Oxygen and nitrogen are pro-carcinogens. Damage to DNA by reactive oxygen, chlorine and nitrogen species: Measurement, mechanism and the effects of nutrition

Mutation Research - Genetic Toxicology and Environmental Mutagenesis

Volumn 443, Issue 1-2, 1999, Pages 37-52

  Halliwell, Barry ^a  

^a NATIONAL UNIVERSITY OF SINGAPORE   (Singapore)

Author keywords

8 hydroxydeoxyguanosine (8OHdG); Carcinogen; DNA damage

Indexed keywords

ANTIOXIDANT; FLAVONOID; FREE RADICAL; HYDROGEN PEROXIDE; HYDROXYL RADICAL; NITRIC OXIDE; NITROGEN DERIVATIVE; OXYGEN RADICAL; PEROXYNITRITE; REACTIVE OXYGEN METABOLITE;

CANCER RISK; DIET; DNA DAMAGE; DNA DETERMINATION; GAS CHROMATOGRAPHY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HUMAN; MASS SPECTROMETRY; PRIORITY JOURNAL; REVIEW; RISK ASSESSMENT;

EID: 0033565994     PISSN: 13835718     EISSN: None     Source Type: Journal    
DOI: 10.1016/S1383-5742(99)00009-5     Document Type: Article

References (153)

1. Ames B.N., Gold L.S. Environmental pollution, pesticides, and the prevention of cancer: misconceptions. FASEB J. 11:1997;1041-1052.
2. .) in the carcinogenic process. Biochim. Biophys. Acta. 1288:1996;F31-F36.
3. Ambs S., Hussain P., Harris C.C. Interactive effects of NO and the p53 tumor suppressor gene in carcinogenesis and tumor progression. FASEB J. 11:1997;443-448.
4. Juedes M.J., Wogan G.N. Peroxynitrite-induced mutation spectra of pSP 189 following replication in bacteria and in human cells. Mutat. Res. 349:1996;51-61.
5. Szabó C., Zingarelli B., O'Connor M., Salzman A.L. DNA strand breakage, activation of poly(ADP-ribose) synthetase, and cellular energy depletion are involved in the cytotoxicity in macrophages and smooth muscle cells exposed to peroxynitrite. Proc. Natl. Acad. Sci. USA. 93:1996;1753-1758.
6. Wink D.A., Kasprzak K.S., Maragos C.M., Elespuru R.K., Misra M., Dunams T.M., Cebula T.A., Koch W.H., Andrews A.W., Allen J.S., Keefer L.K. DNA deaminating ability and genotoxicity of nitric oxide and its progenitors. Science. 254:1991;1001-1003.
7. Ohshima H., Bartsch H. Chronic infections and inflammatory processes as cancer risk factors: possible role of nitric oxide in carcinogenesis. Mutat. Res. 305:1994;253-264.
8. Yermilov V., Rubio J., Ohshima H. Formation of 8-nitroguanine in DNA treated with peroxynitrite in vitro and its rapid removal from DNA by depurination. FEBS Lett. 376:1995;207-210.
9. Douki H., Cadet J. Peroxynitrite mediated oxidation of purine bases of nucleosides and isolated DNA. Free Radical Res. 24:1996;369-380.
10. deRojas-Walker T., Tamir S., Ji H., Wishnock J.S., Tannenbaum S.R. Nitric oxide induces oxidative damage in addition to deamination in macrophage DNA. Chem. Res. Toxicol. 8:1995;473-477.
11. Douki T., Cadet J., Ames B.N. An adduct between peroxynitrite and 2′-deoxyguanosine: 4,5-dihydro-5-hydroxy-4-(nitrosooxy)-2′-deoxyguanosine. Chem. Res. Toxicol. 9:1996;3-7.
12. Spencer J.P.E., Wong J., Jenner A., Aruoma O.I., Cross C.E., Halliwell B. Base modifications and strand breakage in isolated calf thymus DNA and in DNA from human skin epidermal keratinocytes exposed to peroxynitrite or 3-morpholinosydnonimine. Chem. Res. Toxicol. 9:1995;1152-1158.
13. Felley-Bosco E. Role of nitric oxide in genotoxicity: implication for carcinogenesis. Cancer Metastasis Rev. 17:1998;25-37.
14. Lindahl T. Instability and decay of the primary structure of DNA. Nature. 362:1993;709-715.
15. Savva R., McAuley-Hecht K., Brown T., Pearl L. The structural basis of specific base-excision repair by uracil-DNA glycosylase. Nature. 373:1995;487-493.
16. Demple B., Harrison L. Repair of oxidative damage to DNA: enzymology and biology. Annu. Rev. Biochem. 63:1994;915-948.
17. Wilson D.M. III, Thompson L.H. Life without DNA repair. Proc. Natl. Acad. Sci. USA. 94:1997;12754-12757.
18. A. Wennmalm, G. Benthin, L. Jungersten, A. Edlund, A.S. Petersson, Nitric oxide formation in man as reflected by plasma levels of nitrate, with special focus on kinetics, confounding factors and response to immunological challenge, in: S. Moncada, M. Feelish, R. Busse, E.A. Higgs (Eds.), The Biology of Nitric Oxide, Vol. 4., Portland Press, 1994, pp. 474-476.
19. McKnight G.M., Smith L.M., Drummond R.S., Duncan C.W., Golden M., Benjamin N. Chemical synthesis of nitric oxide in the stomach from dietary nitrate in humans. Gut. 40:1997;211-214.
20. Ohshima H., Bartsch H. Quantitative assessment of endogenous nitration in humans by measuring excretion of N-nitrosoproline in the urine. Cancer Res. 41:1981;3658-3662.
21. Shephard S.E., Schlatter C., Lutz W.K. Assessment of the risk of formation of carcinogenic N-nitroso compounds from dietary precursors in the stomach. Food Chem. Toxicol. 25:1987;91-108.
22. Dallinga J.W., Pachen D.M.F.A., Lousberg A.H.P., van Geel J.A.M., Houben G.M.P., Stockbrügger R.W., van Maanen J.M.S., Kleinjans J.C.S. Volatile N-nitrosoamines in gastric juice of patients with various conditions of the gastrointestinal tract determined by gas chromatography-mass spectrometry and related to intragastric pH and nitrate and nitrite levels. Cancer Lett. 124:1998;119-125.
23. B. Halliwell, J.M.C. Gutteridge, Free Radicals in Biology and Medicine, 3rd edn., Clarendon Press, Oxford, UK, 1999.
24. Halliwell B., Aruoma O.I. DNA damage by oxygen-derived species: its mechanism and measurement in mammalian systems. FEBS Lett. 281:1991;9-19.
25. C. von Sonntag, The Chemical Basis of Radiation Biology, Taylor and Francis, London, 1987.
26. 2 with 2′-deoxyguanosine and DNA. Isolation and characterization of the main oxidation products. Chem. Res. Toxicol. 8:1995;379-388.
27. 2. Chem.-Biol. Interact. 80:1992;239-260.
28. Mori T., Tano K., Takimoto K., Utsumi H. Formation of 8-hydroxyguanine and 2,6-diamino-4-hydroxy-5-formamidopyrimidine in DNA by riboflavin mediated photosensitization. Biochem. Biophys. Res. Commun. 242:1998;98-101.
29. Aruoma O.I., Halliwell B., Dizdaroglu M. Iron ion dependent modification of bases in DNA by the superoxide radical-generating system hypoxanthine/xanthine oxidase. J. Biol. Chem. 264:1989;13024-13028.
30. Nackerdien Z., Rao G., Cacciuttolo M.A., Gajewski E., Dizdaroglu M. Chemical nature of DNA-protein cross-links produced in mammalian chromatin by hydrogen peroxide in the presence of iron or copper ions. Biochemistry. 30:1991;4872-4879.
31. Aruoma O.I., Halliwell B., Gajewski E., Dizdaroglu M. Copper-ion-dependent damage to the bases in DNA in the presence of hydrogen peroxide. Biochem. J. 273:1991;601-604.
32. Dizdaroglu M. Gas-chromatography mass-spectrometry of free radical-induced products of pyrimidines and purines in DNA. Methods Enzymol. 193:1990;842-857.
33. 2 in the presence of ferric and cupric ions. Arch. Biochem. Biophys. 285:1991;317-324.
34. Spencer J.P.E., Jenner A., Chimel K., Aruoma O.I., Cross C.E., Wu R., Halliwell B. DNA strand breakage and base modification induced by hydrogen peroxide treatment of human respiratory tract epithelial cells. FEBS Lett. 374:1995;233-236.
35. Fuciarelli A.F., Wegher B.J., Blakely W.F., Dizdaroglu M. Yields of radiation-induced base products in DNA - effects of DNA conformation and gassing conditions. Int. J. Radiat. Biol. 58:1990;397-415.
36. Miller I., Jenner A., Bruchelt G., Niethammer D., Halliwell B. Effect of concentration on the cytotoxic mechanism of doxorubicin - apoptosis and oxidative DNA damage. Biochem. Biophys. Res. Commun. 230:1997;254-257.
37. B. Epe, DNA damage induced by photosensitizers and other photoreactive compounds, in: O.I. Aruoma, B. Halliwell (Eds.), DNA and Free Radicals. Techniques, Mechanisms and Applications, OICA International Press, St. Lucia, 1998.
38. Whiteman M., Jenner A., Halliwell B. Hypochlorous acid-induced base modification in isolated calf thymus DNA. Chem. Res. Toxicol. 10:1997;1240-1246.
39. M. Whiteman, J.P.E. Spencer, A. Jenner, B. Halliwell, Hypochlorous acid-induced DNA base modification: potentiation by nitrite. Biochem. Biophys. Res. Commun., in press.
40. Lyras L., Cairns N.J., Jenner A., Jenner P., Halliwell B. An assessment of oxidative damage to proteins, lipids and DNA in brain from patients with Alzheimer's disease. J. Neurochem. 68:1997;2061-2069.
41. Lyras L., Perry R.H., Perry E.K., Ince P.G., Jenner A., Jenner P., Halliwell B. Oxidative damage to proteins, lipids and DNA in cortical brain regions from patients with Dementia with Lewy bodies. J. Neurochem. 71:1998;302-312.
42. Alam Z.I., Jenner A., Daniel S.E., Lees A.J., Cairns N., Marsden C.D., Jenner P., Halliwell B. Oxidative DNA damage in the Parkinsonian brain: an apparent selective increase in 8-hydroxyguanine levels in substantia nigra. J. Neurochem. 69:1997;1196-1203.
43. Loeb L.A. Endogenous carcinogenesis: molecular oncology into the 21st century - Presidential address. Cancer Res. 49:1989;5489-5496.
44. Wiseman H., Halliwell B. Damage to DNA by reactive oxygen and nitrogen species - role in inflammatory disease and progression to cancer. Biochem. J. 313:1996;17-29.
45. Feig D.I., Loeb L.A. Mechanisms of mutation by oxidative DNA damage: reduced fidelity of mammalian DNA polymerase β Biochemistry. 32:1993;4466-4473.
46. Burdon R.H., Alliangana D., Gill V. Endogenously generated active oxygen species and cellular glutathione levels in relation to BHK-21 cell proliferation. Free Radical Res. 21:1994;121-134.
47. Chaudhary A.K., Nokubo M., Reddy G.R.et al. Detection of endogenous malondialdehyde-deoxyguanosine adducts in human liver. Science. 265:1994;1580-1582.
48. 4-ethenocytosine by lipid peroxidation products and nucleic acid bases. Chem. Res. Toxicol. 8:1995;278-283.
49. 2-propano adducts of 2′-deoxyguanosine with 4-hydroxynonenal and other α,β-unsaturated aldehydes. Chem. Res. Toxicol. 7:1994;511-518.
50. Taguchi T., Ohashi M. Changes in fidelity levels of DNA polymerases α-1, α-2 and β during ageing in rats. Mech. Age Dev. 99:1997;33-47.
51. Floyd R.A. The role of 8-hydroxyguanine in carcinogenesis. Carcinogenesis. 11:1990;1447-1450.
52. Kasai H. Analysis of a form of oxidative DNA damage, 8-hydroxy-2′-deoxyguanosine, as a marker of cellular oxidative stress during carcinogenesis. Mutat. Res. 387:1997;147-163.
53. Helbock H.J., Beckman K.B., Shigenaga M.K., Walter P.B., Woodall A.A., Yeo H.C., Ames B.N. DNA oxidation matters: the HPLC-electrochemical detection assay of 8-oxo-deoxyguanosine and 8-oxo-guanine. Proc. Natl. Acad. Sci. USA. 95:1998;288-293.
54. A. Hartwig, Assessment of oxidative DNA damage by the frequency of formamidopyrimidine glycosylase (FPG) sensitive DNA lesions, in: O.I. Aruoma, B. Halliwell (Eds.), DNA and Free Radicals. Techniques, Mechanisms and Applications, OICA International Press, St. Lucia, 1998.
55. Halliwell B., Dizdaroglu M. The measurement of oxidative damage to DNA by HPLC and GC-MS techniques. Free Radical Res. Commun. 16:1992;75-87.
56. Nackerdien Z., Olinksi R., Dizdaroglu M. DNA base damage in chromatin of γ-irradiated cultured human cells. Free Radical Res. Commun. 16:1992;259-273.
57. Malins D.C., Haimanot R. Major alterations in the nucleotide structure of DNA in cancer of the female breast. Cancer Res. 51:1991;5430-5432.
58. Bridges B.A. MutY directs mutation? Nature. 375:1995;741.
59. Mo J.Y., Maki H., Sekiguchi M. Hydrolytic elimination of a mutagenic nucleotide, 8-oxodGTP, by human 18-kilodalton protein: sanitization of nucleotide pool. Proc. Natl. Acad. Sci. USA. 89:1992;11021-11025.
60. Roldan-Arjona T., Wei Y.F., Carter K.C., Klungland A., Anselinino C., Wang R.P., Augustus M., Lindahl T. Molecular cloning and functional expression of a human cDNA encoding the antimutator enzyme 8-hydroxyguanine-DNA glycosylase. Proc. Natl. Acad. Sci. USA. 94:1997;8016-8020.
61. Wood R.D. Nucleotide excision repair in mammalian cells. J. Biol. Chem. 272:1997;23465-23468.
62. Stillwell W.G., Xu H.X., Adkins J.A.et al. Analysis of methylated and oxidized purines in urine by capillary gas chromatography-mass spectrometry. Chem. Res. Toxicol. 2:1989;94-99.
63. Loft S., Fischer-Nielsen A., Jeding I.B.et al. 8-Hydroxydeoxyguanosine as a urinary marker of oxidative DNA damage. J. Toxicol. Environ. Health. 40:1993;391-404.
64. Loft S., Velthuis-te Wierik E.J.M., van den Berg H., Poulsen H.E. Energy restriction and oxidative DNA damage in humans. Cancer Epidemiol. Biomarkers Prev. 4:1995;515-519.
65. Verhagen V., Poulsen H.E., Loft S.et al. Reduction of oxidative DNA-damage in humans by Brussels sprouts. Carcinogenesis. 16:1995;969-970.
66. Ames B.N. Endogenous oxidative DNA damage, aging and cancer. Free Radical Res. Commun. 7:1989;121-128.
67. Drury J.A., Jeffers G., Cooke R.W.I. Urinary 8-hydroxydeoxyguanosine in infants and children. Free Radical Res. 28:1998;423-428.
68. Halliwell B. Can oxidative DNA damage be used as a biomarker of cancer risk in humans? Problems, resolutions and preliminary results from nutritional supplementation studies. Free Radical Res. 25:1998;469-486.
69. A. Collins, J. Cadet, B. Epe, C. Gedik, Problems in the measurement of 8-oxoguanine in human DNA. Report of a workshop, DNA Oxidation, held in Aberdeen, UK, 19-21 January, 1997. Carcinogenesis, 18 (1997) 1833-1836.
70. Harris G., Bashir S., Winyard P.G. 7,8-Dihydro-8-oxo-2′-deoxyguanosine present in DNA is not simply an artefact of isolation. Carcinogenesis. 15:1994;411-413.
71. Claycamp H.G. Phenol sensitization of DNA to subsequent oxidative damage in 8-hydroxyguanosine assays. Carcinogenesis. 13:1992;1289-1292.
72. A. Rehman, B. Halliwell, Optimization of procedures for the isolation of DNA from human blood, Free Radical Res. (1999) in press.
73. Lunec J. ESCODD: European Standards Committee on Oxidative DNA damage. Free Radical Res. 25:1998;601-608.
74. Gedik C.M., Wood S.G., Collins A.R. Measuring oxidative damage to DNA; HPLC and the comet assay compared. Free Radical Res. 25:1998;609-615.
75. Dizdaroglu M. Facts about the artifacts in the measurement of oxidative DNA base damage by gas chromatography-mass spectrometry. Free Radical Res. 25:1998;551-563.
76. Dizdaroglu M., Bertgold D.S. Characterization of free-radical induced base damage in DNA at biologically relevant levels. Anal. Biochem. 156:1986;182-188.
77. Farooq S., Bailey E., Farmer P.B., Jukes R., Lamb H.H., Hernández H., Sram R., Topinka J. Determination of cis-thymine glycol in DNA by gas chromatography-mass spectrometry with selected ion recording and multiple reaction monitoring. J. Chromatogr. B. 702:1997;49-60.
78. Jenner A., England T.G., Aruoma O.I., Halliwell B. Measurement of oxidative DNA damage by gas chromatography-mass spectrometry: ethanethiol prevents artifactual generation of oxidized DNA bases. Biochem. J. 331:1998;365-369.
79. A.R. Collins, The comet assay: a novel approach to measuring DNA oxidation, in: O.I. Aruoma, B. Halliwell (Eds.), DNA and Free Radicals, Techniques, Mechanisms and Applications, OICA International Press, St. Lucia, 1998.
80. 32P -postlabeling assay and the basal levels in rat tissue Carcinogenesis. 17:1996;917-924.
81. 33P -postlabelling and electrochemical detection Carcinogenesis. 18:1997;2367-2371.
82. 32P -postlabeling assay Carcinogenesis. 18:1997;2415-2419.
83. Ward J.F. Radiation mutagenesis: the initial DNA lesions responsible. Radiat. Res. 142:1995;362-368.
84. Bartsch H. DNA adducts in human carcinogenesis: etiological relevance and structure-activity relationship. Mutat. Res. 340:1996;67-79.
85. Poirier M.C., Weston A. Human DNA adduct measurements: state of the art. Environ. Health Perspect. 104(5):1996;883-893. suppl.
86. Kalyanaraman B., Sohnle P.G. Generation of free radical intermediates from foreign compounds by neutrophil-derived oxidants. J. Clin. Invest. 75:1985;1618-1622.
87. Beckman J.S., Koppenol W.H. Nitric oxide, superoxide and peroxynitrite: the good, the bad and the ugly. Am. J. Physiol. 271:1996;424-437.
88. Prat F., Houk K.N., Foote C.S. Effect of guanine stacking on the oxidation of 8-oxoguanine in B-DNA. J. Am. Chem. Soc. 120:1998;645-646.
89. Floyd R.A., Watson J.J., Wong P.K.et al. Hydroxy-free radical adduct of deoxyguanosine: sensitive detection and mechanisms of formation. Free Radical Res. Commun. 1:1986;163-172.
90. Ames B.N., Shigenaga M.K., Hagen T.M. Oxidants, antioxidants and the degenerative diseases of aging. Proc. Natl. Acad. Sci. USA. 90:1993;7915-7922.
91. Totter J.R. Spontaneous cancer and its possible relationship to oxygen metabolism. Proc. Natl. Acad. Sci. USA. 77:1980;1763-1767.
92. Cerutti P. Oxy-radicals and cancer. Lancet. 344:1994;862-863.
93. K.B. Beckman, B.N. Ames, Oxidative DNA damage: assessing its role in cancer and aging, in: O.I. Aruoma, B. Halliwell (Eds.), DNA and Free Radicals, Techniques, Mechanisms and Applications, OICA International Press, St. Lucia, 1998.
94. Zastawny T.H., Dabrowska M., Jaskolski T., Klimarczyk M., Kulinski L., Koszela A., Szczesniewicz M., Sliwinska M., Witkowski P., Olinski R. Comparison of oxidative base damage in mitochondrial and nuclear DNA. Free Radical Biol. Med. 24:1998;722-725.
95. Yates F.M., Van Houten B. Mitochondrial DNA damage is more extensive and persists longer than nuclear DNA damage in human cells following oxidative stress. Proc. Natl. Acad. Sci. USA. 94:1997;514-519.
96. Suter M., Richter C. Fragmented mitochondrial DNA is the predominant carrier of oxidized DNA bases. Biochemistry. 38:1999;459-464.
97. Wei Y.H. Oxidative stress and mitochondrial DNA mutations in human aging. Proc. Soc. Exp. Biol. Med. 217:1998;53-63.
98. Ravanat J.-L., Turesky R.J., Gremaud E., Trudle L.J., Stadler R.H. Determination of 8-oxoguanine in DNA by gas-chromatography mass-spectrometry and HPLC-electrochemical detection - overestimation of the background level of the oxidized base by the gas-chromatography mass-spectrometry assay. Chem. Res. Toxicol. 8:1995;1039-1045.
99. Douki T., Delatour T., Bianchini F., Cadet J. Observation and prevention of an artifactual formation of oxidized DNA bases and nucleosides in the GC-EIMS method. Carcinogenesis. 17:1996;347-353.
100. Dizdaroglu M. Quantitative-determination of oxidative base damage in DNA by stable isotope-dilution mass-spectrometry. FEBS Lett. 315:1993;1-6.
101. Hamberg M., Zhang L.Y. Quantitative-determination of 8-hydroxyguanine and guanine by isotope-dilution mass spectrometry. Anal. Biochem. 229:1995;336-344.
102. LaFrancois C.J., Fujimoto J., Sowers L.C. Synthesis and chemical characterization of isotopically enriched pyrimidine deoxynucleoside oxidation damage products. Chem. Res. Toxicol. 11:1998;75-83.
103. Halliwell B. Oxidative stress, nutrition and health. Experimental strategies for optimization of nutritional antioxidant intake in humans. Free Radical Res. 25:1996;57-74.
104. England T.G., Jenner A., Aruoma O.I., Halliwell B. Determination of oxidative DNA base damage by gas chromatography-mass spectrometry, Effect of derivatization conditions on artifactual formation of certain base oxidation products. Free Radical Res. 29:1998;321-330.
105. 4 from guanine during trimethylsilylation. Anal. Biochem. 261:1998;57-63.
106. D. Rindgen, A.K. Chaudhary, I.A. Blair, Applications of advanced mass spectrometry to detect oxidative DNA damage: carcinogenic implications, in: O.I. Aruoma, B. Halliwell (Eds.), DNA and Free Radicals, Techniques, Mechanisms and Applications, OICA International Press, St. Lucia, 1998.
107. Kaur H., Halliwell B. Measurement of oxidized and methylated DNA bases by HPLC with electrochemical detection. Biochem. J. 318:1996;21-23.
108. Kasai H., Crain P.F., Kuchino Y., Nishimura S., Ootsuyama A., Tanooka H. Formation of 8-hydroxyguanine moiety in cellular DNA by agents producing oxygen radicals and evidence for its repair. Carcinogenesis. 7:1986;1849-1851.
109. H.E. Poulsen, S. Loft, Interpretation of oxidative DNA modification: relation between tissue levels, excretion of urinary repair products and single cell gel electrophoresis (comet assay), in: O.I. Aruoma, B. Halliwell (Eds.), DNA and Free Radicals, Techniques, Mechanisms and Applications, OICA International Press, St. Lucia, 1998.
110. Kiyosawa H., Suko M., Okudaira H., Murata K., Miyamoto T., Chung M.H., Kasai H., Nishimura S. Cigarette smoking induces formation of 8-hydroxydeoxyguanosine, one of the oxidative DNA damages, in human peripheral leukocytes. Free Radical Res. Commun. 11:1990;23-27.
111. Loft S., Vistisen K., Ewertz M.et al. Oxidative DNA-damage estimated by 8-hydroxydeoxyguanosine excretion in man: influence of smoking, gender and body mass index. Carcinogenesis. 13:1992;2241-2247.
112. Deng X.S., Tuo J., Poulsen H.E., Loft S. Prevention of oxidative DNA damage in rats by Brussels sprouts. Free Radical Res. 28:1998;323-333.
113. Paganga G., Rice-Evans C.A. The identification of flavonoids as glycosides in human plasma. FEBS Lett. 401:1997;78-82.
114. Sian J., Dexter D.T., Lees A.J., Daniel S., Agid Y., Javoy-Agid F., Jenner P., Marsden C.D. Alterations in glutathione levels in Parkinson's disease and other neurodegenerative disorders affecting basal ganglia. Ann. Neurol. 36:1994;348-355.
115. Alam Z.I., Daniel S.E., Lees A.J., Marsden D.C., Jenner P., Halliwell B. A generalised increase in protein carbonyls in the brain in Parkinson's but not incidental Lewy body disease. J. Neurochem. 69:1997;1326-1329.
116. Podmore I.D., Griffiths H.R., Herbert K.E., Mistry N., Mistry P., Lunec J. Vitamin C exhibits pro-oxidant properties. Nature. 392:1998;559.
117. Rehman A., Collis C.S., Yang M., Kelly M., Diplock A.T., Halliwell B., Rice-Evans C. The effects of iron and vitamin C co-supplementation on oxidative damage to DNA in healthy volunteers. Biochem. Biophys. Res. Commun. 246:1998;293-298.
118. Halliwell B., Wasil M., Grootveld M. Biologically significant scavenging of the myeloperoxidase-derived oxidant hypochlorous acid by ascorbic acid. FEBS Lett. 213:1987;15-18.
119. M.J.Davies, R.T. Dean, Radical-Mediated Protein Oxidation, From Chemistry to Medicine, Oxford Univ. Press, Oxford, UK, 1977.
120. Ohshima H., Friesen M., Brouet I., Bartsch H. Nitro-tyrosine as a new marker for endogenous nitrosation and nitration of proteins. Food Chem. Toxicol. 28:1990;647-652.
121. Steinberg D., Parthasarathy S., Carew T.E.et al. Beyond cholesterol. Modifications of low-density lipoprotein that increase its atherogenicity. N. Engl. J. Med. 320:1989;915-924.
122. 2-isoprostanes produced by non-cyclooxygenase free radical-catalyzed mechanism. Methods Enzymol. 233:1994;163-174.
123. Kaur H., Halliwell B. Action of biologically-relevant oxidizing species upon uric acid. Identification of uric acid oxidation products. Chem.-Biol. Interact. 73:1990;235-247.
124. Ogihara H., Ogihara T., Miki M., Yasuda H., Mino M. Plasma copper and antioxidant status in Wilson's disease. Pediatr. Res. 37:1995;219-226.
125. Halliwell B. Vitamin C: antioxidant or pro-oxidant in vivo? Free Radical Res. 25:1996;439-454.
126. Laughton M.J., Evans P.J., Moroney M.A.et al. Inhibition of mammalian 5-lipoxygenase and cyclooxygenase by flavonoids and phenolic dietary additives. Biochem. Pharmacol. 42:1991;1673-1681.
127. Hodnick W.F., Kung F.S., Roettger W.J., Bohmont C.W., Pardini R.S. Inhibition of mitochondrial respiration and production of toxic oxygen radicals by flavonoids. Biochem. Pharmacol. 35:1986;2345-2357.
128. Rahman A., Shahabuddin S., Hadi S.M., Parish J.H., Ainley K. Strand scission in DNA induced by quercetin and Cu(II): role of Cu(I) and oxygen free radicals. Carcinogenesis. 10:1989;1833-1839.
129. Halliwell B., Gutteridge J.M.C. The antioxidants of human extracellular fluids. Arch. Biochem. Biophys. 280:1990;1-8.
130. Bendich A., Machlin L.J., Scandurra O.et al. The anti-oxidant role of vitamin C. Free Radical Biol. Med. 2:1986;419-444.
131. Rice-Evans C.A., Sampson J., Bramley P.M., Holloway D.E. Why do we expect carotenoids to be antioxidant in vivo? Free Radical Res. 26:1997;381-398.
132. α-Tocopherol, β-Carotene Prevention Study Group The effect of vitamin E and beta carotene on the incidence of lung cancer and other cancers in male smokers. N. Engl. J. Med. 330:1994;1029-1035.
133. Rowe P.M. Beta-carotene takes a collective beating. Lancet. 347:1996;249.
134. von Poppel G., Poulsen H., Loft S., Verhagen H. No influence of beta carotene on oxidative DNA damage in male smokers. J. Natl. Cancer Inst. 87:1995;310-311.
135. E.R. Beatty, T.G. England, C.A. Geissler, O.I. Aruoma, B. Halliwell, Effect of antioxidant vitamin supplementation on markers of DNA damage and plasma antioxidants, Proc. Nutr. Soc., in press.
136. Verhagen V., Poulsen H.E., Loft S.et al. Reduction of oxidative DNA-damage in humans by Brussels sprouts. Carcinogenesis. 16:1995;969-970.
137. French M., Dreosti I., Aitken C. Vitamin E supplements and their effect on vitamin-E status in blood and genetic damage rates in peripheral blood lymphocytes. Carcinogenesis. 18:1997;359-364.
138. Pool-Zobel B.L., Bub A., Müller H., Wollowski I., Rechkemmer G. Consumption of vegetables reduces genetic damage in humans: first results of a human intervention trial with carotenoid-rich foods. Carcinogenesis. 18:1997;1847-1850.
139. Priemé H., Loft S., Nyyssönen K., Salonen J.T., Poulsen H.E. No effect of supplementation with vitamin E, ascorbic acid or coenzyme Q10 on oxidative DNA damage estimated by 8-oxo-7,8-dihydro-2′-deoxyguanosine excretion in smokers. Am. J. Clin. Nutr. 65:1997;503-507.
140. Zhang Y., Kensler T.W., Cho C.G.et al. Anti-carcinogenic activities of sulforaphane and structurally related synthetic norbornyl isothiocyanates. Proc. Natl. Acad. Sci. USA. 91:1994;3147-3150.
141. Johnson I.T., Williamson G., Musk S.R.R. Anticarcinogenic factors in plant foods. A new class of nutrients? Nutr. Res. 7:1994;175-204.
142. Prestera T., Talalay P. Electrophile and antioxidant regulation of enzymes that detoxify carcinogens. Proc. Natl. Acad. Sci. USA. 92:1995;8965-8969.
143. Duthie S.J., Ma A., Ross M.A., Collins A.R. Antioxidant supplementation decreases oxidative DNA damage in human lymphocytes. Cancer Res. 56:1996;1291-1295.
144. Phull P.S., Green C.J., Jacyna M.R. A radical view of the stomach: the role of oxygen-derived free radicals and antioxidants in gastroduodenal disease. Eur. J. Gastroenterol. Hepatol. 7:1995;265-274.
145. Babbs C.F. Free radicals and the etiology of colon cancer. Free Radical Biol. Med. 8:1990;191-200.
146. Oldreive C., Zhao K., Paganga G., Halliwell B., Rice-Evans C. Inhibition of nitrous acid-dependent tyrosine nitration and DNA base deamination by flavonoids and other phenolic compounds. Chem. Res. Toxicol. 11:1998;1574-1579.
147. Laughton M.J., Halliwell B., Evans P.J., Hoult J.R.S. Antioxidant and pro-oxidant actions of the plant phenolics quercetin, gossypol and myricetin. Biochem. Pharmacol. 38:1989;2859-2865.
148. Paya M., Halliwell B., Hoult J.R.S. Interaction of a series of coumarins with reactive oxygen species. Scavenging of superoxide, hypochlorous acid and hydroxyl radicals. Biochem. Pharmacol. 44:1992;205-214.
149. Scott B.C., Butler J., Halliwell B., Aruoma O.I. Evaluation of the anti-oxidant actions of ferulic acid and catechins. Free Radical Res. 19:1993;241-253.
150. Paganga G., Al-Hashim H., Khodr H., Scott B.C., Aruoma O.I., Hider R.C., Halliwell B., Rice-Evans C.A. Mechanisms of antioxidant activities of quercetin and catechin. Redox Rep. 2:1996;359-364.
151. Pannala A.S., Rice-Evans C.A., Halliwell B., Singh S. Inhibition of peroxynitrite-mediated tyrosine nitration by catechin polyphenols. Biochem. Biophys. Res. Commun. 232:1997;164-168.
152. MacGregor J.T., Wehr C.M., Hiatt R.A., Peters B., Tucker J.D., Langlois R.G., Jacob R.A., Jensen R.H., Yager J.W., Shigenaga M.K., Frei B., Eynon B.P., Ames B.N. Spontaneous genetic damage in man: evaluation of interindividual variability, relationship among markers of damage, and influence of nutritional status. Mutat. Res. 377:1997;125-135.
153. Wei O., Spitz M.R. The role of DNA repair capacity in susceptibility to lung cancer: a review. Cancer Metastasis Rev. 16:1997;295-307.