Inhibition of recombinant human mitochondrial aldehyde dehydrogenase by two intermediate metabolites of disulfiram

Biochemical Pharmacology

Volumn 55, Issue 7, 1998, Pages 1099-1103

  Mays, Dennis C ^a   Ortiz Bermudez, Patricia ^a   Lam, Jennifer P ^a   Tong, Ik H ^a   Fauq, Abdul H ^a   Lipsky, James J ^a  

^a MAYO CLINIC COLLEGE OF MEDICINE   (United States)

Author keywords

Alcoholism; Disulfiram; Enzyme inactivation; Human recombinanrt aldehyde dehydrogenase; S methyl N,N diethyldithiocarbamate sulfine; S methyl N,N diethylthiocarbamate sulfoxide

Indexed keywords

ALDEHYDE DEHYDROGENASE; DIETHYLDITHIOCARBAMIC ACID METHYL ESTER; DISULFIRAM; DISULFIRAM DERIVATIVE; DRUG METABOLITE; RECOMBINANT ENZYME; SULFOXIDE; UNCLASSIFIED DRUG;

ARTICLE; CONTROLLED STUDY; ENZYME ACTIVITY; ENZYME INHIBITION; HUMAN; IN VITRO STUDY; LIVER MITOCHONDRION; PRIORITY JOURNAL;

ALCOHOL DETERRENTS; ALDEHYDE DEHYDROGENASE; DISULFIRAM; DITIOCARB; ENZYME INHIBITORS; HUMANS; KINETICS; MITOCHONDRIA; RECOMBINANT PROTEINS;

EID: 0032055620     PISSN: 00062952     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0006-2952(97)00686-2     Document Type: Article

References (25)

1. Hald J., Jacobsen E., Larsen V. The sensitizing effect of tetraethylthiuramdisulphide (Antabuse) to ethylalcohol. Acta Pharmacol Toxicol. 4:1948;285-296.
2. Kitson T.M. The disulfiram-ethanol reaction. J Stud Alcohol. 38:1977;96-113.
3. Cobby J., Mayersohn M., Selliah S. The rapid reduction of disulfiram in blood and plasma. J Pharmacol Exp Ther. 202:1977;724-731.
4. Glauser T.A., Nelson A.N., Zembower D.E., Lipsky J.J., Weinshilboum R.M. Diethyldlthiocarbamate S-methylation Evidence for catalysis by human liver thiol methyltransferase and thiopurine methyltransferase. J Pharmacol Exp Ther. 266:1993;23-32.
5. Madan A., Faiman M.D. NADPH-dependent, regioselective S-oxidation of a it thionosulfur- and thioether-containing xenobiotic, diethyldithiocarbamate methyl ester by rat liver microsomes. Drug Metab Dispos. 22:1994;324-330.
6. m aldehyde dehydrogenase inhibitor. Alcohol. 7:1990;165-169.
7. Johansson B., Petersen E.N., Arnold E. Diethylthiocarbamic acid methyl ester. A potent inhibitor of aldehyde dehydrogenase found in rats treated with disulfiram or diethyldithiocarbamic acid methyl ester. Biochem Pharmacol. 38:1989;1053-1059.
8. m aldehyde dehydrogenase. Biochem Pharmacol. 42:1991;1361-1366.
9. Lam J.P., Mays D.C., Lipsky J.J. Inhibition of recombinant human mitochondrial and cytosolic aldehyde dehydrogenases by two candidates for the active metabolites of disulfiram. Biochemistry. 36:1997;13748-13754.
10. Hart B.W., Faiman M.D. In vitro and in vivo inhibition of rat liver aldehyde dehydrogenase by S-methyl N,N-diethylthiocarbamate sulfoxide, a new metabolite of disulfiram. Biochem Pharmacol. 43:1992;403-406.
11. m mitochondrial aldehyde dehydrogenase. Biochem Pharmacol. 49:1995;693-700.
12. Mays D.C., Nelson A.N., Lam-Holt J.P., Fauq A.H., Lipsky J.J. S-Methyl-N,N - diethylthiocarbamate sulfoxide and S-methyl-N-N-diethylthiocarbamate sulfone, two candidates for the active metabolite of disulfiram. Alcohol Clin Exp Res. 20:1996;595-600.
13. m aldehyde dehydrogenase and putative metabolite of disulfiram. Alcohol Clin Exp Res. 18:1994;1013-1017.
14. Madan A., Faiman M.D. Characterization of diethyldithiocarbamate methyl ester sulfine as an intermediate in the bioactivation of disulfiram. J Pharmacol Exp Ther. 272:1995;775-780.
15. Zheng C-F, Wang T.T.Y., Weiner H. Cloning and expression of the full-length cDNAs encoding human liver class 1 and class 2 aldehyde dehydrogenase. Alcohol Clin Exp Res. 17:1993;828-831.
16. 50 in the rat after intraperitoneal administration. Alcohol Clin Exp Res. 7:1983;307-311.
17. Nelson A.N., Lipsky J.J. Microtiter plate-based determination of multiple concentration-inhibition relationships. Anal Biochem. 231:1995;437-439.
18. Segall Y., Casida J.E. Oxidation of sulfallate and related alkyl dialkyldithiocarbamates to dialkylformamides via sulfine and imminium ion intermediates. J Agri Food Chem. 31:1983;242-246.
19. Madan A., Williams T.D., Faiman M.D. Glutathione- and glutathione-S-transferase-dependent oxidative desulfuration of the thione xenobiotic diethyldithiocarbamate methyl ester. Mol Pharmacol. 46:1994;1217-1225.
20. Romero F.J., Galaris D. Compartmentation of cellular glutathione in mitochondrial and cytosolic pools. Viña J. Glutathione Metabolism and Physiological Functions. 1990;29-38 CRC Press, Boca Raton.
21. Ohno Y., Hirota K., Kawanishi T., Takanaka A. Loss of viability after disulfiram treatment without preceding depletion of intracellular GSH. J Toxicol Sci. 15:1990;63-73.
22. Nagendra S.N., Shetty K.T., Rao K.M., Rao BSSR. Effect of disulfiram administration on rat brain glutathione metabolism. Alcohol. 11:1994;7-10.
23. Mitchell J.R., Jollow D.J., Potter W.Z., Gillette J.R., Brodie B.B. Acetaminophen-induced hepatic necrosis. IV. Protective role of glutathione. J Pharmacol Exp Ther. 187:1973;211-217.
24. Weiner H. Subcellular localization of acetaldehyde oxidation in liver. Ann NY Acad Sci. 492:1987;25-34.
25. Klyosov A.A., Rashkovetsky L.G., Tahir M.K., Keung W-M. Possible role of liver cytosolic and mitochondrial aldehyde dehydrogenases in acetaldehyde metabolism. Biochemistry. 35:1996;4445-4456.