Identification of CYP3A4 as the major enzyme responsible for 25- hydroxylation of 5β-cholestane-3α, 7α, 12α-triol in human liver microsomes

Biochimica et Biophysica Acta - Molecular and Cell Biology of Lipids

Volumn 1437, Issue 1, 1999, Pages 46-52

  Furster, Catrin ^a   Wikvall, Kjell ^a  

^a Division of Biochemistry   (Sweden)

Author keywords

12 triol; 25 Hydroxylation; 5 Cholestane 3 ; 7 ; CYP3A4

Indexed keywords

BILE ACID; CYTOCHROME B5; CYTOCHROME P450 3A4; CYTOCHROME P450 ISOENZYME; RECOMBINANT ENZYME; TRANYLCYPROMINE; UNCLASSIFIED DRUG;

ARTICLE; HUMAN; HUMAN CELL; HYDROXYLATION; LIVER MICROSOME METABOLISM; MICHAELIS CONSTANT; PRIORITY JOURNAL;

ARYL HYDROCARBON HYDROXYLASES; BILE ACIDS AND SALTS; CHOLESTANOLS; CHOLESTEROL; CYTOCHROME P-450 CYP27A1; CYTOCHROME P-450 ENZYME SYSTEM; ENZYME INHIBITORS; GAS CHROMATOGRAPHY-MASS SPECTROMETRY; HUMANS; KINETICS; MICROSOMES, LIVER; MIXED FUNCTION OXYGENASES; STEROID HYDROXYLASES; TROLEANDOMYCIN;

EID: 0033613935     PISSN: 13881981     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0005-2760(98)00175-1     Document Type: Article

References (25)

1. Björkhem I. Mechanism of degradation of the steroid side chain in the formation of bile acids. J. Lipid Res. 33:1992;455-471.
2. Shefer S., Cheng F.W., Dayal B., Hauser S., Tint G.S., Salen G., Mosbach E.S. A 25-hydroxylation pathway of cholic acid biosynthesis in man and rat. J. Clin. Invest. 57:1976;897-903.
3. Duane W.C., Pooler P.A., Hamilton J.N. Bile acid synthesis in man. J. Clin. Invest. 82:1988;82-85.
4. Oftebro H., Björkhem I., Skrede S., Schreiner A., Pedersen J.I. Cerebrotendinous anthomatosis. J. Clin. Invest. 65:1980;1418-1430.
5. Salen G., Shefer S., Tint G.S., Nicolau G., Dayal B., Batta A.K. Biosynthesis of bile acids in cerebrotendinous xanthomatosis. J. Clin. Invest. 76:1985;744-751.
6. Björkhem I., Gustafsson J., Johansson G., Persson B. Biosynthesis of bile acids in man. J. Clin. Invest. 55:1975;478-486.
7. Cronholm T., Johansson G. Oxidation of 5β-cholestane-3α,7α,12α-triol by rat liver microsomes. Eur. J. Biochem. 16:1970;373-381.
8. Wikvall K. Hydroxylations in biosynthesis of bile acids. J. Biol. Chem. 259:1984;3800-3804.
9. Lund E., Björkhem I., Furster C., Wikvall K. 24-, 25- and 27-hydroxylation of cholesterol by a purified preparation of 27-hydroxylase from pig liver. Biochim. Biophys. Acta. 1166:1993;177-182.
10. Ono S., Hatanaka T., Hotta H., Satoh T., Gonzalez F.J., Tsutsui M. Specificity of substrate and inhibitor probes for cytochrome P450s: evaluation of in vitro metabolism using cDNA-expressed human P450s and human liver microsomes. Xenobiotica. 26:1996;681-693.
11. Inaba T., Jurima M., Mahon W.A., Kalow W. In vitro inhibition studies of two isozymes of human liver cytochrome P-450. Drug. Metab. Dispos. 13:1985;443-448.
12. Wienkers L.C., Wurden C.J., Storch E., Kunze K.L., Rettie A.E., Trager W.F. Formation of (R)-8-hydroxywarfarin in human liver microsomes. Drug. Metab. Dispos. 24:1996;610-614.
13. Tassaneeyakul W., Birkett D.J., Veronese M.E., McManus M.E., Tukey R.H., Quattrochi L.C., Gelboin H.V., Miners J.O. Specificity of substrate and inhibitor probes for human cytochromes P450 1A1 and 1A2. J. Pharmacol. Exp. Ther. 265:1992;401-407.
14. Baldwin S.J., Bloomer J.C., Smith G.J., Ayrton A.D., Clarke S.E., Chenery R.J. Ketoconazole and sulphaphenazole as the respective selective inhibitors of P4503A and 2C9. Xenobiotica. 25:1995;261-270.
15. Guengerich F.P. Mechanism-based inactivation of human liver microsomal cytochrome P-450 IIIA4 by gestodene. Chem. Res. Toxicol. 3:1990;363-371.
16. F.P. Guengerich, Human cytochrome P450 enzymes, in: P.R. Ortiz de Montellano (Ed.), Cytochrome P450: Structure, Mechanism, and Biochemistry, Plenum, New York, 1995, pp. 473-535.
17. P. Maurel, The CYP3 family, in: C. Ioannides (Ed.), Cytochromes P450: Metabolic and Toxicological Aspects, CRC Press, Boca Raton, FL, 1996, pp. 241-270.
18. Waxman D.J., Attisano C., Guengerich F.P., Lapenson D.P. Human liver microsomal steroid metabolism: Identification of the major microsomal steroid hormone 6β-hydroxylase cytochrome P-450 enzyme. Arch. Biochem. Biophys. 263:1988;424-436.
19. Niwa T., Yabusaki Y., Honma K., Matsuo N., Tatsua K., Ishibashi F., Katagiri M. Contribution of human hepatic cytochrome P450 isoforms to regioselective hydroxylation of steroid hormones. Xenobiotica. 28:1998;539-547.
20. Kerlan V., Dreano Y., Bercovici J.P., Beaune P.H., Floch H.H., Berthou F. Nature of cytochromes P450 involved in the 2-/4-hydroxylations of estradiol in human liver microsomes. Biochem. Pharmacol. 44:1992;1745-1756.
21. Ged C., Rouillon J.M., Pichard L., Combalbert J., Bressot N., Bories P., Michel H., Beaune P., Maurel P. The increase in urinary excretion of 6β-hydroxycortisol as a marker of human hepatic cytochrome P450IIIA induction. Br. J. Clin. Pharmacol. 28:1989;373-387.
22. Salen G., Shefer S., Cheng F.W., Dayal B., Batta A.K., Tint G.S. Cholic acid biosynthesis. J. Clin. Invest. 63:1978;38-44.
23. Hanson R.F., Staples A.B., Williams G.C. Metabolism of 5β-cholestane-α,7α,12α,26-tetrol and 5β-cholestane-3α,7α,12α,25-tetrol into cholic acid in normal human subjects. J. Lipid Res. 20:1979;489-493.
24. Holmberg Betsholtz I., Wikvall K. Studies on sterol 27-hydroxylase-catalyzed oxidation of 5β-cholestane-3α,7α,12α-triol into 3α,7α,12α-trihydroxy-5β-cholestanoic cid. J. Steroid Biochem. Mol. Biol. 55:1995;115-119.
25. P. Zimniak, D.J. Waxman, Liver cytochrome P450 metabolism of endogenous steroid hormones, bile acids, and fatty acids, in: J.B. Schenkman, H. Greim (Eds.), Handbook of Experimental Pharmacology, vol. 105 Springer, Berlin, 1993, pp. 123-144.