Oxidation of methanol, ethylene glycol, and isopropanol with human alcohol dehydrogenases and the inhibition by ethanol and 4-methylpyrazole

Chemico-Biological Interactions

Volumn 191, Issue 1-3, 2011, Pages 26-31

  Lee, Shou Lun ^a   Shih, Hsuan Ting ^b   Chi, Yu Chou ^b   Li, Yeung Pin ^b,c   Yin, Shih Jiun ^b  

^a CHINA MEDICAL UNIVERSITY   (Taiwan)

^b NATIONAL DEFENSE MEDICAL CENTER   (Taiwan)

^c NATIONAL SUN YAT SEN UNIVERSITY   (Taiwan)

Author keywords

4 Methypyrazole; Ethylene glycol; Human alcohol dehydrogenase family; Isopropanol; Methanol; Treatment of poisoning

Indexed keywords

2 PROPANOL; 4 METHYLPYRAZOLE; ALCOHOL; ALCOHOL DEHYDROGENASE; ALCOHOL DEHYDROGENASE 1A CLASS I; ALCOHOL DEHYDROGENASE 1B1; ALCOHOL DEHYDROGENASE 1B2; ALCOHOL DEHYDROGENASE 1B3; ALCOHOL DEHYDROGENASE 1C1; ALCOHOL DEHYDROGENASE 1C2; ALCOHOL DEHYDROGENASE 2 CLASS II; ALCOHOL DEHYDROGENASE 4 CLASS IV; ETHYLENE GLYCOL; METHANOL; UNCLASSIFIED DRUG;

ALCOHOL METABOLISM; ALCOHOL OXIDATION; CATALYSIS; COMPUTER SIMULATION; CONFERENCE PAPER; CONTROLLED STUDY; ENZYME ACTIVITY; ENZYME INHIBITION; ENZYME KINETICS; ENZYME PURIFICATION; ENZYME SUBSTRATE; ENZYMOLOGY; HUMAN; LIPID PEROXIDATION; PROTEIN EXPRESSION;

2-PROPANOL; ALCOHOL DEHYDROGENASE; ENZYME INHIBITORS; ETHANOL; ETHYLENE GLYCOL; HUMANS; KINETICS; METHANOL; OXIDATION-REDUCTION; PYRAZOLES;

EID: 79957571572     PISSN: 00092797     EISSN: 18727786     Source Type: Journal    
DOI: 10.1016/j.cbi.2010.12.005     Document Type: Conference Paper

References (36)

1. S.J. Yin, C.L. Han, A.I. Lee, C.W.Wu, Human alcohol dehydrogenase family: functional classification, ethanol/retinol metabolism, and medical implications, Adv. Exp. Med. Biol. 463 (1999) 265-274.
2. H. Jornvall, J.O. Hoog, B. Persson, X. Pares, Pharmacogenetics of the alcohol dehydrogenase system, Pharmacology 61 (2000) 184-191.
3. H.J. Edenberg, W.F. Bosron, Alcohol dehydrogenases, in: C.A. McQueen (Ed.), Comprehensive Toxicology, vol. 4, Academic Press, Oxford, 2010, pp. 111-130.
4. G. Duester, J. Farres, M.R. Felder, R.S. Holmes, J.O. Hoog, X. Pares, B.V. Plapp, S.J. Yin, H. Jornvall, Recommended nomenclature for the vertebrate alcohol dehydrogenase gene family, Biochem. Pharmacol. 58 (1999) 389-395.
5. S.P. Lee, C.P. Chiang, S.L. Lee, Y.J. Hsia, T.L. Chuang, J.C. Lin, S.C. Liang, S. Nieh, S.J. Yin, Immunochemical features in the classification of human alcohol dehydrogenase family, Alcohol 39 (2006) 13-20. (Pubitemid 44287277)
6. Y.C. Chen, G.S. Peng, M.F. Wang, T.P. Tsao, S.J. Yin, Polymorphism of ethanolmetabolism genes and alcoholism: correlation of allelic variations with the pharmacokinetic and pharmacodynamic consequences, Chem. Biol. Interact. 178 (2009) 2-7.
7. J.O. Hoog, P. Stromberg, J.J. Hedberg, W.J. Griffiths, The mammalian alcohol dehydrogenases interact in several metabolic pathways, Chem. Biol. Interact. 143-144 (2003) 175-181. (Pubitemid 36246440)
8. S. Abramson, A.K. Singh, Treatment of the alcohol intoxications: ethylene glycol, methanol and isopropanol, Curr. Opin. Nephrol. Hypertens. 9 (2000) 695-701.
9. B. Megarbane, S.W. Borron, F.J. Baud, Current recommendations for treatment of severe toxic alcohol poisonings, Intensive Care Med. 31 (2005) 189-195. (Pubitemid 40362266)
10. J.A. Kraut, I. Kurtz, Toxic alcohol ingestions: clinical features, diagnosis, and management, Clin. J. Am. Soc. Nephrol. 3 (2008) 208-225.
11. J. Brent, K. McMartin, S. Phillips, K.K. Burkhart, J.W. Donovan, M. Wells, K. Kulig, Fomepizole for the treatment of ethylene glycol poisoning, N. Engl. J. Med. 340 (1999) 832-838. (Pubitemid 29142626)
12. S.W. Borron, B. Megarbane, F.J. Baud, Fomepizole in treatment of uncomplicated ethylene glycol poisoning, Lancet 354 (1999) 831.
13. J. Brent, K. McMartin, S. Phillips, C. Aaron, K. Kulig, Fomepizole for the treatment of methanol poisoning, N. Engl. J. Med. 344 (2001) 424-429. (Pubitemid 32128675)
14. D.G. Barceloux, G.R. Bond, E.P. Krenzelok, H. Cooper, J.A. Vale, American Academy of Clinical Toxicology practice guidelines on the treatment of methanol poisoning, J. Toxicol. Clin. Toxicol. 40 (2002) 415-446. (Pubitemid 34976720)
15. C.F. Chou, C.L. Lai, Y.C. Chang, G. Duester, S.J. Yin, Kinetic mechanism of human class IV alcohol dehydrogenase functioning as retinol dehydrogenase, J. Biol. Chem. 277 (2002) 25209-25216.
16. S.L. Lee, J.O. Hoog, S.J. Yin, Functionality of allelic variations in human alcohol dehydrogenase gene family: assessment of a functional window for protection against alcoholism, Pharmacogenetics 14 (2004) 725-732.
17. S.L. Lee, G.Y. Chau, C.T. Yao, C.W.Wu, S.J. Yin, Functional assessment of human alcohol dehydrogenase family in ethanol metabolism: significance of first-pass metabolism, Alcohol. Clin. Exp. Res. 30 (2006) 1132-1142.
18. O.H. Lowry, N.J. Rosebrough, A.L. Farr, R.J. Randall, Protein measurement with the Folin phenol reagent, J. Biol. Chem. 193 (1951) 265-275.
19. T. Bucher, B. Brauser, A. Conze, F. Klein, O. Langguth, H. Sies, State of oxidation-reduction and state of binding in the cytosolic NADH-system as disclosed by equilibration with extracellular lactate-pyruvate in hemoglobin-free perfused rat liver, Eur. J. Biochem. 27 (1972) 301-317.
20. W.W. Cleland, Statistical analysis of enzyme kinetic data, Methods Enzymol. 63 (1979) 103-138.
21. M. Dixon, E.C. Webb, Enzymes, 3rd ed., Academic Press, New York, 1979, pp. 72-75.
22. S.J. Yin, Alcohol dehydrogenase: enzymology and metabolism, Alcohol Alcohol. 29 (Suppl. 2) (1994) 113-119.
23. S.J. Yin, C.F. Chou, C.L. Lai, S.L. Lee, C.L. Han, Human class IV alcohol dehydrogenase: kinetic mechanism, functional roles and medical relevance, Chem. Biol. Interact. 143-144 (2003) 219-227.
24. S.L. Lee, M.F. Wang, A.I. Lee, S.J. Yin, The metabolic role of human ADH3 functioning as ethanol dehydrogenase, FEBS Lett. 544 (2003) 143-147.
25. F.W.Wagner, X. Pares, B. Holmquist, B.L. Vallee, Physical and enzymatic properties of a class III isozyme of human liver alcohol dehydrogenase: chi-ADH, Biochemistry 23 (1984) 2193-2199.
26. T.D. Hurley, W.F. Bosron, C.L. Stone, L.M. Amzel, Structures of three human beta alcohol dehydrogenase variants: correlations with their functional differences, J. Mol. Biol. 239 (1994) 415-429.
27. G.J. Davis, W.F. Bosron, C.L. Stone, K. Owusu-Dekyi, T.D. Hurley, X-ray structure of human beta3 beta3 alcohol dehydrogenase: the contribution of ionic interactions to coenzyme binding, J. Biol. Chem. 271 (1996) 17057-17061.
28. P. Xie, S.H. Parsons, D.C. Speckhard, W.F. Bosron, T.D. Hurley, X-ray structure of human class IV sigma sigma alcohol dehydrogenase: structural basis for substrate specificity, J. Biol. Chem. 272 (1997) 18558-18563.
29. M.S. Niederhut, B.J. Gibbons, S. Perez-Miller, T.D. Hurley, Three-dimensional structures of the three human class I alcohol dehydrogenases, Protein Sci. 10 (2001) 697-706. (Pubitemid 32240495)
30. C.L. Stone, T.K. Li, W.F. Bosron, Stereospecific oxidation of secondary alcohols by human alcohol dehydrogenases, J. Biol. Chem. 264 (1989) 11112-11116.
31. T.K. Li, H. Theorell, Human liver alcohol dehydrogenase: inhibition by pyrazole and pyrazole analogs, Acta Chem. Scand. 23 (1969) 892-902.
32. R. Pietruszko, Human liver alcohol dehydrogenase: inhibition of methanol activity by pyrazole, 4-methylpyrazole, 4-hydroxymethylpyrazole and 4-carboxypyrazole, Biochem. Pharmacol. 24 (1975) 1603-1607.
33. P.T. Xie, T.D. Hurley, Methionine-141 directly influences the binding of 4-methylpyrazole in human sigma sigma alcohol dehydrogenase, Protein Sci. 8 (1999) 2639-2644. (Pubitemid 30007625)
34. W.F. Bosron, T.K. Li, W.P. Dafeldecker, B.L. Vallee, Human liver pi-alcohol dehydrogenase: kinetic and molecular properties, Biochemistry 18 (1979) 1101-1105. (Pubitemid 9145383)
35. M.I. Schimerlik, W.W. Cleland, Inhibition and alternate-substrate studies on the mechanism of malic enzyme, Biochemistry 16 (1977) 565-570. (Pubitemid 8047789)
36. T.H. Venkataramaiah, B.V. Plapp, Formamides mimic aldehydes and inhibit liver alcohol dehydrogenases and ethanol metabolism, J. Biol. Chem. 278 (2003) 36699-36706.