Alcohol
Volume 35, Issue 3 , Pages 187-193 , April 2005

DNA adducts from acetaldehyde: implications for alcohol-related carcinogenesis

Received 11 February 2005 ,Revised 28 March 2005 ,Accepted 29 March 2005.

References 

  1. Bogdanffy MS, Sarangapani R, Kimbell JS, Frame SR, Plowchalk DR. Analysis of vinyl acetate metabolism in rat and human nasal tissues by an in vitro gas uptake technique. Toxicol Sci. 1998;46:235–246
  2. Brooks PJ, Theruvathu JA, Nath RG. DNA damage from alcohol abuse with special reference to the brain. In:  Preedy VR,  Watson RR editor. Comprehensive Handbook of Alcohol Related Pathology. London: Elsevier; 2004;
  3. Cahill A, Cunningham CC, Adachi M, Ishii H, Bailey SM, Fromenty B, et al. Effects of alcohol and oxidative stress on liver pathology: the role of the mitochondrion. Alcohol Clin Exp Res. 2002;26:907–915
  4. Chung F-L, Zhang L, Ocando JE, Nath RG. Role of 1,N2-propanodeoxyguanosine adducts as endogenous DNA lesions in rodents and humans. IARC Sci Publ. 1999;150:45–54
  5. Cornell NW, Veech RL. Enzymatic measurement of ethanol or NAD in acid extracts of biological samples. Anal Biochem. 1983;132:418–423
  6. D'Andrea AD. Cellular function of the Fanconi anemia pathway. Nat Med. 2001;7:1259–1260
  7. de los Santos C, Zaliznyak T, 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. 2001;276:9077–9082
  8. Eder E, Budiawan . Cancer risk assessment for the environmental mutagen and carcinogen crotonaldehyde on the basis of TD50 and comparison with 1,N2-propanodeoxyguanosine adduct levels. Cancer Epidemiol Biomarkers Prev. 2001;10:883–888
  9. Fang JL, Vaca CE. Development of a 32P-postlabelling method for the analysis of adducts arising through the reaction of acetaldehyde with 2′-deoxyguanosine-3′-monophosphate and DNA. Carcinogenesis. 1995;16:2177–2185
  10. Fang JL, Vaca CE. Detection of DNA adducts of acetaldehyde in peripheral white blood cells of alcohol abusers. Carcinogenesis. 1997;18:627–632
  11. Frank A, Seitz HK, Bartsch H, Frank N, Nair J. Immunohistochemical detection of 1,N6-ethenodeoxyadenosine in nuclei of human liver affected by diseases predisposing to hepato-carcinogenesis. Carcinogenesis. 2004;25:1027–1031
  12. Friedberg EC, Wagner R, Radman M. Specialized DNA polymerases, cellular survival, and the genesis of mutations. Science. 2002;296:1627–1630
  13. Fukunaga T, Sillanaukee P, Eriksson CJ. Problems involved in the determination of endogenous acetaldehyde in human blood. Alcohol Alcohol. 1993;28:535–541
  14. Garro AJ, Espina N, Farinati F, Salvagnini M. The effects of chronic ethanol consumption on carcinogen metabolism and on O6-methylguanine transferase–mediated repair of alkylated DNA. Alcohol Clin Exp Res. 1986;10(6 Suppl):73S–77S
  15. Hagmar L, Stromberg U, Tinnerberg H, Mikoczy Z. The usefulness of cytogenetic biomarkers as intermediate endpoints in carcinogenesis. Int J Hyg Environ Health. 2001;204:43–47
  16. Hengstler JG, Bogdanffy MS, Bolt HM, Oesch F. Challenging dogma: thresholds for genotoxic carcinogens? The case of vinyl acetate. Annu Rev Pharmacol Toxicol. 2003;43:485–520
  17. Homann N, Jousimies-Somer H, Jokelainen K, Heine R, Salaspuro M. High acetaldehyde levels in saliva after ethanol consumption: methodological aspects and pathogenetic implications. Carcinogenesis. 1997;18:1739–1743
  18. Koivisto P, Robins P, Lindahl T, Sedgwick B. Demethylation of 3-methylthymine in DNA by bacterial and human DNA dioxygenases. J Biol Chem. 2004;279:40470–40474
  19. Kozekov ID, Nechev LV, Moseley MS, Harris CM, Rizzo CJ, Stone MP, et al. DNA interchain cross-links formed by acrolein and crotonaldehyde. J Am Chem Soc. 2003;125:50–61
  20. Kurtz AJ, Lloyd RS. 1,N2-deoxyguanosine adducts of acrolein, crotonaldehyde, and trans-4-hydroxynonenal cross-link to peptides via Schiff base linkage. J Biol Chem. 2003;278:5970–5976
  21. Kuykendall JR, Bogdanffy MS. Reaction kinetics of DNA–histone crosslinking by vinyl acetate and acetaldehyde. Carcinogenesis. 1992;13:2095–2100
  22. Mao H, Schnetz-Boutaud NC, Weisenseel JP, Marnett LJ, Stone MP. Duplex DNA catalyzes the chemical rearrangement of a malondialdehyde deoxyguanosine adduct. Proc Natl Acad Sci U S A. 1999;96:6615–6620
  23. Matsuda T, Kawanishi M, Yagi T, Matsui S, Takebe H. Specific tandem GG to TT base substitutions induced by acetaldehyde are due to intra-strand crosslinks between adjacent guanine bases. Nucleic Acids Res. 1998;26:1769–1774
  24. Matsuda T, Terashima I, Matsumoto Y, Yabushita H, Matsui S, Shibutani S. Effective utilization of N2-ethyl-2′-deoxyguanosine triphosphate during DNA synthesis catalyzed by mammalian replicative DNA polymerases. Biochemistry. 1999;38:929–935
  25. Minko IG, Washington MT, Kanuri M, Prakash L, Prakash S, Lloyd RS. Translesion synthesis past acrolein-derived DNA adduct, γ-hydroxypropanodeoxyguanosine, by yeast and human DNA polymerase η. J Biol Chem. 2003;278:784–790
  26. Nath RG, Ocando JE, Chung F-L. Detection of 1,N2-propanodeoxyguanosine adducts as potential endogenous DNA lesions in rodent and human tissues. Cancer Res. 1996;56:452–456
  27. Nath RG, Ocando JE, Guttenplan JB, Chung F-L. 1,N2-propanodeoxyguanosine adducts: potential new biomarkers of smoking-induced DNA damage in human oral tissue. Cancer Res. 1998;58:581–584
  28. Niedernhofer LJ, Odijk H, Budzowska M, van Drunen E, Maas A, Theil AF, et al. The structure-specific endonuclease Ercc1-Xpf is required to resolve DNA interstrand cross-link-induced double-strand breaks. Mol Cell Biol. 2004;24:5776–5787
  29. Obe G, Anderson D. International Commission for Protection against Environmental Mutagens and Carcinogens. ICPEMC Working Paper No. 15/1. Genetic effects of ethanol. Mutat Res. 1987;186:177–200
  30. Obe G, Natarajan AT, Meyers M, Hertog AD. Induction of chromosomal aberrations in peripheral lymphocytes of human blood in vitro, and of SCEs in bone-marrow cells of mice in vivo by ethanol and its metabolite acetaldehyde. Mutat Res. 1979;68:291–294
  31. Obe G, Ristow H. Acetaldehyde, but not ethanol, induces sister chromatid exchanges in Chinese hamster cells in vitro. Mutat Res. 1977;56:211–213
  32. Perrino FW, Blans P, Harvey S, Gelhaus SL, McGrath C, Akman SA, et al. The N2-ethylguanine and the O6-ethyl- and O6-methylguanine lesions in DNA: contrasting responses from the “bypass” DNA polymerase η and the replicative DNA polymerase α. Chem Res Toxicol. 2003;16:1616–1623
  33. Quievryn G, Zhitkovich A. Loss of DNA–protein crosslinks from formaldehyde-exposed cells occurs through spontaneous hydrolysis and an active repair process linked to proteosome function. Carcinogenesis. 2000;21:1573–1580
  34. Sako M, Inagaki S, Esaka Y, Deyashiki Y. Histones accelerate the cyclic 1,N2-propanoguanine adduct-formation of DNA by the primary metabolite of alcohol and carcinogenic crotonaldehyde. Bioorg Med Chem Lett. 2003;13:3497–3498
  35. Sako M, Yaekura I, Deyashiki Y. Chemo- and regio-selective modifications of nucleic acids by acetaldehyde and crotonaldehyde. Nucleic Acids Res Suppl. 2002;21–22
  36. Simanowski UA, Stickel F, Maier H, Gärtner U, Seitz HK. Effect of alcohol on gastrointestinal cell regeneration as a possible mechanism in alcohol-associated carcinogenesis. Alcohol. 1995;12:111–115
  37. Terashima I, Matsuda T, Fang T-W, Suzuki N, Kobayashi J, Kohda K, et al. Miscoding potential of the N2-ethyl-2′-deoxyguanosine DNA adduct by the exonuclease-free Klenow fragment of Escherichia coli DNA polymerase I. Biochemistry. 2001;40:4106–4114
  38. Theruvathu, J. A., Jaruga, P., Nath, R. G., Dizdaroglu, M., & Brooks, P. J. (In press). Polyamines stimulate the formation of mutagenic 1,N2-propano-deoxyguanosine adducts from acetaldehyde. Nucleic Acids Research.
  39. U.S. Department of Health and Human Services, Public Health Service, National Toxicology Program . Alcoholic beverage consumption. In: Report on Carcinogens. Tenth Edition. Research Triangle Park, NC: Author; 2002;
  40. Vaca CE, Fang JL, Schweda EK. Studies of the reaction of acetaldehyde with deoxynucleosides. Chem Biol Interact. 1995;98:51–67
  41. Visapää J-P, Götte K, Benesova M, Li J, Homann N, Conradt C, et al. Increased cancer risk in heavy drinkers with the alcohol dehydrogenase 1C∗1 allele, possibly due to salivary acetaldehyde. Gut. 2004;53:871–876
  42. Wang M, McIntee EJ, Cheng G, Shi Y, Villalta PW, Hecht SS. Identification of DNA adducts of acetaldehyde. Chem Res Toxicol. 2000;13:1149–1157
  43. Wang X, D'Andrea AD. The interplay of Fanconi anemia proteins in the DNA damage response. DNA Repair (Amst). 2004;3:1063–1069
  44. Woodgate R. A plethora of lesion-replicating DNA polymerases. Genes Dev. 1999;13:2191–2195
  45. Woutersen RA, Appelman LM, Van Garderen-Hoetmer A, Feron VJ. Inhalation toxicity of acetaldehyde in rats. III. Carcinogenicity study. Toxicology. 1986;41:213–231
  46. Yang I-Y, Chan G, Miller H, Huang Y, Torres MC, Johnson F, et al. Mutagenesis by acrolein-derived propanodeoxyguanosine adducts in human cells. Biochemistry. 2002;41:13826–13832
  47. Yang I-Y, Hossain M, Miller H, Khullar S, Johnson F, Grollman A, et al. Responses to the major acrolein-derived deoxyguanosine adduct in Escherichia coli. J Biol Chem. 2001;276:9071–9076
  48. Yang I-Y, Miller H, Wang Z, Frank EG, Ohmori H, Hanaoka F, et al. 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. 2003;278:13989–13994
  49. Yokoyama A, Omori T. Genetic polymorphisms of alcohol and aldehyde dehydrogenases and risk for esophageal and head and neck cancers. Jpn J Clin Oncol. 2003;33:111–121

PII: S0741-8329(05)00094-7

doi: 10.1016/j.alcohol.2005.03.009

Alcohol
Volume 35, Issue 3 , Pages 187-193 , April 2005

Article Tools

* Image Usage & Resolution