Manipulation of kinetic profiles in 2-aryl propionic acid cyclooxygenase inhibitors

Bioorganic and Medicinal Chemistry Letters

Volumn 14, Issue 3, 2004, Pages 667-671

  Gupta, Kushol ^a,b   Kaub, Carl J ^c   Carey, Kristen N ^c   Casillas, Eduard G ^c   Selinsky, Barry S ^c   Loll, Patrick J ^a  

^a DREXEL UNIVERSITY COLLEGE OF MEDICINE   (United States)

^b UNIVERSITY OF PENNSYLVANIA   (United States)

^c VILLANOVA UNIVERSITY   (United States)

Author keywords

Flurbiprofen; Ibuprofen; NSAIDS; Slow tight binding inhibitors

Indexed keywords

AMIDE; CARBOXYLIC ACID; ESTER; FLURBIPROFEN; IBUPROFEN; NONSTEROID ANTIINFLAMMATORY AGENT; PROPIONIC ACID DERIVATIVE; PROSTAGLANDIN SYNTHASE INHIBITOR;

ARTICLE; CHEMICAL MODIFICATION; CRYSTAL STRUCTURE; DRUG BINDING; HALOGENATION; KINETICS; POLYACRYLAMIDE GEL ELECTROPHORESIS;

EID: 0346556196     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2003.11.034     Document Type: Article

References (27)

1. Breitner J.C. Annu. Rev. Med. 47:1996;401.
2. DuBois R.N. Progress in Experimental Tumor Research. 37:2003;124.
3. Smith W.L., DeWitt D.L., Garavito R.M. Annu. Rev. Biochem. 69:2000;145.
4. Dannhardt G., Kiefer W. Eur. J. Med. Chem. 36:2001;109.
5. Morrison J.F., Walsh C.T. Adv. Enz. Relat. Areas Mol. Biol. 61:1988;201.
6. Kulmacz R.J., Lands W.E.M. J. Biol. Chem. 260:1985;12572.
7. Rome L.H., Lands W.E.M. Proc. Natl. Acad. Sci. U.S.A. 72:1975;4863.
8. Marnett L.J. Prostaglandins and Other Lipid Mediators. 68-69:2002;153.
9. Copeland R.A., Williams J.M., Biannaras J., Nurnberg S., Covington M., Pinto D., Pick S., Trzaskos J.M. Proc. Natl. Acad. Sci. U.S.A. 91:1994;11202.
10. Gierse J.K., Koboldt C.M., Walker M.C., Seibert K., Isakson P.C. Biochem. J. 339:1999;607.
11. Ouellet M., Percival M.D. Biochem. J. 306:1995;247.
12. Picot D., Loll P.J., Garavito R.M. Nature. 367:1994;243.
13. 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. 384:1996;644.
14. Selinsky B.S., Gupta K., Sharkey C.T., Loll P.J. Biochemistry. 40:2001;5172.
15. Kozak K.R., Prusakiewicz J.J., Rowlinson S.W., Marnett L.J. Bioorg. Med. Chem. Lett. 12:2002;1315.
16. Kalgutkar A.S., Marnett A.B., Crews B.C., Remmel R.P., Marnett L.J. J. Med. Chem. 43:2000;2860.
17. Kalgutkar A.S., Rowlinson S.W., Crews B.C., Marnett L.J. Bioorg. Med. Chem. Lett. 12:2002;521.
18. Laneuville O., Breuer D.K., DeWitt D.L., Hla T., Funk C.D., Smith W.L. J. Pharm. Exp. Ther. 271:1995;927.
19. Mevkh A.T., Sud'ina G.F., Golub N.B., Varfolomeev S.D. Anal. Biochem. 150:1985;91.
20. Kulmacz, R. J.; Lands, W. E. M. In Prostaglandins and Related Substances, A Practical Approach; Benedetto, C.; McDonald-Gibson, R. G.; Nigam, S.; Slater, T. F. Eds.; IRL Press: Washington, DC, 1987; pp 209.
21. Gupta, K.; Selinsky, B. S.; Kaub, C. J.; Katz, A. K.; Loll, P. J. J. Mol. Biol. 2003, in press.
22. Blicke F.F., Grier N. J. Am. Chem. Soc. 65:1943;1725.
23. Loll P.J., Picot D., Ekabo O., Garavito R.M. Biochemistry. 35:1996;7330.
24. Callan O.H., So O.Y., Swinney D.C. J. Biol. Chem. 271:1996;3548.
25. Rowlinson S.W., Kiefer J.R., Prusakiewicz J., Pawlitz J.L., Kozak K.R., Kalgutkar A.S., Stallings W.C., Kurumbail R.G., Marnett L.J. J. Biol. Chem. 278:2003;45763.
26. Kalgutkar A.S., Crews B.C., Rowlinson S.W., Marnett A.B., Kozak K.R., Remmel R.P., Marnett L.J. Proc. Natl. Acad. Sci. U.S.A. 97:2000;925.
27. Cignarella G., Curuzu M.M., Grella G., Loriga M., Anania V., Desole M.S. Farmaco [Sci]. 28:1983;187.