Advertisement

DNA Damage by Free Radicals. Mechanism, Meaning and Measurement

  • B. Halliwell
Conference paper
Part of the Ernst Schering Research Foundation Workshop book series (SCHERING FOUND, volume 10)

Abstract

It is well established that aerobes constantly produce small amounts of oxygen-derived species, such as superoxide radical (O2 ·−), hydrogen peroxide (H2O2), and hypochlorous acid (HOC1), the latter being generated by the enzyme myeloperoxidase in neutrophils (for reviews, see di Guiseppi and Fridovich 1984; Halliwell and Gutteridge 1989; Weiss 1989). Exposure of living organism to background levels of ionizing radiation leads to homolytic fission of oxygen-hydrogen bonds in water to produce highly reactive hydroxyl radicals, OH· (for review, see von Sonntag 1987). Hydroxyl radicals can also be generated when H2O2 comes into contact with certain transition metal ion chelates, especially those of iron and copper. In general, the reduced forms of these metal ions (Fe2+, Cu2+) produce OH· at a faster rate upon reaction with H2O2 than the oxidized forms (Fe3+, Cu2+), and so reducing agents such as O2·− and ascorbic acid can often accelerate OH· generation by metal ion/H2O2 mixtures (Halliwell and Gutteridge 1990a). Another potentially physiologically important source of OH· is the interaction of nitric oxide radical (NO·) with 02·− (Beckman et al. 1990).

Keywords

High Performance Liquid Chromatography Homolytic Fission High Performance Liquid Chromatography Technique Thymine Glycol Thymidine Glycol 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. Adachi S, Takemoto K, Hirosue T, Hosogai Y (1993) Spontaneous and 2-nitropropane induced levels of 8-hydroxy-2’-deoxyguanosine in liver DNA of rats fed iron-deficient or manganese-and copper-deficient diets. Carcinogenesis 14: 265–268PubMedCrossRefGoogle Scholar
  2. Agarwal RP, Parks Jr RE (1978) Adenosine deaminase from human erythrocytes. Meth Enzymol L1: 502–507.CrossRefGoogle Scholar
  3. Aida M, Nishimura S (1987) An ab initio molecular orbital study on the characteristics of 8-hydroxyguanine. Mut Res 192: 83–89.CrossRefGoogle Scholar
  4. Aiyar J, Berkovits HJ, Floyd RA, Wetterhahn KE (1990) Reaction of chromium (VI) with hydrogen peroxide in the presence of glutathione: reactive intermediates and resulting DNA damage. Chem Res Tox 3: 595–603.CrossRefGoogle Scholar
  5. Alam S, Ali S, Ali R (1993) The effect of hydroxyl radical on the antigenicity of native DNA. FEBS Lett 319: 66–70.PubMedCrossRefGoogle Scholar
  6. Ames BN (1989) Endogenous oxidative DNA damage, aging and cancer. Free Rad Res Comms 7: 121–128.CrossRefGoogle Scholar
  7. Aruoma OI, Halliwell B, Dizdaroglu M (1989a) Iron ion-dependent modification of bases in DNA by the superoxide radical-generating system hypoxanthine/oxidase. J Biol Chem 264: 13024–13028.PubMedGoogle Scholar
  8. Aruoma OI, Halliwell B, Gajewski E, Dizdaroglu M (1989b) Damage to the bases in DNA induced by hydrogen peroxide and ferric ion chelates. J Biol Chem 264: 20509–20512.PubMedGoogle Scholar
  9. Aruoma GI, Halliwell B, Gajewski E, Dizdaroglu M (1991) Copper-ion-dependent damage to the bases in DNA in the presence of hydrogen peroxide. Biochem J 273: 601–604.PubMedGoogle Scholar
  10. Beckman JS, Beckman TW, Chen J, Marshall PA, Freeman BA (1990) Apparent hydroxyl radical production by peroxynitrite: implications for endotheliai injury from nitric oxide and superoxide. Proc Natl Acad Sci USA 87: 1620–1624.PubMedCrossRefGoogle Scholar
  11. Berger M, Anselmino C, Mouret JF, Cadet J (1990) High performance liquid chromatography-electrochemical assay for monitoring the formation of 8oxo-7,8-dihydro-adenine and its related 2’-deoxyribonucleoside. J Liquid Chromatog 13: 929–940.CrossRefGoogle Scholar
  12. Birnboim HC (1988) A superoxide anion induced DNA strand-break metabolic pathway in human leukocytes: effect of vanadium. Biochem Cell Biol 66: 374–381.PubMedCrossRefGoogle Scholar
  13. Blount S, Griffiths HR, Staines NA, Lunec J (1992) Probing molecular changes induced in DNA by reactive oxygen species with monoclonal antibodies. Immunol Lett 34: 115–126.PubMedCrossRefGoogle Scholar
  14. Breimer LH (1988) Ionizing radiation-induced mutation. Br J Cancer 57:6–18 Breimer LH (1990) Molecular mechanisms of oxygen radical carcinogenesis and mutagenesis. The role of DNA base damage. Mol Carcinog 3:188–197.Google Scholar
  15. Breimer LH (1991) Repair of DNA damage induced by reactive oxygen species. Free Rad Res Comms 14: 159–171.CrossRefGoogle Scholar
  16. Burdon RH, Rice-Evans C (1989) Free radicals and the regulation of mammalian cell proliferation. Free Rad Res Comms 6: 346–348.Google Scholar
  17. Canonero R, Martelli A, Marinari UR, Brambilla G (1990) Mutation induction in Chinese hamster lung V79 cells by five alk-2-enals produced by lipid peroxidation. Mutat Res 244: 153–156.PubMedCrossRefGoogle Scholar
  18. Cantoni O, Sestili P, Cattabeni F, Bellomo G, Pou S, Cohen M, Cerutti P (1989) Calcium chelator quin 2 prevents hydrogen-peroxide-induced DNA breakage and cytotoxicity. Eur J Biochem 181: 209–212.CrossRefGoogle Scholar
  19. Carmichael PL, She MN, Phillips DH (1992) Detection and characterization by 32P-postlabelling of DNA adducts induced by a Fenton-type oxygen radical-generating system. Carcinogenesis 13: 1127–1135.PubMedCrossRefGoogle Scholar
  20. Cerutti P, Larsson R, Krupitza G, Muehlmatter D, Crawford D, Amstad P (1989) Pathophysiological mechanisms of active oxygen. Mutat Res 214: 81–88.PubMedCrossRefGoogle Scholar
  21. Cheng KC, Cahill DS, Kasai H, Nishimura S, Loeb LA (1992) 8-Hydroxyguanine, an abundant form of oxidative DNA damage, causes G —> T and A — C substitutions. J Biol Chem 267: 166–172.Google Scholar
  22. Chung FL, Xu Y (1992) Increased 8-oxodeoxyguanosine levels in lung DNA of A/J mice and F344 rats treated with the tobacco-specific nitrosamine 4(methyl-nitrosamine)-1-(3-pyridyl)-1-butanone. Carcinogenesis 13: 1269–1272.PubMedCrossRefGoogle Scholar
  23. Claycamp HG (1992) Phenol sensitization of DNA to subsequent oxidative damage in 8-hydroxyguanine assays. Carcinogenesis 13: 1289–1292.PubMedCrossRefGoogle Scholar
  24. Conway CC, Nie G, Huesain NS, Fiala ES (1991) Comparison of oxidative damage to rat liver DNA and RNA by primary nitroalkanes, secondary nitroalkanes, cyclopentanone oxime and related compounds. Cancer Res 51: 3143–3147.Google Scholar
  25. Denda A, Sai K, Tang Q, Tsujuchi T, Tsutsumi M, Amanuwa T, Murata Y, Nakoe D, Maruyama H, Kurokawa Y, Konishi Y (1991) Induction of 8-hydroxydeoxyguanosine but not initiation of carcinogenesis by redox enzyme modulations with or without menadione in rat liver. Carcinogenesis 12: 719–726.PubMedCrossRefGoogle Scholar
  26. Devasagayam TPA, Steenken S, Obendorf MSW, Schultz WA, Sies H (1991) Formation of 8-hydroxy(deoxy)guanosine and generation of strand breaks at guanine residues in DNA by singlet oxygen. Biochemistry 30: 6283–6289.PubMedCrossRefGoogle Scholar
  27. Di Guiseppi G, Fridovich I (1984) The toxicology of molecular oxygen. CRC Crit Rev Toxicol 12: 315–342.CrossRefGoogle Scholar
  28. Dijkwel PA, Wenink PW (1986) Structural integrity of the nuclear matrix; dif- ferential effects of thiol agents and metal chelators. J Cell Sci 84: 53–67.PubMedGoogle Scholar
  29. Dizdaroglu M (1991) Chemical determination of free radical-induced damage to DNA. Free Rad Biol Med 10: 225–242.PubMedCrossRefGoogle Scholar
  30. Dizdaroglu M (1993) Quantitative determination of oxidative base damage in DNA by stable isotope-dilution mass spectrometry. FEBS Lett 315: 1–6.PubMedCrossRefGoogle Scholar
  31. Dizdaroglu M, Hermes W, Schulte-Frohlinde D, von Sonntag C (1978) Enzymatic digestion of DNA y-irradiated in aqueous solution. Separation of the digests by ion-exchange chromatography. Int J Radiat Biol 33: 563–569.Google Scholar
  32. Dizdaroglu M, Rao G, Halliwell B, Gajewski E (1991a) Damage to the DNA bases in mammalian chromatin by hydrogen peroxide in the presence of ferric and cupric ions. Arch Biochem Biophys 285: 317–324.PubMedCrossRefGoogle Scholar
  33. Dizdaroglu M, Nackerdien Z, Chao BC, Gajewski E, Rao G (199 lb) Chemical nature of in vivo DNA base damage in hydrogen peroxide-treated mammalian cells. Arch Biochem Biophys 285: 388–390.Google Scholar
  34. Djuric A, Luongo DA, Harper DA (1991) Quantitation of 5-(hydroxymethyl) uracil in DNA by gas chromatography with mass spectral detection. Chem Res Tox 4: 687–691.CrossRefGoogle Scholar
  35. Epe B, Mutzel R, Adam W (1988) DNA damage by oxygen radicals and excited state species: a comparative study using enzymatic probes in vitro. Chem-Biol Interac 67: 149–165.CrossRefGoogle Scholar
  36. Epe B, Pflaum M, Haring M, Hegler J, Rudiger H (1993) Use of repair endonucleases to characterize DNA damage induced by reactive oxygen species in cellular systems. Toxicol Lett 67: 57–72.PubMedCrossRefGoogle Scholar
  37. Essigmann JM, Wood ML (1993) The relationship between the chemical structures and mutagenic specificities of the DNA lesions formed by chemical and physical mutagens. Toxicol Lett 67: 29–39.PubMedCrossRefGoogle Scholar
  38. Evans J, Maccabee M, Hatahet Z, Courcelle J, Bockrath R, Ide H, Wallace S (1993) Thymine ring saturation and fragmentation products: lesion bypass, misinsertion and implications for mutagenesis. Mut Res 299: 147–156.CrossRefGoogle Scholar
  39. Farber JL (1990) The role of calcium in lethal cell injury. Chem Res Toxicol 3: 503–508.PubMedCrossRefGoogle Scholar
  40. Faux SP, Francis JE, Smith AG, Chipman JK (1992) Induction of 8-hydroxydeoxyguanosine in Ah-responsive mouse liver by iron and Aroclor 1254. Carcinogenesis 13: 247–250.PubMedCrossRefGoogle Scholar
  41. Feig DI, Loeb LA (1993) Mechanisms of mutation by oxidative DNA damage: reduced fidelity of mammalian DNA polymerase P. Biochemistry 32: 4466–4473.PubMedCrossRefGoogle Scholar
  42. Floyd RA (1990) The role of 8-hydroxyguanine in carcinogenesis. Carcinogenesis 11: 1447–1450.PubMedCrossRefGoogle Scholar
  43. Floyd RA, Watson JJ, Wong PK, Altmiller DH, Rickard RC (1986) Hydroxyl-free radical adduct of deoxyguanosine: sensitive detection and mechanisms of formation. Free Rad Res Comms 1: 163–172.CrossRefGoogle Scholar
  44. Floyd RA, West MS, Eneff KL, Hogsett WE, Tingey DT (1988) Hydroxyl free radical mediated formation of 8-hydroxyguanine in isolated DNA. Arch Biochem Biophys 262: 266–272.PubMedCrossRefGoogle Scholar
  45. Floyd RA, West MS, Eneff KL, Schneider JE (1989) Methylene blue plus light mediates 8-hydroxyguanine formation in DNA. Arch Biochem Biophys 273: 106–111.PubMedCrossRefGoogle Scholar
  46. Fraga CC, Shigenaga MK, Park JW, Degan P, Ames BN (1990) Oxidative damage to DNA during aging: 8-hydroxy-2’-deoxyguanosine in rat organ DNA and urine. Proc Natl Acad Sci USA 87: 4533–4537.PubMedCrossRefGoogle Scholar
  47. Fraga CG, Motchnik PA, Shigenaga MK, Helbock HJ, Jacob RA, Ames BN (1991) Ascorbic acid protects against endogenous oxidative DNA damage in human sperm. Proc Natl Acad Sci USA 88: 11006–11033.CrossRefGoogle Scholar
  48. Frebourg T, Friend SH (1992) Cancer risks from germline P53 mutations. J Clin Invest 90: 1637–1641.PubMedCrossRefGoogle Scholar
  49. Frenkel K (1992) Carcinogen-mediated oxidant formation and oxidative DNA damage. Pharmac Ther 53: 127–166.CrossRefGoogle Scholar
  50. Frenkel K, Zhong Z, Wei H, Karkoszka J, Patel U, Rashid K, Georgescu M, Solomon JJ (1991) Quantitative high-performance liquid chromatography analysis of DNA oxidized in vitro and in vivo. Anal Biochem 196: 126–136.PubMedCrossRefGoogle Scholar
  51. Gajewski E, Rao G, Nackerdien Z, Dizdaroglu M (1990) Modification of DNA bases in mammalian chromatin by radiation-generated free radicals. Biochemistry 29: 7876–7882.PubMedCrossRefGoogle Scholar
  52. Geborek P, Mansson B, Hellmer G, Saxne T (1992) Cytidine deaminase and lactoferrin in inflammatory synovial fluids — indicators of local polymorphonuclear cell function. Br J Rheumatol 31: 235–240.PubMedCrossRefGoogle Scholar
  53. Geierstanger BH, Kagawa TF, Chen SL, Quigley GJ, Ho PS (1991) Base-specific binding of copper ( II) to Z-DNA. J Biol Chem 266: 20185–20191Google Scholar
  54. Glantz MD, Lewis AS (1978) Guanine deaminase from rabbit liver. Meth Enzymol L1: 512–517.CrossRefGoogle Scholar
  55. Goligorsky MS, Morgan MA, Suh H, Safirstein R, Johnson R (1992) Mild oxidative stress: cellular mode of mitogenic effect. Renal Failure 14: 385–389PubMedCrossRefGoogle Scholar
  56. Gutteridge JMC, Halliwell B (1990) The measurement and mechanism of lipid peroxidation in biological systems. Trends Biochem Sci 15: 129–135.PubMedCrossRefGoogle Scholar
  57. Hadley M, Draper HH (1990) Isolation of a guanine-malondialdehyde adduct from rat and human urine. Lipids 25: 82–85.PubMedCrossRefGoogle Scholar
  58. Halliwell B (1987) Oxidants and human disease; some new concepts. FASEB J 1: 358–362.PubMedGoogle Scholar
  59. Halliwell B, Aruoma OI (1991) DNA damage by oxygen-derived species. Its mechanism and measurement in mammalian systems. FEBS Lett 281: 9–19.Google Scholar
  60. Halliwell B, Dizdaroglu M (1992) The measurement of oxidative damage to DNA by HPLC and GC/MS techniques. Free Rad Res Comms 16: 75–87.CrossRefGoogle Scholar
  61. Halliwell B, Gutteridge JMC (1984) Lipid peroxidation, oxygen radicals, cell damage and antioxidant therapy. Lancet 1: 1396–1398.PubMedCrossRefGoogle Scholar
  62. Halliwell B, Gutteridge JMC (1989) Free radicals in biology and medicine, 2nd edn. Clarendon, OxfordGoogle Scholar
  63. Halliwell B, Gutteridge JMC (1990a) Role of free radicals and catalytic metal ions in human disease. Methods Enzymol 186: 1–185.PubMedCrossRefGoogle Scholar
  64. Halliwell B, Gutteridge JMC (1990b) The antioxidants of human extracellular fluids. Arch Biochem Biophys 280: 1–8.PubMedCrossRefGoogle Scholar
  65. Hayakawa M, Ogawa T, Sugiyama S, Tanaka M, Ozawa T (1991) Massive conversion of guanine to 8-hydroxyguanosine in mouse liver mitochondrial DNA by administration of azidothymidine. Biochem Biophys Res Commun 176: 87–93.PubMedCrossRefGoogle Scholar
  66. Hayakawa M, Hattori K, Sugiyama S, Ozawa T (1992) Age-associated oxygen damage and mutations in mitochondrial DNA in human hearts. Biochem Biophys Res Commun 189: 979–985.PubMedCrossRefGoogle Scholar
  67. Heig ME, Ulrich D, Sagelsdorff P, Richter C, Lutz WK (1990) No measurable increase in thymidine glycol or 8-hydroxydeoxyguanosine in liver DNA of rats treated with nafenopin or choline-devoid low-methionine diet. Mut Res 238: 325–329.CrossRefGoogle Scholar
  68. Hinrichsen LI, Floyd RA, Sudilovsky 0 (1990) Is 8-hydroxydeoxyguanosine a mediator of carcinogenesis by a choline-devoid diet in the rat liver? Carcinogenesis 11: 1879–1881.Google Scholar
  69. Imlay JA, Linn S (1988) DNA damage and oxygen radical toxicity. Science 240: 1302–1309.PubMedCrossRefGoogle Scholar
  70. Kasai H, Nishimura S (1984) Hydroxylation of deoxyguanosine at the C-8 position by ascorbic acid and other reducing agents. Nucleic Acids Res 12: 2137–2145.PubMedCrossRefGoogle Scholar
  71. Kasai H, Tanooka H, Nishimura S (1984) Formation of 8-hydroxyguanine residues in DNA by X-irradiation. Gann 75: 1037–1039.PubMedGoogle Scholar
  72. Kasai H, Crain PF, Kuchino Y, Nishimura S, Ootsuyama A, Tanooka H (1986) Formation of 8-hydroxyguanine moiety in cellular DNA by agents producing oxygen radicals and evidence for its repair. Carcinogenesis 7: 1849–1851.PubMedCrossRefGoogle Scholar
  73. Kasprzak KS (1991) The role of oxidative damage in metal carcinogenicity. Chem Res Tox 4: 604–615.CrossRefGoogle Scholar
  74. Kasprzak KS, Diwan BA, Rice JM, Misra M, Riggs CW, Olinski R, Dizdaroglu M (1992) Nickel(II)-mediated oxidative DNA base damage in renal and hepatic chromatin of pregnant rats and their fetuses. Possible relevance to carcinogenesis. Chem Res Tox 5: 810–815.Google Scholar
  75. Kass GE, Duddy SK, Ossenius S (1989) Activation of hepatroyte protein kinase C by redox-cycling quinones. Biochem J 260: 499–507.PubMedGoogle Scholar
  76. Kelly JD, Orner GA, Hendricks JD, Williams DE (1992) Dietary hydrogen peroxide enchances hepato-carcinogenesis in trout: correlation with 8-hydroxy-2’-deoxyguanosine levels in liver DNA. Carcinogenesis 13: 1639–1642.PubMedCrossRefGoogle Scholar
  77. Kiyosawa T, Suko M, Okudaira H, Murata K, Miyamoto T, Chung MH, Kasai H Nishimura S (1990) Cigarette smoke induces formation of 8-hydroxydeoxyguanosine, one of the oxidative DNA damages in human peripheral leukocytes. Free Rad Res Comms 11: 23–27.CrossRefGoogle Scholar
  78. Kojima T, Nishina T, Kitamura M, Kamatani N, Nishioka K (1989) Reversed-phase high-performance liquid-chromatography of 2,8-dihydroxyadenine in serum and urine with electrochemical detection. Clin Chim Acta 181: 109–114.PubMedCrossRefGoogle Scholar
  79. Kyle ME, Nakae D, Sakaida I, Miccadei S, Farber JL (1988) Endocytosis of superoxide dismutase is required in order for the enzyme to protect hepatocytes from the cytotoxicity of hydrogen peroxide. J Biol Chem 263: 3784–3789.PubMedGoogle Scholar
  80. Larrick JW, Wright SC (1990) Cytotoxic mechanism of tumor necrosis factor alpha. FASEB J 4: 3215–3223.PubMedGoogle Scholar
  81. Larsson R, Cerutti P (1989) Translocation and enhancement of phosphotransferase activity of protein kinase C following exposure of mouse epidermal cells to oxidants. Cancer Res 49: 5627–5632.PubMedGoogle Scholar
  82. Leanderson P, Tagesson C (1989) Cigarette smoke potentiates the DNA-da- maging effect of manmade mineral fibres. Am J Indust Med 16: 697–706.Google Scholar
  83. Leanderson P, Tegesson C (1992) Cigarette smoke-induced DNA damage in cultured human lung cells: role of hydroxyl radicals and endonuclease activation. Chem Biol Interac 81: 197–208.CrossRefGoogle Scholar
  84. Lewis CD, Laemmli UK (1982) Higher order metaphase chromosome structure: evidence for metalloprotein interactions. Cell 29: 171–181PubMedCrossRefGoogle Scholar
  85. Lindahl T (1993) Instability and decay of the primary structure of DNA. Nature 362: 709–715.PubMedCrossRefGoogle Scholar
  86. Loft S, Vistisen K, Ewertz M, Tjonneland A, Overvad K, Poulsen HE (1992) Oxidative DNA damage estimated by 8-hydroxydeoxyguanosine excretion in humans: influence of smoking, gender and body mass index. Carcinogenesis 13: 2441–2447.CrossRefGoogle Scholar
  87. Lu LJW, Tasake F, Hokanson JA, Kohda K (1991) Detection of 8-hydroxy2’deoxyguanosine in deoxyribonucleic acid by the 32P-postlabelling method. Chem Pharm Bull 39: 1880–1882.PubMedCrossRefGoogle Scholar
  88. Lutgerink JT, de Graaf E, Hoebee B, Staenuitez HFC, Westra JG, Kriek E (1992) Detection of 8-hydroxyguanine in small amounts of DNA by 32P postlabelling. Anal Biochem 201: 127–133.PubMedCrossRefGoogle Scholar
  89. Maccubbin A, Evans M, Paul CR, Budzinski EL, Przybyszewski J, Box HC (1991) Enzymatic excision of radiation-induced lesions from DNA model compounds. Radiat Res 126: 21–26.PubMedCrossRefGoogle Scholar
  90. Malins DC, Haimanot R (1990) 4,6,-Diamino-5-formamido-pyrimidine, 8-hydroxyguanine and 8-hydroxyadenine in DNA from neoplastic liver of English sole exposed to carcinogens. Biochem Biophys Res Commun 173: 614–619.Google Scholar
  91. Malins DC, Haimanot R (1991) Major alterations in the nucleotide structure of DNA in cancer of the female breast. Cancer Res 51: 5430–5432.PubMedGoogle Scholar
  92. McBride TJ, Preston BD, Loeb LA (1991) Mutagenic spectrum resulting from DNA damage by oxygen radicals. Biochemistry 30: 207–213.PubMedCrossRefGoogle Scholar
  93. Meier B, Radeke H, Selle S, Raspe HH, Sies H, Resch K, Habermehl GG (1990) Human fibroblasts release reactive oxygen species in response to treatment with synovial fluids from patients suffering from arthritis. Free Rad Res Comms 8: 149–160.CrossRefGoogle Scholar
  94. Mello-Filho AC, Hoffman RE, Meneghini R (1984) Cell killing and DNA damage by hydrogen peroxide are mediated by intracellular iron. Biochem J 218: 273–276.PubMedGoogle Scholar
  95. Mo JY, Maki H, Sekiguchi M (1992) Hydrolytic elimination of a mutagenic nucleotide, 8-oxodGTP, by human 18-kilodalton protein: sanitization of nucleotide pool. Proc Natl Acad Sci USA 89: 11021–11025.PubMedCrossRefGoogle Scholar
  96. Moraes EC, Keyse SM, Tyrrell RM (1990) Mutagenesis by hydrogen peroxide treatment of mammalian cells: a molecular analysis. Carcinogenesis 11: 283–293.PubMedCrossRefGoogle Scholar
  97. Mouret JF, Polverelli M, Sarrazini F, Cadet J (1991) Ionic and radical oxidations of DNA by hydrogen peroxide. Chem-Biol Interac 77: 187–201.CrossRefGoogle Scholar
  98. Murrell GAC, Francis MJO, Bromley L (1990) Modulation of fibroblast proliferation by oxygen free radicals. Biochem J 265: 659–665.PubMedGoogle Scholar
  99. Nackerdien Z, Rao G, Cacciuttolo MA, Gajewski E, Dizdaroglu M (1991) Chemical nature of DNA-protein cross-links produced in mammalian chromatin by hydrogen peroxide in the presence of iron or copper ions. Biochemistry 30: 4872–4879.CrossRefGoogle Scholar
  100. Nackerdien Z, Olinski R, Dizdaroglu M (1992) DNA base damage in chromatin of y-irradiated human cells. Free Rad Res Comms 16: 259–273.CrossRefGoogle Scholar
  101. Nakae D, Yoshiji H, Amanuma T, Kinugasa T, Farber JL, Konishi Y (1990) Endocytosis-independent uptake of liposome-encapsulated superoxide dismutase prevents the killing of cultured hepatocytes by tert-butyl hydroperoxide. Arch Biochem Biophys 279: 315–319.PubMedCrossRefGoogle Scholar
  102. Nassi-Calo L, Mello-Filho AC, Meneghini R (1989) 0-phenanthroline protects mammalian cells from hydrogen peroxide-induced gene mutation and morphological transformation. Carcinogenesis 10: 1055–1057.Google Scholar
  103. Oda Y, Uesugi S, Ikehara M, Nishimura S, Kawase Y, Ishikawa H, Inoue H, Ohtsuka E (1991) NMR studies of a DNA containing 8-hydroxydeoxyguanosine. Nucleic Acids Res 19: 1407–1412.PubMedCrossRefGoogle Scholar
  104. Olinski R, Zastawny T, Budzbon J, Skokowski J, Zegarski W, Dizdaroglu M (1992) DNA base modifications in chromatin of human cancerous tissues. FEBS Lett 309: 193–198.PubMedCrossRefGoogle Scholar
  105. Oller AR, Thilly WG (1992) Mutational spectra in human [3-cells. Spontaneous, oxygen and hydrogen peroxide-induced mutations at the hprt gene. J Mol Biol 228: 813–826.Google Scholar
  106. Orrenius S, McConkey DJ, Bellomo G, Nicotera P (1989) Role of Ca++ in toxic cell killing. Trends Pharmacol Sci 10: 281–285.PubMedCrossRefGoogle Scholar
  107. Park JW, Floyd RA (1992) Lipid peroxidation products mediate the formation of 8-hydroxydeoxyguanosine in DNA. Free Rad Biol Med 12: 245–250PubMedCrossRefGoogle Scholar
  108. Prieto-Alamo MJ, Abril N, Pueyo C (1993) Mutagenesis in Escherichia coli K12 mutants defective in superoxide dismutase or catalase. Carcinogenesis 14: 237–244.PubMedCrossRefGoogle Scholar
  109. Prutz WA, Butler J, Land EJ (1990) Interaction of copper ( I) with nucleic acids. Int J Radiat Biol 58: 215–234.Google Scholar
  110. Retel J, Hoebee B, Braun JEF, Lutgerink JT, van den Akker E, Wanamarta AH, Joenje H, Lafleur MJM (1993) Mutational specificity of oxidative DNA damage. Mut Res 299: 165–182.CrossRefGoogle Scholar
  111. Richter C (1988) Do mitochondrial DNA fragments promote cancer and aging? FEBS Lett 241: 1–5.PubMedCrossRefGoogle Scholar
  112. Richter C, Park JW, Ames BN (1988) Normal oxidative damage to mitochondria) and nuclear DNA is extensive. Proc Natl Acad Sci USA 85: 6465–6467.PubMedCrossRefGoogle Scholar
  113. Rowley DA, Halliwell B (1983) DNA damage by superoxide-generating systems in relation to the mechanism of action of the anti-tumor antibiotic adriamycin. Biochim Biophys Acta 761: 86–93PubMedCrossRefGoogle Scholar
  114. Roy D, Floyd RA, Liehr JG (1991) Elevated 8-hydroxy-deoxyguanosine levels in DNA of diethylstilbestrol-treated Syrian hamsters; covalent DNA damage by free radicals generated by redox cycling of diethylstilbestrol. Cancer Res 51: 3882–3885.PubMedGoogle Scholar
  115. Sai K, Takagi A, Umemura T, Hasegawa R, Kurokawa Y (1991) Relation of 8-hydroxydeoxyguanosine formation in rat kidney to lipid peroxidation, glutathione level and relative organ weight after a single administration of potassium bromate. Japan J Cancer Res 82: 165–169CrossRefGoogle Scholar
  116. Shibutani S, Takeshita M, Grollman AP (1991) Insertion of specific bases during DNA synthesis past the oxidation-damaged base 8-oxodG. Nature 349: 431–434.PubMedCrossRefGoogle Scholar
  117. Shigenaga MK, Park JW, Cundy KC, Gimeno CJ, Ames BN (1990) In vivo oxidative DNA damage: measurement of 8-hydroxy-2’-deoxyguanosine in DNA and urine by high-performance liquid chromatography with electrochemical detection. Meth Enzymol 186: 521–530.PubMedCrossRefGoogle Scholar
  118. Sies H ed (1991) Oxidative stress, oxidants and antioxidants. Academic, New YorkGoogle Scholar
  119. Sies H (1993) Damage to plasmid DNA by singlet oxygen and its protection. Mut Res 299: 183–191.CrossRefGoogle Scholar
  120. Sodum RS, Chung FL (1988) INZ-ethenodeoxyguanosine as a potential marker for DNA adduct formation by trans-4-hydroxy-2-nonenal. Cancer Res 48: 320–323.PubMedGoogle Scholar
  121. Steenken S (1989) Purine bases, nucleosides and nucleotides: aqueous solution redox chemistry and transformation reactions of their radical cations and e and OH adducts. Chem Rev 89: 503–520.CrossRefGoogle Scholar
  122. Stillwell WG, Xu HX, Adkins JA, Wishnok JS, Tannenbaum SR (1989) Analysis of methylated and oxidized purines in urine by capillary gas chromatography-mass spectrometry. Chem Res Tox 2: 94–99.CrossRefGoogle Scholar
  123. Stone K, Ksebati M, Marnett LJ (1990a) Identification of the adducts formed by reaction of malondialdehyde with adenosine. Chem Res Tox 3:33–38.Google Scholar
  124. Stone K, Uzieblo A, Marnett LJ (1990b) Studies of the reaction of malondial-dehyde with cytosine nucleosides. Chem Res Tox 3: 467–472.CrossRefGoogle Scholar
  125. Tchou J, Grollman AP (1993) Repair of DNA containing the oxidatively-damaged base, 8-oxoguanine Mut Res 299: 277–287.Google Scholar
  126. Totter JR (1980) Spontaneous cancer and its possible relationship to oxygen metabolism. Proc Natl Acad Sci USA 77: 1763–1767.PubMedCrossRefGoogle Scholar
  127. Touati D (1989) The molecular genetics of superoxide dismutase in E. coli. Free Rad Res Comms 8: 1–8.CrossRefGoogle Scholar
  128. Trush MA, Kensler TW (1991) An overview of the relationship between oxidative stress and chemical carcinogenesis. Free Rad Biol Med 10: 201–209.PubMedCrossRefGoogle Scholar
  129. Ueda N, Shah SV (1992) Endonuclease-induced DNA damage and cell death in oxidant injury to renal tubular epithelial cells. J Clin Invest 90: 2593–2597.PubMedCrossRefGoogle Scholar
  130. Umemura T, Sai K, Takagi A, Hasegawa R, Kurokawa Y (1991) The effects of exogenous glutathione and cysteine on oxidative stress induced by ferric nitrilotriacetate. Cancer Lett 58: 49–56.PubMedCrossRefGoogle Scholar
  131. von Sonntag C (1987) The chemical basis of radiation biology. Taylor and Francis, LondonGoogle Scholar
  132. Wagner JR, Hu CC, Ames BN (1992) Endogenous oxidative damage of deoxycytidine in DNA. Proc Natl Acad Sci USA 89: 3380–3384PubMedCrossRefGoogle Scholar
  133. Weiss SJ (1989) Tissue destruction by neutrophils. N Engl J Med 320: 365–376.PubMedCrossRefGoogle Scholar
  134. Weitberg AB, Corvese D (1990) Translocation of chromosomes 16 and 18 in oxygen radical-transformed human lung fibroblasts. Biochem Biophys Res Commun 169: 70–74.PubMedCrossRefGoogle Scholar
  135. Weitzman SA, Gordon LI (1990) Inflammation and cancer: role of phagocyte-generated oxidants in carcinogenesis. Blood 76: 655–663.PubMedGoogle Scholar
  136. Weitzman SA, Weitberg AB, Clark EP, Clark TP, Stossel TP (1985) Phagocytes as carcinogens: malignant transformation produced by human neutrophils. Science 227: 1231–1233.PubMedCrossRefGoogle Scholar
  137. Weitzman S, Schmeichel C, Turk P, Stevens C, Tolsma S, Bouck N (1988) Phagocyte-mediated carcinogenesis: DNA from phagocyte-transformed C3H 10T1/2 cells can transform NIH/3T3 cells. Ann NY Acad Sci 551: 103–109.PubMedCrossRefGoogle Scholar
  138. Wink DA, Kasprzak KS, Maragos CM, Elespura RK, Misra M, Dunams TM, Cebula TA, Koch WH, Andrews AW, Allen JS, Keefer LK (1991) DNA deaminating ability and genotoxicity of nitric oxide and its progenitors. Science 254: 1001–1003.PubMedCrossRefGoogle Scholar
  139. Wyllie AH (1980) Glucocorticoid-induced thymocyte apoptosis is associated with endogenous endonuclease activation. Nature 284: 555–556.PubMedCrossRefGoogle Scholar
  140. Zimmerman R, Cerutti P (1984) Active oxygen acts as a promoter of carcinogenesis in C3H/10T1/2/C18 fibroblasts. Proc Natl Acad Sci USA 81: 2085–2087.PubMedCrossRefGoogle Scholar
  141. Zimmerman RI, Chan A, Leadon SA (1989) Oxidative damage in murine tumor cells treated in vitro by recombinant human tumor necrosis factor. Cancer Res 49: 1644–1648.PubMedGoogle Scholar

Copyright information

© Springer-Verlag Berlin Heidelberg 1994

Authors and Affiliations

  • B. Halliwell

There are no affiliations available

Personalised recommendations