Metabolism of trans, trans-muconaldehyde, a cytotoxic metabolite of benzene, in mouse liver by alcohol dehydrogenase Adh1 and aldehyde reductase AKR1A4

Toxicology and Applied Pharmacology

Volumn 210, Issue 1-2, 2006, Pages 163-170

  Short, Duncan M ^a,d   Lyon, Robert ^a   Watson, David G ^a   Barski, Oleg A ^b   McGarvie, Gail ^c   Ellis, Elizabeth M ^a  

^a UNIVERSITY OF STRATHCLYDE   (United Kingdom)

^b University of Louisville School of Medicine   (United States)

^c UNIVERSITY OF THE WEST OF SCOTLAND   (United Kingdom)

^d UNIVERSITY OF EDINBURGH   (United Kingdom)

Author keywords

Alcohol dehydrogenase; Aldehyde reductase; Benzene; Mouse liver; trans, trans muconaldehyde

Indexed keywords

ALCOHOL DEHYDROGENASE; ALDEHYDE REDUCTASE; BENZENE DERIVATIVE; HYDROXYL GROUP; MUCONALDEHYDE; PYRAZOLE; REDUCED NICOTINAMIDE ADENINE DINUCLEOTIDE;

AFFINITY CHROMATOGRAPHY; ANALYTIC METHOD; ANIMAL TISSUE; ARTICLE; CHROMATOGRAPHY; CONTROLLED STUDY; CYTOTOXICITY; ENZYME ACTIVITY; ENZYME ANALYSIS; ENZYME INHIBITION; ENZYME PURIFICATION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; KINETICS; LIVER METABOLISM; MALE; MOUSE; NONHUMAN;

ALCOHOL DEHYDROGENASE; ALDEHYDE REDUCTASE; ALDEHYDES; ANIMALS; BENZENE; CLONING, MOLECULAR; LIVER; MALE; METABOLIC DETOXICATION, DRUG; MICE; MICE, INBRED STRAINS; STEREOISOMERISM;

ANIMALIA;

EID: 29044446774     PISSN: 0041008X     EISSN: 10960333     Source Type: Journal    
DOI: 10.1016/j.taap.2005.09.017     Document Type: Article

References (46)

1. D.J. Abernethy, E.V. Kleymenova, J. Rose, L. Recio, and B. Faiola Human CD34+ hematopoietic progenitor cells are sensitive targets for toxicity induced by 1,4-benzoquinone Toxicol. Sci. 79 2004 82 89
2. M. Aksoy, K. Dincol, T. Akgun, S. Erdem, and G. Dincol Haematological effects of chronic benzene poisoning in 217 workers Br. J. Ind. Med. 28 1972 296 301
3. E.M. Algar, T.L. Seeley, and R.S. Holmes Purification and molecular properties of mouse alcohol dehydrogenase isozymes Eur. J. Biochem. 137 1983 139 147
4. D. Allan, and D. Lohnes Cloning and developmental expression of mouse aldehyde reductase (AKR1A4) Mech. Dev. 94 2000 271 275
5. O.A. Barski, V.Z. Papusha, G.R. Kunkel, and K.H. Gabbay Regulation of aldehyde reductase expression by STAF and CHOP Genomics 83 2004 119 129
6. A.K. Bauer, B. Faiola, D.J. Abernethy, R. Marchan, L.J. Pluta, V.A. Wong, K. Roberts, and A.K. Jaiswal Genetic susceptibility to benzene-induced toxicity: role of NADPH:quinone oxidoreductase-1 Cancer Res. 63 2003 929 935
7. K.M. Bohren, B. Bullock, B. Wermuth, and K.H. Gabbay The aldo-keto reductase superfamily. cDNAs and deduced amino acid sequences of human aldehyde and aldose reductases J. Biol. Chem. 264 1989 9547 9551
8. M.D. Boleda, N. Saubi, J. Farres, and X. Pares Physiological substrates for rat alcohol dehydrogenase classes: aldehydes of lipid peroxidation, omega-hydroxyfatty acids, and retinoids Arch. Biochem. Biophys. 307 1993 85 90
9. R. Chang, C. Wong, S. Kline, A. Conney, B. Goldstein, and G. Witz Mutagenicity of trans, trans-muconaldehyde and its metabolites in V79 cells Environ. Mol. Mutagen. 24 1994 112 115
10. E.P. Cronkite, J. Bullis, T. Inoue, and R.T. Drew Benzene inhalation produces leukemia in mice Toxicol. Appl. Pharmacol. 75 1984 358 361
11. W.S. Davidson, L. Weihrauch, and T.G. Flynn Purification and compositional relatedness of aldehyde reductase from several species Biochem. Soc. Trans. 6 1978 940 942
12. J.S. Deetz, C.A. Luehr, and B.L. Vallee Human liver alcohol dehydrogenase isozymes: reduction of aldehydes and ketones Biochemistry 23 1984 6822 6828
13. L. Deltour, M.H. Foglio, and G. Duester Metabolic deficiencies in alcohol dehydrogenase Adh1, Adh3, and Adh4 null mutant mice. Overlapping roles of Adh1 and Adh4 in ethanol clearance and metabolism of retinol to retinoic acid J. Biol. Chem. 274 1999 16796 16801
14. H.J. Edenberg, K. Zhang, K. Fong, W.F. Bosron, and T.K. Li Cloning and sequencing of cDNA encoding the complete mouse liver alcohol dehydrogenase Proc. Natl. Acad. Sci. U.S.A. 82 1985 2262 2266
15. A. Gaikwad, D.J. Long II, J.L. Stringer, and A.K. Jaiswal In vivo role of NAD(P)H:quinone oxidoreductase 1 (NQO1) in the regulation of intracellular redox state and accumulation of abdominal adipose tissue J. Biol. Chem. 276 2001 22559 22564
16. M. Gaskell, K.I. McLuckie, and P.B. Farmer Comparison of the mutagenic activity of the benzene metabolites, hydroquinone and para-benzoquinone in the supF forward mutation assay: a role for minor DNA adducts formed from hydroquinone in benzene mutagenicity Mutat. Res. 554 2004 387 398
17. D. Goon, X. Cheng, J.A. Ruth, D.R. Petersen, and D. Ross Metabolism of trans, trans-muconaldehyde by aldehyde and alcohol dehydrogenases: identification of a novel metabolite Toxicol. Appl. Pharmacol. 114 1992 147 155
18. D. Goon, J. Matsuura, and D. Ross Metabolism and cytotoxicity of trans, trans-muconaldehyde and its derivatives: potential markers of benzene ring cleavage reactions Chem-Biol. Interact. 88 1993 37 53
19. V.L. Grotz, S. Ji, S.A. Kline, B.D. Goldstein, and G. Witz Metabolism of benzene and trans, trans-muconaldehyde in the isolated perfused rat liver Toxicol. Lett. 70 1994 281 290
20. J.D. Hayes, and D.J. Pulford The glutathione S-transferase supergene family: regulation of GST and the contribution of the isoenzymes to cancer chemoprotection and drug resistance Crit. Rev. Biochem. Mol. Biol. 30 1995 445 600
21. A. Hinshelwood, G. McGarvie, and E. Ellis Characterisation of a novel mouse liver aldo-keto reductase AKR7A5 FEBS Lett. 523 2002 213 218
22. G.F. Kalf, and R. Snyder A survey of studies on benzene-induced human leukaemogenesis Adv. Occup. Med. Rehabil. 1 1995 39 68
23. T.A. Kirley, B.D. Goldstein, W.M. Maniara, and G. Witz Metabolism of trans, trans-muconaldehyde, a microsomal hematotoxic metabolite of benzene, by purified yeast aldehyde dehydrogenase and a mouse liver soluble fraction Toxicol. Appl. Pharmacol. 100 1989 360 367
24. Q. Lan, L. Zhang, G. Li, R. Vermeulen, R.S. Weinberg, M. Dosemeci, S.M. Rappaport, and M. Shen Hematotoxicity in workers exposed to low levels of benzene Science 306 2004 1774 1776
25. L. Latriano, B. Goldstein, and G. Witz Formation of muconaldehyde, an open-ring metabolite of benzene, in mouse-liver microsomes-An additional pathway for toxic metabolites Proc. Natl. Acad. Sci. U.S.A. 83 1986 8356 8360
26. G. Levay, D. Ross, and W.J. Bodell Peroxidase activation of hydroquinone results in the formation of DNA adducts in HL-60 cells, mouse bone marrow macrophages and human bone marrow Carcinogenesis 14 1993 2329 2334
27. Y. Oshiro, P.S. Balwierz, and G. Witz Micronucleus formation in mouse bone marrow cells in vivo in response to trans, trans-muconaldehyde Toxicol. Lett. 121 2001 159 166
28. M.V. Osier, A.J. Pakstis, H. Soodyall, D. Comas, D. Goldman, A. Odunsi, F. Okonofua, and J. Parnas A global perspective on genetic variation at the ADH genes reveals unusual patterns of linkage disequilibrium and diversity Am. J. Hum. Genet. 71 2002 84 99
29. D.V. Parke, and R.T. Williams Studies in detoxication. XLIX. The metabolism of benzene containing (14C1) benzene Biochem. J. 54 1953 231 238
30. N.R. Rao, and R. Snyder Oxidative modifications produced in HL-60 cells on exposure to benzene metabolites J. Appl. Toxicol. 15 1995 403 409
31. E. Rivedal, and G. Witz Metabolites of benzene are potent inhibitors of gap-junction intercellular communication Arch. Toxicol. 79 2005 303 311
32. H. Schoenfeld, and G. Witz DNA-protein cross-link levels in bone marrow cells of mice treated with benzene or trans, trans-muconaldehyde J. Toxicol. Environ. Health, Part A 56 1999 379 395
33. R. Snyder Overview of the toxicology of benzene J. Toxicol. Environ. Health, Part A 61 2000 339 346
34. R. Snyder Xenobiotic metabolism and the mechanism(s) of benzene toxicity Drug Metab. Rev. 36 2004 531 547
35. T. Sorahan, L.J. Kinlen, and R. Doll Cancer risks in a historical UK cohort of benzene exposed workers Occup. Environ. Med. 62 2005 231 236
36. J.L. Valentine, S.S. Lee, M.J. Seaton, B. Asgharian, G. Farris, J.C. Corton, F.J. Gonzalez, and M.A. Medinsky Reduction of benzene metabolism and toxicity in mice that lack CYP2E1 expression Toxicol. Appl. Pharmacol. 141 1996 205 213
37. N.J. Vianna, and A. Polan Lymphomas and occupational benzene exposure Lancet 1 1979 1394 1395
38. L. Wallace Environmental exposure to benzene: an update Environ. Health Perspect. 104 1996 1129 1136
39. B. Wermuth, J.D. Munch, and J.P. von Wartburg Purification and properties of NADPH-dependent aldehyde reductase from human liver J. Biol. Chem. 252 1977 3821 3828
40. G. Witz Biological interactions of α,β-unsaturated aldehydes Free Radical Biol. Med. 7 1989 333 349
41. G. Witz, G.S. Rao, and B.D. Goldstein Short-term toxicity of trans, trans-muconaldehyde Toxicol. Appl. Pharmacol. 80 1985 511 516
42. G. Witz, L. Latriano, and B.D. Goldstein Metabolism and toxicity of trans, trans-muconaldehyde, an open-ring microsomal metabolite of benzene Environ. Health Perspect. 82 1989 19 22
43. G. Witz, S.C. Gad, R.R. Tice, Y. Oshiro, C.E. Piper, and B.D. Goldstein Genetic toxicity of the benzene metabolite trans, trans-muconaldehyde in mammalian and bacterial cells Mutat. Res. 240 1990 295 306
44. Z. Zhang, S.A. Kline, T.A. Kirley, B.D. Goldstein, and G. Witz Pathways of trans, trans-muconaldehyde metabolism in mouse liver cytosol: reversibility of monoreductive metabolism and formation of end products Arch. Toxicol. 67 1993 461 467
45. Z. Zhang, B.D. Goldstein, and G. Witz Iron-stimulated ring-opening of benzene in a mouse liver microsomal system. Mechanistic studies and formation of a new metabolite Biochem. Pharmacol. 50 1995 1607 1617
46. Z. Zhang, K. Cooper, B.D. Goldstein, and G. Witz Distribution studies in CD-1 mice administered [14C]muconaldehyde Arch. Toxicol. 71 1997 703 708