6α-Hydroxylation of taurochenodeoxycholic acid and lithocholic acid by CYP3A4 in human liver microsomes

Biochimica et Biophysica Acta - Molecular and Cell Biology of Lipids

Volumn 1438, Issue 1, 1999, Pages 47-54

  Araya, Zufan ^a   Wikvall, Kjell ^a  

^a Division of Biochemistry   (Sweden)

Author keywords

6 Hydroxylation; Bile acid; CYP3A4; Human liver

Indexed keywords

CYTOCHROME B5; CYTOCHROME P450; CYTOCHROME P450 INHIBITOR; LITHOCHOLIC ACID; TAUROCHENODEOXYCHOLIC ACID; TESTOSTERONE; TROLEANDOMYCIN; CYP3A PROTEIN, HUMAN; CYP3A4 PROTEIN, HUMAN; MIXED FUNCTION OXIDASE; TAURODEOXYCHOLIC ACID;

ARTICLE; CATALYSIS; CONTROLLED STUDY; ENZYME ACTIVITY; ENZYME ANALYSIS; HUMAN; HYDROXYLATION; INHIBITION KINETICS; LIVER MICROSOME; PRIORITY JOURNAL; PROTEIN EXPRESSION; BIOSYNTHESIS; GENE EXPRESSION; GENETICS; KINETICS; METABOLISM;

CYTOCHROME P-450 ENZYME SYSTEM; GENE EXPRESSION; HUMANS; HYDROXYLATION; KINETICS; LITHOCHOLIC ACID; MICROSOMES, LIVER; MIXED FUNCTION OXYGENASES; TAUROCHENODEOXYCHOLIC ACID; TAURODEOXYCHOLIC ACID;

EID: 0033583336     PISSN: 13881981     EISSN: None     Source Type: Journal    
DOI: 10.1016/S1388-1981(99)00031-1     Document Type: Article

References (34)

1. H. Danielsson, J. Gustafsson, Biochemistry of bile acids in health and disease, in: H.L. Ioachim (Ed.), Pathobiology Annual, Vol. 11, Raven Press, New York, 1981, pp. 259-298.
2. A.F. Hofmann, Bile acids, in: I.M. Arias, J.L. Boyer, N. Fausto, W.B. Jakoby, D. Schachter, D.A. Shafritz (Eds.), The Liver: Biology and Pathobiology, Raven Press, New York, 1994, pp. 677-718.
3. Araya Z., Hellman U., Hansson R. Characterisation of taurochenodeoxycholic acid 6α-hydroxylase from pig liver microsomes. Eur. J. Biochem. 231:1995;855-861.
4. Boström H. Characterisation of 6α-hydroxylation of taurochenodeoxycholic acid in pig liver. J. Lipid Res. 27:1986;807-812.
5. Almé B., Bremmelgaard A., Sjövall J., Thomassen P. Analysis of metabolic profiles of bile acids in urine using a lipophilic anion exchange and computerized gas-liquid chromatography-mass spectrometry. J. Lipid Res. 18:1977;339-362.
6. Wietholtz H., Marschall H.U., Sjövall J., Matern S. Stimulation of bile acid 6α-hydroxylation by rifampin. J. Hepatol. 24:1996;713-718.
7. Summerfield J.A., Billing B.H., Shackleton C.H.L. Identification of bile acids in the serum and urine in cholestasis. Biochem. J. 154:1976;507-516.
8. Bremmelgaard A. Bile acids in plasma of patients without kidneys. Scand. J. Clin. Lab. Invest. 43:1983;603-607.
9. Shoda J., Osuga T., Mahara R., Tohma M., Matsuura K., Tanaka N., Matsuzaki Y., Miyazak H. Altered metabolism of bile acids in cholestasis: determination of 1β- and 6α-hydroxylated metabolites. J. Chromatogr. 488:1989;315-328.
10. Shoda J., Tanaka N., Osuga T., Matsuura K K., Miyazaki H. Altered bile acid metabolism in liver disease: concurrent occurrence of C-1 and C-6 hydroxylated bile acid metabolites and their preferential excretion into urine. J. Lipid Res. 31:1990;249-259.
11. Hansson R., Wikvall K. Hydroxylations in biosynthesis and metabolism of bile acids. Catalytic properties of different forms of cytochrome P-450. J. Biol. Chem. 255:1980;1643-1649.
12. Björkhem I., Danielsson H., Wikvall K. Hydroxylations of bile acids by reconstituted systems from rat liver microsomes. J. Biol. Chem. 249:1974;6439-6445.
13. Teixeira J., Gil G. Cloning, expression and regulation of lithocholic acid 6β-hydroxylase. J. Biol. Chem. 266:1991;21030-21036.
14. 3 by isotope dilution-mass fragmentography. Clin. Chem. 25:1979;584-588.
15. Guengerich F.P., Shimada T. Oxidation of toxic and cancerogenic chemicals by human cytochrome P-450 enzymes. Chem. Res. Toxicol. 4:1991;391-407.
16. Guengerich F.P. Characterization of human cytochrome P-450 enzymes. FASEB J. 6:1992;745-748.
17. Baldvin S.J., Bloomer J.C., Smith G.J., Ayrton A.D., Clark S.E., Chenery R.J. Ketoconazole and sulfaphenazole as the respective inhibitors of P450 3A and 2C9. Xenobiotica. 25:1995;261-271.
18. Inaba J., Jurima M., Mahon W.A., Kalow W. In vitro inhibition studies of two isoenzymes of human liver cytochrome P-450: mephenytoin p-hydroxylase and sparteine monooxygenase. Drug Metab. Dispos. 13:1985;443-448.
19. Zimniak P., Holsztynska E.J., Lester R., Waxman D.J., Radominska A. Detoxification of lithocholic acid. Elucidation of the pathways of oxidative metabolism in rat liver microsomes. J. Lipid Res. 30:1989;907-918.
20. D. Trülzsch, J. Roboz, H. Green, P. Czygan, J. Rudick, F. Hutterer, F. Schaffner, H. Popper, Hydroxylation of taurolithocholate and taurodeoxycholate by human liver microsomes, in: P. Back, W. Gerock (Eds.), Bile Acids in Human Diseases, Schattauer Verlag, Stuttgart, 1972, p. 71.
21. Trülzsch D., Roboz J., Greim H., Czygan P., Rudick J., Hutterer F., Schaffner F., Popper H. Hydroxylation of taurolithocholate by isolated human liver microsomes. Biochem. Med. 9:1974;158-166.
22. Björkhem I., Einarsson K., Hellers G. Metabolism of mono- and dihydroxylated bile acids in preparations of human liver. Eur. J. Clin. Invest. 3:1973;459-465.
23. Gustafsson J., Anderson S., Sjövall J. Bile acid metabolism during development. Metabolism of lithocholic acid in human fetal liver. Pediatr. Res. 21:1987;99-103.
24. Wietholtz H., Marschall H.U., Reuschenbach R., Matern H., Matern S. Urinary excretion of bile acid glucosides and glucuronides in extrahepatic cholestasis. Hepatology. 13:1991;656-662.
25. Nakashima T., Sano A., Seto Y., Nakajima T., Shima T., Sakamoto Y., Okuno T., Kashima K., Hasegawa T. Unusual trihydroxy bile acids in the urine of patients treated with chenodeoxycholate, ursodeoxycholate, or rifampicin and those with intrahepatic cholestasis. Hepatology. 11:1990;255-260.
26. Jönsson G., Hedenborg G., Wisén O., Norman A. Presence of bile acid metabolites in serum, urine, and faeces in cirrhosis. Scand. J. Clin. Lab. Invest. 52:1992;555-564.
27. A. Radminska, P. Zimniak, J. Falany, M. Iscan, R. Lester, D.J. Waxman, Bile acid hydroxylation by human liver microsomes and vaccinia virus-expressed cytochrome P-450 hPCN1 and hPCN3, FASEB J. 4 (1990) A1972 (Abstract 1619).
28. Gad 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.
29. Guengerich F.P. Mechanism-based inactivation of human liver microsomal cytochrome P-450 IIIA4 by gestodene. Chem. Res. Toxicol. 3:1990;363-371.
30. F.P. Guengerich, Human cytochrome P450 enzymes, in: P.R. Ortiz de Montellano (Ed.), Cytochrome P450: Structure, Mechanism, and Biochemistry, Plenum Press, New York, 1995, pp. 473-535.
31. P. Maurel, The CYP3 family, in: C. Ioannides (Ed.), Cytochromes P450: Metabolic and Toxicological Aspects, CRC Press, Boca Raton, FL, 1996, pp. 241-270.
32. Waxman D.J., Attisano C., Guengerich FP 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.
33. Niwa T., Yabusaki Y., Honma K., Natsuo N., Tatsua K., Ishibashi F., Katagiri M. Contribution of human hepatic cytochrome P450 isoforms to regioselective hydroxylation of steroid hormones. Xenobiotika. 28:1998;539-547.
34. 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.