Differential inhibition of human CYP3A4 and Candida albicans CYP51 with azole antifungal agents

Chemico-Biological Interactions

Volumn 125, Issue 3, 2000, Pages 165-175

  Lamb, David C ^a   Kelly, Diane E ^a   Baldwin, Brian C ^b   Kelly, Steven L ^a  

^a ABERYSTWYTH UNIVERSITY   (United Kingdom)

^b JEALOTT S HILL RESEARCH STATION   (United Kingdom)

Author keywords

Azole; Cytochrome P450; Inhibition; Toxicity

Indexed keywords

ANTIFUNGAL AGENT; CYTOCHROME P450; CYTOCHROME P450 3A4; DICLOBUTRAZOL; GENACONAZOLE; ISOENZYME; ITRACONAZOLE; KETOCONAZOLE; STEROL 14ALPHA DEMETHYLASE; UNCLASSIFIED DRUG; UNSPECIFIC MONOOXYGENASE;

ARTICLE; CANDIDA ALBICANS; CONTROLLED STUDY; ENANTIOMER; ENZYME BINDING; ENZYME INHIBITION; HUMAN; HUMAN CELL; IN VITRO STUDY; SPECTROPHOTOMETRY; STEROL SYNTHESIS; STRUCTURE ACTIVITY RELATION;

ANTIFUNGAL AGENTS; AZOLES; CANDIDA ALBICANS; CYTOCHROME P-450 ENZYME SYSTEM; HUMANS; ISOENZYMES; MIXED FUNCTION OXYGENASES; OXIDOREDUCTASES; SPECIES SPECIFICITY; SUBSTRATE SPECIFICITY;

CANDIDA ALBICANS; SACCHAROMYCES CEREVISIAE;

EID: 0034653493     PISSN: 00092797     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0009-2797(99)00169-6     Document Type: Article

References (30)

1. Vanden Bossche H., Marichal P., Gorrens J., Bellens D., Moerells H., Janssen P.A.J. Interaction of azole derivatives with cytochrome P450 isozymes in yeast, fungi, plant and mammalian cells. Pestic. Sci. 21:1987;306-309.
2. Lamb D.C., Kelly D.E., Kelly S.L. Molecular diversity of sterol 14α-demethylase substrates in plants, fungi and humans. FEBS Lett. 425:1998;263-265.
3. Kelly S.L., Lamb D.C., Corran A.J., Baldwin B.C., Kelly D.E. Mode of action and resistance to azole antifungals associated with the formation of 14α-methylergosta-8,24(28)-dien-3β,6α-diol. Biochem. Biophys. Res. Commun. 207:1995;910-915.
4. Watson P.F., Rose M.E., Ellis S.W., England H., Kelly S.L. Defective sterol C5-6 desaturation and azole resistance: a new hypothesis for the mode of action of azole antifungals. Biochem. Biophys. Res. Commun. 164:1989;1170-1175.
5. Yoshida Y., Aoyama Y. Interaction of azole antifungal agents with cytochrome P45014DM purified from Saccharomyces cerevisiae microsomes. Biochem. Pharmacol. 36:1987;229-235.
6. Feldman D. Ketoconazole and other imidazole derivatives as inhibitors of steroidogenesis. Endocr. Rev. 7:1986;409-420.
7. Kraemer F.B., Spilman S.D. Effects of ketoconazole on cholesterol synthesis. J. Pharmacol. Exp. Ther. 238:1986;905-911.
8. Trzaskos J.M., Henry M.J. Comparative effects of the azole-based fungicide flusilazole on yeast and mammalian lanosterol 14α-methyl demethylase. Antimicrob. Agents Chemother. 33:1989;1228-1231.
9. Kelly S.L., Lamb D.C., Kelly D.E., Loeffler J., Einsele H. Resistance to fluconazole and amphotericin in Candida albicans from AIDS patients. Lancet. 348:1996;1523-1524.
10. Miettinen T.A. Cholesterol metabolism during ketoconazole treatment in man. J. Lipid Res. 29:1988;43-51.
11. Guengerich F.P., Martin M.V., Beaunne P.H., Kremers P., Wolff T., Waxman D.J. Characterisation of rat and human liver microsomal cytochrome P450 forms involved in nifedipine oxidation, a prototype for genetic polymorphism in oxidative drug metabolism. J. Biol. Chem. 261:1986b;5051-5060.
12. Bargetzi M.J., Aoyama T., Gonzalez F.J., Meyer U.A. Lidocaine metabolism in human liver microsomes by cytochrome P450IIIA4. Clin. Pharmacol. Ther. 46:1989;521-527.
13. Aoyama T., Yamano S., Waxman D.J., Lapenson D.P., Meyer U.A., Fischer V., Tyndale R., Inaba T., Kalow W., Gelboin H.V., Gonzalez F.J. Cytochrome P450 hpCN3, a novel cytochrome P450 IIIA gene product that is differentially expressed in adult human liver: Complementary DNA and deduced amino acid sequence and distinct specifities of complementary DNA-expressed hpCN1 and hpCN3 for the metabolism of steroid hormones and cyclosporine. J. Biol. Chem. 264:1989;10388-10395.
14. Renaud J.P., Cullin C., Pompon D., Beaune P., Mansuy D. Expression of human liver cytochrome P450 IIIA4 in yeast. A functional model for the hepatic enzyme. Eur. J. Biochem. 194:1990;889-896.
15. Guengerich F.P. Characterisation of human microsomal cytochrome P450 enzymes. Annu. Rev. Pharmacol. Toxicol. 29:1989b;241-264.
16. 22-desaturase. FEBS Lett. 377:1995;217-220.
17. Kelly S.L., Rowe J., Watson P.F. Molecular genetic studies on the mode of action of azole antifungal agents. Biochem. Soc. Trans. 19:1991;796-798.
18. Guengerich F.P., Brian W.R., Sari M.A., Ross J.T. Expression of mammalian cytochrome P450 enzymes using yeast-based vectors. Methods Enzymol. 206:1991;130-145.
19. Ito H., Fukuda Y., Murata K., Kimura A. Transformation of intact yeast cells treated with alkali cations. J. Bacteriol. 153:1983;163-168.
20. Omura T., Sato R. The carbon monoxide binding pigment of liver microsomes. I. Evidence for its haemoprotein nature. J. Biol. Chem. 239:1964;2370-2378.
21. Wiggins T., Baldwin B.C. Binding of azole fungicides related to diclobutrazol to cytochrome P450. Pestic. Sci. 15:1984;206-209.
22. Vanden Bossche H., Marichal P., Odds F.C., Le Jeune L., Coene M.C. Characterisation of an azole resistant Candida glabrata isolate. Antimicrob. Agents Chemother. 36:1992;2602-2610.
23. Ballard S.A., Ellis S.W., Kelly S.L., Troke P.F. A novel method for studying ergosterol biosynthesis by a cell-free preparation of Aspergillus fumigatus and its inhibition by azole antifungal agents. J. Med. Vet. Mycol. 28:1990;335-344.
24. Nebert D.W., Gelboin H.V. Substrate-inducible microsomal aryl hydroxylase in mammalian cell culture. I. Assay and properties of induced enzyme. J. Biol. Chem. 243:1968;6242-6249.
25. S.L. Kelly, D.C. Lamb, B.C. Baldwin, D.E. Kelly, P450 and azole tolerance in fungi. In: M.C. Lechner (ed.), Proceedings of the Cytochrome P450 8th International Conference, John Libbey Eurotext, Paris, 1994, pp. 209-212.
26. Jefcoate C.R., Gaylor J.L., Calabrese R.L. Ligand interactions with cytochrome P-450. I. Binding of primary amines. Biochemistry. 8:1969;3455-3463.
27. Kelly S.L., Arnoldi A., Kelly D.E. Molecular genetic analysis of azole antifungal mode of action. Biochem. Soc. Trans. 21:1993;1034-1038.
28. Lamb D.C., Kelly D.E., Baldwin B.C., Gozzo F., Boscott P., Richards W.G., Kelly S.L. Differential inhibition of Candida albicans CYP51 with azole antifungal stereoisomers. FEMS Microbiol. Lett. 149:1997;25-30.
29. Boscott P.E., Grant G.H. Modeling cytochrome P450 14α-demethylase (Candida albicans) from P450cam. J. Mol. Graph. 12:1994;185-195.
30. Lamb D.C., Kelly D.E., Waterman M.R., Stromstadt M., Rozman D., Kelly S.L. Characterisitics of the heterologously expressed human lanosterol 14α-demethylase (P45014DM, CYP51) and inhibition of the purified human and Candida albicans P45014DM with azole antifungal agents. Yeast. 15:1999;755-763.