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Oxidatively Damaged DNA and Inflammation

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Book cover Oxidative Damage to Nucleic Acids

Part of the book series: Molecular Biology Intelligence Unit ((MBIU))

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Abstract

Chronic inflammation has long been associated with diseases such as cancer and cardiovascular disease, with infectious processes playing a causal role in many types of cancer. One potential link between chronic inflammation and human disease involves the release of highly reactive oxygen and nitrogen species by macrophages and neutrophils in inflamed tissues. In addition to their intended targets, these species also attack surrounding host tissue cells, with damage to virtually all cellular components, including DNA, RNA, proteins, carbohydrates and lipids. This chapter addresses the role of inflammatory processes in DNA damage in cells and tissues, whether by direct attack on DNA or by indirect mechanisms involving generation of electrophiles that subsequently react with DNA to form adducts.

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References

  1. Ohshima H, Tatemichi M, Sawa T. Chemical basis of inflammation-induced carcinogenesis. Arch Biochem Biophys 2003; 417:3–11.

    Article  PubMed  CAS  Google Scholar 

  2. Ohshima H. Genetic and epigenetic damage induced by reactive nitrogen species: Implications in carcinogenesis. Toxicol Lett 2003; 140–141:99–104.

    Article  PubMed  CAS  Google Scholar 

  3. Balkwill F, Mantovani A. Inflammation and cancer: Back to Virchow? Lancet 2001; 357:539–45.

    Article  PubMed  CAS  Google Scholar 

  4. Shacter E, Weitzman SA. Chronic inflammation and cancer. Oncology (Huntingt) 2002; 16:217–26, 29.

    Google Scholar 

  5. Levin B. Ulcerative colitis and colon cancer: Biology and surveillance. J Cell Biochem Suppl 1992; 16G:47–50.

    Article  PubMed  CAS  Google Scholar 

  6. Farrell RJ, Peppercorn MA. Ulcerative colitis. Lancet 2002; 359:331–340.

    Article  PubMed  Google Scholar 

  7. Asaka M, Takeda H, Sugiyama T et al. What role does Helicobacter pylori play in gastric cancer? Gastroenterology 1997; 113:S56–S60.

    PubMed  CAS  Google Scholar 

  8. Ebert MP, Yu J, Sung JJ et al. Molecular alterations in gastric cancer: The role of Helicobacter pylori. Eur J Gastroenterol Hepatol 2000; 12:795–798.

    Article  PubMed  CAS  Google Scholar 

  9. Badawi AF, Mostafa MH, Probert A et al. Role of schistosomiasis in human bladder cancer: Evidence of association, aetiological factors, and basic mechanisms of carcinogenesis. Eur J Cancer Prev 1995; 4:45–59.

    Article  PubMed  CAS  Google Scholar 

  10. Mostafa MH, Sheweita SA, O’Connor PJ. Relationship between schistosomiasis and bladder cancer. Clin Microbiol Rev 1999; 12:97–111.

    PubMed  CAS  Google Scholar 

  11. Nathan C, Shiloh MU. Reactive oxygen and nitrogen intermediates in the relationship between mammalian hosts and microbial pathogens. Proc Natl Acad Sci USA 2000; 97:8841–8848.

    Article  PubMed  CAS  Google Scholar 

  12. Nathan CF. Secretory products of macrophages. J Clin Invest 1987; 79:319–326.

    Article  PubMed  CAS  Google Scholar 

  13. Li J, Billiar TR, Talanian RV et al. Nitric oxide reversibly inhibits seven members of the caspase family via S-nitrosylation. Biochem Biophys Res Commun 1997; 240:419–424.

    Article  PubMed  CAS  Google Scholar 

  14. Kim PK, Zamora R, Petrosko P et al. The regulatory role of nitric oxide in apoptosis. Int Immunopharmacol 2001; 1:1421–1441.

    Article  PubMed  CAS  Google Scholar 

  15. Rosin MP, Saad el Din Zaki S, Ward AJ et al. Involvement of inflammatory reactions and elevated cell proliferation in the development of bladder cancer in schistosomiasis patients. Mutat Res 1994; 305:283–292.

    PubMed  CAS  Google Scholar 

  16. Ambs S, Ogunfusika MO, Merriam WG et al. Up-regulation of inducible nitric oxide synthase expression in cancer-prone p53 knockout mice. Proc Natl Acad Sci USA 1998; 95:8823–8828.

    Article  PubMed  CAS  Google Scholar 

  17. Jenkins DC, Charles IG, Thomsen LL et al. Roles of nitric oxide in tumor growth. Proc Natl Acad Sci USA 1995; 92:4392–4396.

    Article  PubMed  CAS  Google Scholar 

  18. Feig DI, Reid TM, Loeb LA. Reactive oxygen species in tumorigenesis. Cancer Res 1994; 54:1890s–1894s.

    PubMed  CAS  Google Scholar 

  19. Grisham MB, Jourďheuil D, Wink DA. Review article: Chronic inflammation and reactive oxygen and nitrogen metabolism—Implications in DNA damage and mutagenesis. Aliment Pharmacol Ther 2000; 14(Suppl 1):3–9.

    Article  PubMed  CAS  Google Scholar 

  20. Dedon PC, Tannenbaum SR. Reactive nitrogen species in the chemical biology of inflammation. Arch Biochem Biophys 2004; 423:12–22.

    Article  PubMed  CAS  Google Scholar 

  21. Bredt DS, Snyder SH. Nitric Oxide: A physiologic messenger molecule. Neuron 1994; 63:175–95.

    CAS  Google Scholar 

  22. Gross SS, Wolin MS. Nitric Oxide: Pathophysiological Mechanisms. Annual Rev Physiol 1995; 57:737–769.

    Article  PubMed  CAS  Google Scholar 

  23. Lancaster Jr JR. Nitric Oxide in Cells. American Scientist 1992; 80:248–59.

    Google Scholar 

  24. MacMicking J, Xie Q, Nathan C. Nitric oxide and macrophage function. Annual Rev Immunol 1997; 15:323–350.

    Article  CAS  Google Scholar 

  25. Moncada S, Palmer RMJ, Higgs EA. Nitric oxide: Physiology, pathophysiology, and pharmacology. Pharmacol Rev 1991; 43:109–142.

    PubMed  CAS  Google Scholar 

  26. Nathan C. Nitric oxide as a secretory product of mammalian cells. FASEB J 1992; 6:3051–64.

    PubMed  CAS  Google Scholar 

  27. Tamir S, Tannenbaum SR. The role of nitric oxide (NO) in the carcinogenic process. Biochem Biophys Acta 1996; 1288:F31–F36.

    PubMed  Google Scholar 

  28. Miwa M, Stuehr DJ, Marletta MA et al. Nitrosation of amines by stimulated macrophages. Carcinogenesis 1987; 8:955–958.

    Article  PubMed  CAS  Google Scholar 

  29. Stuehr DJ, Marletta MA. Synthesis of nitrite and nitrate in murine macrophage cell lines. Cancer Res 1987; 47:5590–5594.

    PubMed  CAS  Google Scholar 

  30. Lewis RS, Tamir S, Tannenbaum SR et al. Kinetic analysis of the fate of nitric oxide synthesized by macrophages in vitro. J Biol Chem 1995; 270:29350–29355.

    Article  PubMed  CAS  Google Scholar 

  31. Chen B, Keshive M, Deen WM. Diffusion and reaction of nitric oxide in suspension cell cultures. Biophys J 1998; 75:745–754.

    Article  PubMed  CAS  Google Scholar 

  32. Chen B, Deen WM. Analysis of the effects of cell spacing and liquid depth on nitric oxide and its oxidation products in cell cultures. Chem Res Toxicol 2001; 14:135–147.

    Article  PubMed  CAS  Google Scholar 

  33. Dong M, Wang C, Deen WM et al. Absence of 2′-deoxyoxanosine and presence of abasic sites in DNA exposed to nitric oxide at controlled physiological concentrations. Chem Res Toxicol 2003; 16:1044–1055.

    Article  PubMed  CAS  Google Scholar 

  34. Lucas LT, Gatehouse D, Jones GDD et al. Characterization of DNA damage at purine residues in oligonucleotides and calf thymus DNA induced by the mutagen 1-nitrosoindole-3-acetonitrile. Chem Res Toxicol 2001; 14:158–164.

    Article  PubMed  CAS  Google Scholar 

  35. Lucas LT, Gatehouse D, Shuker DE. Efficient nitroso group transfer from N-nitrosoindoles to nucleotides and 2′-deoxyguanosine at physiological pH. A new pathway for N-nitrosocompounds to exert genotoxicity. J Biol Chem 1999; 274:18319–18326.

    Article  PubMed  CAS  Google Scholar 

  36. Suzuki T, Yamaoka R, Nishi M et al. Isolation and characterization of a novel product, 2′-deoxyoxanosine, from 2′-deoxyguanosine, oligodeoxynucleotide, and calf thymus DNA treated with nitrous acid and nitric oxide. J Am Chem Soc 1996; 118:2515–2516.

    Article  CAS  Google Scholar 

  37. Suzuki T, Kanaori K, Tajima K et al. Mechanism and intermediate for formation of 2′-deoxyoxanosine. Nucleic Acids Symp Ser 1997; 313–314.

    Google Scholar 

  38. Dong M, Dedon PC. Relatively small increases in the steady-state levels of nucleobase deamination products in DNA from human TK6 cells exposed to toxic levels of nitric oxide. Chem Res Toxicol 2006; 19:50–57.

    Article  PubMed  CAS  Google Scholar 

  39. Glaser R, Wu H, Lewis M. Cytosine catalysis of nitrosative guanine deamination and interstrand cross-link formation. J Am Chem Soc 2005; 127:7346–7358.

    Article  PubMed  CAS  Google Scholar 

  40. Lim KS, Huang SH, Jenner A et al. Potential artifacts in the measurement of DNA deamination. Free Radicals in Biology and Medicine 2006; 40:1939–1948.

    Article  CAS  Google Scholar 

  41. Burney S, Caulfield JL, Niles JC et al. The chemistry of DNA damage from nitric oxide and peroxynitrite. Mutat Res 1999; 424:37–49.

    PubMed  CAS  Google Scholar 

  42. Shafirovich V, Cadet J, Gasparutto D et al. Nitrogen dioxide as an oxidizing agent of 8-oxo-7,8-dihydro-2′-deoxyguanosine but not of 2′-deoxyguanosine. Chem Res Toxicol 2001; 14:233–241.

    Article  PubMed  CAS  Google Scholar 

  43. Tretyakova NY, Burney S, Pamir B et al. Peroxynitrite-induced DNA damage in the supF gene: Correlation with the mutational spectrum. Mutat Res 2000; 447:287–303.

    PubMed  CAS  Google Scholar 

  44. Yermilov V, Yoshie Y, Rubio J et al. Effects of carbon dioxide/bicarbonate on induction of DNA single-strand breaks and formation of 8-nitroguanine, 8-oxoguanine and base propenal mediated by peroxynitrite. FEBS Lett 1996; 399:67–70.

    Article  PubMed  CAS  Google Scholar 

  45. Niles JC, Wishnok JS, Tannenbaum SR. Peroxynitrite-induced oxidation and nitration products of guanine and 8-oxoguanine: Structures and mechanisms of product formation. Nitric Oxide 2006; 14:109–121.

    Article  PubMed  CAS  Google Scholar 

  46. Cadet J, Douki T, Gasparutto D et al. Oxidative damage to DNA: Formation, measurement and biochemical features. Mutat Res 2003; 531:5–23.

    PubMed  CAS  Google Scholar 

  47. Cadet J, Douki T, Ravanat JL. One-electron oxidation of DNA and inflammation processes. Nat Chem Biol 2006; 2:348–349.

    Article  PubMed  CAS  Google Scholar 

  48. von Sonntag C. The Chemical Basis of Radiation Biology. New York: Taylor and Francis, 1987.

    Google Scholar 

  49. Pogozelski WK, Tullius TD. Oxidative strand scission of nucleic acids: Routes initiated by hydrogen abstraction from the sugar moiety. Chem Rev 1998; 98:1089–1107.

    Article  PubMed  CAS  Google Scholar 

  50. Dedon PC, Goldberg IH. Free-radical mechanisms involved in the formation of sequence-dependent bistranded DNA lesions by the antitumor antibiotics bleomycin, neocarzinostatin, and calicheamicin. Chem Res Toxicol 1992; 5:311–332.

    Article  PubMed  CAS  Google Scholar 

  51. Angeloff A, Dubey I, Pratviel G et al. Characterization of a 5′-aldehyde terminus resulting from the oxidative attack at C5′ of a 2-deoxyribose on DNA. Chem Res Toxicol 2001; 14:1413–1420.

    Article  PubMed  CAS  Google Scholar 

  52. Kennedy LJ, Moore Jr K, Caulfield JL et al. Quantitation of 8-oxoguanine and strand breaks produced by four oxidizing agents. Chem Res Toxicol 1997; 10:386–392.

    Article  PubMed  CAS  Google Scholar 

  53. Guyton AC, Hall JE. Textbook of medical physiology. 10th ed. Philadelphia: Saunders, 2000.

    Google Scholar 

  54. Zhou X, Taghizadeh K, Dedon PC. Chemical and biological evidence for base propenals as the major source of the endogenous M1dG adduct in cellular DNA. J Biol Chem 2005; 280:25377–25382.

    Article  PubMed  CAS  Google Scholar 

  55. Steenken S, Jovanovic SV. How easily oxidized is DNA? One-Electron Reduction Potentials of Adenosine and Guanosine Radicals in Aqueous Solution. J Am Chem Soc 1997; 119:617–618.

    Article  CAS  Google Scholar 

  56. Uppu RM, Cueto R, Squadrito GL et al. Competitive reactions of peroxynitrite with 2′-deoxyguanosine and 7,8-dihydro-8-oxo-2′-deoxyguanosine (8-oxodG): Relevance to the formation of 8-oxodG in DNA exposed to peroxynitrite. Free Rad Biol Med 1996: 21:407–411.

    Article  PubMed  CAS  Google Scholar 

  57. Yanagawa H, Ogawa Y, Ueno M. Redox Ribonucleosides Isolation and Characterization of 5-Hydroxyuridine, 8-Hydroxyguanosine and 8-Hydroxyadenosine from Torula Yeast RNA. J Biol Chem 1992; 267:13320–13326.

    PubMed  CAS  Google Scholar 

  58. Hailer MK, Slade PG, Martin BD et al. Nei deficient Escherichia coli are sensitive to chromate and accumulate the oxidized guanine lesion spiroiminodihydantoin. Chem Res Toxicol 2005; 18:1378–1383.

    Article  PubMed  CAS  Google Scholar 

  59. Hall DB, Holmlin RE, Barton JK. Oxidative DNA damage through long-range electron transfer. Nature 1996; 382:731–735.

    Article  PubMed  CAS  Google Scholar 

  60. Ly D, Kan Y, Armitage B et al. Cleavage of DNA by irradiation of substituted anthraquinones: Intercalation promotes electron transfer and efficient reaction at GG steps. J Am Chem Soc 1996; 118:8747–8748.

    Article  CAS  Google Scholar 

  61. Saito I, Takayama M, Sugiyama H et al. Photoinduced DNA cleavage via electron transfer: Demonstration that guanine residues located 5′-to a guanine are the most electron-donating sites. J Am Chem Soc 1995; 117:6406–6407.

    Article  CAS  Google Scholar 

  62. Saito I, Nakamura T, Nakatani K et al. Mapping of hot spots for DNA damage by one-electron oxidation: Efficacy of GG doublets and GGG triplets as a trap in long-range hole migration. J Am Chem Soc 1998; 120:12686–12687.

    Article  CAS  Google Scholar 

  63. Kawanishi S, Oikawa S, Murata M et al. Site-specific oxidation at GG and GGG sequences in double-stranded DNA by benzoyl peroxide as a tumor promoter. Biochemistry 1999; 38:16733–16739.

    Article  PubMed  CAS  Google Scholar 

  64. Spassky A, Angelov D. Influence of the local helical conformation on the guanine modifications generated from one-electron DNA oxidation. Biochemistry 1997; 36:6571–6576.

    Article  PubMed  CAS  Google Scholar 

  65. Giese B. Electron transfer in DNA. Curr Opin Chem Biol 2002; 6:612–618.

    Article  PubMed  CAS  Google Scholar 

  66. Schuster GB. Long-range charge transfer in DNA: Transient structural distortions control the distance dependence. Acc Chem Res 2000; 33:253–260.

    Article  PubMed  CAS  Google Scholar 

  67. Kanvah S, Schuster GB. The sacrificial role of easily oxidizable sites in the protection of DNA from damage. Nucleic Acids Res 2005; 33:5133–5138.

    Article  PubMed  CAS  Google Scholar 

  68. Sugiyama H, Saito I. Theoretical studies of GG-specific photocleavage of DNA via electron transfer: Significant lowering of ionization potential and 5′-localization of HOMO of stacked GG bases in B-form DNA. J Am Chem Soc 1996; 118:7063–7068.

    Article  CAS  Google Scholar 

  69. Senthilkumar K, Grozema FC, Guerra CF et al. Mapping the sites of selective oxidation of guanines in DNA. J Am Chem Soc 2003; 125:13658–13659.

    Article  PubMed  CAS  Google Scholar 

  70. Margolin Y, Cloutier JF, Shafirovich V et al. Paradoxical hotspots for guanine oxidation by a chemical mediator of inflammation. Nat Chem Biol 2006; 2:365–366.

    Article  PubMed  CAS  Google Scholar 

  71. Shafirovich V, Cadet J, Gasparutto D et al. Nitrogen dioxide as an oxidizing agent of 8-oxo-7,8-dihydro-2′-deoxyguanosine but not of 2′-deoxyguanosine. Chem Res Toxicol 2001; 14:233–241.

    Article  PubMed  CAS  Google Scholar 

  72. Shafirovich V, Dourandin A, Huang W et al. The carbonate radical is a site-selective oxidizing agent of guanine in double-stranded oligonucleotides. J Biol Chem 2001; 276:24621–24626.

    Article  PubMed  CAS  Google Scholar 

  73. Rodriguez H, Valentine MR, Holmquist GP et al. Mapping of peroxyl radical induced damage on genomic DNA. Biochemistry 1999; 38:16578–16588.

    Article  PubMed  CAS  Google Scholar 

  74. Haraguchi K, Delaney MO, Wiederholt CJ et al. Synthesis and characterization of oligodeoxynucleotides containing formamidopyrimidine lesions and nonhydrolyzable analogues. J Am Chem Soc 2002; 124:3263–3269.

    Article  PubMed  CAS  Google Scholar 

  75. Tretyakova NY, Wishnok JS, Tannenbaum SR. Peroxynitrite-induced secondary oxidative lesions at guanine nucleobases: Chemical stability and recognition by the Fpg DNA repair enzyme. Chem Res Toxicol 2000; 13:658–664.

    Article  PubMed  CAS  Google Scholar 

  76. Marnett LJ. Oxy radicals, lipid peroxidation and DNA damage. Toxicology 2002; 181–182:219–222.

    Article  PubMed  Google Scholar 

  77. Montine TJ, Neely MD, Quinn JF et al. Lipid peroxidation in aging brain and Alzheimer’s disease. Free Radic Biol Med 2002; 33:620–626.

    Article  PubMed  CAS  Google Scholar 

  78. Bartsch H, Nair J. Oxidative stress and lipid peroxidation-derived DNA-lesions in inflammation driven carcinogenesis. Cancer Detect Prev 2004; 28:385–391.

    Article  PubMed  CAS  Google Scholar 

  79. Ahmed N, Thornalley PJ. Quantitative screening of protein biomarkers of early glycation, advanced glycation, oxidation and nitrosation in cellular and extracellular proteins by tandem mass spectrometry multiple reaction monitoring. Biochem Soc Trans 2003; 31:1417–1422.

    Article  PubMed  CAS  Google Scholar 

  80. Thornalley PJ. Glycation in diabetic neuropathy: Characteristics, consequences, causes, and therapeutic options. Int Rev Neurobiol 2002; 50:37–57.

    Article  PubMed  CAS  Google Scholar 

  81. Stadtman ER. Role of oxidant species in aging. Curr Med Chem 2004; 11:1105–1112.

    PubMed  CAS  Google Scholar 

  82. Stadtman ER, Levine RL. Free radical-mediated oxidation of free amino acids and amino acid residues in proteins. Amino Acids 2003; 25:207–218.

    Article  PubMed  CAS  Google Scholar 

  83. Stadtman ER, Moskovitz J, Levine RL. Oxidation of methionine residues of proteins: Biological consequences. Antioxid Redox Signal 2003; 5:577–582.

    Article  PubMed  CAS  Google Scholar 

  84. Williams MV, Lee SH, Pollack M et al. Endogenous lipid hydroperoxide-mediated DNA-adduct formation in min mice. J Biol Chem 2006; 281:10127–10133.

    Article  PubMed  CAS  Google Scholar 

  85. Lee SH, Williams MV, Dubois RN et al. Cyclooxygenase-2-mediated DNA damage. J Biol Chem 2005; 280:28337–28346.

    Article  PubMed  CAS  Google Scholar 

  86. Schmid K, Nair J, Winde G et al. Increased levels of promutagenic etheno-DNA adducts in colonic polyps of FAP patients. Int J Cancer 2000; 87:1–4.

    Article  PubMed  CAS  Google Scholar 

  87. Nair J, Barbin A, Velic I et al. Etheno DNA-base adducts from endogenous reactive species. Mutat Res 1999; 424:59–69.

    PubMed  CAS  Google Scholar 

  88. Lee SH, Arora JA, Oe T et al. 4-Hydroperoxy-2-nonenal-induced formation of 1,N2-etheno-2′-deoxyguanosine adducts. Chem Res Toxicol 2005; 18:780–786.

    Article  PubMed  CAS  Google Scholar 

  89. Lee SH, Blair IA. Oxidative DNA damage and cardiovascular disease. Trends Cardiovasc Med 2001; 11:148–155.

    Article  PubMed  CAS  Google Scholar 

  90. Blair IA. Lipid hydroperoxide-mediated DNA damage. Exp Gerontol 2001; 36:1473–1481.

    Article  PubMed  CAS  Google Scholar 

  91. Chung FL, Zhang L, Ocando JE et al. Role of 1,N2-propanodeoxyguanosine adducts as endogenous DNA lesions in rodents and humans. IARC Sci Publ 1999:45–54.

    Google Scholar 

  92. Chung FL, Nath RG, Nagao M et al. Endogenous formation and significance of 1,N2-propanodeoxyguanosine adducts. Mutat Res 1999; 424:71–81.

    PubMed  CAS  Google Scholar 

  93. Chung FL, Chen HJC, Nath RG. Lipid peroxidation as a potential endogenous source for the formation of exocyclic DNA adducts. Carcinogenesis 1996; 17:2105–2111.

    Article  PubMed  CAS  Google Scholar 

  94. Loeppky RN, Cui W, Goelzer P et al. Glyoxal-guanine DNA adducts: Detection, stability and formation in vivo from nitrosamines. IARC Sci Publ 1999:155–168.

    Google Scholar 

  95. Kasai H, Iwamoto-Tanaka N, Fukada S. DNA Modifications by the Mutagen Glyoxal: Adduction to G and C, Deamination of C and GC and GA Cross-linking. Carcinogenesis 1998; 19:1459–1465.

    Article  PubMed  CAS  Google Scholar 

  96. Dedon PC, Plastaras JP, Rouzer CA et al. Indirect mutagenesis by oxidative DNA damage: Formation of the pyrimidopurinone adduct of deoxyguanosine by base propenal. Proc Natl Acad Sci USA 1998; 95:11113–11116.

    Article  PubMed  CAS  Google Scholar 

  97. Awada M, Dedon PC. Formation of the 1,N2-glyoxal adduct of deoxyguanosine by phosphoglycolaldehyde, a product of 3′-deoxyribose oxidation in DNA. Chem Res Toxicol 2001; 14:1247–1253.

    Article  PubMed  CAS  Google Scholar 

  98. Gingipalli L, Dedon PC. Reaction of cis-and trans-2-butene-1,4-dial with 2′-deoxycytidine to form stable oxadiazabicyclooctaimine adducts. J Am Chem Soc 2001; 123:2664–2665.

    Article  PubMed  CAS  Google Scholar 

  99. Plastaras JP, Dedon PC, Marnett LJ. Effects of DNA structure on oxopropenylation by the endogenous mutagens malondialdehyde and base propenal. Biochemistry 2002; 41:5033–5042.

    Article  PubMed  CAS  Google Scholar 

  100. Bohnert T, Gingipalli L, Dedon PC. Reaction of 2′-deoxyribonucleosides with cis-and trans-1,4-dioxo-2-butene. Biochem Biophys Res Commun 2004; 323:838–844.

    Article  PubMed  CAS  Google Scholar 

  101. Lee SH, Oe T, Arora JS et al. Analysis of FeII-mediated decomposition of a linoleic acid-derived lipid hydroperoxide by liquid chromatography/mass spectrometry. J Mass Spectrom 2005; 40:661–668.

    Article  PubMed  CAS  Google Scholar 

  102. Esterbauer H, Gebicki J, Puhl H et al. The role of lipid peroxidation and antioxidants in oxidative modification of LDL. Free Radic Biol Med 1992; 13:341–390.

    Article  PubMed  CAS  Google Scholar 

  103. Pollack M, Oe T, Lee SH et al. Characterization of 2′-deoxycytidine adducts derived from 4-oxo-2-nonenal, a novel lipid peroxidation product. Chem Res Toxicol 2003; 16:893–900.

    Article  PubMed  CAS  Google Scholar 

  104. Jian W, Lee SH, Arora JS et al. Unexpected formation of etheno-2′-deoxyguanosine adducts from 5(S)-hydroperoxyeicosatetraenoic acid: Evidence for a bis-hydroperoxide intermediate. Chem Res Toxicol 2005; 18:599–610.

    Article  PubMed  CAS  Google Scholar 

  105. Yocum AK, Oe T, Yergey AL et al. Novel lipid hydroperoxide-derived hemoglobin histidine adducts as biomarkers of oxidative stress. J Mass Spectrom 2005; 40:754–764.

    Article  PubMed  CAS  Google Scholar 

  106. Price MA, Tullius TD. Using hydroxyl radical to probe DNA structure. Meth Enz 1992; 212:194–218.

    Article  CAS  Google Scholar 

  107. Rashid R, Langfinger D, Wagner R et al. Bleomycin versus OH-radial-induced malondialdehydeproduct formation in DNA. Int J Radiat Biol 1999; 75:101–109.

    Article  PubMed  CAS  Google Scholar 

  108. Chin DH, Kappen LS, Goldberg IH. 3′-formyl phosphate-ended DNA: High energy intermediate in antibiotic-induced DNA sugar damage. Proc Natl Acad Sci USA 1987; 84:7070–7074.

    Article  PubMed  CAS  Google Scholar 

  109. Chen B, Bohnert T, Zhou X et al. 5′-(2-Phosphoryl-1,4-dioxobutane) as a product of 5′-oxidation of deoxyribose in DNA: Elimination as trans-1,4-dioxo-2-butene and approaches to analysis. Chem Res Toxicol 2004; 17:1406–1413.

    Article  PubMed  CAS  Google Scholar 

  110. Pratviel G, Pitie M, Bernadou J et al. Furfural as a marker of DNA cleavage by hydroxylation at the 5′ carbon of deoxyribose. Angew Chem Int Ed Engl 1991; 30:702–704.

    Article  Google Scholar 

  111. Collins C, Zhou X, Wang R et al. Differential Oxidation of Deoxyribose in DNA by gamma and alpha-Particle Radiation. Radiat Res 2005; 163:654–662.

    Article  PubMed  CAS  Google Scholar 

  112. Collins C, Awada MM, Zhou X et al. Analysis of 3′-phosphoglycolaldehyde residues in oxidized DNA by gas chromatography/negative chemical ionization/mass spectrometry. Chem Res Toxicol 2003; 16:1560–1566.

    Article  PubMed  CAS  Google Scholar 

  113. Sitlani A, Long EC, Pyle AM et al. DNA photocleavage by phenanthrenequinone diimine complexes with rhodium (III): Shape-selective recognition and reaction. J Am Chem Soc. 1992; 114:2303–2312.

    Article  CAS  Google Scholar 

  114. Stubbe J, Kozarich JW. Mechanisms of bleomycin-induced DNA degradation. Chem Rev 1987; 87:1107–1136.

    Article  CAS  Google Scholar 

  115. Yu L, Golik J, Harrison R et al. The deoxyfucose-anthranilate of esperamicin A1 confers intercalative DNA binding and causes a switch in the chemistry of bistranded DNA lesions. Journal of the American Chemical Society 1994; 116:9733–9738.

    Article  CAS  Google Scholar 

  116. Dedon PC, Goldberg IH. Mechanism of DNA damage by neocarzinostatin and other bicyclic enediyne antibiotics. In: Probst C, Perun T, eds. Nucleic Acid Targeted Drug Design. New York: Marcel Dekker Inc., 1992:475–523.

    Google Scholar 

  117. Sigman DS. Nuclease activity of 1,10-phenanthroline-copper ion. Acc Chem Res 1986; 19:180–186.

    Article  CAS  Google Scholar 

  118. Hashimoto M, Greenberg MM, Kow YW et al. The 2-deoxyribonolactone lesion produced in DNA by neocarzinostatin and other damaging agents forms cross-links with the base-excision repair enzyme endonuclease III. J Am Chem Soc 2001; 123:3161–3162.

    Article  PubMed  CAS  Google Scholar 

  119. DeMott MS, Beyret E, Wong D et al. Covalent trapping of human DNA polymerase beta by the oxidative DNA lesion 2-deoxyribonolactone. J Biol Chem 2002.

    Google Scholar 

  120. Roginskaya M, Bernhard WA, Marion RT et al. The release of 5-methylene-2-furanone from irradiated DNA catalyzed by cationic polyamines and divalent metal cations. Radiat Res 2005; 163:85–89.

    Article  PubMed  CAS  Google Scholar 

  121. Kadlubar FF, Anderson KE, Haussermann S et al. Comparison of DNA adduct levels associated with oxidative stress in human pancreas. Mutat Res 1998; 405:125–133.

    PubMed  CAS  Google Scholar 

  122. Marnett LJ. DNA adducts of alpha, beta-unsaturated aldehydes and dicarbonyl compounds. IARC Sci Publ 1994; 125:151–163.

    PubMed  CAS  Google Scholar 

  123. Thornalley PJ. Glutathione-dependent detoxification of alpha-oxoaldehydes by the glyoxalase system: Involvement in disease mechanisms and antiproliferative activity of glyoxalase I inhibitors. Chem Biol Interact 1998; 111–112:137–151.

    Article  PubMed  Google Scholar 

  124. Shapiro R, Sodum RS, Everett DW et al. Reactions of nucleosides with glyoxal and acrolein. IARC Sci Publ 1986:165–173.

    Google Scholar 

  125. Mazurenko NN, Broude NE, Budowsky EI. Reaction of glyoxal with nucleic acid components. IV. Reduction of guanine-glyoxal adduct with sodium borohydride. Biochim Biophys Acta 1971; 254:389–392.

    PubMed  CAS  Google Scholar 

  126. Basu AK, O’Hara SM, Valladier P et al. Identification of adducts formed by the reaction of guanine nucleosides with malondialdehyde and structurally related aldehydes. Chem Res Toxicol 1988; 1:53–59.

    Article  PubMed  CAS  Google Scholar 

  127. Murata-Kamiya N, Kamiya H, Iwamoto N et al. Formation of a mutagen, glyoxal, from DNA treated with oxygen free radicals. Carcinogenesis 1995; 16:2251–2253.

    Article  PubMed  CAS  Google Scholar 

  128. Kawabata H, Takeshita H, Fujiwara T et al. Chemistry of neocarzinostatin-mediated degradation of d(GCATGC). Mechanism of spontaneous thymine release. Tetrahedron Lett 1989; 30:4263–4266.

    Article  CAS  Google Scholar 

  129. Chen LJ, Hecht SS, Peterson LA. Identification of cis-2-butene-1,4-dial as a microsomal metabolite of furan. Chem Res Toxicol 1995; 8:903–906.

    Article  PubMed  CAS  Google Scholar 

  130. Maga JA. Furans in foods. CRC Crit Rev Food Sci Nutr 1979; 11:355–400.

    Article  PubMed  CAS  Google Scholar 

  131. Egle Jr JL, Gochberg BJ. Respiratory retention and acute toxicity of furan. Am Ind Hyg Assoc J 1979; 40:310–314.

    PubMed  CAS  Google Scholar 

  132. Byrns MC, Predecki DP, Peterson LA. Characterization of nucleoside adducts of cis-2-butene-1, 4-dial, a reactive metabolite of furan. Chem Res Toxicol 2002; 15:373–379.

    Article  PubMed  CAS  Google Scholar 

  133. Byrns MC, Vu CC, Neidigh JW et al. Detection of DNA adducts derived from the reactive metabolite of furan, cis-2-butene-1,4-dial. Chem Res Toxicol 2006; 19:414–420.

    Article  PubMed  CAS  Google Scholar 

  134. Peterson LA, Naruko KC, Predecki DP. A reactive metabolite of furan, cis-2-butene-1,4-dial, is mutagenic in the Ames assay. Chem Res Toxicol 2000; 13:531–534.

    Article  PubMed  CAS  Google Scholar 

  135. Nair J, Gal A, Tamir S et al. Etheno adducts in spleen DNA of SJL mice stimulated to overproduce nitric oxide. Carcinogenesis 1998; 19:2081–2084.

    Article  PubMed  CAS  Google Scholar 

  136. Gal A, Tamir S, Tannenbaum SR et al. Nitric oxide production in SJL mice bearing the RcsX lymphoma: A model for in vivo toxicological evaluation of NO. Proc Natl Acad Sci USA 1996; 93:11499–11503.

    Article  PubMed  CAS  Google Scholar 

  137. Gal A, Wogan GN. Mutagenesis associated with nitric oxide production in transgenic SJL mice. Proc Natl Acad Sci USA 1996; 93:15102–14107.

    Article  PubMed  CAS  Google Scholar 

  138. Tamir S, deRojas-Walker T, Gal A et al. Nitric oxide production in relation to spontaneous B-cell lymphoma and myositis in SJL mice. Cancer Res 1995; 55:4391–4397.

    PubMed  CAS  Google Scholar 

  139. Gal A, Tamir S, Kennedy LJ et al. Nitrotyrosine formation, apoptosis, and oxidative damage: Relationships to nitric oxide production in SJL mice bearing the RcsX tumor. Cancer Res 1997; 57:1823–1828.

    PubMed  CAS  Google Scholar 

  140. Nair J, Carmichael PL, Fernando RC et al. Lipid peroxidation-induced etheno-DNA adducts in the liver of patients with the genetic metal storage disorders Wilson’s disease and primary hemochromatosis. Cancer Epidemiol Biomarkers Prev 1998; 7:435–440.

    PubMed  CAS  Google Scholar 

  141. Nair J, Sone H, Nagao M et al. Copper-dependent formation of miscoding etheno-DNA adducts in the liver of Long Evans Cinnamon (LEC) rats developing hereditary hepatitis and hepatocellular carcinoma. Cancer Res 1996; 56:1267–1271.

    PubMed  CAS  Google Scholar 

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Authors and Affiliations

  1. Center for Environmental Health Sciences and Biological Engineering Division, Massachusetts Institute of Technology, NE47-277, 77 Massachusetts Avenue, Cambridge, MA, 02139, USA

    Peter C. Dedon & Marita C. Barth

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  1. Peter C. Dedon
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  2. Marita C. Barth
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  1. Radiation and Oxidative Stress Group Department of Cancer Studies and Molecular Medicine RKCSB, Leicester Royal Infirmary, University of Leicester, Leicester, UK

    Mark D. Evans B.Sc., Ph.D.

  2. Department of Cancer Studies and Molecular Medicine and Department of Genetics, University of Leicester, Leicester, UK

    Marcus S. Cooke B.Sc., M.Sc., Ph.D.

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Dedon, P.C., Barth, M.C. (2007). Oxidatively Damaged DNA and Inflammation. In: Evans, M.D., Cooke, M.S. (eds) Oxidative Damage to Nucleic Acids. Molecular Biology Intelligence Unit. Springer, New York, NY. https://doi.org/10.1007/978-0-387-72974-9_15

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