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DNA damage induced by endogenous aldehydes: Current state of knowledge

Voulgaridou, Georgia-Persephoni, Anestopoulos, Ioannis, Franco, Rodrigo, Panayiotidis, Mihalis I., Pappa, Aglaia·2011·Mutation Research - Fundamental and Molecular Mechanisms of Mutagenesis
DOI 10.1016/j.mrfmmm.2011.03.006
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  1. Vasiliou, 2000, Role of aldehyde dehydrogenases in endogenous and xenobiotic metabolism, Chem. Biol. Interact., 129, 1, 10.1016/S0009-2797(00)00211-8 · DOI · Paper page
  2. Vasiliou, 2004, Role of human aldehyde dehydrogenases in endobiotic and xenobiotic metabolism, Drug Metab. Rev., 36, 279, 10.1081/DMR-120034001 · DOI · Paper page
  3. Niki, 2009, Lipid peroxidation: physiological levels and dual biological effects, Free Radic. Biol. Med., 47, 469, 10.1016/j.freeradbiomed.2009.05.032 · DOI · Paper page
  4. Petersen, 2004, Reactions of 4-hydroxynonenal with proteins and cellular targets, Free Radic. Biol. Med., 37, 937, 10.1016/j.freeradbiomed.2004.06.012 · DOI · Paper page
  5. Dmitriev, 2010, Lipid peroxidation in relation to ageing and the role of endogenous aldehydes in diabetes and other age-related diseases, Ageing Res. Rev., 9, 200, 10.1016/j.arr.2009.09.004 · DOI
  6. Forman, 2010, Reactive oxygen species and alpha,beta-unsaturated aldehydes as second messengers in signal transduction, Ann N. Y. Acad. Sci., 1203, 35, 10.1111/j.1749-6632.2010.05551.x · DOI
  7. Davydov, 2003, Metabolism of endogenous aldehydes: participation in oxidative stress-induced lesions and its age aspects, Biomed. Khim., 49, 374
  8. Esterbauer, 1991, Chemistry and biochemistry of 4-hydroxynonenal, malonaldehyde and related aldehydes, Free Radic. Biol. Med., 11, 81, 10.1016/0891-5849(91)90192-6 · DOI · Paper page
  9. Roberts, 2003, DNA damage by carbonyl stress in human skin cells, Mutat. Res., 522, 45
  10. Cadet, 2010, Oxidatively generated base damage to cellular DNA, Free Radic. Biol. Med., 49, 9, 10.1016/j.freeradbiomed.2010.03.025 · DOI · Paper page
  11. Zarkovic, 2003, 4-hydroxynonenal as a bioactive marker of pathophysiological processes, Mol. Aspects Med., 24, 281, 10.1016/S0098-2997(03)00023-2 · DOI · Paper page
  12. Huang, 2010, DNA cross-link induced by trans-4-hydroxynonenal, Environ. Mol. Mutagen, 51, 625, 10.1002/em.20599 · DOI
  13. Siddiqui, 2010, Protective potential of trans-resveratrol against 4-hydroxynonenal induced damage in PC12 cells, Toxicol. in Vitro, 24, 1592, 10.1016/j.tiv.2010.06.008 · DOI
  14. Esterbauer, 1986, Studies on the mechanism of formation of 4-hydroxynonenal during microsomal lipid peroxidation, Biochim. Biophys. Acta, 876, 154, 10.1016/0005-2760(86)90329-2 · DOI · Paper page
  15. Schneider, 2008, Routes to 4-hydroxynonenal: fundamental issues in the mechanisms of lipid peroxidation, J. Biol. Chem., 283, 15539, 10.1074/jbc.R800001200 · DOI · Paper page
  16. Kuiper, 2008, Mercapturic acid conjugates of 4-hydroxy-2-nonenal and 4-oxo-2-nonenal metabolites are in vivo markers of oxidative stress, J. Biol. Chem., 283, 17131, 10.1074/jbc.M802797200 · DOI
  17. LoPachin, 2009, Molecular mechanisms of 4-hydroxy-2-nonenal and acrolein toxicity: nucleophilic targets and adduct formation, Chem. Res. Toxicol., 22, 1499, 10.1021/tx900147g · DOI · Paper page
  18. Jomova, 2010, Metals, oxidative stress and neurodegenerative disorders, Mol. Cell. Biochem., 345, 91, 10.1007/s11010-010-0563-x · DOI · Paper page
  19. Minko, 2009, Chemistry and biology of DNA containing 1,N(2)-deoxyguanosine adducts of the alpha,beta-unsaturated aldehydes acrolein, crotonaldehyde, and 4-hydroxynonenal, Chem. Res. Toxicol., 22, 759, 10.1021/tx9000489 · DOI · Paper page
  20. Nair, 2007, Lipid peroxidation-induced DNA damage in cancer-prone inflammatory diseases: a review of published adduct types and levels in humans, Free Radic. Biol. Med., 43, 1109, 10.1016/j.freeradbiomed.2007.07.012 · DOI · Paper page
  21. Wang, 2003, Site-specific synthesis and reactivity of oligonucleotides containing stereochemically defined 1,N2-deoxyguanosine adducts of the lipid peroxidation product trans-4-hydroxynonenal, J. Am. Chem. Soc., 125, 5687, 10.1021/ja0288800 · DOI
  22. Liu, 2006, Replication-coupled repair of crotonaldehyde/acetaldehyde-induced guanine-guanine interstrand cross-links and their mutagenicity, Biochemistry, 45, 12898, 10.1021/bi060792v · DOI
  23. Hussain, 2000, Increased p53 mutation load in nontumorous human liver of wilson disease and hemochromatosis: oxyradical overload diseases, Proc. Natl. Acad. Sci. U.S.A., 97, 12770, 10.1073/pnas.220416097 · DOI · Paper page
  24. Chung, 2000, Deoxyguanosine adducts of t-4-hydroxy-2-nonenal are endogenous DNA lesions in rodents and humans: detection and potential sources, Cancer Res., 60, 1507
  25. Nair, 2007, Lipid peroxidation-derived etheno-DNA adducts in human atherosclerotic lesions, Mutat. Res., 621, 95, 10.1016/j.mrfmmm.2007.02.013 · DOI
  26. Bartsch, 2004, Oxidative stress and lipid peroxidation-derived DNA-lesions in inflammation driven carcinogenesis, Cancer Detect. Prev., 28, 385, 10.1016/j.cdp.2004.07.004 · DOI · Paper page
  27. Nair, 2006, Increased etheno-DNA adducts in affected tissues of patients suffering from Crohn's disease, ulcerative colitis, and chronic pancreatitis, Antioxid. Redox. Signal., 8, 1003, 10.1089/ars.2006.8.1003 · DOI
  28. Nair, 2010, High urinary excretion of lipid peroxidation-derived DNA damage in patients with cancer-prone liver diseases, Mutat. Res., 683, 23
  29. Young, 2010, Levels of oxidative damage and lipid peroxidation in thyroid neoplasia, Head Neck, 32, 750, 10.1002/hed.21247 · DOI
  30. Hu, 2002, The major lipid peroxidation product, trans-4-hydroxy-2-nonenal, preferentially forms DNA adducts at codon 249 of human p53 gene, a unique mutational hotspot in hepatocellular carcinoma, Carcinogenesis, 23, 1781, 10.1093/carcin/23.11.1781 · DOI · Paper page
  31. Meerang, 2008, Increased urinary 1,N6-ethenodeoxyadenosine and 3,N4-ethenodeoxycytidine excretion in thalassemia patients: markers for lipid peroxidation-induced DNA damage, Free Radic. Biol. Med., 44, 1863, 10.1016/j.freeradbiomed.2008.02.009 · doi:10.1016/j.freeradbiomed.2008.02.009
  32. Nair, 2005, Age-dependent increase of etheno-DNA-adducts in liver and brain of ROS overproducing OXYS rats, Biochem. Biophys. Res. Commun., 336, 478, 10.1016/j.bbrc.2005.08.114 · DOI
  33. Gotz, 2002, Unaltered brain levels of 1,N2-propanodeoxyguanosine adducts of trans-4-hydroxy-2-nonenal in Alzheimer's disease, Neurosci. Lett., 324, 49, 10.1016/S0304-3940(02)00163-5 · DOI
  34. Stevens, 2008, Acrolein: sources, metabolism, and biomolecular interactions relevant to human health and disease, Mol. Nutr. Food Res., 52, 7, 10.1002/mnfr.200700412 · DOI · Paper page
  35. Zaliznyak, 2010, NMR structure of duplex DNA containing the alpha-OH-PdG.dA base pair: a mutagenic intermediate of acrolein, Biopolymers, 93, 391, 10.1002/bip.21366 · doi:10.1002/bip.21366
  36. Singh, 2010, Role of by-products of lipid oxidation in Alzheimer's disease brain: a focus on acrolein, J. Alzheimers. Dis., 21, 741, 10.3233/JAD-2010-100405 · DOI · Paper page
  37. Monteil, 1999, Acrolein toxicity: comparative in vitro study with lung slices and pneumocytes type II cell line from rats, Toxicology, 133, 129, 10.1016/S0300-483X(99)00015-3 · doi:10.1016/s0300-483x(99)00015-3
  38. Kaminskas, 2004, Strong protein adduct trapping accompanies abolition of acrolein-mediated hepatotoxicity by hydralazine in mice, J. Pharmacol. Exp. Ther., 310, 1003, 10.1124/jpet.104.067330 · DOI
  39. Uchida, 1999, Current status of acrolein as a lipid peroxidation product, Trends Cardiovasc. Med., 9, 109, 10.1016/S1050-1738(99)00016-X · DOI · Paper page
  40. Pan, 2009, Acrolein-derived DNA adduct formation in human colon cancer cells: its role in apoptosis induction by docosahexaenoic acid, Chem. Res. Toxicol., 22, 798, 10.1021/tx800355k · DOI
  41. Liu, 2010, Mutagenicity of acrolein and acrolein-induced DNA adducts, Toxicol. Mech. Methods, 20, 36, 10.3109/15376510903530845 · doi:10.3109/15376510903530845
  42. Minetti, 2010, Impact of alpha-hydroxy-propanodeoxyguanine adducts on DNA duplex energetics: opposite base modulation and implications for mutagenicity and genotoxicity, Biopolymers, 93, 370, 10.1002/bip.21355 · DOI
  43. Feng, 2006, Acrolein is a major cigarette-related lung cancer agent: preferential binding at p53 mutational hotspots and inhibition of DNA repair, Proc. Natl. Acad. Sci. U.S.A., 103, 15404, 10.1073/pnas.0607031103 · DOI · Paper page
  44. Stone, 2008, Interstrand DNA cross-links induced by alpha,beta-unsaturated aldehydes derived from lipid peroxidation and environmental sources, Acc. Chem. Res., 41, 793, 10.1021/ar700246x · DOI · Paper page
  45. Nam, 2010, Potential role of acrolein in neurodegeneration and in Alzheimer's disease, Curr. Mol. Pharmacol., 3, 66, 10.2174/1874-470211003020066 · DOI
  46. Nath, 1994, Detection of exocyclic 1,N2-propanodeoxyguanosine adducts as common DNA lesions in rodents and humans, Proc. Natl. Acad. Sci. U.S.A., 91, 7491, 10.1073/pnas.91.16.7491 · DOI · Paper page
  47. Kawai, 2003, Formation of acrolein-derived 2′-deoxyadenosine adduct in an iron-induced carcinogenesis model, J. Biol. Chem., 278, 50346, 10.1074/jbc.M309057200 · DOI
  48. Chen, 2009, Simultaneous quantification of 1,N2-propano-2′-deoxyguanosine adducts derived from acrolein and crotonaldehyde in human placenta and leukocytes by isotope dilution nanoflow LC nanospray ionization tandem mass spectrometry, Anal. Chem., 81, 9812, 10.1021/ac9019472 · DOI
  49. Liu, 2005, Development of a method for quantification of acrolein-deoxyguanosine adducts in DNA using isotope dilution-capillary LC/MS/MS and its application to human brain tissue, Anal. Chem., 77, 5982, 10.1021/ac050624t · DOI
  50. Liu, 2006, Detection and quantification of endogenous cyclic DNA adducts derived from trans-4-hydroxy-2-nonenal in human brain tissue by isotope dilution capillary liquid chromatography nanoelectrospray tandem mass spectrometry, Chem. Res. Toxicol., 19, 710, 10.1021/tx0502903 · DOI
  51. Sezer, 2010, DNA damage and its relationship with other oxidative stress parameters in Behcet's disease, Rheumatol. Int.
  52. Del, 2005, A review of recent studies on malondialdehyde as toxic molecule and biological marker of oxidative stress, Nutr. Metab Cardiovasc. Dis., 15, 316, 10.1016/j.numecd.2005.05.003 · DOI · Paper page
  53. Bono, 2010, Malondialdehyde-deoxyguanosine adduct formation in workers of pathology wards: the role of air formaldehyde exposure, Chem. Res. Toxicol., 23, 1342, 10.1021/tx100083x · DOI
  54. Marnett, 2002, Oxy radicals, lipid peroxidation and DNA damage, Toxicology, 181–182, 219, 10.1016/S0300-483X(02)00448-1 · DOI · Paper page
  55. Marnett, 1999, Lipid peroxidation-DNA damage by malondialdehyde, Mutat. Res., 424, 83
  56. Jacobs, 2010, Systems analysis of protein modification and cellular responses induced by electrophile stress, Acc. Chem. Res., 43, 673, 10.1021/ar900286y · DOI · Paper page
  57. Kew, 2009, Hepatic iron overload and hepatocellular carcinoma, Cancer Lett., 286, 38, 10.1016/j.canlet.2008.11.001 · DOI
  58. Kanner, 2007, Dietary advanced lipid oxidation endproducts are risk factors to human health, Mol. Nutr. Food Res., 51, 1094, 10.1002/mnfr.200600303 · DOI · Paper page
  59. Agadjanyan, 2005, A new role of phosphoglucose isomerase. Involvement of the glycolytic enzyme in aldehyde metabolism, Biochemistry (Mosc.), 70, 1251, 10.1007/s10541-005-0255-4 · doi:10.1007/s10541-005-0255-4
  60. Dmitriev, 2007, Aldehydes and disturbance of carbohydrate metabolism: some consequences and possible approaches to its normalization, Arch. Physiol. Biochem., 113, 87, 10.1080/13813450701384783 · DOI
  61. Maddukuri, 2010, In vitro bypass of the major malondialdehyde- and base propenal-derived DNA adduct by human Y-family DNA polymerases kappa, iota, and Rev1, Biochemistry, 49, 8415, 10.1021/bi1009024 · doi:10.1021/bi1009024
  62. Cline, 2010, Arrest of human mitochondrial RNA polymerase transcription by the biological aldehyde adduct of DNA, M1dG, Nucleic Acids Res., 38, 7546, 10.1093/nar/gkq656 · DOI
  63. Marnett, 1999, Chemistry and biology of DNA damage by malondialdehyde, IARC Sci. Publ., 17
  64. Pluskota-Karwatka, 2010, Identification of adducts formed in the reactions of malonaldehyde–glyoxal and malonaldehyde–methylglyoxal with adenosine and calf thymus DNA, Chem. Biodivers., 7, 959, 10.1002/cbdv.200800320 · doi:10.1002/cbdv.200800320
  65. Wang, 1996, Lipid peroxidation-induced putative malondialdehyde-DNA adducts in human breast tissues, Cancer Epidemiol. Biomarkers Prev., 5, 705
  66. Voss, 2006, Clinical oxidation parameters of aging, Free Radic. Res., 40, 1339, 10.1080/10715760600953859 · DOI
  67. Cai, 1996, Age-dependent increase of indigenous DNA adducts in rat brain is associated with a lipid peroxidation product, Exp. Gerontol., 31, 373, 10.1016/0531-5565(95)02027-6 · DOI
  68. Peluso, 2011, Breast fine-needle aspiration malondialdehyde deoxyguanosine adduct in breast cancer, Free Radic. Res., 45, 477, 10.3109/10715762.2010.549485 · DOI
  69. Munnia, 2006, Bronchial malondialdehyde DNA adducts, tobacco smoking, and lung cancer, Free Radic. Biol. Med., 41, 1499, 10.1016/j.freeradbiomed.2006.08.007 · DOI
  70. Munnia, 2004, Exocyclic malondialdehyde and aromatic DNA adducts in larynx tissues, Free Radic. Biol. Med., 37, 850, 10.1016/j.freeradbiomed.2004.05.024 · DOI
  71. Singh, 2001, Lobe-specific increases in malondialdehyde DNA adduct formation in the livers of mice following infection with Helicobacter hepaticus, Carcinogenesis, 22, 1281, 10.1093/carcin/22.8.1281 · DOI
  72. Gungor, 2010, Transcriptional profiling of the acute pulmonary inflammatory response induced by LPS: role of neutrophils, Respir. Res., 11, 24, 10.1186/1465-9921-11-24 · doi:10.1186/1465-9921-11-24
  73. Jeong, 2008, Accumulation of M1dG DNA adducts after chronic exposure to PCBs, but not from acute exposure to polychlorinated aromatic hydrocarbons, Free Radic. Biol. Med., 45, 585, 10.1016/j.freeradbiomed.2008.04.043 · DOI
  74. Chung, 2003, Formation of trans-4-hydroxy-2-nonenal- and other enal-derived cyclic DNA adducts from omega-3 and omega-6 polyunsaturated fatty acids and their roles in DNA repair and human p53 gene mutation, Mutat. Res., 531, 25
  75. Fernandes, 2005, Mammalian cell mutagenesis of the DNA adducts of vinyl chloride and crotonaldehyde, Environ. Mol. Mutagen., 45, 455, 10.1002/em.20117 · doi:10.1002/em.20117
  76. Liu, 2010, Crotonaldehyde induces oxidative stress and caspase-dependent apoptosis in human bronchial epithelial cells, Toxicol. Lett., 195, 90, 10.1016/j.toxlet.2010.02.004 · doi:10.1016/j.toxlet.2010.02.004
  77. Liu, 2010, Gene expression profile and cytotoxicity of human bronchial epithelial cells exposed to crotonaldehyde, Toxicol. Lett., 197, 113, 10.1016/j.toxlet.2010.05.005 · DOI
  78. Huang, 2008, Rearrangement of the (6S,8R 11S) and (6R,8S,11R) exocyclic 1,N2-deoxyguanosine adducts of trans-4-hydroxynonenal to N2-deoxyguanosine cyclic hemiacetal adducts when placed complementary to cytosine in duplex DNA, J. Am. Chem. Soc., 130, 10898, 10.1021/ja801824b · DOI
  79. Cho, 2006, Orientation of the crotonaldehyde-derived N2-[3-Oxo-1(S)-methyl-propyl]-dG DNA adduct hinders interstrand cross-link formation in the 5′-CpG-3′ sequence, Chem. Res. Toxicol., 19, 1019, 10.1021/tx0600604 · DOI
  80. Stein, 2006, Genotoxicity of acetaldehyde- and crotonaldehyde-induced 1,N2-propanodeoxyguanosine DNA adducts in human cells, Mutat. Res., 608, 1, 10.1016/j.mrgentox.2006.01.009 · DOI
  81. Zhang, 2006, Analysis of crotonaldehyde- and acetaldehyde-derived 1,n(2)-propanodeoxyguanosine adducts in DNA from human tissues using liquid chromatography electrospray ionization tandem mass spectrometry, Chem. Res. Toxicol., 19, 1386, 10.1021/tx060154d · DOI
  82. Dexheimer, 2008, The modulation of topoisomerase I-mediated DNA cleavage and the induction of DNA-topoisomerase I crosslinks by crotonaldehyde-derived DNA adducts, Nucleic Acids Res., 36, 4128, 10.1093/nar/gkn334 · DOI
  83. Cho, 2006, Stereospecific formation of interstrand carbinolamine DNA cross-links by crotonaldehyde- and acetaldehyde-derived alpha-CH3-gamma-OH-1,N2-propano-2′-deoxyguanosine adducts in the 5′-CpG-3′ sequence, Chem. Res. Toxicol., 19, 195, 10.1021/tx050239z · DOI
  84. Nath, 1996, Detection of 1, N2-propanodeoxyguanosine adducts as potential endogenous DNA lesions in rodent and human tissues, Cancer Res., 56, 452
  85. Nath, 1998, 1,N2-propanodeoxyguanosine adducts: potential new biomarkers of smoking-induced DNA damage in human oral tissue, Cancer Res, 58, 581
  86. Jha, 2007, Genotoxicity of crotonaldehyde in the bone marrow and germ cells of laboratory mice, Mutat. Res., 632, 69, 10.1016/j.mrgentox.2007.04.008 · doi:10.1016/j.mrgentox.2007.04.008
  87. Kawaguchi-Niida, 2006, Crotonaldehyde accumulates in glial cells of Alzheimer's disease brain, Acta Neuropathol., 111, 422, 10.1007/s00401-006-0044-1 · DOI
  88. Blair, 2001, Lipid hydroperoxide-mediated DNA damage, Exp. Gerontol., 36, 1473, 10.1016/S0531-5565(01)00133-4 · DOI · Paper page
  89. Long, 2010, Sr. Trans-4-hydroxy-2-hexenal, a product of n-3 fatty acid peroxidation: make some room HNE, Free Radic. Biol. Med., 49, 1, 10.1016/j.freeradbiomed.2010.03.015 · DOI · Paper page
  90. Guillen, 2008, Toxic oxygenated alpha,beta-unsaturated aldehydes and their study in foods: a review, Crit. Rev. Food Sci. Nutr., 48, 119, 10.1080/10408390601177613 · DOI · Paper page
  91. Zhu, 2009, Mass spectrometric characterization of protein modification by the products of nonenzymatic oxidation of linoleic acid, Chem. Res. Toxicol., 22, 1386, 10.1021/tx9000072 · doi:10.1021/tx9000072
  92. Lee, 2001, Oxidative DNA damage and cardiovascular disease, Trends Cardiovasc. Med., 11, 148, 10.1016/S1050-1738(01)00094-9 · DOI
  93. Kuiper, 2010, Quantitation of mercapturic acid conjugates of 4-hydroxy-2-nonenal and 4-oxo-2-nonenal metabolites in a smoking cessation study, Free Radic. Biol. Med., 48, 65, 10.1016/j.freeradbiomed.2009.10.025 · DOI
  94. Saito, 2010, Reaction products of gamma-tocopherol with (E)-4-oxo-2-nonenal in acidic acetonitrile, Biosci. Biotechnol. Biochem., 74, 168, 10.1271/bbb.90681 · DOI
  95. Shimozu, 2009, Identification of advanced reaction products originating from the initial 4-oxo-2-nonenal-cysteine Michael adducts, Chem. Res. Toxicol., 22, 957, 10.1021/tx900059k · doi:10.1021/tx900059k
  96. Doorn, 2002, Covalent modification of amino acid nucleophiles by the lipid peroxidation products 4-hydroxy-2-nonenal and 4-oxo-2-nonenal, Chem. Res. Toxicol., 15, 1445, 10.1021/tx025590o · DOI · Paper page
  97. Zhu, 2009, Covalent cross-linking of glutathione and carnosine to proteins by 4-oxo-2-nonenal, Chem. Res. Toxicol., 22, 1050, 10.1021/tx9000144 · DOI
  98. Sakuma, 2010, Xanthine oxidase-derived reactive oxygen species mediate 4-oxo-2-nonenal-induced hepatocyte cell death, Toxicol. Appl. Pharmacol., 249, 127, 10.1016/j.taap.2010.08.025 · DOI
  99. Chou, 2010, Detection of lipid peroxidation-induced DNA adducts caused by 4-oxo-2(E)-nonenal and 4-oxo-2(E)-hexenal in human autopsy tissues, Chem. Res. Toxicol., 23, 1442, 10.1021/tx100047d · DOI
  100. Christov, 2010, Comparison of the in vitro replication of the 7-(2-oxoheptyl)-1,N2-etheno-2′-deoxyguanosine and 1,N2-etheno-2′-deoxyguanosine lesions by Sulfolobus solfataricus P2 DNA polymerase iv (Dpo4), Chem. Res. Toxicol., 23, 1330, 10.1021/tx100082e · DOI
  101. Rindgen, 1999, Covalent modifications to 2′-deoxyguanosine by 4-oxo-2-nonenal, a novel product of lipid peroxidation, Chem. Res. Toxicol., 12, 1195, 10.1021/tx990034o · DOI
  102. Rindgen, 2000, Formation of a substituted 1,N(6)-etheno-2′-deoxyadenosine adduct by lipid hydroperoxide-mediated generation of 4-oxo-2-nonenal, Chem. Res. Toxicol., 13, 846, 10.1021/tx0000771 · DOI
  103. Pollack, 2003, Characterization of 2′-deoxycytidine adducts derived from 4-oxo-2-nonenal, a novel lipid peroxidation product, Chem. Res. Toxicol., 16, 893, 10.1021/tx030009p · DOI
  104. Teng, 2001, The formaldehyde metabolic detoxification enzyme systems and molecular cytotoxic mechanism in isolated rat hepatocytes, Chem. Biol. Interact., 130–132, 285, 10.1016/S0009-2797(00)00272-6 · DOI · Paper page
  105. Lu, 2010, Structural characterization of formaldehyde-induced cross-links between amino acids and deoxynucleosides and their oligomers, J. Am. Chem. Soc., 132, 3388, 10.1021/ja908282f · DOI · Paper page
  106. Lu, 2009, Formation of S-[1-(N2-deoxyguanosinyl)methyl]glutathione between glutathione and DNA induced by formaldehyde, J. Am. Chem. Soc., 131, 3414, 10.1021/ja808048c · doi:10.1021/ja808048c
  107. Cheng, 2003, Reactions of formaldehyde plus acetaldehyde with deoxyguanosine and DNA: formation of cyclic deoxyguanosine adducts and formaldehyde cross-links, Chem. Res. Toxicol., 16, 145, 10.1021/tx025614r · DOI
  108. Zhang, 2010, Formaldehyde and leukemia: epidemiology, potential mechanisms, and implications for risk assessment, Environ. Mol. Mutagen., 51, 181, 10.1002/em.20534 · DOI
  109. Zhang, 2009, Formaldehyde exposure and leukemia: a new meta-analysis and potential mechanisms, Mutat. Res., 681, 150, 10.1016/j.mrrev.2008.07.002 · DOI · Paper page
  110. Neuss, 2010, Gene expression changes in primary human nasal epithelial cells exposed to formaldehyde in vitro, Toxicol. Lett., 198, 289, 10.1016/j.toxlet.2010.07.010 · doi:10.1016/j.toxlet.2010.07.010
  111. Cheng, 2008, Formation of formaldehyde adducts in the reactions of DNA and deoxyribonucleosides with alpha-acetates of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone (NNK) 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanol (NNAL), and N-nitrosodimethylamine (NDMA), Chem. Res. Toxicol., 21, 746, 10.1021/tx7003823 · DOI
  112. Lu, 2010, Distribution of DNA adducts caused by inhaled formaldehyde is consistent with induction of nasal carcinoma but not leukemia, Toxicol. Sci., 116, 441, 10.1093/toxsci/kfq061 · DOI · Paper page
  113. Wang, 2009, Clear differences in levels of a formaldehyde-DNA adduct in leukocytes of smokers and nonsmokers, Cancer Res., 69, 7170, 10.1158/0008-5472.CAN-09-1571 · DOI
  114. Lu, 2011, Molecular dosimetry of N(2)-hydroxymethyl-dG DNA adducts in rats exposed to formaldehyde, Chem. Res. Toxicol., 24, 159, 10.1021/tx1003886 · DOI
  115. McGregor, 2006, Formaldehyde and glutaraldehyde and nasal cytotoxicity: case study within the context of the 2006 IPCS Human Framework for the Analysis of a cancer mode of action for humans, Crit. Rev. Toxicol., 36, 821, 10.1080/10408440600977669 · DOI
  116. Han, 2007, Plasma methylglyoxal and glyoxal are elevated and related to early membrane alteration in young, complication-free patients with Type 1 diabetes, Mol. Cell. Biochem., 305, 123, 10.1007/s11010-007-9535-1 · DOI
  117. Wuenschell, 2010, Mutagenic potential of DNA glycation: miscoding by (R)- and (S)-N2-(1-carboxyethyl)-2′-deoxyguanosine, Biochemistry, 49, 1814, 10.1021/bi901924b · DOI
  118. Kim, 2010, Methylglyoxal induces cellular damage by increasing argpyrimidine accumulation and oxidative DNA damage in human lens epithelial cells, Biochem. Biophys. Res. Commun., 391, 346, 10.1016/j.bbrc.2009.11.061 · DOI
  119. Nakadate, 2009, The formation of argpyrimidine, a methylglyoxal–arginine adduct, in the nucleus of neural cells, Biochem. Biophys. Res. Commun., 378, 209, 10.1016/j.bbrc.2008.11.028 · DOI
  120. Kim, 2010, Renal podocyte apoptosis in Zucker diabetic fatty rats: involvement of methylglyoxal-induced oxidative DNA damage, J. Comp. Pathol., 144, 41, 10.1016/j.jcpa.2010.04.008 · doi:10.1016/j.jcpa.2010.04.008
  121. Pampati, 2010, Monitoring nonenzymatic glycation of human immunoglobulin G by methylglyoxal and glyoxal: a spectroscopic study, Anal. Biochem., 408, 59, 10.1016/j.ab.2010.08.038 · DOI
  122. Thornalley, 2010, Imidazopurinones are markers of physiological genomic damage linked to DNA instability and glyoxalase 1-associated tumour multidrug resistance, Nucleic Acids Res., 38, 5432, 10.1093/nar/gkq306 · DOI
  123. Breyer, 2008, Analysis and biological relevance of advanced glycation end-products of DNA in eukaryotic cells, FEBS J., 275, 914, 10.1111/j.1742-4658.2008.06255.x · DOI
  124. Sartori, 2008, Aminoacetone, a putative endogenous source of methylglyoxal, causes oxidative stress and death to insulin-producing RINm5f cells, Chem. Res. Toxicol., 21, 1841, 10.1021/tx8001753 · DOI
  125. Thornalley, 2007, Endogenous alpha-oxoaldehydes and formation of protein and nucleotide advanced glycation endproducts in tissue damage, Novartis. Found. Symp., 285, 229, 10.1002/9780470511848.ch17 · doi:10.1002/9780470511848.ch17
  126. Lankin, 2007, Mechanisms of oxidative modification of low density lipoproteins under conditions of oxidative and carbonyl stress, Biochemistry (Mosc.), 72, 1081, 10.1134/S0006297907100069 · DOI
  127. Kim, 2010, KIOM-79 prevents methyglyoxal-induced retinal pericyte apoptosis in vitro and in vivo, J. Ethnopharmacol., 129, 285, 10.1016/j.jep.2010.03.027 · DOI
  128. Yuan, 2008, Efficient and accurate bypass of N2-(1-carboxyethyl)-2′-deoxyguanosine by DinB DNA polymerase in vitro and in vivo, Proc. Natl. Acad. Sci. U.S.A., 105, 8679, 10.1073/pnas.0711546105 · DOI
  129. Synold, 2008, Advanced glycation end products of DNA: quantification of N2-(1-Carboxyethyl)-2′-deoxyguanosine in biological samples by liquid chromatography electrospray ionization tandem mass spectrometry, Chem. Res. Toxicol., 21, 2148, 10.1021/tx800224y · DOI
  130. Tatone, 2010, Female reproductive dysfunction during ageing: role of methylglyoxal in the formation of advanced glycation endproducts in ovaries of reproductively-aged mice, J. Biol. Regul. Homeost. Agents, 24, 63
  131. Loeppky, 2002, Microsome-mediated oxidation of N-nitrosodiethanolamine (NDELA), a bident carcinogen, Chem. Res. Toxicol., 15, 457, 10.1021/tx000267b · doi:10.1021/tx000267b
  132. Kasai, 1998, DNA modifications by the mutagen glyoxal: adduction to G and C, deamination of C and GC and GA cross-linking, Carcinogenesis, 19, 1459, 10.1093/carcin/19.8.1459 · DOI
  133. Olsen, 2005, Reaction of glyoxal with 2′’-deoxyguanosine, 2′-deoxyadenosine, 2′-deoxycytidine, cytidine, thymidine, and calf thymus DNA: identification of DNA adducts, Chem. Res. Toxicol., 18, 730, 10.1021/tx0496688 · doi:10.1021/tx0496688
  134. Brock, 2004, Coupling products of nucleosides with the glyoxal adduct of deoxyguanosine, Chem. Res. Toxicol., 17, 1047, 10.1021/tx049906z · doi:10.1021/tx049906z
  135. Pluskota-Karwatka, 2008, Formation of adducts in the reaction of glyoxal with 2′-deoxyguanosine and with calf thymus DNA, Bioorg. Chem., 36, 57, 10.1016/j.bioorg.2007.10.004 · DOI
  136. Balbo, 2008, N2-ethyldeoxyguanosine as a potential biomarker for assessing effects of alcohol consumption on DNA, Cancer Epidemiol. Biomarkers Prev., 17, 3026, 10.1158/1055-9965.EPI-08-0117 · DOI
  137. Speit, 2008, Low sensitivity of the comet assay to detect acetaldehyde-induced genotoxicity, Mutat. Res., 657, 93, 10.1016/j.mrgentox.2008.07.010 · doi:10.1016/j.mrgentox.2008.07.010
  138. Mechilli, 2008, DNA repair deficiency and acetaldehyde-induced chromosomal alterations in CHO cells, Mutagenesis, 23, 51, 10.1093/mutage/gem042 · DOI
  139. Kayani, 2010, The in vitro genotoxicity of ethanol and acetaldehyde, Toxicol. in Vitro, 24, 56, 10.1016/j.tiv.2009.09.003 · DOI
  140. Nagayoshi, 2009, Increased formation of gastric N(2)-ethylidene-2′-deoxyguanosine DNA adducts in aldehyde dehydrogenase-2 knockout mice treated with ethanol, Mutat. Res., 673, 74, 10.1016/j.mrgentox.2008.11.009 · DOI
  141. Yu, 2010, Formation of acetaldehyde-derived DNA adducts due to alcohol exposure, Chem. Biol. Interact., 188, 367, 10.1016/j.cbi.2010.08.005 · DOI · Paper page
  142. Rulten, 2008, Alcohol induces DNA damage and the Fanconi anemia D2 protein implicating FANCD2 in the DNA damage response pathways in brain, Alcohol. Clin. Exp. Res., 32, 1186, 10.1111/j.1530-0277.2008.00673.x · DOI
  143. Matsuda, 2006, Increased DNA damage in ALDH2-deficient alcoholics, Chem. Res. Toxicol., 19, 1374, 10.1021/tx060113h · DOI
  144. McKillop, 2009, Role of alcohol in liver carcinogenesis, Semin. Liver Dis., 29, 222, 10.1055/s-0029-1214377 · DOI
  145. Toh, 2010, Alcohol drinking, cigarette smoking, and the development of squamous cell carcinoma of the esophagus: molecular mechanisms of carcinogenesis, Int. J. Clin. Oncol., 15, 135, 10.1007/s10147-010-0057-6 · DOI
  146. Seitz, 2007, Alcohol metabolism and cancer risk, Alcohol Res. Health, 30, 38
  147. Lorenti, 2009, Relationship between DNA lesions, DNA repair and chromosomal damage induced by acetaldehyde, Mutat. Res., 662, 3
  148. Singh, 2009, Evaluation of the DNA damaging potential of cannabis cigarette smoke by the determination of acetaldehyde derived N2-ethyl-2′-deoxyguanosine adducts, Chem. Res. Toxicol., 22, 1181, 10.1021/tx900106y · DOI
  149. Chen, 2007, Quantitation of an acetaldehyde adduct in human leukocyte DNA and the effect of smoking cessation, Chem. Res. Toxicol., 20, 108, 10.1021/tx060232x · DOI
  150. Fang, 1995, 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, 16, 2177, 10.1093/carcin/16.9.2177 · DOI
  151. Fang, 1997, Detection of DNA adducts of acetaldehyde in peripheral white blood cells of alcohol abusers, Carcinogenesis, 18, 627, 10.1093/carcin/18.4.627 · DOI · Paper page
  152. Oyama, 2010, Effects of acetaldehyde inhalation in mitochondrial aldehyde dehydrogenase deficient mice (Aldh2−/−), Front. Biosci. (Elite Ed.), 2, 1344, 10.2741/e194 · DOI
  153. Matsuda, 2007, Increased formation of hepatic N2-ethylidene-2′-deoxyguanosine DNA adducts in aldehyde dehydrogenase 2-knockout mice treated with ethanol, Carcinogenesis, 28, 2363, 10.1093/carcin/bgm057 · DOI
  154. Inagaki, 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, 10.1248/bpb.27.273 · DOI
  155. Theruvathu, 2005, Polyamines stimulate the formation of mutagenic 1,N2-propanodeoxyguanosine adducts from acetaldehyde, Nucleic Acids Res., 33, 3513, 10.1093/nar/gki661 · DOI
  156. Matter, 2007, Sequence distribution of acetaldehyde-derived N2-ethyl-dG adducts along duplex DNA, Chem. Res. Toxicol., 20, 1379, 10.1021/tx7001146 · DOI
  157. Takeuchi, 2008, Possible involvement of advanced glycation end-products (AGEs) in the pathogenesis of Alzheimer's disease, Curr. Pharm. Des., 14, 973, 10.2174/138161208784139693 · DOI · Paper page
  158. Dutta, 2006, In vitro nonenzymatic glycation of DNA nucleobases: an evaluation of advanced glycation end products under alkaline pH, Anal. Bioanal. Chem., 386, 1633, 10.1007/s00216-006-0753-2 · DOI
  159. Dutta, 2005, Nonenzymatic glycation of DNA nucleosides with reducing sugars, Anal. Biochem., 345, 171, 10.1016/j.ab.2005.07.034 · DOI
  160. Li, 2007, Nonenzymatic glycation of guanosine 5′-triphosphate by glyceraldehyde: an in vitro study of AGE formation, Bioorg. Chem., 35, 417, 10.1016/j.bioorg.2007.08.004 · DOI
  161. Li, 2008, The structural modification of DNA nucleosides by nonenzymatic glycation: an in vitro study based on the reactions of glyoxal and methylglyoxal with 2′-deoxyguanosine, Anal. Bioanal. Chem., 390, 679, 10.1007/s00216-007-1682-4 · DOI
  162. Bidmon, 2007, Analysis of DNA-bound advanced glycation end-products by LC and mass spectrometry, J. Chromatogr. B Analyt. Technol. Biomed. Life Sci., 855, 51, 10.1016/j.jchromb.2006.11.033 · DOI
  163. Koivisto, 2010, Analytical methods in DNA and protein adduct analysis, Anal. Bioanal. Chem., 398, 2563, 10.1007/s00216-010-4217-3 · DOI
  164. Gedik, 2005, Establishing the background level of base oxidation in human lymphocyte DNA: results of an interlaboratory validation study, FASEB J., 19, 82, 10.1096/fj.04-1767fje · DOI · Paper page
  165. Jeong, 2005, Pyrimido[1,2-a]-purin-10(3H)-one M1G, is less prone to artifact than base oxidation, Nucleic Acids Res., 33, 6426, 10.1093/nar/gki944 · DOI
  166. Rouzer, 1997, 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., 10, 181, 10.1021/tx9601216 · DOI
  167. Xue, 2011, Glyoxalase in ageing, Semin. Cell Dev. Biol., 10.1016/j.semcdb.2011.02.013 · DOI · Paper page
  168. Miyazawa, 2010, Lipid glycation and protein glycation in diabetes and atherosclerosis, Amino. Acids

Cited by

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Metadata

Authors
Voulgaridou, G.-P., Anestopoulos, I., Franco, R., Panayiotidis, M. I., & Pappa, A.
Venue
Mutation Research - Fundamental and Molecular Mechanisms of Mutagenesis
Publisher
Elsevier BV
Published
2011-06
Volume
711
Issue
1-2
Pages
13-27
ISSN
  • 0027-5107 (ISSN-L)
  • 1386-1964
DOI
10.1016/j.mrfmmm.2011.03.006
OpenAlex
W2079709169
Cited by
304
References
4
FWCI
6.77
Type
journal article
Language
en
Open access
closed
Licence
Funders
  • National Institutes of Health (P20RR17675)
  • University of Nebraska-Lincoln
  • Israeli Centers for Research Excellence

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CoChat. (2026). Citation check: DNA damage induced by endogenous aldehydes: Current state of knowledge. https://app.cochat.ai/papers/10.1016/j.mrfmmm.2011.03.006
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Voulgaridou, G.-P., Anestopoulos, I., Franco, R., Panayiotidis, M. I., & Pappa, A. (2011). DNA damage induced by endogenous aldehydes: Current state of knowledge. Mutation Research - Fundamental and Molecular Mechanisms of Mutagenesis. https://doi.org/10.1016/j.mrfmmm.2011.03.006

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