Oxidation of tienilic acid by human yeast-expressed cytochromes P-450 2C8, 2C9, 2C18 and 2C19. Evidence that this drug is a mechanism-based inhibitor specific for cytochrome P-450 2C9

European Journal of Biochemistry

Volumn 241, Issue 3, 1996, Pages 797-804

  Jean, Pascale ^a   Lopez Garcia, Pilar ^b   Dansette, Patrick ^a   Mansuy, Daniel ^a   Goldstein, Joyce L ^c  

^a CNRS   (France)

^b UNIVERSITY OF VALENCIA   (Spain)

^c Natl Institutes Environ Hlth Sci   (United States)

Author keywords

Covalent binding; Cytochromes P 450 2C; Ionic strength; Suicide inhibition; Tienilic acid

Indexed keywords

CYTOCHROME P450; ISOENZYME; RECOMBINANT PROTEIN; TIENILIC ACID;

ARTICLE; CONTROLLED STUDY; COVALENT BOND; DRUG HYDROXYLATION; DRUG METABOLISM; ENZYME ACTIVITY; ENZYME BINDING; ENZYME INDUCTION; ENZYME ISOLATION; GENE EXPRESSION; HUMAN; HUMAN TISSUE; IONIC STRENGTH; LIVER; LIVER MICROSOME; MALE; PRIORITY JOURNAL; YEAST;

FELIS CATUS;

EID: 0029910243     PISSN: 00142956     EISSN: None     Source Type: Journal    
DOI: 10.1111/j.1432-1033.1996.00797.x     Document Type: Article

References (33)

1. Beaune, P. H., Dansette, P. M., Mansuy, D., Kiffel, L., Finck, M., Amar, C., Leroux, J. P. & Homberg, J. C. (1987) Proc. Natl Acad. Sci. USA 84, 551-555.
2. Bellamine, A., Gauthier, J. C., Urban, P. & Pompon, P. (1994) Eur. J. Biochem. 225, 1005-1013.
3. Brian, W. R., Srivastava, P. K., Umbenhauer, D. R., Lloyd, S. R. & Guengerich, F. P. (1989) Biochemistry 28, 4993-4999.
4. Correia, M. A. (1995) in Cytochrome P450, structure, mechanism and biochemistry (de Montellano, P. O. R., ed.) pp. 607-630. Plenum Press, New York.
5. Dansette, P. M., Amar, C., Valadon, P., Pons, C., Beaune, P. & Mansuy, D. (1991) Biochem. Pharmacol. 41, 553-560.
6. Ged, C., Umbenhauer, D., Bellew, T., Bork, R., Srivastava, P., Shinriki, N., Lloyd, R. S. & Guengerich, F. P. (1988) Biochemistry 27, 6929.
7. Gemzik, B., Halvorson, M & Parkinson, A. (1990) J. Biochem. 35, 429-440.
8. Goldstein, J. A. & de Morais, S. M. F. (1994a) Pharmacogenetics 4, 285-299.
9. Goldstein, J. A., Faletto, M. B., Romkes-Sparks, M., Sullivan, T., Kitareewan, S., Rancy, J. L., Lasker, J. M. & Ghonayem, B. I. (1994b) Biochemistry 33, 1743-1752.
10. Guengerich, F. P. (1995) in Cytochrome P-450, structure, mechanism and biochemistry (de Montellano, P. O. R., ed.) pp. 473-536. Plenum Press, New-York.
11. Kaminsky, L. S., de Morais, S. M. K. Faletto, M. B., Dunbar, D. A. & Goldstein, J. A. (1992) Mol. Pharmacol. 43, 234-239.
12. Kedzie, K., Philpot, R. & Halpert, J. (1991) Arch. Biochem. Biophys. 291, 176-186.
13. Lecœur, S., Bonierbale, F., Challine, D., Gautier, J. C., Valadon, P., Dansette, P. M., Mansuy, D. & Beaune, P. H. (1994) Chem. Res. Toxicol. 7, 434-442.
14. Lopez-Garcia, P., Dansette, P. M., Valadon, P., Amar, C., Beaune, P. H., Guengerich, F. P. & Mansuy, D. (1993) Eur. J. Biochem. 213, 223-232.
15. Lopez-Garcia, P., Dansette, P. M. & Mansuy, D. (1994) Biochemistry 33, 166-175.
16. Lowry, O. H., Rosebrough, N. J., Farr, A. L. & Randall, R. J. (1951) J. Biol. Chem. 193, 265-275.
17. Mancy, A., Broto, P., Dijols, S., Dansette, P. M. & Mansuy, D. (1995) Biochemistry 34, 10 365-10 375.
18. Mansuy, D., Valadon, P., Erdelmeier, I., Lopez-Garcia, M. P., Amar, C., Girault, J. P. & Dansette, P. M. (1991) J. Am. Chem. Soc. 113, 7825-7826.
19. Miners, J. O., Kerry, J. S., Robson, R. A., Veronese, M. K. & Birkett, D. J. (1988) Biochem. Pharmacol. 37, 1137-1144.
20. Neau, K., Dansette, P. M., Andronik, V. & Mansuy, D. (1991) Biochem. Pharmacol. 39, 1101-1107.
21. Omura, T. & Sato, P. (1964) J. Biol. Chem. 239, 2370-2378.
22. Pernecky, S. J., Pater, T. D. & Coon, M. J. (1990) Biochem. Biophys. Res. Commun. 172, 1331-1337.
23. Relling, M. V., Aoyama, T., Gonzalez, F. J. & Meyer, U. A. (1990) J. Pharmacol. Exp. Ther. 252, 442-447.
24. Romkes, M., Faletto, M. B., Blaisdell, J. A., Raucy, J. L. & Goldstein, J. A. (1991) Biochemistry 30, 3247-3255.
25. Strobel, H. W. & Dignam, J. D. (1978) Methods. Enzymol. 52, 89-96.
26. Silverman, H. (1995) in Enzyme kinetics and mechanism (Purich, D. L., ed.) part D, pp. 240-283. Academic Press Inc., San Diego.
27. Truan, G., Cullin, C., Reisdorf, P., Urban, P. & Pompon, P. (1993) Gene (Amst.) 125, 49-55.
28. Tipton, K. F. (1989) in Design of enzyme inhibitors as drugs (Sandler, M. & Smith, H. J., eds) pp. 70-93. Oxford University Press, Oxford.
29. Urban, P., Truan, G., Bellamine, A., Laine, R., Gauthier, J. C. & Pompon, D. (1994) Drug Metab. and Drug Interact. 12, 169-200.
30. Vinay, P., Paquin, J., Lemieux, G., Gougoux, A. & Bertrand, M. (1980) Eur. J. Drug Metab. Pharmacokinet. 5, 113-125.
31. Walley, S. G. (1980) Biochem. J. 185, 771-773
32. Walsh, C. (1982) Tetrahedron 38, 871-902.
33. Yoshida, Y., Kumaoka, H. & Sato, R. (1974) J. Biochem. (Tokyo) 75, 1201-1210.