The importance of 3,4-epoxy-1,2-butanediol and hydroxymethylvinyl ketone in 3-butene-1,2-diol associated mutagenicity

Chemico-Biological Interactions

Volumn 166, Issue 1-3, 2007, Pages 182-190

  Powley, Mark W ^a   Walker, Vernon E ^b   Li, Yutai ^a   Upton, Patricia B ^a   Swenberg, James A ^a  

^a The University of North Carolina at Chapel Hill   (United States)

^b LOVELACE RESPIRATORY RESEARCH INSTITUTE   (United States)

Author keywords

1,3 Butadiene; 1,N2 Propanodeoxyguanosine; 3,4 Epoxy 1,2 butanediol; 3 Butene 1,2 diol; DNA adduct; Hydroxymethylvinyl ketone

Indexed keywords

3 BUTENE 1,2 DIOL; 3,4 EPOXY 1,2 BUTANEDIOL; BUTADIENE DIEPOXIDE; DNA; GLUTATHIONE; HEMOGLOBIN; HYDROXYMETHYLVINYL KETONE; KETONE DERIVATIVE; MUTAGENIC AGENT; UNCLASSIFIED DRUG; VINYL DERIVATIVE;

ANIMAL EXPERIMENT; ANIMAL MODEL; ANIMAL TISSUE; ARTICLE; CHEMICAL MUTAGENESIS; CONTROLLED STUDY; DNA ADDUCT; FEMALE; GENE; GENE MUTATION; HPRT GENE; LIQUID CHROMATOGRAPHY; LIVER; MUTATION RATE; MUTATIONAL ANALYSIS; NONHUMAN; RAT; TANDEM MASS SPECTROMETRY;

ANIMALS; BUTANONES; BUTYLENE GLYCOLS; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; CHROMATOGRAPHY, LIQUID; DNA ADDUCTS; DOSE-RESPONSE RELATIONSHIP, DRUG; FEMALE; GLYCOLS; HYDROLYSIS; HYPOXANTHINE PHOSPHORIBOSYLTRANSFERASE; LIVER; MASS SPECTROMETRY; MICE; MUTAGENESIS; MUTAGENICITY TESTS; RATS; RATS, INBRED F344; RATS, SPRAGUE-DAWLEY; REFERENCE STANDARDS; REPRODUCIBILITY OF RESULTS; STEREOISOMERISM;

MUS; RATTUS; RODENTIA;

EID: 33947132399     PISSN: 00092797     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.cbi.2007.02.001     Document Type: Article

References (32)

1. Huff J.E., Melnick R.L., Solleveld H.A., Haseman J.K., Powers M., and Miller R.A. Multiple organ carcinogenicity of 1,3-butadiene in B6C3F1 mice after 60 weeks of inhalation exposure. Science 227 (1985) 548-549
2. Melnick R.L., Huff J., Chou B.J., B.J., and Miller R.A. Carcinogenicity of 1,3-butadiene in C57BL/6 × C3HF1 mice at low exposure concentrations. Cancer Res. 50 (1990) 6592-6599
3. Melnick R.L., Huff J.E., Roycroft J.H., Chou B.J., and Miller R.A. Inhalation toxicology and carcinogenicity of 1,3-butadiene in B6C3F1 mice following 65 weeks of exposure. Environ. Health Perspect. 86 (1990) 27-36
4. Owen P.E., Glaister J.R., Graunt I.F., and Pullinger D.H. Inhalation toxicity studies with 1,3-butadiene. 3. Two-year toxicity/carcinogenicity study in rats. Am. Ind. Hyg. Assoc. J. 48 (1987) 407-413
5. Owen P.E., and Glaister J.R. Inhalation toxicity and carcinogenicity of 1,3-butadiene in Sprague-Dawley rats. Environ. Health Perspect. 86 (1990) 19-25
6. Delzell E., Sathiakumar N., Hovinga M., Macaluso M., Julian J., Larson J.R., Cole P., and Muir D.C.F. A follow-up study of synthetic rubber workers. Toxicology 113 (1996) 182-189
7. Divine B.J., and Hartman C.M. Mortality update of butadiene production workers. Toxicology 113 (1996) 169-181
8. V.E. Walker, D.M. Walker, Q. Meng, J. McDonald, B.R. Scott, M.J. Bauer, D.J. Claffey, M.W. Powley, P.B. Upton, J.A. Swenberg, R.F. Henderson, Genotoxicity of 1,3-butadiene and its epoxy intermediates, HEI Research Report, Health Effects Institute, Capital City Press, Montpelier, VT, in press.
9. Powley M.W., Li Y., Upton P.B., Walker V.E., and Swenberg J.A. Quantification of DNA and hemoglobin adducts of 3,4-epoxy-1,2-butanediol in rodents exposed to 3-butene-1,2-diol. Carcinogenesis 26 (2005) 1573-1580
10. Krause R.J., Kemper R.A., and Elfarra A.A. Hydroxymethylvinyl ketone: a reactive Michael acceptor formed by the oxidation of 3-butene-1,2-diol by cDNA-expressed human cytochrome P450s and mouse, rat, and human liver microsomes. Chem. Res. Toxicol. 14 (2001) 1590-1595
11. Cottrell L., Golding B.T., Munter T., and Watson W.P. In vitro metabolism of chloroprene: species differences, epoxide stereochemistry and a de-chlorination pathway. Chem. Res. Toxicol. 14 (2001) 1552-1562
12. Bechtold W.E., Strunk M.R., Chang I.Y., Ward J.B., and Henderson R.F. Species differences in urinary butadiene metabolites: comparisons of metabolite ratios between mice, rats, and humans. Toxicol. Appl. Pharmacol. 127 (1994) 44-49
13. Sabourin P.J., Burka L.T., Bechtold W.E., Dahl A.R., Hoover M.D., Chang I.Y., and Henderson R.F. Species differences in urinary butadiene metabolites; identification of 1,2-dihydroxy-4(N-acetylcysteinyl)butane, a novel metabolite of butadiene. Carcinogenesis 13 (1992) 1633-1638
14. Sprague C.L., and Elfarra A.A. Mercapturic acid urinary metabolites of 3-butene-1,2-diol as in vivo evidence for the formation of hydroxymethylvinyl ketone in mice and rats. Chem. Res. Toxicol. 17 (2004) 819-826
15. Eder E., Scheckenbach S., Deininger C., and Hoffman C. The possible role of α,β-unsaturated carbonyl compounds in mutagenesis and carcinogenesis. Toxicol. Lett. 67 (1993) 87-103
16. 2-propanodeoxyguanosine adducts of the 1,3-butadiene metabolite, hydroxymethylvinyl ketone. Chem. Res. Toxicol. 16 (2003) 1448-1454
17. Sanchez A.M., Minko I.G., Kurtz A.J., Kanuri M., Moriya M., and Lloyd R.S. Comparative evaluation of the bioreactivity and mutagenic spectra of acrolein-derived alpha-HOPdG and gamma-HOPdG regioisomeric deoxyguanosine adducts. Chem. Res. Toxicol. 16 (2003) 1019-1028
18. Yang I.Y., Chan G., Miller H., Huang Y., Torres M.C., Johnson J., and Moriya M. Mutagenesis by acrolein-derived propanodeoxyguanosine adducts in human cells. Biochemistry 41 (2002) 13826-13832
19. Yang I.Y., Johnson F., Grollman A.P., and Moriya M. Genotoxic mechanism for the major acrolein-derived deoxyguanosine adduct in human cells. Chem. Res. Toxicol. 15 (2002) 160-194
20. Yang I.Y., Miller H., Wang Z., Frank E.G., Ohmort H., Hanoaka F., and Moriya M. Mammalian translesion DNA synthesis across an acrolein-derived deoxyguanosine adduct: participation of DNA polymerase η in error-prone synthesis in human cells. J. Biol. Chem. 278 (2003) 13989-13994
21. de los Santos C., Zaliznyak T., and Johnson F. NMR characterization of a DNA duplex containing the major acrolein-derived deoxyguanosine adduct γ-OH-1,-N2-propano-2′-deoxyguanosine. J. Biol. Chem. 276 (2001) 9071-9076
22. VanderVeen L.A., Hashim M.F., Nechev L.V., Harris T.M., Harris C.M., and Marnett L.J. Evaluation of the mutagenic potential of the principal DNA adduct of acrolein. J. Biol. Chem. 276 (2001) 9066-9070
23. Yang I.Y., Hossain M., Miller H., Khullar S., Johnson F., Grollman A., and Moriya M. Responses to the major acrolein-derived deoxyguanosine adduct in Escherichia coli. J. Biol. Chem. 276 (2001) 9071-9076
24. Minko I.G., Washington M.T., Kanuri M., Prakash L., Prakash S., and Lloyd R.S. Translesion synthesis past acrolein-derived DNA adduct, γ-hydroxypropanodeoxyguanosine, by yeast and human DNA polymerase η. J. Biol. Chem. 278 (2003) 784-790
25. Kanuri M., Minko I.G., Nechev L.V., Harris T.M., Harris C.M., and Lloyd R.S. Error prone translesion synthesis past γ-hydroxypropano deoxyguanosine, the primary acrolein-derived adduct in mammalian cells. J. Biol. Chem. 277 (2002) 18257-18265
26. Bevan C., Keller D.A., Panepinto A.S., and Bentley K.S. Effect of 4-vinylcyclohexene on micronucleus formation in the bone marrow of rats and mice. Drug Chem. Toxicol. 24 (2001) 273-285
27. 2-propanodeoxyguanosine adducts in DNA upon reaction with acrolein or crotonaldehyde. Cancer Res. 44 (1984) 990-995
28. Nath R.G., Ocando J.E., Richie J.P., and Chung F.L. Effect of glutathione depletion on exocyclic adduct levels in the liver DNA of F344 rats. Chem. Res. Toxicol. 10 (1997) 1250-1253
29. Chung F.L., Komninou D., Zhang L., Nath R., Pan J., Amin S., and Richie J. Glutathione depletion enhances formation of endogenous cyclic DNA adducts derived form t-4-hydroxy-2-nonenal in rat liver. Chem. Res. Toxicol. 18 (2005) 24-27
30. Johnson K.A., Fink S.P., and Marnett L.J. Repair of propanodeoxyguanosine by nucleotide excision repair in vivo and in vitro. J. Biol. Chem. 272 (1997) 11434-11438
31. 2-propanodeoxyguanosine DNA adducts by human cell nuclear extracts. Biochemistry 43 (2004) 7514-7521
32. Johnson K.A., Mierzwa M.L., Fink S.P., and Marnett L.J. MutS recognition of exocyclic DNA adducts that are endogenous products of lipid oxidation. J. Biol. Chem. 274 (1999) 27112-27118