Increased toxicity of cocaine on human hepatocytes induced by ethanol: Role of GSH

Biochemical Pharmacology

Volumn 58, Issue 10, 1999, Pages 1579-1585

  Ponsoda, Xavier ^a,b   Bort, Roque ^a,b   Jover, Ramiro ^a,b   Gómez Lechón, María José ^a   Castell, José V ^a,b  

^a HOSPITAL UNIVERSITARIO LA FE   (Spain)

^b UNIVERSITY OF VALENCIA   (Spain)

Author keywords

Cocaine, cocaethylene; Ethanol; GSH; Human hepatocytes; Toxicity

Indexed keywords

ALCOHOL; COCAINE;

ALCOHOL ABUSE; ARTICLE; CONTROLLED STUDY; DRUG ABUSE; HUMAN; HUMAN CELL; LIVER CELL; LIVER TOXICITY; PRIORITY JOURNAL; TOXICITY TESTING;

AGED; CELL SURVIVAL; CELLS, CULTURED; COCAINE; DOPAMINE UPTAKE INHIBITORS; DRUG SYNERGISM; ETHANOL; FEMALE; GLUTATHIONE TRANSFERASE; HUMANS; LIVER; MALE; MIDDLE AGED; OXIDATIVE STRESS;

EID: 0032880904     PISSN: 00062952     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0006-2952(99)00249-X     Document Type: Article

References (48)

1. Kloss M.W., Rosen G.M., Rauckman E.J. Cocaine-mediated hepatotoxicity A critical review . Biochem Pharmacol. 33:1984;169-173.
2. Perino L.E., Warren G.H., Levine J.S. Cocaine-induced hepatotoxicity in humans. Gastroenterology. 93:1987;176-180.
3. Wanless I.R., Dore S., Gopinath N., Tan J., Cameron R., Heathcote E.J., Blendis L.M., Levy G. Histopathology of cocaine hepatotoxicity Report of four patients . Gastroenterology. 98:1990;497-501.
4. McCance-Katz E.F., Price L.H., McDougle C.J., Kosten T.R., Black J.E., Jatlow P.I. Concurrent cocaine-ethanol ingestion in humans Pharmacology, physiology, behavior, and the role of cocaethylene . Psychopharmacology. 111:1993;39-46.
5. Boyer C.S., Petersen D.R. Potentiation of cocaine-mediated hepatotoxicity by acute and chronic ethanol. Alcohol Clin Exp Res. 14:1990;28-31.
6. Gorelik D.A. Alcohol and cocaine Clinical and pharmacological interactions . Recent Dev Alcohol. 10:1992;37-56.
7. Haberman P.W., Noble J.A., Dufour M.C. Alcohol use in combination with cocaine, heroin and methadone by medical examiner cases. J Stud Alcohol. 56:1995;344-347.
8. Odeleye O.E., Watson R.R., Eskelson C.D., Earnest D. Enhancement of cocaine-induced hepatotoxicity by ethanol. Drug Alcohol Depend. 31:1993;253-263.
9. Smith A.C., Freeman R.W., Harbison R.D. Ethanol enhancement of cocaine-induced hepatotoxicity. Biochem Pharmacol. 30:1981;453-458.
10. Smith D.E. Cocaine-alcohol abuse Epidemiological, diagnostic and treatment considerations . J Psychoactive Drugs. 18:1986;117-129.
11. Jover R., Ponsoda X., Gómez-Lechón M.J., Herrero C., del Pino J., Castell J.V. Potentiation of cocaine hepatotoxicity by ethanol in human hepatocytes. Toxicol Appl Pharmacol. 107:1991;526-534.
12. Boelsterli U.A., Lanzotti A., Göldlin C., Oertle M. Identification of cytochrome P-450IIB1 as a cocaine-bioactivating isoform in rat hepatic microsomes and in cultured rat hepatocytes. Drug Metab Dispos. 20:1992;96-101.
13. LeDuc B.W., Sinclair P.R., Shuster L., Sinclair J.F., Evans J.E., Greenblatt D.J. Norcocaine and N-hydroxynorcocaine formation in human liver microsomes Role of cytochrome P-450 3A4 . Pharmacology. 46:1993;294-300.
14. Pellinen P., Honkakoski P., Stenbäck F., Niemitz M., Alhava E., Pelkonen O., Lang M.A., Pasanen M. Cocaine N-demethylation and the metabolism-related hepatotoxicity can be prevented by cytochrome P450 3A inhibitors. Eur J Pharmacol. 270:1994;35-43.
15. Boelsterli U.A., Goldlin C. Biomechanisms of cocaine-induced hepatocyte injury mediated by the formation of reactive metabolites. Arch Toxicol. 65:1991;351-360.
16. Mets B., Virag L. Lethal toxicity from equimolar infusions of cocaine and cocaine metabolites in conscious and anesthetized rats. Anesth Analg. 81:1995;1033-1038.
17. Rauckman E.J., Kloss M.W., Rosen G.M. Involvement of nitroxide radicals in cocaine-induced hepatotoxicity. Can J Chem. 60:1981;1614-1620.
18. Roberts S.M., Harbison R.D., James R.C. Human microsomal N-oxidative metabolism of cocaine. Drug Metab Dispos. 19:1991;1046-1051.
19. Shuster L., Casey E., Welankiwar S.S. Metabolism of cocaine and norcocaine to N-hydroxynorcocaine. Biochem Pharmacol. 32:1983;3045-3051.
20. Jover R., Ponsoda X., Gómez-Lechón M.J., Castell J.V. Cocaine hepatotoxicity Two different toxicity mechanisms for phenobarbital-induced and non-induced rat hepatocytes . Biochem Pharmacol. 46:1993;1967-1974.
21. Boyer C.S., Petersen D.R. Enzymatic basis for the transesterification of cocaine in the presence of ethanol Evidence for the participation of microsomal carboxylesterases . J Pharmacol Exp Ther. 260:1992;939-946.
22. Brzezinski M.R., Abraham T.L., Stone C.L., Dean R.A., Bosron W.F. Purification and characterization of a human liver cocaine carboxylesterase that catalyzes the production of benzoylecgonine and the formation of cocaethylene from alcohol and cocaine. Biochem Pharmacol. 48:1994;1747-1755.
23. Dean R.A., Christian C.D., Sample R.H.B., Bosron W.F. Human liver cocaine esterases Ethanol-mediated formation of ethyl cocaine . FASEB J. 5:1991;2735-2739.
24. Dean R.A., Harper E.T., Dumaual N., Stoeckel D.A., Bosron W.F. Effects of ethanol on cocaine metabolism Formation of cocaethylene and norcocaethylene . Toxicol Appl Pharmacol. 117:1992;1-8.
25. Roberts S.M., Roth L., Harbison R.D., James R.C. Cocaethylene hepatotoxicity in mice. Biochem Pharmacol. 43:1992;1989-1995.
26. Bailey D.N. Serial plasma concentrations of cocaethylene, cocaine, and ethanol in trauma victims. J Anal Toxicol. 17:1993;79-83.
27. Farré M., De la Torre R., Llorente M., Lamas X., Ugena B., Segura J., Camí J. Alcohol and cocaine interactions in humans. J Pharmacol Exp Ther. 266:1993;1364-1373.
28. Farré M., De la Torre R., González M.L., Terán M.T., Roset P.N., Menoyo E., Camí J. Cocaine and alcohol interactions in humans Neuroendocrine effects and cocaethylene metabolism . J Pharmacol Exp Ther. 283:1997;164-176.
29. Boelsterli U.A., Wolf A., Goldlin C. Oxygen free radical production mediated by cocaine and its ethanol-derived metabolite, cocaethylene, in rat hepatocytes. Hepatology. 18:1993;1154-1161.
30. Hearn W.L., Rose S., Wagner J., Ciarleglio A., Mash D.C. Cocaethylene is more potent than cocaine in mediating lethality. Pharmacol Biochem Behav. 39:1991;531-533.
31. Roberts S.M., Harbison R.D., James R.C. Inhibition by ethanol of the metabolism of cocaine to benzoylecgonine and ecgonine methyl ester in mouse and human liver. Drug Metab Dispos. 21:1993;537-541.
32. Schechter M.D., Meehan S.M. The lethal effects of ethanol and cocaine and their combination in mice Implications for cocaethylene formation . Pharmacol Biochem Behav. 52:1995;245-248.
33. Gómez-Lechón M.J., López P., Donato T., Montoya A., Larrauri A., Giménez P., Trullenque R., Fabra R., Castell J.V. Culture of human hepatocytes from small surgical liver biopsies. Biochemical characterization and comparison with in vivo. In Vitro Cell Dev Biol. 26:1990;67-74.
34. Donato M.T., Castell J.V., Gómez-Lechón M.J. Effect of model inducers on cytochrome P450 activities of human hepatocytes in primary culture. Drug Metab Dispos. 23:1995;553-558.
35. Gómez-Lechón M.J., Donato T., Ponsoda X., Fabra R., Trullenque R., Castell J.V. Isolation, culture and use of human hepatocytes in drug research. Castell J.V., Gómez-Lechón M.J. In Vitro Methods in Pharmaceutical Research. 1997;129-153 Academic Press, San Diego.
36. Dicker E., McHugh T., Cederbaum A.I. Increased oxidation of p-nitrophenol and aniline by intact hepatocytes isolated from pyrazole-treated rats. Biochim Biophys Acta. 1035:1990;249-256.
37. Borenfreund E., Babich H., Martin-Alguacil N. Comparisons of two in vitro cytotoxicity assays The neutral red (NR) and tetrazolium MTT tests . Toxicol In Vitro. 2:1988;1-6.
38. Hissin P.J., Hilf R.A. A fluorimetric method for determination of oxidized and reduced glutathione in tissues. Anal Biochem. 74:1976;214-226.
39. Castell J.V., Gómez-Lechón M.J., Ponsoda X., Bort R. In vitro investigation of the molecular mechanisms of hepatotoxicity. Castell J.V., Gómez-Lechón M.J. In Vitro Methods in Pharmaceutical Research. 1997;375-410 Academic Press, San Diego.
40. Masugi F., Nakamura T. Measurement of thiobarbituric acid value in liver homogenate solubilized with sodium dodecyl sulphate and variation of the values affected by vitamin E and drugs. Vitamins. 51:1977;21-29.
41. Lau C.E., Ma F., Falk J.L. Simultaneous determination of cocaine and its metabolites with caffeine in rat serum microsamples by high-performance liquid chromatography. J Chromatogr. 532:1990;95-103.
42. Lloyd R.V., Shuster L., Mason R.P. Reexamination of the microsomal transformation of N-hydroxynorcocaine to norcocaine nitroxide. Mol Pharmacol. 43:1993;645-648.
43. Ndikum-Moffor F.M., Shoeb T.R., Roberts S.M. Liver toxicity from norcocaine nitroxide, an N-oxidative metabolite of cocaine. J Pharmacol Exp Ther. 284:1998;413-419.
44. Kostrubsky V.E., Strom S.C., Wood S.G., Wrighton S.A., Sinclair P.R., Sinclair J.F. Ethanol and isopentanol increase CYP3A and CYP2E in primary cultures of human hepatocytes. Arch Biochem Biophys. 322:1995;516-520.
45. Boelsterli U.A., Atanasoski S., Goldlin C. Ethanol-induced enhancement of cocaine bioactivation and irreversible protein binding Evidence against a role of cytochrome P-450IIE1 . Alcohol Clin Exp Res. 15:1991;779-784.
46. Kron J.E., Konkol R.J., Olsen G.D. In vivo pharmacokinetics and in vitro production of cocaethylene in pregnant guinea pigs. Life Sci. 58:1996;1695-1704.
47. Younes M., Strubelt O. Alcohol-induced hepatotoxicity A role for oxygen free radicals . Free Radic Res Commun. 3:1987;19-26.
48. Lieber C.S. Ethanol metabolism, cirrhosis and alcoholism. Clin Chim Acta. 257:1997;59-84.