In vitro metabolism of acitretin by human liver microsomes: Evidence of an acitretinoyl-coenzyme A thioester conjugate in the transesterification to etretinate

Biochemical Pharmacology

Volumn 60, Issue 4, 2000, Pages 507-516

  Knights, Kathleen M ^a   Gasser, Rodolfo ^b   Klemisch, Wolfgang ^b  

^a Faculty of Health Sciences   (Australia)

^b F HOFFMANN LA ROCHE LTD   (Switzerland)

Author keywords

Acitretin; Acitretinoyl CoA; Conjugation; Etretinate; Human liver microsomes; Transesterification

Indexed keywords

ADENOSINE TRIPHOSPHATE; ALCOHOL; ALCOHOL DERIVATIVE; COENZYME A; ETRETIN; ETRETINATE;

ARTICLE; CONJUGATE; CONTROLLED STUDY; DRUG METABOLISM; ESTERIFICATION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HUMAN; HUMAN TISSUE; HYDROLYSIS; IN VITRO STUDY; LIQUID CHROMATOGRAPHY; LIVER MICROSOME; MASS SPECTROMETRY; PRIORITY JOURNAL; THIN LAYER CHROMATOGRAPHY;

ACETALDEHYDE; ACETATES; ACITRETIN; ACYL COENZYME A; COENZYME A LIGASES; ESTERIFICATION; ETHANOL; ETRETINATE; HUMANS; MICROSOMES, LIVER; REPRESSOR PROTEINS; SACCHAROMYCES CEREVISIAE PROTEINS;

EID: 0034664222     PISSN: 00062952     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0006-2952(00)00339-7     Document Type: Article

References (35)

1. Wiegand U.W., Jensen B.K. Pharmacokinetics of acitretin in humans. Saurat J.H. Retinoids 10 Years On . 1991;192-203 Karger, Basel.
2. Chou RC, Wyss R, Huselton CA and Wiegand UW, A newly discovered xenobiotic metabolic pathway: Ethyl ester formation. Life Sci 49: PL 169-172, 1991.
3. Chou R.C., Wyss R., Huselton C.A., Wiegand U.W. A potentially new metabolic pathway Ethyl esterification of acitretin . Xenobiotica. 22:1992;993-1002.
4. Laugier J.P., de Sousa G., Bun H., Geiger J.M., Surber C., Rahmani R. Acitretin biotransformation into etretinate Role of ethanol on in vitro hepatic metabolism . Dermatology. 188:1994;122-125.
5. Schmitt-Hoffmann AH, Dittrich S, Saulnier E, Schenk P and Chou RC, Mechanistic studies on the ethyl esterification of acitretin by human liver preparations in vitro. Life Sci 57: PL 407-412, 1995.
6. Knights K.M. Role of hepatic fatty acid:coenzyme A ligases in the metabolism of xenobiotic carboxylic acids. Clin Exp Pharmacol Physiol. 25:1998;776-782.
7. Skare K.L., Schnoes H.K., DeLuca H.F. Biliary metabolites of all-trans-retinoic acid in the rat Isolation and identification of a novel polar metabolite . Biochemistry. 21:1982;3308-3317.
8. Miller D.A., DeLuca H.F. Activation of retinoic acid by coenzyme A for the formation of ethyl retinoate. Proc Natl Acad Sci USA. 82:1985;6419-6422.
9. Alleryani S., Kabakibi A., Cluette-Brown J., Laposata M. Fatty acid ethyl ester synthase, an enzyme for nonoxidative ethanol metabolism, is present in serum after liver and pancreatic injury. Clin Chem. 42:1996;24-27.
10. Polokoff M.A., Bell R.M. Limited palmitoyl-CoA penetration into microsomal vesicles as evidenced by a highly latent ethanol acyltransferase activity. J Biol Chem. 253:1978;7173-7178.
11. McKinnon R.A., Hall P.D., Quattrochi L.C., Tukey R.H., McManus M.E. Localization of CYP1A1 and CYP 1A2 messenger RNA in normal human liver and in hepatocellular carcinoma by in situ hybridization. Hepatology. 14:1991;848-856.
12. Krisans S.K., Mortensen R.M., Lazarow P.B. Acyl-CoA synthetase in rat liver peroxisomes Computer-assisted analysis of cell fractionation experiments . J Biol Chem. 255:1980;9599-9607.
13. Becker C.-M., Harris R.A. Influence of valproic acid on hepatic carbohydrate and lipid metabolism. Arch Biochem Biophys. 223:1983;381-392.
14. Toennies G., Kolb J.J. Techniques and reagents for paper chromatography. Anal Chem. 23:1951;823-826.
15. Knights K.M., Roberts B.J. Xenobiotic acyl-CoA formation Evidence of kinetically distinct hepatic microsomal long-chain fatty acid and nafenopin-CoA ligases . Chem Biol Interact. 90:1994;215-223.
16. Bronfman M., Morales M.N., Amigo L., Orellana A., Nunez L., Cardenas L., Hidalgo P.C. Hypolipidaemic drugs are activated to acyl-CoA esters in isolated rat hepatocytes. Biochem J. 284:1992;289-295.
17. Shirley M.A., Bennani Y.L., Boehm M.F., Breau A.P., Pathirana C., Ulm E.H. Oxidative and reductive metabolism of 9-cis-retinoic acid in the rat. Identification of 13,14-dihydro-9-cis-retinoic acid and its taurine conjugate. Drug Metab Dispos. 24:1996;293-302.
18. Marsden J.R. Lipid metabolism and retinoid therapy. Pharmacol Ther. 40:1989;55-65.
19. Roberts B.J., Knights K.M. Differential induction of rat hepatic microsomal and peroxisomal long-chain and nafenopin-CoA ligases by clofibric acid and di-(2-ethylhexyl)phthalate. Xenobiotica. 25:1995;469-476.
20. Abe T., Fujino T., Fukuyama R., Minoshima S., Shimizu N., Toh H., Suzuki H., Yamamoto T. Human long-chain acyl-CoA synthetase Structure and chromosomal location . J Biochem. 111:1992;123-128.
21. Ghosh B., Barbosa E., Singh I. Molecular cloning and sequencing of human palmitoyl-CoA ligase and its tissue specific expression. Mol Cell Biochem. 151:1995;77-81.
22. Mentlein R., Lembke B., Vik H., Berge R.K. Different induction of microsomal carboxylesterases, palmitoyl-CoA hydrolase and acyl-L-carnitine hydrolase in rat liver after treatment with clofibrate. Biochem Pharmacol. 35:1986;2727-2730.
23. Gaustad R., Johnsen H., Fonnum F. Carboxylesterases in guinea pig. A comparison of the different isoenzymes with regard to inhibition by organophosphorus compounds in vivo and in vitro. Biochem Pharmacol. 42:1991;1335-1343.
24. McCracken N.W., Blain P.G., Williams F.M. Nature and role of xenobiotic metabolizing esterases in rat liver, lung, skin and blood. Biochem Pharmacol. 45:1993;31-36.
25. Yamada J., Matsumoto I., Furihata T., Sakuma M., Suga T. Purification and properties of long-chain acyl-CoA hydrolases from the liver cytosol of rats treated with peroxisome proliferator. Arch Biochem Biophys. 308:1994;118-125.
26. Tsujita T., Okuda H. Fatty acid ethyl ester-synthesizing activity of lipoprotein lipase from rat postheparin plasma. J Biol Chem. 269:1994;5884-5889.
27. Tsujita T., Okuda H. Fatty acid ethyl ester synthase in rat adipose tissue and its relationship to carboxylesterase. J Biol Chem. 267:1992;23489-23494.
28. Bearer C.F., Gould S., Emerson R., Kinnunen P., Cook C.S. Fetal alcohol syndrome and fatty acid ethyl esters. Pediatr Res. 31:1992;492-495.
29. Mogelson S., Pieper S.J., Lange L.G. Thermodynamic bases for fatty acid ethyl ester synthase catalyzed esterification of free fatty acid with ethanol and accumulation of fatty acid ethyl esters. Biochemistry. 23:1984;4082-4087.
30. Treloar T., Madden L.J., Winter J.S., Smith J.L., de Jersey J. Fatty acid ethyl ester synthesis by human liver microsomes. Biochim Biophys Acta. 1299:1996;160-166.
31. Grigor M.R., Bell I.C. Synthesis of fatty acid esters of short-chain alcohols by an acyltransferase in rat liver microsomes. Biochim Biophys Acta. 306:1973;26-30.
32. Heith A.M., Morse C.R., Tsujita T., Volpacelli S.A., Flood J.G., Laposata M. Fatty acid ethyl ester synthase catalyzes the esterification of ethanol to cocaine. Biochem Biophys Res Commun. 208:1995;549-554.
33. Yisak W., Agurell S., Lindgren J.E., Widman M. In vivo metabolites of cannabinol identified as fatty acid conjugates. J Pharm Pharmacol. 30:1978;462-463.
34. Leighty E.G. Metabolism and distribution of cannabinoids in rats after different methods of administration. Biochem Pharmacol. 22:1973;1613-1621.
35. Leighty E.G., Fentiman A.F., Foltz R.L. Long-retained metabolites of delta9- and delta8-tetrahydrocannabinols identified as novel fatty acid conjugates. Res Commun Chem Pathol Pharmacol. 14:1976;13-28.