Formation of acetaldehyde-derived DNA adducts due to alcohol exposure

Chemico-Biological Interactions

Volumn 188, Issue 3, 2010, Pages 367-375

  Yu, Hsu Sheng ^a   Oyama, Tsunehiro ^a   Isse, Toyohi ^b   Kitagawa, Kyoko ^c   Pham, Thi Thu Phuong ^a   Tanaka, Masayuki ^a   Kawamoto, Toshihiro ^a  

^a UNIVERSITY OF OCCUPATIONAL AND ENVIRONMENTAL HEALTH   (Japan)

^b UNIVERSITY OF OCCUPATIONAL AND ENVIRONMENTAL HEALTH   (Japan)

^c HAMAMATSU UNIVERSITY SCHOOL OF MEDICINE   (Japan)

Author keywords

Acetaldehyde; ALDH2; DNA adducts; Ethanol metabolism

Indexed keywords

ACETALDEHYDE; ALCOHOL; ALCOHOL DEHYDROGENASE; ALDEHYDE DEHYDROGENASE ISOENZYME 2; DEOXYGUANOSINE; DNA; N2 ETHYL 2' DEOXYGUANOSINE; UNCLASSIFIED DRUG;

ALCOHOL CONSUMPTION; ALCOHOL METABOLISM; ALLELE; ARTICLE; CANCER RISK; CARCINOGENESIS; CARCINOGENICITY; CHEMICAL STRUCTURE; DNA ADDUCT; DNA BINDING; DNA DAMAGE; DNA SYNTHESIS; DRINKING BEHAVIOR; ENVIRONMENTAL EXPOSURE; ENZYME ACTIVITY; ENZYME SPECIFICITY; GENE LOCATION; GENETIC IDENTIFICATION; GENETIC VARIABILITY; HETEROZYGOTE; HUMAN; NONHUMAN; OXIDATIVE STRESS; PROTEIN DNA INTERACTION; RISK FACTOR; SINGLE NUCLEOTIDE POLYMORPHISM;

EID: 78149464376     PISSN: 00092797     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.cbi.2010.08.005     Document Type: Review

References (107)

1. IARC Alcohol drinking. IARC Monogr. Eval. Carcinog. Risks Hum. 1988, 44:1-378.
2. Stickel F., Schuppan D., Hahn E.G., Seitz H.K. Cocarcinogenic effects of alcohol in hepatocarcinogenesis. Gut 2002, 51(1):132-139.
3. Austoker J. Reducing alcohol intake. BMJ 1994, 308(6943):1549-1552.
4. IARC, Alcohol consumption and ethyl carbamate (urethane), IARC Monogr. Eval. Carcinog. Risks Hum. 96 (2010) (in press).
5. Fang J.L., Vaca C.E. Detection of DNA adducts of acetaldehyde in peripheral white blood cells of alcohol abusers. Carcinogenesis 1997, 18(4):627-632.
6. Poschl G., Seitz H.K. Alcohol and cancer. Alcohol Alcohol. 2004, 39(3):155-165.
7. Brooks P.J., Theruvathu J.A. DNA adducts from acetaldehyde: implications for alcohol-related carcinogenesis. Alcohol 2005, 35(3):187-193.
8. 2-ethyldeoxyguanosine as a potential biomarker for assessing effects of alcohol consumption on DNA. Cancer Epidemiol. Biomarkers Prev. 2008, 17(11):3026-3032.
9. Seitz H.K., Meier P. The role of acetaldehyde in upper digestive tract cancer in alcoholics. Transl. Res. 2007, 149(6):293-297.
10. Matsuo K., Hamajima N., Shinoda M., Hatooka S., Inoue M., Takezaki T., Tajima K. Gene-environment interaction between an aldehyde dehydrogenase-2 (ALDH2) polymorphism and alcohol consumption for the risk of esophageal cancer. Carcinogenesis 2001, 22(6):913-916.
11. Lewis S.J., Smith G.D. Alcohol, ALDH2, and esophageal cancer: a meta-analysis which illustrates the potentials and limitations of a Mendelian randomization approach, Cancer Epidemiol. Biomarkers Prev. 2005, 14(8):1967-1971.
12. Oze I., Matsuo K., Suzuki T., Kawase T., Watanabe M., Hiraki A., Ito H., Hosono S., Ozawa T., Hatooka S., Yatabe Y., Hasegawa Y., Shinoda M., Kiura K., Tajima K., Tanimoto M., Tanaka H. Impact of multiple alcohol dehydrogenase gene polymorphisms on risk of upper aerodigestive tract cancers in a Japanese population. Cancer Epidemiol. Biomarkers Prev. 2009, 18(11):3097-3102.
13. Druesne-Pecollo N., Tehard B., Mallet Y., Gerber M., Norat T., Hercberg S., Latino-Martel P. Alcohol and genetic polymorphisms: effect on risk of alcohol-related cancer. Lancet Oncol. 2009, 10(2):173-180.
14. Seitz H.K., Stickel F. Molecular mechanisms of alcohol-mediated carcinogenesis. Nat. Rev. Cancer 2007, 7(8):599-612.
15. Secretan B., Straif K., Baan R., Grosse Y., El Ghissassi F., Bouvard V., Benbrahim-Tallaa L., Guha N., Freeman C., Galichet L., Cogliano V. A review of human carcinogens-Part E: Tobacco, areca nut, alcohol, coal smoke, and salted fish. Lancet Oncol. 2009, 10(11):1033-1034.
16. Brennan P., Boffetta P. Mechanistic considerations in the molecular epidemiology of head and neck cancer. IARC Sci. Publ. 2004, 157:393-414.
17. Eagon P.K. Alcoholic liver injury: influence of gender and hormones. World J. Gastroenterol. 2010, 16(11):1377-1384.
18. Gill J. The effects of moderate alcohol consumption on female hormone levels and reproductive function. Alcohol Alcohol. 2000, 35(5):417-423.
19. Seitz H.K., Stickel F., Homann N. Pathogenetic mechanisms of upper aerodigestive tract cancer in alcoholics. Int. J. Cancer 2004, 108(4):483-487.
20. Boccia S., Hashibe M., Galli P., De Feo E., Asakage T., Hashimoto T., Hiraki A., Katoh T., Nomura T., Yokoyama A., van Duijn C.M., Ricciardi G., Boffetta P. Aldehyde dehydrogenase 2 and head and neck cancer: a meta-analysis implementing a Mendelian randomization approach. Cancer Epidemiol. Biomarkers Prev. 2009, 18(1):248-254.
21. Fang J.L., Vaca C.E. 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(9):2177-2185.
22. Vaca C.E., Fang J.L., Schweda E.K. Studies of the reaction of acetaldehyde with deoxynucleosides. Chem. Biol. Interact. 1995, 98(1):51-67.
23. Brien J.F., Loomis C.W. Pharmacology of acetaldehyde. Can. J. Physiol. Pharmacol. 1983, 61(1):1-22.
24. Agarwal D.P., Goedde H.W. Pharmacogenetics of alcohol metabolism and alcoholism. Pharmacogenetics 1992, 2(2):48-62.
25. Yin S.J. Alcohol dehydrogenase: enzymology and metabolism. Alcohol Alcohol. Suppl. 1994, 2:113-119.
26. Kanda J., Matsuo K., Suzuki T., Kawase T., Hiraki A., Watanabe M., Mizuno N., Sawaki A., Yamao K., Tajima K., Tanaka H. Impact of alcohol consumption with polymorphisms in alcohol-metabolizing enzymes on pancreatic cancer risk in Japanese. Cancer Sci. 2009, 100(2):296-302.
27. Seitz H.K., Stickel F. Acetaldehyde as an underestimated risk factor for cancer development: role of genetics in ethanol metabolism. Gene Nutr. 2010, 5:121-128.
28. Yokoyama A., Kato H., Yokoyama T., Tsujinaka T., Muto M., Omori T., Haneda T., Kumagai Y., Igaki H., Yokoyama M., Watanabe H., Fukuda H., Yoshimizu H. Genetic polymorphisms of alcohol and aldehyde dehydrogenases and glutathione S-transferase M1 and drinking, smoking, and diet in Japanese men with esophageal squamous cell carcinoma. Carcinogenesis 2002, 23(11):1851-1859.
29. Hashibe M., Boffetta P., Zaridze D., Shangina O., Szeszenia-Dabrowska N., Mates D., Janout V., Fabianova E., Bencko V., Moullan N., Chabrier A., Hung R., Hall J., Canzian F., Brennan P. Evidence for an important role of alcohol- and aldehyde-metabolizing genes in cancers of the upper aerodigestive tract. Cancer Epidemiol. Biomarkers Prev. 2006, 15(4):696-703.
30. Peters E.S., McClean M.D., Liu M., Eisen E.A., Mueller N., Kelsey K.T. The ADH1C polymorphism modifies the risk of squamous cell carcinoma of the head and neck associated with alcohol and tobacco use. Cancer Epidemiol. Biomarkers Prev. 2005, 14(2):476-482.
31. Asakage T., Yokoyama A., Haneda T., Yamazaki M., Muto M., Yokoyama T., Kato H., Igaki H., Tsujinaka T., Kumagai Y., Yokoyama M., Omori T., Watanabe H. Genetic polymorphisms of alcohol and aldehyde dehydrogenases, and drinking, smoking and diet in Japanese men with oral and pharyngeal squamous cell carcinoma. Carcinogenesis 2007, 28(4):865-874.
32. Bouchardy C., Hirvonen A., Coutelle C., Ward P.J., Dayer P., Benhamou S. Role of alcohol dehydrogenase 3 and cytochrome P-4502E1 genotypes in susceptibility to cancers of the upper aerodigestive tract. Int. J. Cancer 2000, 87(5):734-740.
33. Osier M., Pakstis A.J., Kidd J.R., Lee J.F., Yin S.J., Ko H.C., Edenberg H.J., Lu R.B., Kidd K.K. Linkage disequilibrium at the ADH2 and ADH3 loci and risk of alcoholism. Am. J. Hum. Genet. 1999, 64(4):1147-1157.
34. Kawase T., Matsuo K., Hiraki A., Suzuki T., Watanabe M., Iwata H., Tanaka H., Tajima K. Interaction of the effects of alcohol drinking and polymorphisms in alcohol-metabolizing enzymes on the risk of female breast cancer in Japan. J. Epidemiol. 2009, 19(5):244-250.
35. Yoshida A., Ikawa M., Hsu L.C., Tani K. Molecular abnormality and cDNA cloning of human aldehyde dehydrogenases. Alcohol 1985, 2(1):103-106.
36. Higuchi S., Matsushita S., Murayama M., Takagi S., Hayashida M. Alcohol and aldehyde dehydrogenase polymorphisms and the risk for alcoholism. Am. J. Psychiatry 1995, 152(8):1219-1221.
37. Muramatsu T., Higuchi S., Shigemori K., Saito M., Sasao M., Harada S., Shigeta Y., Yamada K., Muraoka H., Takagi S., et al. Ethanol patch test-a simple and sensitive method for identifying ALDH phenotype. Alcohol. Clin. Exp. Res. 1989, 13(2):229-231.
38. Baan R., Straif K., Grosse Y., Secretan B., El Ghissassi F., Bouvard V., Altieri A., Cogliano V. Carcinogenicity of alcoholic beverages. Lancet Oncol. 2007, 8(4):292-293.
39. Oyama T., Isse T., Kagawa N., Kinaga T., Kim Y.D., Morita M., Sugio K., Weiner H., Yasumoto K., Kawamoto T. Tissue-distribution of aldehyde dehydrogenase 2 and effects of the ALDH2 gene-disruption on the expression of enzymes involved in alcohol metabolism. Front. Biosci. 2005, 10:951-960.
40. Mizoi Y., Yamamoto K., Ueno Y., Fukunaga T., Harada S. Involvement of genetic polymorphism of alcohol and aldehyde dehydrogenases in individual variation of alcohol metabolism. Alcohol Alcohol. 1994, 29(6):707-710.
41. Morimoto K., Takeshita T. Low Km aldehyde dehydrogenase (ALDH2) polymorphism, alcohol-drinking behavior, and chromosome alterations in peripheral lymphocytes, Environ. Health Perspect. 1996, 104(Suppl. 3):563-567.
42. Vakevainen S., Tillonen J., Agarwal D.P., Srivastava N., Salaspuro M. High salivary acetaldehyde after a moderate dose of alcohol in ALDH2-deficient subjects: strong evidence for the local carcinogenic action of acetaldehyde. Alcohol. Clin. Exp. Res. 2000, 24(6):873-877.
43. Oyama T., Isse T., Ogawa M., Muto M., Uchiyama I., Kawamoto T. Susceptibility to inhalation toxicity of acetaldehyde in Aldh2 knockout mice. Front. Biosci. 2007, 12:1927-1934.
44. Shibuya A., Yoshida A. Genotypes of alcohol-metabolizing enzymes in Japanese with alcohol liver diseases: a strong association of the usual Caucasian-type aldehyde dehydrogenase gene (ALDH1(2)) with the disease. Am. J. Hum. Genet. 1988, 43(5):744-748.
45. Yokoyama A., Muramatsu T., Omori T., Matsushita S., Yoshimizu H., Higuchi S., Yokoyama T., Maruyama K., Ishii H. Alcohol and aldehyde dehydrogenase gene polymorphisms influence susceptibility to esophageal cancer in Japanese alcoholics. Alcohol. Clin. Exp. Res. 1999, 23(11):1705-1710.
46. Yokoyama A., Muramatsu T., Ohmori T., Makuuchi H., Higuchi S., Matsushita S., Yoshino K., Maruyama K., Nakano M., Ishii H. Multiple primary esophageal and concurrent upper aerodigestive tract cancer and the aldehyde dehydrogenase-2 genotype of Japanese alcoholics. Cancer 1996, 77(10):1986-1990.
47. IARC Allyl compounds, aldehydes, epoxides and peroxides. IARC Monogr. Eval. Carcinog. Risks Hum. 1985, 36:101-132.
48. He S.M., Lambert B. Acetaldehyde-induced mutation at the hprt locus in human lymphocytes in vitro. Environ. Mol. Mutagen. 1990, 16(2):57-63.
49. Espina N., Lima V., Lieber C.S., Garro A.J. In vitro and in vivo inhibitory effect of ethanol and acetaldehyde on O6-methylguanine transferase. Carcinogenesis 1988, 9(5):761-766.
50. Woutersen R.A., Appelman L.M., Van Garderen-Hoetmer A., Feron V.J. Inhalation toxicity of acetaldehyde in rats. III. Carcinogenicity study. Toxicology 1986, 41(2):213-231.
51. Feron V.J., Kruysse A., Woutersen R.A. Respiratory tract tumours in hamsters exposed to acetaldehyde vapour alone or simultaneously to benzo(a)pyrene or diethylnitrosamine. Eur. J. Cancer Clin. Oncol. 1982, 18(1):13-31.
52. 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(3):111-121.
53. Oyama T., Nagayoshi H., Matsuda T., Oka M., Isse T., Yu H.S., Pham T.T., Tanaka M., Kagawa N., Kaneko K., Kawamoto T. Effects of acetaldehyde inhalation in mitochondrial aldehyde dehydrogenase deficient mice (Aldh2-/-). Front. Biosci. (Elite Ed.) 2010, 2:1344-1354.
54. Wang M., McIntee E.J., Cheng G., Shi Y., Villalta P.W., Hecht S.S. Identification of DNA adducts of acetaldehyde. Chem. Res. Toxicol. 2000, 13(11):1149-1157.
55. 2-ethylidene-2′-deoxyguanosine DNA adducts in aldehyde dehydrogenase 2-knockout mice treated with ethanol. Carcinogenesis 2007, 28(11):2363-2366.
56. Matsuda T., Yabushita H., Kanaly R.A., Shibutani S., Yokoyama A. Increased DNA damage in ALDH2-deficient alcoholics. Chem. Res. Toxicol. 2006, 19(10):1374-1378.
57. Ogawa M., Oyama T., Isse T., Saito K., Tomigahara Y., Endo Y., Kawamoto T. A comparison of covalent binding of ethanol metabolites to DNA according to Aldh2 genotype. Toxicol. Lett. 2007, 168(2):148-154.
58. Lutz W.K. In vivo covalent binding of organic chemicals to DNA as a quantitative indicator in the process of chemical carcinogenesis. Mutat. Res. 1979, 65(4):289-356.
59. 2-ethyl-dG adducts along duplex DNA. Chem. Res. Toxicol. 2007, 20(10):1379-1387.
60. Harris C.C. Interindividual variation among humans in carcinogen metabolism, DNA adduct formation and DNA repair. Carcinogenesis 1989, 10(9):1563-1566.
61. 2-ethyl-2′-deoxyguanosine adducts. Chem. Res. Toxicol. 2009, 22(6):1181-1188.
62. 2-ethyl-2′-deoxyguanosine triphosphate during DNA synthesis catalyzed by mammalian replicative DNA polymerases. Biochemistry 1999, 38(3):929-935.
63. 2-ethyldeoxyguanosine DNA adducts in the human embryonic kidney cell line 293. Chem. Res. Toxicol. 2006, 19(7):960-967.
64. Marietta C., Thompson L.H., Lamerdin J.E., Brooks P.J. Acetaldehyde stimulates FANCD2 monoubiquitination, H2AX phosphorylation, and BRCA1 phosphorylation in human cells in vitro: implications for alcohol-related carcinogenesis. Mutat. Res. 2009, 664(1-2):77-83.
65. Liu X., Lao Y., Yang I.Y., Hecht S.S., Moriya M. Replication-coupled repair of crotonaldehyde/acetaldehyde-induced guanine-guanine interstrand cross-links and their mutagenicity. Biochemistry 2006, 45(42):12898-12905.
66. Mechilli M., Schinoppi A., Kobos K., Natarajan A.T., Palitti F. DNA repair deficiency and acetaldehyde-induced chromosomal alterations in CHO cells. Mutagenesis 2008, 23(1):51-56.
67. De Silva I.U., McHugh P.J., Clingen P.H., Hartley J.A. Defining the roles of nucleotide excision repair and recombination in the repair of DNA interstrand cross-links in mammalian cells. Mol. Cell. Biol. 2000, 20(21):7980-7990.
68. Ristow H., Obe G. Acetaldehyde induces cross-links in DNA and causes sister-chromatid exchanges in human cells. Mutat. Res. 1978, 58(1):115-119.
69. Wu D., Cederbaum A.I. Oxidative stress mediated toxicity exerted by ethanol-inducible CYP2E1. Toxicol. Appl. Pharmacol. 2005, 207(2 Suppl.):70-76.
70. Song M.F., Li Y.S., Ootsuyama Y., Kasai H., Kawai K., Ohta M., Eguchi Y., Yamato H., Matsumoto Y., Yoshida R., Ogawa Y. Urea, the most abundant component in urine, cross-reacts with a commercial 8-OH-dG ELISA kit and contributes to overestimation of urinary 8-OH-dG. Free Radic. Biol. Med. 2009, 47(1):41-46.
71. Ekstrom G., Ingelman-Sundberg M. Rat liver microsomal NADPH-supported oxidase activity and lipid peroxidation dependent on ethanol-inducible cytochrome P-450 (P-450IIE1). Biochem. Pharmacol. 1989, 38(8):1313-1319.
72. Marnett L.J. Oxyradicals and DNA damage. Carcinogenesis 2000, 21(3):361-370.
73. De Bont R., van Larebeke N. Endogenous DNA damage in humans: a review of quantitative data. Mutagenesis 2004, 19(3):169-185.
74. Ichihashi K., Osawa T., Toyokuni S., Uchida K. Endogenous formation of protein adducts with carcinogenic aldehydes: implications for oxidative stress. J. Biol. Chem. 2001, 276(26):23903-23913.
75. Ishii T., Kumazawa S., Sakurai T., Nakayama T., Uchida K. Mass spectroscopic characterization of protein modification by malondialdehyde. Chem. Res. Toxicol. 2006, 19(1):122-129.
76. Ishino K., Wakita C., Shibata T., Toyokuni S., Machida S., Matsuda S., Matsuda T., Uchida K. Lipid peroxidation generates body odor component trans-2-nonenal covalently bound to protein in vivo. J. Biol. Chem. 2010, 285(20):15302-15313.
77. Tuma D.J. Role of malondialdehyde-acetaldehyde adducts in liver injury. Free Radic. Biol. Med. 2002, 32(4):303-308.
78. Wang R.S., Nakajima T., Kawamoto T., Honma T. Effects of aldehyde dehydrogenase-2 genetic polymorphisms on metabolism of structurally different aldehydes in human liver. Drug Metab. Dispos. 2002, 30(1):69-73.
79. Yoshida A., Rzhetsky A., Hsu L.C., Chang C. Human aldehyde dehydrogenase gene family. Eur. J. Biochem. 1998, 251(3):549-557.
80. Vasiliou V., Bairoch A., Tipton K.F., Nebert D.W. Eukaryotic aldehyde dehydrogenase (ALDH) genes: human polymorphisms, and recommended nomenclature based on divergent evolution and chromosomal mapping. Pharmacogenetics 1999, 9(4):421-434.
81. Crabb D.W., Matsumoto M., Chang D., You M. Overview of the role of alcohol dehydrogenase and aldehyde dehydrogenase and their variants in the genesis of alcohol-related pathology. Proc. Nutr. Soc. 2004, 63(1):49-63.
82. Wang M., Cheng G., Balbo S., Carmella S.G., Villalta P.W., Hecht S.S. Clear differences in levels of a formaldehyde-DNA adduct in leukocytes of smokers and nonsmokers. Cancer Res. 2009, 69(18):7170-7174.
83. 6-ethenodeoxyadenosine, a DNA adduct highly mutagenic in mammalian cells. Biochemistry 1996, 35(35):11487-11492.
84. Kenney W.C. Acetaldehyde adducts of phospholipids. Alcohol. Clin. Exp. Res. 1982, 6(3):412-416.
85. Davis V.E., Walsh M.J. Alcohol, amines, and alkaloids: a possible biochemical basis for alcohol addiction. Science 1970, 167(920):1005-1007.
86. Sjoquist B., Liljequist S., Engel J. Increased salsolinol levels in rat striatum and limbic forebrain following chronic ethanol treatment. J. Neurochem. 1982, 39(1):259-262.
87. Pfohl-Leszkowicz A., Grosse Y., Carriere V., Cugnenc P.H., Berger A., Carnot F., Beaune P., de Waziers I. High levels of DNA adducts in human colon are associated with colorectal cancer. Cancer Res. 1995, 55(23):5611-5616.
88. Chen C.L., Chi C.W., Chang K.W., Liu T.Y. Safrole-like DNA adducts in oral tissue from oral cancer patients with a betel quid chewing history. Carcinogenesis 1999, 20(12):2331-2334.
89. Saad A.A., O'Connor P.J., Mostafa M.H., Metwalli N.E., Cooper D.P., Margison G.P., Povey A.C. Bladder tumor contains higher N7-methylguanine levels in DNA than adjacent normal bladder epithelium. Cancer Epidemiol. Biomarkers Prev. 2006, 15(4):740-743.
90. Tang D., Santella R.M., Blackwood A.M., Young T.L., Mayer J., Jaretzki A., Grantham S., Tsai W.Y., Perera F.P. A molecular epidemiological case-control study of lung cancer. Cancer Epidemiol. Biomarkers Prev. 1995, 4(4):341-346.
91. Kriek E., Van Schooten F.J., Hillebrand M.J., Van Leeuwen F.E., Den Engelse L., De Looff A.J., Dijkmans A.P. DNA adducts as a measure of lung cancer risk in humans exposed to polycyclic aromatic hydrocarbons. Environ. Health Perspect. 1993, 99:71-75.
92. Marjani H.A., Biramijamal F., Rakhshani N., Hossein-Nezhad A., Malekzadeh R. Investigation of NQO1 genetic polymorphism, NQO1 gene expression and PAH-DNA adducts in ESCC. A case-control study from Iran. Genet. Mol. Res. 2010, 9(1):239-249.
93. Warnakulasuriya S., Parkkila S., Nagao T., Preedy V.R., Pasanen M., Koivisto H., Niemela O. Demonstration of ethanol-induced protein adducts in oral leukoplakia (pre-cancer) and cancer. J. Oral Pathol. Med. 2008, 37(3):157-165.
94. Kitagawa K., Kawamoto T., Kunugita N., Tsukiyama T., Okamoto K., Yoshida A., Nakayama K. Aldehyde dehydrogenase (ALDH) 2 associates with oxidation of methoxyacetaldehyde; in vitro analysis with liver subcellular fraction derived from human and Aldh2 gene targeting mouse. FEBS Lett. 2000, 476(3):306-311.
95. Mitchell D.Y., Petersen D.R. The oxidation of alpha-beta unsaturated aldehydic products of lipid peroxidation by rat liver aldehyde dehydrogenases. Toxicol. Appl. Pharmacol. 1987, 87(3):403-410.
96. 2-propanodeoxyguanosine adducts of 2-hexenal in vivo. Arch. Toxicol. 2000, 74(10):642-648.
97. Ohsawa I., Kamino K., Nagasaka K., Ando F., Niino N., Shimokata H., Ohta S. Genetic deficiency of a mitochondrial aldehyde dehydrogenase increases serum lipid peroxides in community-dwelling females. J. Hum. Genet. 2003, 48(8):404-409.
98. Moon K.H., Kim B.J., Song B.J. Inhibition of mitochondrial aldehyde dehydrogenase by nitric oxide-mediated S-nitrosylation. FEBS Lett. 2005, 579(27):6115-6120.
99. Marnett L.J. Oxy radicals, lipid peroxidation and DNA damage. Toxicology 2002, 181-182:219-222.
100. Churchill E.N., Disatnik M.H., Mochly-Rosen D. Time-dependent and ethanol-induced cardiac protection from ischemia mediated by mitochondrial translocation of varepsilonPKC and activation of aldehyde dehydrogenase 2. J. Mol. Cell. Cardiol. 2009, 46(2):278-284.
101. Ohta S., Ohsawa I. Dysfunction of mitochondria and oxidative stress in the pathogenesis of Alzheimer's disease: on defects in the cytochrome c oxidase complex and aldehyde detoxification. J. Alzheimers Dis. 2006, 9(2):155-166.
102. Dosanjh M.K., Chenna A., Kim E., Fraenkel-Conrat H., Samson L., Singer B. All four known cyclic adducts formed in DNA by the vinyl chloride metabolite chloroacetaldehyde are released by a human DNA glycosylase. Proc. Natl. Acad. Sci. U. S. A. 1994, 91(3):1024-1028.
103. Rouzer C.A., Chaudhary A.K., Nokubo M., Ferguson D.M., Reddy G.R., Blair I.A., Marnett L.J. Analysis of the malondialdehyde-2′-deoxyguanosine adduct pyrimidopurinone in human leukocyte DNA by gas chromatography/electron capture/negative chemical ionization/mass spectrometry. Chem. Res. Toxicol. 1997, 10(2):181-188.
104. Fink S.P., Reddy G.R., Marnett L.J. Mutagenicity in Escherichia coli of the major DNA adduct derived from the endogenous mutagen malondialdehyde. Proc. Natl. Acad. Sci. U. S. A. 1997, 94(16):8652-8657.
105. Winter C.K., Segall H.J., Haddon W.F. Formation of cyclic adducts of deoxyguanosine with the aldehydes trans-4-hydroxy-2-hexenal and trans-4-hydroxy-2-nonenal in vitro. Cancer Res. 1986, 46(11):5682-5686.
106. Isse T., Kitagawa K., Matsuno K., Matsuda T., Oyama T., Kawamoto T. Alcohol-mediated organ damage and acetaldehyde adducts. Jpn. J. Psychiatr. Res. Alcohol. 2007, 14:3-9. (in Japanese).
107. Wang M., McIntee E.J., Cheng G., Shi Y., Villalta P.W., Hecht S.S. Identification of paraldol-deoxyguanosine adducts in DNA reacted with crotonaldehyde. Chem. Res. Toxicol. 2000, 13(10):1065-1074.