 1995, 44, 1.
2. Smith, W. L.; Garavito, R. M.; DeWitt, D. L. J. Biol. Chem. 1996, 271, 33157.
3. Picot, D.; Loll, P. J.; Garavito, R. M. Nature 1994, 367, 243.
4. McKeever, B. M.; Pandya, S.; Percival, M. D.; Ouellet, M.; Bayly, C.; O'Neill, G. P.; Bastien, L.; Kennedy, B. P.; Adam, M.; Cromlish, W.; Roy, P.; Black, W. C.; Guay, D.; LeBlanc, Y., submitted for publication. Coordinates have been submitted to the Brookhaven Protein Databank with accession number 2CX2.
5. Luong, C.; Miller, A.; Barnett, J.; Chow, J.; Ramesha, C.; Browner, M. F. Nature Struc Biol. 1996, 3, 927.
6. Kurumbail, R. G.; Stevens, A. M.; Gierse, J. K.; McDonald, J. J.; Stegeman, R. A.; Pak, J. Y.; Gildehaus D.; Miyashiro, J. M.; Penning T. D.; Seibert, K.; Isakson, P. C.; Stallings, W. C. Nature 1996, 384, 644.
7. Gans, K. R.; Galbraith, W.; Roman, R. J.; Haber, S. B.; Kerr, J. S.; Schmidt, W. K.; Smith, C.; Hewes. W. E.; Ackerman, N. R. J. Pharmacol Exp. Ther. 1990, 254, 180.
8. Futaki, N.; Yoshikawa, K.; Hamasaka, Y.; Arai, I.; Higuchi, S.; Iizuka, H.; Otomo, S. Gen. Pharmacol. 1993, 24, 105.
9. Copeland, R. A.; Williams, J. M.; Giannaras, J.; Nurnberg, S.; Covington, M.; Pinto D.; Pick, S.; Trzaskos, J. M. Proc. Natl. Acad. Sci. U.S.A. 1994, 91, 11202.
10. Ouellet, M.; Percival, M. D. Biochem. J. 1995, 306, 247.
11. Molecular dynamics simulations were carried out using AMBER .1: Pearlman, D. A., Case, D. A., Caldwell, J. W., Ross, W. S., Cheatham, T. E., Ferguson, D. M., Seibel, G. L., Singh, U. C., Weiner, P. J., Kollman, P. A., AMBER 4.1, University of California, San Francisco, 1995.
12. Ma, J. C.; Dougherty, D. A. Chem. Rev. 1997, 97, 1303.
13. (a) Yamauchi, T.; Nakao, K.; Fujii, K. J. Chem. Soc. Perkin Trans. 1 1987, 1433. (b) Yamauchi, T.; Hattori, K.; Nakao, K.; Tamaki, K. J. Org. Chem. 1988, 53, 4858. (c) Fujii, K.; Nakao, K.; Yamauchi, T. Synthesis 1982, 456.
14. (a) Yamauchi, T.; Nakao, K.; Fujii, K. J. Chem. Soc. Perkin Trans. 1 1987, 1433. (b) Yamauchi, T.; Hattori, K.; Nakao, K.; Tamaki, K. J. Org. Chem. 1988, 53, 4858. (c) Fujii, K.; Nakao, K.; Yamauchi, T. Synthesis 1982, 456.
15. (a) Yamauchi, T.; Nakao, K.; Fujii, K. J. Chem. Soc. Perkin Trans. 1 1987, 1433. (b) Yamauchi, T.; Hattori, K.; Nakao, K.; Tamaki, K. J. Org. Chem. 1988, 53, 4858. (c) Fujii, K.; Nakao, K.; Yamauchi, T. Synthesis 1982, 456.
16. Farina, V.; And Roth, G. P. Tetrahedron Lett. 1991, 4243-4246.