Vinyl acetate monomer (VAM) genotoxicity profile: Relevance for carcinogenicity

Critical Reviews in Toxicology

Volumn 43, Issue 8, 2013, Pages 671-706

  Albertini, Richard J ^a  

^a UNIVERSITY OF VERMONT   (United States)

Author keywords

Acetaldehyde; Aldehyde dehydrogenase; Carboxylesterase; DNA adducts; DNA DNA crosslinks; DNA protein crosslinks; Mode of action; Mutation threshold

Indexed keywords

ACETALDEHYDE; ALDEHYDE DEHYDROGENASE; CARCINOGEN; MALONALDEHYDE; UNCLASSIFIED DRUG; VINYL ACETATE; VINYL ACETATE MONOMER;

CARCINOGENESIS; CARCINOGENICITY; CELL FREE SYSTEM; CHROMOSOME MUTATION; DNA ADDUCT; DNA CROSS LINKING; DNA DAMAGE; DROSOPHILA MELANOGASTER; GENE MUTATION; GENOTOXICITY; HUMAN; METABOLISM; MUTAGENICITY; MUTATION; NONHUMAN; REVIEW;

ACETALDEHYDE; ALDEHYDE DEHYDROGENASE; ANIMALS; CARCINOGENS; CELLS, CULTURED; DISEASE MODELS, ANIMAL; DNA DAMAGE; DOSE-RESPONSE RELATIONSHIP, DRUG; HUMANS; MUTAGENS; VINYL COMPOUNDS;

EID: 84883436781     PISSN: 10408444     EISSN: 15476898     Source Type: Journal    
DOI: 10.3109/10408444.2013.827151     Document Type: Review

References (186)

1. Aaron CS, Bolcsfoldi G, Glatt HR, et al. (1994). Mammalian cell gene mutation assays working group report. Mutat Res 312:235-9.
2. Abrahamson S, Wurgler FE, DeJongh C, et al. (1980). How many loci on the X-chromosome of Drosophila melanogaster can mutate to recessive lethals? Environ Mutagen 2:447-53.
3. ACGIH. (1991-1992, 1994-1995). Threshold limit values for chemical substances and physical agents and biological exposure indices. Cincinnati, OH: American Conference of Governmental Industrial Hygienists.
4. Ames BN, Shigenaga MK, Hagen TM. (1993). Oxidants, antioxidants, and the degenerative diseases of aging. Proc Natl Acad Sci USA 90: 7915-22.
5. Andersen ME, Green T, Fredrick CB, Bogdanffy MS. (2002). Physiologically based pharmacokinetic (PBPK) models for nasal tissue dosimetry of organic esters: Assessing state-of-knowledge and risk assessment applications with methyl methacrylate and vinyl acetate. Regul Toxicol Pharmacol 116:234-45.
6. Balbo S, Hashibe M, Gundy S, et al. (2008). N2-ethyldeoxyguanosine as a potential biomarker for assessing effects of alcohol consumption on DNA. Cancer Epidemiol Biomarkers Prev 17:3026-32.
7. Balbo S, Meng L, Bliss RL, et al. (2012a). Kinetics if DNA adduct formation in the oral cavity after drinking alcohol. Cancer Epidemiol Biomarkers Prev 21:601-8.
8. Balbo S, Meng L, Bliss RL, et al. (2012b). Time course of DNA adduct formation in peripheral blood granulocytes and lymphocytes after drinking alcohol. Mutagenesis 27:485-90.
9. Badr FM, Hussain F. (1977). Action of ethanol and its metabolite acetaldehyde in human lymphocytes: In vivo and in vitro study. Abstracts of papers presented at the 1977 meetings of the Genetics Society of America; Austin, Texas, August 14-17.
10. Bandas EL. (1982). Studies on the role of metabolites and contaminants in the mutagenic action of ethanol on the yeast mitochondria. Genetika 18:1056-61.
11. Bariliak R, Kozachuk SI. (1983). Embryotoxic and mutagenic activity of ethanol and acetaldehyde in intra-amniotic exposure. Tsitologiia I Genetika 17:57-60.
12. Bartsch H, Malaveille C, Barbin A, et al. (1979). Mutagenic and alkylating metabolites of halo-ethylenes, chlorobutadienes and dichlorobutenes produced by rodent or human liver tissues. Arch Toxicol 41:249-77.
13. Bird RP, Draper HH, Basrur PK. (1982). Effect of malonaldehyde and acetaldehyde on cultured mammalian cells production of micronuclei and chromosomal aberrations. Mutat Res 101:237-46.
14. Blasiak J, Trzeciak A, Malecka-Panas E, et al. (2000). in vitro genotoxicity of ethanol and acetaldehyde in human lymphocytes and the gastrointestinal tract mucosa cells. Toxicol in Vitro 14:287-95.
15. Bogdanffy MS, Valentine R. (2003). Differentiating between local cytotoxicity, mitogenesis, and genotoxicity in carcinogen risk assessments: The case of vinyl acetate. Toxicol Lett 140-141:83-98.
16. Bogdanffy MS, Dreef-van der Meulen HC, Beems RB, et al. (1994a). Chronic toxicity and oncogenicity inhalation study with vinyl acetate in the rat and mouse. Fundam Appl Toxicol 23:215-29.
17. Bogdanffy MS, Tyler TR, Vinegar MB, et al. (1994b). Chronic toxicity and oncogenicity study with vinyl acetate in the rat: In utero exposure in drinking water. Fundam Appl Toxicol 23:206-24.
18. Bogdanffy MS, Plowchalk DR, Sarangapani R, et al. (2001). Modeof- action-based dosimeters for interspecies extrapolation of vinyl acetate Inhalation risk. Inhal Toxicol 13:377-96.
19. Bogdanffy MS, Gladnick NL, Kegelman T, et al. (1997). Four-week inhalation cell proliferation study of the effects of vinyl acetate on rat nasal epithelium. Inhal Toxicol 9:331-50.
20. Bohlke JU, Singh S, Goedde HW. (1983). Cytogenetic effects of acetaldehyde in lymphocytes of Germans and Japanese: SCE, clastogenic activity, and cell cycle delay. Hum Genet 63:285-9.
21. Boobis AR, Daston GP, Preston RJ, et al. (2009). Application of key events analysisto chemical carcinogens and noncarcinogens. Crit Rev Food Sci Nutr 49:690-707.
22. Brams A, Buchet JP, Crutzen-Fayt MC, et al. (1987). Comparative study, with 40 chemicals, of the efficiency of the salmonella assay and the SOS chromotest (kit procedure). Toxicol Lett 38:123-33.
23. Brooks PJ, Theruvathu JA. (2005). DNA adducts from acetaldehyde: Implications for alcohol-related carcinogenesis. Alcohol 35: 187-93.
24. Budinsky R, Gollapudi B, Albertini RJ, et al. (2013). Micronuclei, HPRT and TK loci mutation studies in tk6 cells with vinyl acetate monomer and acetaldehyde. Environ Mol Mutagen (Paper accepted for publication).
25. Canadian Draft Assessment for VAM.(2008). Draft Screening Assessment for Vinyl Acetate, Acetic acid ethenyl ester (vinyl acetate monomer), CAS RN 108-05-04.
26. Casanova-Schmitz M, David RM, Heck HD. (1984). Oxidation of formaldehyde and acetaldehyde by NAD?-dependent dehydrogenases in rat nasal mucosal homogenates. Biochem Pharmacol 33:1137-42.
27. CFR (29 CFR 1910.1000, Table Z-1 A). (2006). Code of Federal Regulations, Washington, DC: U.S. government Printing Office, Office of Federal Register.
28. Chen L, Wang M, Villalta PW, et al. (2007). Quantitation of an acetaldehyde adduct in human leukocyte DNA and the effect of smoking cessation. Chem Res Toxicol 20:108-13.
29. Costa M, Zhitkovich A, Harris M, et al. (1997). DNA-protein cross-links produced by various chemicals in cultured human lymphoma cells. J Toxicol Environ Health 50:433-49.
30. Crebelli R, Conti G, Conti L, et al. (1989). A comparative study on ethanol and acetaldehyde as inducers of chromosome malsegregation in Aspergillus nidulans. Mutat Res 215:187-95.
31. de Raat WK, Davis PB, Bakker GL. (1983). Induction of sisterchromatid exchanges by alcohol and alcoholic beverages after metabolic activation by rat-liver homogenate. Mutat Res 124:85-90.
32. Deese DE, Joyner RE. (1969). Vinyl acetate: A study of chronic human exposure. Am Ind Hygiene Assoc J Sept/Oct:449-57.
33. Doak SH, Jenkins GJS, Johnson GE, et al. (2007). Mechanistic influences for mutation induction curves after exposure to DNAreactive carcinogens. Cancer Res 67:1-8.
34. Dulout FN, Furnus CC. (1988). Acetaldehyde-induced aneuploidy in cultured Chinese hamster cells. Mutagenesis 3:207-11.
35. Environment Canada. (2008) Screening assessment for the challenge: Acetic acid ethenyl ester (vinyl acetate monomer). Ottawa: Environment Canada.
36. Eriksson CJP. (1987). Human acetaldehyde levels: Aspects of current interest. ICPEMC Working Paper No. 15/3, Mutat Res 186: 235-40.
37. EU Risk Assessment, Vinyl Acetate CAS No. 108-05-05, EINECS-No. 203-545-4, Final Approved Version, August 19, 2008.
38. Fang JL, Vaca CE. (1995). Development of a 32P-postlabelling method for the analysis of adducts arising through the reaction of acetaldehyde with 20-deoxyguanosine-30-monophosphate and DNA. Carcinogenesis 16:2177-85.
39. Fang JL, Vaca CE. (1997). Detection of DNA adducts of acetaldehyde in peripheral white blood cells of alcohol abusers. Carcinogenesis 18: 627-32.
40. Flaman JM, Frebourg T, Moreau V, et al. (1995). A simple p53 functional assay for screening cell lines, blood, and tumors. Proc Natl Acad Sci USA 92:3963-7.
41. Florin I, Rutberg L, Curvall M, et al. (1980). Screening of tobacco smoke constituents for mutagenicity using the Ames test. Toxicology 15: 219-32.
42. Fraenkel-Conrat R, Singer B. (1988). Nucleoside adducts are formed by cooperative reaction of acetaldehyde and alcohols: possible mechanism for the role of ethanol in carcinogenesis. Proc Natl Acad Sci USA 85:3758-61.
43. Gale EP. (1980a). Vinyl acetate: 13-week oral (drinking water) toxicity study in the rat. Report No. 2146-51/4, Hazleton, UK.
44. Gale EP. (1980b). Vinyl acetate: 13-week oral (drinking water) toxicity study in the mouse. Report No. 2146-51/5, Hazleton, UK.
45. Garcia CCM, Angeli JPF, Freitas FP, et al. (2011). [13C2] Acetaldehyde promotes unequivocal formation of 1,N2-propano-deoxyguanosine in human cells. J Am Chem Soc 133:9140-3.
46. Garcia CL, Mechilli M, De Santis LP, et al. (2009). Relationship between DNA lesions, DNA repair and chromosomal damage induced by acetaldehyde. Mutat Res 662:3-9.
47. Gocke E, Wall M. (2009). In vivo genotoxicity of EMS: Statistical assessment of the dose response curves. Toxicol Lett 190:298-302.
48. Graf U, Frei H, Ka?gi A, et al. (1989). Thirty compounds tested in the Drosophila wing spot test. Mutat Res 222:359-73.
49. Grafstrom RC, Dypbukt JM, Sundqvist K, et al. (1994). Pathobiological effects of acetaldehyde in cultured human epithelial cells and fibroblasts. Carcinogenesis 15:985-90.
50. Green MH, Muriel WJ. (1976). Mutagen testing using TRP? reversion in Escherichia coli. Mutat Res 38:3-32.
51. He SM, Lambert B. (1985). Induction and persistence of SCE-inducing damage in human lymphocytes exposed to vinyl acetate and acetaldehyde in vitro. Mutat Res 158:201-8.
52. He SM, Lambert B. (1990). Acetaldehyde-induced mutation at the hprt locus in human lymphocytes in vitro. Environ Mol Mutagenisis 16: 57-63.
53. Hecht SS, McIntee EJ, Wang M. (2001). New DNA adducts of crotonaldehyde and acetaldehyde. Toxicology 166:31-6.
54. Helander A, Lindahl-Kiessling K. (1991). Increased frequency of acetaldehyde-induced sister-chromatid exchanges in human lymphocytes treated with an aldehyde dehydrogenase inhibitor. Mutat Res 264:103-7.
55. Hellmer L, Bolesfoldi G. (1992). An evaluation of the E. coli K-12 uvrB/recA DNA repair host-mediated assay. I. In vitro sensitivity of the bacteria to 61 compounds. Mutat Res 272:145-60.
56. Hemminki K, Suni R. (1984). Sites of reaction of glutaraldehyde and acetaldehyde with nucleosides. Arch Toxicol 55:186-90.
57. Hengstler JG, Bogdanffy MS, Bolt HM, et al. (2003). Challenging dogma: Thresholds for genotoxic carcinogens? the case of vinyl acetate. Annu Rev Pharmacol Toxicol 43:485-520.
58. Hori K, Miyamoto S, Yukawa Y, et al. (2012). Stability of acetaldehydederived DNA adduct in vitro. Biochem Biophys Res Commun 423: 642-6.
59. IARC. (1995). IARC monographs on the evaluation of carcinogenic risks to humans. Section on Vinyl Acetate. Vol. 63. Lyon, 373-91. Geneva: World Health Organization.
60. IARC.(1999). IARC monographs on the evaluation of carcinogenic risks to humans: Re-evaluation of some organic chemicals, hydrazine and hydrogen peroxide. Geneva World Health Organization.
61. Inagaki S, Esaka Y, Goto M, et al. (2004). LC-MS study on the formation of cyclic 1,N2-propano guanine adduct in the reactions of DNA with acetaldehyde in the presence of histone. Biol Pharm Bull 27:273-6.
62. Inagaki S, Esake Y, Deyashiki Y, et al. (2003). Analysis of DNA adducts of acetaldehyde by liquid chromatography-mass spectrometry. J Chromoatgr A 987:341-7.
63. Ishikawa H, Miyatsu Y, Kurihara K, et al. (2006). Gene-environmental interactions between alcohol-drinking behavior and ALDH2 and CYP2E1 polymorphisms and their impact on micronuclei frequency in human lymphocytes. Mutat Res 594:1-9.
64. Ishikawa H, Ishikawa T, Yamamoto H, et al. (2007). Genotoxic effects of alcohol in human peripheral lymphocytes modulated by ADH1B and ALDH2 gene polymorphisms. Mutat Res 615:134-42.
65. Jansson T. (1982). The frequency of sister chromatid exchanges in human lymphocytes treated with ethanol and acetaldehyde. Hereditas 97:301-3.
66. Jantunen K, Ma?ki-Paakkanen J, Norppa H. (1986). Induction of chromosome aberrations by styrene and vinyl acetate in cultured human lymphocytes: dependence on erythrocytes. Mutat Res 159: 109-16.
67. JETCO. (1997). Mutagenicity test data of existing chemical substances, supplement. Tokyo: Japanese Chemical Industry Ecology-Toxicology and Information Center.
68. Jung R, Engelhart G, Herbold B, et al. (1992). Collaborative study of mutagenicity with Salmonella typhimurium TA102. Mutat Res 278: 265-70.
69. Kayani MA, Parry JM. (2010). The in vitro genotoxicity of ethanol and acetaldehyde. Toxicol In Vitro 24:56-60.
70. Kim JS, Kim YJ, Kim TY, et al. (2005). Association of ALDH2 polymorphism with sensitivity to acetaldehyde-induced micronuclei and facial flushing after alcohol intake. Toxicology 210:169-74.
71. Kirby PE. (1983). Mouse lymphoma mutagenesis assay with 40171 (ML-NCI 78), Microbiological Associates; NO1-CP-15739.
72. Kligerman AD, Hu Y. (2007). Some insights into the mode of action of butadiene by examining the genotoxicity of its metabolites. Chemico- Biol Interactions 166:132-9.
73. Kligerman AD, DeMarini DM, Doerr CL, et al. (1999a). Comparison of cytogenetic effects of 3,4-epoxy-1-butene and 1,2:3,4-diepoxybutane in mouse, rat and human lymphocytes following in vitro G0 exposures. Mutat Res 439:13-23.
74. Kligerman AD, Doerr CL, Tennant AM. (1999b). Cell cycle specificity of cytogenetic damage induced by 3,4-epoxy-1-butene. Mutat Res 444:151-8.
75. Knadle S. (1985). Synergistic interaction between hydroquinone and acetaldehyde in the induction of sister chromatid exchange in human lymphocytes. Cancer Res 45:4852-7.
76. Korte A, Obe G. (1981). Influence of chronic ethanol uptake and acute acetaldehyde treatment on the chromosomes of bone marrow cells and peripheral lymphocytes of Chinese hamsters. Mutat Res 88:389-95.
77. Kunugita N, Isse T, Oyama T, et al. (2008). Increased frequencies of micronucleated reticulocytes and T-cell receptor mutation in ALDH2 knockout mice exposed to acetaldehyde. J Toxicol Sci 33:31-6.
78. Kuykendall JR, Taylor ML, Bogdanffy MS. (1993). Cytotoxicity and DNA-protein crosslink formation in rat nasal tissues exposed to vinyl acetate are carboxylesterase-mediated. Toxicol Appl Pharmacol 123: 283-92.
79. Kuykendall JR, Bogdanffy MS. (1994). Formation and stability of acetaldehyde-induced crosslinks between poly-lysine and polydeoxyguanosine. Mutat Res: Fundam Mol Mechanisms Mutagen 311:49-56.
80. Kuykendall JR, Bogdanffy MS. (1992a). Reaction kinetics of DNA-histone crosslinking by vinyl acetate and acetaldehyde. Carcinogenesis 13:2095-100.
81. Kuykendall JR, Bogdanffy MS. (1992b). Efficiency of DNA-histone crosslinking induced by saturated and unsaturated aldehydes in vitro. Mutat Res 283:131-6.
82. La?hdetie J. (1988). Effects of vinyl acetate and acetaldehyde on sperm morphology and meiotic micronuclei in mice. Mutat Res 202:171-8.
83. Laib RJ, Bolt HM. (1986). Vinyl acetate, a structural analog of vinyl carbamate, fails to induce enzyme-altered foci in rat liver. Carcinogenesis 7:841-3.
84. Lam CW, Casanova M, Heck HD. (1986). Decreased extractability of DNA from proteins in the rat nasal mucosa after acetaldehyde exposure. Fund Appl Toxicol 6:541-50.
85. Lambert B, Andersson B, Bastlova T, et al. (1994). Mutations induced in the hypoxanthine phosphoribosyl transferase gene by three urban air pollutants: Acetaldehyde, benzo[a]pyrene diolepoxide, and ethylene oxide. Environ Health Persp 102:135-8.
86. Lambert B, Chen Y, He SM, et al. (1985). DNA crosslinks in human leucocytes treated with vinyl acetate and acetaldehyde in vitro. Mutat Res 146:301-3.
87. Lee MK, Yoo JW, Lin H, et al. (2005). Air-liquid interface culture of serially passaged human nasal epithelial cell monolayer for in vitro drug transport studies. Drug Deliv 12:305-311.
88. Li SY, Gomelsky M, Duan J, et al. (2004). Overexpression of aldehyde dehydrogenase (ALDH2) transgene prevents acetaldehyde-induced cell injury in human umbilical vein endothelial cells. J Biol Chem 279:11244-52.
89. Li SY, Li Q, Shen JJ, et al. (2006). Attenuation of acetaldehyde-induced cell injury by overexpression of acetaldehyde dehydrogenase-2 (ALDH2) transgene in human cardiac myocytes: Role of MAP kinase signaling. J Mol Cell Cardiol 40:283-94.
90. Lijinsky W, Andrews AW. (1980). Mutagenicity of vinyl compounds in Salmonella typhimurium. Teratogenesis Carcinogenesis Mutagenesis 1:259-67.
91. Lijinsky W, Reuber MD. (1983). Chronic toxicology studies of vinyl acetate in fisher rats. Toxicol Appl Pharmacol 68:43-53.
92. Lin YC, Ho IC, Lee TC. (1989). Ethanol and acetaldehyde potentiate the clastogenicity of ultraviolet light, methyl methanesulfonate, mitomycin C and bleomycin in Chinese hamster ovary cells. Mutat Res 216: 93-9.
93. Madrigal-Bujaidar E, Velazquez-Guadarrama N, Morales-Ramirez P, et al. (2002). Effect of disulfiram on the genotoxic potential of acetaldehyde in mouse spermatogonial cells. Teratogenesis Carcinogenesis Mutagenesis 22:83-91.
94. Maki-Paakkanen J, Norppa H. (1987). Induction of micronuclei by vinyl acetate in mouse bone marrow cells and cultured human lymphocytes. Mutat Res 190:41-5.
95. Maltoni C, Ciliberti A, Lefemine G, et al. (1997). Results of a long-term experimental study on the carcinogenicity of vinyl acetate monomer in mice. Ann NY Acad Sci 837:209-38.
96. Marnett LJ, Riggins JN, West JD. (2003). Endogenous generation of reactive oxidants and electrophiles and their reactions with DNA and proteins. J Clin Invest 111:583-93.
97. Marnett LJ, Hurd HK, Hollstein MC, et al. (1985). Naturally occurring carbonyl compounds are mutagens in Salmonella tester strain TA104. Mutat Res 148:25-34.
98. Matsuda T, Matsumoto A, Uchida M, et al. (2007). Increased formation of hepatic N2-ethylidene-20-46 deoxyguanosine DNA adducts in aldehyde dehydrogenase 2-knockout mice treated with ethanol. Carcinogenesis 47:2363-6.
99. Matsuda T, Yabushita H, Kanaly RA, et al. (2006). Increased DNA damage in ALDH2-deficient alcoholics. Chem Res Toxicol 19: 1374-8.
100. Matsuda T, Terashima L, Matsumoto Y, et al. (1999). Effective utilization of N2-ethyl-20-deoxyguanosine triphosphate during DNA synthesis catalyzed by mammalian replicative DNA polymerases. Biochemistry 38:929-35.
101. Matsuda T, Kawanishi M, Yagi T, et al. (1998). Specific Tandem GG to TT base substitutions induced by acetaldehyde are due to intra-strand crosslinks between adjacent guanine bases. Nucleic Acids Res 7: 1769-74.
102. Matter B, Guza R, Zhao J, et al. (2007). Sequence distribution of acetaldehyde-derived N2-ethyl-dG adducts along duplex DNA. Chem Res Toxicol 20:1379-87.
103. McCann J, Choi E, Yamasaki E, et al. (1975). Detection of carcinogens as mutagens in the salmonella/microsome test: Assay of 300 chemicals. Proc Natl Acad Sci USA 72:5135-9.
104. Mechilli M, Schinoppi A, Kobos K, et al. (2008). DNA repair deficiency and acetaldehyde-induced chromosomal 50 alterations in CHO cells. Mutagenesis 23:51-6.
105. Migliore L, Nieri M. (1991). Evaluation of twelve potential aneuploidogenic chemicals by the in vitro human lymphocyte micronucleus assay. Toxicol in Vitro 5:325-36.
106. Migliore L, Cocchi L, Scarpato R. (1996). Detection of the centromere in micronuclei by fluorescence in situ hybridization: Its application to the human lymphocyte micronucleus assay after treatment with four suspected aneugens. Mutagenesis 11:285-90.
107. Minardi F, Belpoggi F, Soffritti M, et al. (2002). Results of a long-term carcinogenicity bioassay on vinyl acetate monomer in sprague-dawley rats. Ann NY Acad Sci 982:106-22.
108. Moeller BC, Recio L, Green A, et al. (2013). Biomarkers of exposure and effect in human lymphoblastoid TK6 cells following [13C2]- acetaldehyde exposure. Toxicol Sci 133:1-12.
109. Mortelmans K, Zeiger E. (2000). The Ames Salmonella/microsome mutagenicity assay. Mutat Res 455:29-60.
110. Mortelmans K, Haworth S, Lawlor T, et al. (1986). Salmonella mutagenicity tests: II. results from the testing of 270 chemicals. Environ Mutagenesis 8:1-119.
111. Morita T. (1995). Low pH leads to sister-chromatid exchanges and chromosomal aberrations andits clastogenicity is S-dependent. Mutat Res 344:301-8.
112. Morita T, Nagaki T, Fukuda I, et al. (1992). Clastogenicity of low pH to various cultured mammalian cells. Mutat Res 268:297-305.
113. Mustonen R, Kangas J, Vuojolahti P, et al. (1986). Effects of phenoxyacetic acids on the induction of chromosome aberrations in vitro and vivo. Mutagenesis 1:241-5.
114. Nagayoshi H, Matsumoto A, Nishi R, et al. (2009). Increased formation of gastric N2-ethylidine-20-deoxyguanosine DNA adducts in aldehyde dehydrogenase-2 knockout mice treated with ethanol. Mutat Res 673: 74-7.
115. Nersesyan AK, Kukumadzhyan VA, Zil?fyan VN. (1990). Evaluation of activity of some chemical substances being in use in the industry of Armenia. Biol Zh Arm 9:796-7.
116. Noori P, Hou SM. (2001). Mutational spectrum induced by acetaldehyde in the HPRT gene of human T lymphocytes resembles that in the p53 gene of esophageal cancers. Carcinogenesis 22:1825-30.
117. Norppa H, Tursi F, Pfa?ffli P, et al. (1985). Chromosome damage induced by vinyl acetate through in vitro formation of acetaldehyde in human lymphocytes and Chinese hamster ovary cells. Cancer Res 45: 4816-21.
118. NRC. (1987). Biological markers in environmental health research, Committee on biological markers of the National Research Council. Environ Health Persp 74 3-9.
119. Obe G, Beek B. (1979). Mutagenic activity of aldehydes. Drug Alcohol Depend 4:91-4.
120. Obe G, Ristow H. (1977). Acetaldehyde, but not ethanol, induces sister chromatid exchanges in Chinese hamster cells in vitro. Mutat Res 56: 211-13.
121. Obe G, Ristow H, Herha J (1978). Mutagenic activity of alcohol in man: In: Mutations: Their origin, nature and potential relevance to genetic risk in man. Proceedings Yearly Conference 1977 of German Research Society. Boppard: Harald Boldt, 151-61.
122. Obe G, Natarajan AT, Meyers M, et al. (1979). Induction of chromosomal aberrations in peripheral lymphocytes of human blood in vitro and SCEs in bone marrow cells of mice in vivo by ethanol and its metabolite acetaldehyde. Mutat Res 68:291-4.
123. Obe G, Jonas R, Schmidt S. (1986). Metabolism of ethanol in vitro produces a compound which induces sister-chromatid exchanges in human peripheral lymphocytes in vitro: Acetaldehyde not ethanol is mutagenic. Mutat Res 174:47-51.
124. OECD 476. (1997). Guideline for the testing of chemicals: In vitro mammalian cell gene mutation tests. Adopted 21 July 1997.
125. Ogawa M, Isse T, Oyama T, et al. (2006). Urinary 8-hydroxydeoxyguanosine (8-OHdG) and plasma malondialdehydr (MDA) levels in ALDH2 knock-out mice under acetaldehyde exposure. Indl Health 44: 179-83.
126. Olin KL, Cherr GN, Rifkin E, et al. (1996). The effects of some redoxactive metals and reactive aldehydes on DNA-protein cross-links in vitro. Toxicology 110:1-8.
127. Ott MG, Teta MJ, Greenberg HL. (1989). Lymphatic and hematopoietic tissue cancer in a chemical manufacturing environment. Am J Ind Med 16:631-43.
128. Owen PE. (1980a). Vinyl acetate: 3 month inhalation toxicity study in the mouse. Report No. 2303-51/5, Hazelton Lab Europe.
129. Owen PE. (1980b). Vinyl acetate: 3 month inhalation toxicity study in the rat. Report-No. 2286-51/5, Hazleton Lab Europe.
130. Owen PE. (1988). Vinyl acetate: 104 week inhalation combined chronic toxicity and carcinogenicity study in the rat and mouse. Report-No. 5547-51/15, Hazleton, UK.
131. Oyama T, Isse T, Ogawa M, et al. (2007). Susceptibility to inhalation toxicity of acetaldehyde in Aldh2 knockout mice. Front Biosci 12: 1927-34.
132. Oyama T, Nagayoshi H, Matsuda T, et al. (2010). Effects of acetaldehyde inhalation in mitochondrial aldehyde dehydrogenase deficient mice (Aldh2). Front Biosci E2:1344-54.
133. Paget V, Lechevrel M, Sichel F. (2008). Acetaldehyde-induced mutational pattern in the tumour suppressor gene TP53 analysed by use of a functional assay, the FASAY (functional analysis of separated alleles in yeast). Mutat Res 652:12-19.
134. Peng GS, Yin SJ. (2009). Effect of the allelic variants of aldehyde dehydrogenase ALDH22 and alcohol dehydrogenase ADH1B2 on blood acetaldehyde concentrations. Hum Genomics 3: 121-7.
135. Perrino FW, Blans P, Harvey S, et al. (2003). The N2-ethylguanine and the O6-ethyl- and O6-methylguanine lesions in DNA: Contrasting responses from the bypass DNA polymerase Z and the replicative DNA polymerase a. Chem Res Toxicol 16:1616-23.
136. Pluskota-Karwatka D, Pawlowicz AJ, Kronberg L. (2007). Reactions of malonaldehyde and acetaldehyde with calf thymus DNA: Formation of conjugate adducts. Nucleosides Nucleotides Nucleic Acids 26: 567-71.
137. Pluskota-Karwatka D, Pawlowicz AJ, Kronberg L. (2006). Formation of malonaldehyde-acetaldehyde conjugate adducts in calf thymus DNA. Chem Res Toxicol 19:921-926.
138. Pluskota-Karwatka D, Le CF, Munter T, et al. (2005). Formation of conjugate adducts in the reactions of malonaldehyde-acetaldehyde and malonaldehyde-formaldehyde with guanosine. Chem Rec Toxicol 18: 300-7.
139. Pluskota-Karwatka D, Le CF, Munter T, et al. (2002). Identification of conjugate adducts formed in the reactions of malonaldehydeacetaldehyde and malonaldehyde-formaldehyde with cytidine. Chem Rec Toxicol 15:110-17.
140. Preston R J, Williams GM. (2005). DNA-reactive carcinogens: Mode of action and human cancer hazard. Crit Rev Toxicol 35:673-83.
141. Rey M, Palermo AM, Munoz ER. (1994). Lack of effect of acute acetaldehyde treatment on X chromosome segregation in Drosophila melanogaster females. Mutat Res 320:1-7.
142. Ristow H, Seyfarth A, Lochmann ER. (1995). Chromosomal damages by ethanol and acetaldehyde in Saccharomyces cerevisiae as studied by pulsed field gel electrophoresis. Mutat Res 326:165-70.
143. Ristow H, Obe G. (1978). Acetaldhyde induces cross-links in DNA and cause sister-chromatid- exchanges in human cells. Mutat Res 58: 115-19.
144. Rogers-Back.(1985). NCI 73527, (ML-NCI-121), Microbiological Associates NO1-CP-41004.
145. Rosenkranz HS. (1977). Mutagenicity of halogenated alkanes and their derivatives. Environ Health Persp 21:79-84.
146. Sako M, Inagaki S, Esaka Y, et al. (2003). Histones accelerate the cyclic 1,N2-propanoguanine adduct formation of DNA by the primary metabolite of alcohol and carcinogenic crotonaldehyde. Bioorganic Med Chem Lett 13:3497-8.
147. Saladino AJ, Willey JC, Lechner JF, et al. (1985). Effects of formaldehyde, acetaldehyde, benzoyl peroxide, and hydrogen peroxide on cultured normal human bronchial epithelial cells. Cancer Res 45: 2522-6.
148. Shirinian GS, Arutyunyan RM. (1980). Study of cytogenetic change levels under PVA production. Biol Z Armenii XXXIII: 748-52.
149. Simon P, Epe B, Mutzel P, et al. (1986). Synthesis and genotoxicity of acetoxyoxirane, the epoxide of vinyl acetate. J Biochem Toxicol 1: 43-55.
150. Simon P, Ottenwalder H, Bolt HM. (1985). Vinyl acetate: DNA-binding assay in vivo. Toxicol Lett 27:115-20.
151. Singer B, Grunberger D. (1983). Molecular biology of mutagens and carcinogens: Reactions of directly acting agents with nucleic acids. New York: Plenum Press.
152. Singh NP, Khan A. (1985). Acetylaldehyde:genotoxicity and cytotoxicity in human lymphocytes. Mutat Res 337:9-17.
153. Sipi P, Ja?rventaus H, Norppa H. (1992). Sister-chromatid exchanges induced by vinyl esters and respective carboxylic acids in cultured human lymphocytes. Mutat Res 279:75-82.
154. Sobels FH. (1972). The role of Drosophila in the field of Mutat Res. Arch Genet (Zur) 45:101-25.
155. Stanek JJ, Morris JB. (1999). The effect of inhibition of aldehyde dehydrogenase on nasal uptake of inspired acetaldehyde. Toxicol Sci 49:225-31.
156. Stein S, Lao Y, Yang IY, et al. (2006). Genotoxicity of acetaldehyde- and crotonaldehyde-induced 1, N2-propanodeoxyguanosine DNA adducts in human cells. Mutat Res 608:1-7.
157. Stevens G, Rank K, Sauer J, et al. (1991). Evaluation of unscheduled DNA synthesis induced in acetaldehyde treated primary rat hepatocytes. Environ Mol Mutagenesis 17:71.
158. Swenberg JA, Fryar-Tita E, Jeong YC, et al. (2008). Biomarkers in toxicology and risk assessment: Informing critical dose-response relationships. Chem Res Toxicol 21:253-65.
159. Takeshita T, Iijima S, Higurashi M. (1986). Vinyl acetate-induced sister chromatid exchanges in murine bone marrow cells. Proc Japan Acad Ser B 62:239-42.
160. Terashima I, Matsude T, Fang, T-W, et al. (2001). Miscoding potential of the N2-ethyl-20-deoxyguanosine DNA adduct by the exonuclease-free Klenow fragment of Escherichia coli DNA polymerase I. Biochemistry 40:4106-14.
161. Theruvathu JA, Jaruga O, Nath RG, et al. (2005). Polyamines stimulate the formulation of mutagenic 1, N2-propanodeoxyguanosine adducts from acetaldehyde. Nucleic Acids Res 33:3513-20.
162. Tuma DJ, Thiele GM, Xu D, et al. (1996). Acetaldehyde and malondialdehyde react together to generate distinct protein adducts in the liver during long-therm ethanol administration. Hepatology 23: 872-80.
163. UK Food Standards Agency. (2004). Chemicals used in plastic materials and articles in contact with food: Compliance with statutory limits on composition and migration-year 2. Food-Survey-Information-Sheet. (55/04): 41. London, UK: Food standards Agency.
164. Umeda Y, Matsumoto M, Yamazaki K, et al. (2004). Carcinogenicity and chronic toxicity in mice and rats administered vinyl acetate monomer in drinking water. J Occup Health 46:87-99.
165. Upton DC, Wang X, Blans P, et al. (2006a). Mutagenesis by exocyclic alkylamino purine adducts in escherichia coli. Mutat Res 599:1-10.
166. Upton DC, Wang X, Blans P, et al. (2006b). Replication of N2- Ethyldeoxyguanosine ANA adducts in the human embryonic kidney cell line 293. Chem Res Toxicol 19:960-7.
167. U.S. EPA. (2007). Draft Document: Framework for determining a mutagenic mode of action fort carcinogenicity: Using EPA?s 2005 cancer guidelines and supplemental guidance for assessing susceptibility from early-life exposures to carcinogens, EPA 120.R-0/002-A. September 2007.
168. U.S. EPA. (2006). Hazardous Pollutants Release Inventory. Available from: Http://www2.epa.gov/toxics-release-inventory-tri-program [last accessed 27 Aug 2013].
169. U.S. EPA. (2005). Guideline for carcinogen risk assessment. EPA/630/P- 03/001F. March 2005.
170. Vaca CE, Fangay JL, Schwedab EKH. (1995). Studies of the reaction of acetaldehyde with deoxynucleosides. Chemico-Biol Interactions 98: 51-67.
171. Vaca CE, Nilsson JA, Fanf JL, et al. (1998). Formation of DNA adducts in human buccal epithelial cells exposed to acetaldehyde and methylglyoxal in vitro. Chemico-Biol Interactions 108:197-208.
172. Valko M, Rhodes CJ, Moncol J, et al. (2006). Free radicals, metals and antioxidants in oxidative stress-induced cancer. Chemico-Biol Interactions 160:1-40.
173. Valentine R, Bamberger JR, Szostek B, et al. (2002). Time- and concentration-dependent increases in cell proliferation in rats and mice administered vinyl acetate in drinking water. Toxicol Sci: Official J Soc Toxicol 67:190-7.
174. Van Houten B, Albertini RJ. (1995). DNA damage and repair. In: Craighead JE, ed. Pathology of environmental and occupational disease. St. Louis, MO: Mosby-Year Book, Inc, 311-27.
175. Veghelyi PV, Osztovics M, Kardos G, et al. (1978). The fetal alcohol syndrome: Symptoms and pathogenesis. Acta Paediatr Acad Sci Hungaricae 19:171-89.
176. Velez-Cruz R, Riggins JN, Daniels JS, et al. (2005). Exocyclic DNA lesions stimulate DNA cleavage mediated by human topoisomerase IIa in in vitro and in cultured cells. Biochemistry 44:3972-81.
177. Vogel EW, Barbin A, Nivard MJM, et al. (1998). Heritable and cancer risks of exposures to anticancer drugs: Inter-species comparisons of covalent deoxyribonucleic acid-binding agents. Mutat Res 400: 509-40.
178. Wang M, McIntee EJ, Cheng G, et al. (2000). Identification of DNA adducts of acetaldehyde. Chemico-Biol Interactions 13:1149-57.
179. Wang M, Yu N, Chen L, et al. (2006). Identification of an acetaldehyde adduct in human liver DNA and quantitation as N2-ethyldeoxyguanosine. Chem Res Toxicol 19:319-24.
180. Wangenheim J, Bolcsfoldi G. (1988). Mouse lymphoma L5178Y thymidine kinase locus assay of 50 compounds. Mutagenesis 3: 193-205.
181. Watanabe K, Sasaki T, Kawakami K. (1998). Comparisons of chemically-induced mutation among four bacterial strains, Salmonella typhimurium TA102 and TA2638, and Escherichia coli WP2/pKM101 and WP2 uvrA/pKM101: Collaborative study III and evaluation of the usefulness of these strains. Mutat Res 416:169-81.
182. Waxweiler RJ, Smith AH, Falk H, et al. (1981). Excess lung cancer risk in a synthetic chemicals plant. Environ Health Persp 41:159-65.
183. Wenzel P, Muller J, Zurmeyer S, et al. (2008). ALDH-2 deficiency increases cardiovascular oxidative stress-evidence for indirect antioxidative properties. Biochem Biophys Res Commun 367:137-43.
184. Wilcox P, Naidoo A, Wedd DJ, et al. (1990). Comparison of Salmonella typhimurium TA102 with Escherichia coli WP2 tester strains. Mutagenesis 5:285-91.
185. Wilson III DM, Thompson LH. (2007). Molecular mechanisms of sisterchromatid exchange. Mutat Res 616:11-23.
186. Woodruff RC, Mason JM, Valencia R, et al. (1985). Chemical mutagenesis testing in Drosophila. V. Results of 53 coded compounds tested for the National Toxicology Program. Environ Mutagen 7: 677-702.