Role of Oxidative DNA Damage in Dietary Carcinogenesis

Genes and Environment

Volumn 28, Issue 4, 2006, Pages 127-140

  Hiraku, Yusuke ^a   Murata, Mariko ^a   Kawanishi, Shosuke ^a,b  

^a MIE UNIVERSITY GRADUATE SCHOOL OF MEDICINE   (Japan)

^b SUZUKA UNIVERSITY OF MEDICAL SCIENCE   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 77950337778     PISSN: 18807046     EISSN: 18807062     Source Type: Journal    
DOI: 10.3123/jemsge.28.127     Document Type: Article

References (128)

1. Doll R, Peto R. The causes of cancer: quantitative estimates of avoidable risks of cancer in the United States today. J Natl Cancer Inst. 1981; 66: 1191-308.
2. Ames BN, Gold LS. The causes and prevention of cancer: gaining perspective. Environ Health Perspect. 1997; 105 Suppl 4: 865-73.
3. Pitot HC, Dragan YP. Chemical Carcinogenesis. In: Casarett and Doull's Toxicology: The Basic Science of Poisons, 6th ed. pp. 241-319, McGraw-Hill, New York, 2001.
4. Sugimura T. Overview of carcinogenic heterocyclic amines. Mutat Res. 1997; 376: 211-9.
5. Kawanishi S, Hiraku Y. Oxidative and nitrative DNA damage as biomarker for carcinogenesis with special reference to inflammation. Antioxid Redox Signal. 2006; 8: 1047-58.
6. Dijkwel PA, Wenink PW. Structural integrity of the nuclear matrix: differential effects of thiol agents and metal chelators. J Cell Sci. 1986; 84: 53-67.
7. Saucier MA, Wang X, Re RN, Brown J, Bryan SE. Effects of ionic strength on endogenous nuclease activity in chelated and nonchelated chromatin. J Inorg Biochem. 1991; 41: 117-24.
8. Overvad K, Wang DY, Olsen J, Allen DS, Thorling EB, Bulbrook RD, Hayward JL. Copper in human mammary carcinogenesis: a case-cohort study. Am J Epidemiol. 1993; 137: 409-14.
9. Hems G. The contributions of diet and childbearing to breast-cancer rates. Br J Cancer. 1978; 37: 974-82.
10. Chow WH, Gridley G, McLaughlin JK, Mandel JS, Wacholder S, Blot WJ, Niwa S, Fraumeni JF, Jr. Protein intake and risk of renal cell cancer. J Natl Cancer Inst. 1994; 86: 1131-9.
11. Youngman LD, Campbell TC. The sustained development of preneoplastic lesions depends on high protein intake. Nutr Cancer. 1992; 18: 131-42.
12. Fukagawa NK, Galbraith RA. Advancing age and other factors influencing the balance between amino acid requirements and toxicity. J Nutr. 2004; 134: 1569S-74S.
13. Davis AJ, Austic RE. Dietary threonine imbalance alters threonine dehydrogenase activity in isolated hepatic mitochondria of chicks and rats. J Nutr. 1994; 124: 1667-77.
14. Hiraku Y, Sugimoto J, Yamaguchi T, Kawanishi S. Oxidative DNA damage induced by aminoacetone, an amino acid metabolite. Arch Biochem Biophys. 1999; 365: 62-70.
15. Boyland E, Watson G. 3-Hydroxyanthranilic acid, a carcinogen produced by endogenous metabolism. Nature. 1956; 177: 837-8.
16. Bryan GT, Brown RR, Price JM. Mouse bladder carcinogenicity of certain tryptophan metabolites and other aromatic nitrogen compounds suspended in cholesterol. Cancer Res. 1964; 24: 596-602.
17. Abul-Fadl MA, Khalafallah AS. Studies on the urinary excretion of certain tryptophan metabolites in bilharzia-sis and its possible relation to bladder cancer in Egypt. Br J Cancer. 1961; 15: 479-82.
18. Bryan GT. The role of urinary tryptophan metabolites in the etiology of bladder cancer. Am J Clin Nutr. 1971; 24: 841-7.
19. Ehrhart H, Ried W, Benoit W, Dorfler H. Studies on experimental leukemias (VII). Adenocarcinomas, sarcomas and leukemias in mice following subcutaneous injections of 3-hydroxykynurenine. Z Krebsforsch. 1968; 71: 1-6.
20. Kuznezova LE. Mutagenic effect of 3-hydroxykynure-nine and 3-hydroxyanthranilic acid. Nature. 1969; 222: 484-5.
21. Hiraku Y, Inoue S, Oikawa S, Yamamoto K, Tada S, Nishino K, Kawanishi S. Metal-mediated oxidative damage to cellular and isolated DNA by certain trypto-phan metabolites. Carcinogenesis. 1995; 16: 349-56.
22. Laberge C, Lescault A, Tanguay RM. Hereditary tyrosinemias (type I): a new vista on tyrosine toxicity and cancer. Adv Exp Med Biol. 1986; 206: 209-21.
23. Rauschenbach MO, Zharova EI, Sergeeva TI, Ivanova VD, Probatova NA. Blastomogenic activity of p-hydroxyphenyllactic acid in mice. Cancer Res. 1975; 35: 577-85.
24. Weinberg AG, Mize CE, Worthen HG. The occurrence of hepatoma in the chronic form of hereditary tyrosine-mia. J Pediatr. 1976; 88: 434-8.
25. Vogel A, van Den Berg IE, Al-Dhalimy M, Groopman J, Ou CN, Ryabinina O, Iordanov MS, Finegold M, Grompe M. Chronic liver disease in murine hereditary tyrosinemia type 1 induces resistance to cell death. Hepatology. 2004; 39: 433-43.
26. Glatt H. Endogenous mutagens derived from amino acids. Mutat Res. 1990; 238: 235-43.
27. Hiraku Y, Yamasaki M, Kawanishi S. Oxidative DNA damage induced by homogentisic acid, a tyrosine metabolite. FEBS Lett. 1998; 432: 13-6.
28. von Studnitz W. Urinary excretion of aminoacetone following administration of L-threonine in man. Scand J Clin Lab Invest. 1967; 20: 29-32.
29. Cascino A, Muscaritoli M, Cangiano C, Conversano L, Laviano A, Ariemma S, Meguid MM, Rossi Fanelli F. Plasma amino acid imbalance in patients with lung and breast cancer. Anticancer Res. 1995; 15: 507-10.
30. Scioscia KA, Snyderman CH, Wagner R. Altered serum amino acid profiles in head and neck cancer. Nutr Cancer. 1998; 30: 144-7.
31. Pisani W, Bonzanino A, Franco G. The aminoacetone in neoplastic tissues. Boll Soc Ital Biol Sper. 1966; 42: 399-402.
32. Felton JS, Knize MG, Wood C, Wuebbles BJ, Healy SK, Stuermer DH, Bjeldanes LF, Kimble BJ, Hatch FT. Isolation and characterization of new mutagens from fried ground beef. Carcinogenesis. 1984; 5: 95-102.
33. Fay LB, Turesky RJ. Electron impact and fast atom bombardment mass spectrometric analysis of the food-borne carcinogens 2-amino-3-methylimidazo [4,5-/] quinoline, 2-amino-3,8-dimethylimidazo [4,5-/] quinox-aline and their metabolites. Biol Mass Spectrom. 1992; 21: 463-9.
34. Yamashita M, Wakabayashi K, Nagao M, Sato S, Yamaizumi Z, Takahashi M, Kinae N, Tomita I, Sugimura T. Detection of 2-amino-3-methylimi-dazo[4,5-/]quinoline in cigarette smoke condensate. Jpn J Cancer Res. 1986; 77: 419-22.
35. Nagao M. A new approach to risk estimation of food-borne carcinogens-heterocyclic amines-based on molecular information. Mutat Res. 1999; 431: 3-12.
36. Wakata A, Oka N, Hiramoto K, Yoshioka A, Negishi K, Wataya Y, Hayatsu H. DNA strand cleavage in vitro by 3-hydroxyamino-1-methyl-5H-pyrido[4,3-b]-indole, a direct-acting mutagen formed in the metabolism of carcinogenic 3-amino-1-methyl-5H-pyrido [4,3-b]indole. Cancer Res. 1985; 45: 5867-71.
37. Wataya Y, Yamane K, Hiramoto K, Ohtsuka Y, Okubata Y, Negishi K, Hayatsu H. Generation of intracellular active oxygens in mouse FM3A cells by 3-hydroxyamino-1-methyl-5H-pyrido[4,3-b]indole, the activated Trp-P-2. Jpn J Cancer Res. 1988; 79: 576-9.
38. Esumi H, Ohgaki H, Kohzen E, Takayama S, Sugimura T. Induction of lymphoma in CDF1 mice by the food mutagen, 2-amino-1-methyl-6-phenylimidazo[4,5-b]-pyridine. Jpn J Cancer Res. 1989; 80: 1176-8.
39. Ito N, Hasegawa R, Sano M, Tamano S, Esumi H, Takayama S, Sugimura T. A new colon and mammary carcinogen in cooked food, 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP). Carcinogenesis. 1991; 12: 1503-6.
40. Ohta T, Nakatsugi S, Watanabe K, Kawamori T, Ishikawa F, Morotomi M, Sugie S, Toda T, Sugimura T, Wakabayashi K. Inhibitory efi'ects of Bifidobac-terium-fermented soy milk on 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine-induced rat mammary carcinogenesis, with a partial contribution of its component isoflavones. Carcinogenesis. 2000; 21: 937-41.
41. Fretland AJ, Devanaboyina US, Feng Y, Leff MA, Xiao GH, Webb SJ, Hein DW. Oral administration of 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP) yields PhIP-DNA adducts but not tumors in male Syrian hamsters congenic at the N-acetyltransferase 2 (NAT2) locus. Toxicol Sci. 2001; 59: 226-30.
42. Takahashi S, Tamano S, Hirose M, Kimoto N, Ikeda Y, Sakakibara M, Tada M, Kadlubar FF, Ito N, Shirai T. Immunohistochemical demonstration of carcinogen-DNA adducts in tissues of rats given 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP): detection in paraffin-embedded sections and tissue distribution. Cancer Res. 1998; 58: 4307-13.
43. El-Bayoumy K, Chae YH, Rosa JG, Williams LK, Desai D, Amin S, Fiala E. The effects of 1-nitropyrene, 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine and 7,12-dimethylbenz[a]anthracene on 8-hydroxy-2'-deox-yguanosine levels in the rat mammary gland and modulation by dietary 1,4-phenylenebis(methylene) selenoc-yanate. Cancer Lett. 2000; 151: 7-13.
44. Weisburger JH, Dolan L, Pittman B. Inhibition of PhIP mutagenicity by caffeine, lycopene, daidzein, and genistein. Mutat Res. 1998; 416: 125-8.
45. Murata M, Kawanishi S. Oxidation of 5'-site guanine at GG and GGG sequences induced by a metabolite of carcinogenic heterocyclic amine PhIP in the presence of Cu(II) and NADH. Carcinogenesis. 2002; 23: 855-60.
46. Ohgaki H, Hasegawa H, Suenaga M, Sato S, Takayama S, Sugimura T. Carcinogenicity in mice of a mutagenic compound, 2-amino-3,8-dimethylimidazo[4,5-/]quinox-aline (MeIQx) from cooked foods. Carcinogenesis. 1987; 8: 665-8.
47. Dooley KL, Von Tungeln LS, Bucci T, Fu PP, Kadlubar FF. Comparative carcinogenicity of 4-aminobiphenyl and the food pyrolysates, Glu-P-1, IQ, PhIP, and MeIQx in the neonatal B6C3F1 male mouse. Cancer Lett. 1992; 62: 205-9.
48. Kato T, Ohgaki H, Hasegawa H, Sato S, Takayama S, Sugimura T. Carcinogenicity in rats of a mutagenic compound, 2-amino-3,8-dimethylimidazo[4,5-/]quinox-aline. Carcinogenesis. 1988; 9: 71-3.
49. Kushida H, Wakabayashi K, Sato H, Katami M, Kurosaka R, Nagao M. Dose-response study of MeIQx carcinogenicity in F344 male rats. Cancer Lett. 1994; 83: 31-5.
50. Turesky RJ, Lang NP, Butler MA, Teitel CH, Kadlubar FF. Metabolic activation of carcinogenic heterocyclic aromatic amines by human liver and colon. Carcinogen-esis. 1991; 12: 1839-45.
51. Yanagawa Y, Sawada M, Deguchi T, Gonzalez FJ, Kamataki T. Stable expression of human CYP1A2 and N-acetyltransferases in Chinese hamster CHL cells: mutagenic activation of 2-amino-3-methylimidazo[4,5-/]quinoline and 2-amino-3,8-dimethylimidazo[4,5-/]-quinoxaline. Cancer Res. 1994; 54: 3422-7.
52. Snyderwine EG, Davis CD, Nouso K, Roller PP, Schut HA. 32P-postlabeling analysis of IQ, MeIQx and PhIP adducts formed in vitro in DNA and polynucleotides and found in vivo in hepatic DNA from IQ-, MeIQx-and PhIP-treated monkeys. Carcinogenesis. 1993; 14: 1389-95.
53. Hirose M, Futakuchi M, Tanaka H, Orita SI, Ito T, Miki T, Shirai T. Prevention by antioxidants of heter-ocyclic amine-induced carcinogenesis in a rat medium-term liver bioassay: results of extended and combination treatment experiments. Eur J Cancer Prev. 1998; 7: 61-7.
54. Hirose M, Hasegawa R, Kimura J, Akagi K, Yoshida Y, Tanaka H, Miki T, Satoh T, Wakabayashi K, Ito N, et al. Inhibitory effects of 1-O-hexyl-2,3,5-trimethylhydro-quinone (HTHQ), green tea catechins and other antioxidants on 2-amino-6-methyldipyrido[1,2-a:3',2'-d]-imidazole (Glu-P-1)-induced rat hepatocarcinogenesis and dose-dependent inhibition by HTHQ of lesion induction by Glu-P-1 or 2-amino-3,8-dimethylimidazo-[4,5-./]quinoxaline (MeIQx). Carcinogenesis. 1995; 16: 3049-55.
55. Kato T, Hasegawa R, Nakae D, Hirose M, Yaono M, Cui L, Kobayashi Y, Konishi Y, Ito N, Shirai T. Dose-dependent induction of 8-hydroxyguanine and preneoplastic foci in rat liver by a food-derived carcinogen, 2-amino-3,8-dimethylimidazo[4,5-/]quinoxaline, at low dose levels. Jpn J Cancer Res. 1996; 87: 127-33.
56. Murata M, Kobayashi M, Kawanishi S. Mechanism of oxidative DNA damage induced by a heterocyclic amine, 2-amino-3,8-dimethylimidazo[4,5/]quinoxaline. Jpn J Cancer Res. 1999; 90: 268-75.
57. Sasagawa C, Muramatsu M, Matsushima T. Formation of direct mutagens from amino-imidazoazaarenes by nitrite treatment. Mutat Res. 1988; 203: 386.
58. Hirose M, Wakabayashi K, Grivas S, De Flora S, Arakawa N, Nagao M, Sugimura T. Formation of a nitro derivative of 2-amino-3,4-dimethylimidazo[4,5-/]quinoline by photo-irradiation. Carcinogenesis. 1990; 11: 869-71.
59. Morrison LD, Eling TE, Josephy PD. Prostaglandin H synthase-dependent formation of the direct-acting mutagen 2-nitro-3-methylimidazo[4,5-/]quinoline (nitro-IQ) from IQ. Mutat Res. 1993; 302: 45-52.
60. Dirr A, Wild D. Synthesis and mutagenic activity of nitro-imidazoarenes. A study on the mechanism of the genotoxicity of heterocyclic arylamines and nitroarenes. Mutagenesis. 1988; 3: 147-52.
61. Asan E, Fasshauer I, Wild D, Henschler D. Heterocyclic aromatic amine-DNA-adducts in bacteria and mammalian cells detected by 32P-postlabeling analysis. Car-cinogenesis. 1987; 8: 1589-93.
62. Graf U, Wild D, Wurgler FE. Genotoxicity of 2-amino-3-methylimidazo [4,5-/]quinoline (IQ) and related compounds in Drosophila. Mutagenesis. 1992; 7: 145-9.
63. Sawada S, Daimon H, Asakura S, Kawaguchi T, Yamatsu K, Furihata C, Matsushima T. Cumulative effects of chromosome aberrations and sister chromatid exchanges in rat liver induced in vivo by heterocyclic amines. Carcinogenesis. 1994; 15: 285-90.
64. Murata M, Kobayashi M, Kawanishi S. Nonenzymatic reduction of nitro derivative of a heterocyclic amine IQ by NADH and Cu(II) leads to oxidative DNA damage. Biochemistry. 1999; 38: 7624-9.
65. Dandona P, Thusu K, Cook S, Snyder B, Makowski J, Armstrong D, Nicotera T. Oxidative damage to DNA in diabetes mellitus. Lancet. 1996; 347: 444-5.
66. Murata M, Mizutani M, Oikawa S, Hiraku Y, Kawanishi S. Oxidative DNA damage by hyper-glycemia-related aldehydes and its marked enhancement by hydrogen peroxide. FEBS Lett. 2003; 554: 138-42.
67. Brooks PJ, Theruvathu JA. DNA adducts from acetal-dehyde: implications for alcohol-related carcinogenesis. Alcohol. 2005; 35: 187-93.
68. Krokan H, Grafstrom RC, Sundqvist K, Esterbauer H, Harris CC. Cytotoxicity, thiol depletion and inhibition of O6-methylguanine-DNA methyltransferase by various aldehydes in cultured human bronchial fibroblasts. Carcinogenesis. 1985; 6: 1755-9.
69. Wilson DM, 3rd, Tentler JJ, Carney JP, Wilson TM, Kelley MR. Acute ethanol exposure suppresses the repair of O6-methylguanine DNA lesions in castrated adult male rats. Alcohol Clin Exp Res. 1994; 18: 1267-71.
70. Dey A, Cederbaum AI. Alcohol and oxidative liver injury. Hepatology. 2006; 43: S63-74.
71. Seitz HK, Stickel F. Risk factors and mechanisms of hepatocarcinogenesis with special emphasis on alcohol and oxidative stress. Biol Chem. 2006; 387: 349-60.
72. Kaneko T, Tahara S, Takabayashi F, Harada N. Suppression of 8-oxo-2'-deoxyguanosine formation and carcinogenesis induced by N-nitrosobis (2-oxopropyl)-amine in hamsters by esculetin and esculin. Free Radic Res. 2004; 38: 839-46.
73. Nair J, Gansauge F, Beger H, Dolara P, Winde G, Bartsch H. Increased etheno-DNA adducts in affected tissues of patients suffering from Crohn's disease, ulcer-ative colitis, and chronic pancreatitis. Antioxid Redox Signal. 2006; 8: 1003-10.
74. Mori Y, Koide A, Kobayashi Y, Morimura K, Kaneko M, Fukushima S. Effect of ethanol treatment on metabolic activation and detoxification of esophagus carcinogenic N-nitrosamines in rat liver. Mutagenesis. 2002; 17: 251-6.
75. Lofroth G, Gejvall T. Diethyl pyrocarbonate: formation of urethan in treated beverages. Science. 1971; 174: 1248-50.
76. Ough CS. Ethylcarbamate in fermented beverages and foods. I. Naturally occurring ethylcarbamate. J Agric Food Chem. 1976; 24: 323-8.
77. Canas BJ, Havery DC, Robinson LR, Sullivan MP, Joe FL, Jr., Diachenko GW. Ethyl carbamate levels in selected fermented foods and beverages. J Assoc Off Anal Chem. 1989; 72: 873-6.
78. Miller JA, Miller EC. The metabolic activation and nucleic acid adducts of naturally-occurring carcinogens: recent results with ethyl carbamate and the spice flavors safrole and estragole. Br J Cancer. 1983; 48: 1-15.
79. Mori I, Yasuhara K, Hayashi SM, Nonoyama T, Nomura T, Mitsumori K. Carcinogen dose-dependent variation in the transgene mutation spectrum in urethane-induced lung tumors in transgenic mice carrying the human prototype c-Ha-ras gene. Cancer Lett. 2000; 153: 199-209.
80. Simmon VF. In vitro mutagenicity assays of chemical carcinogens and related compounds with Salmonella typhimurium. J Natl Cancer Inst. 1979; 62: 893-9.
81. Scherer E, Winterwerp H, Emmelot P. Modification of DNA and metabolism of ethyl carbamate in vivo: formation of 7-(2-oxoethyl)guanine and its sensitive determination by reductive tritiation using 3H-sodium boro-hydride. IARC Sci Publ. 1986; 109-25.
82. Park KK, Liem A, Stewart BC, Miller JA. Vinyl carba-mate epoxide, a major strong electrophilic, mutagenic and carcinogenic metabolite of vinyl carbamate and ethyl carbamate (urethane). Carcinogenesis. 1993; 14: 441-50.
83. Bartsch H, Barbin A, Marion MJ, Nair J, Guichard Y. Formation, detection, and role in carcinogenesis of ethenobases in DNA. Drug Metab Rev. 1994; 26: 349-71.
84. Ioannou YM, Sanders JM, Matthews HB. Methyl car-bamate. Species-dependent variations in metabolism and clearance in rats and mice. Drug Metab Dispos. 1988; 16: 435-40.
85. Sakano K, Oikawa S, Hiraku Y, Kawanishi S. Metabolism of carcinogenic urethane to nitric oxide is involved in oxidative DNA damage. Free Radic Biol Med. 2002; 33: 703-14.
86. Knight DC, Eden JA. A review of the clinical effects of phytoestrogens. Obstet Gynecol. 1996; 87: 897-904.
87. Nagata C, Takatsuka N, Kawakami N, Shimizu H. A prospective cohort study of soy product intake and stomach cancer death. Br J Cancer. 2002; 87: 31-6.
88. Skibola CF, Smith MT. Potential health impacts of excessive flavonoid intake. Free Radic Biol Med. 2000; 29: 375-83.
89. Newbold RR, Banks EP, Bullock B, Jefferson WN. Uterine adenocarcinoma in mice treated neonatally with genistein. Cancer Res. 2001; 61: 4325-8.
90. Thigpen JE, Locklear J, Haseman JK, Saunders H, Grant MF, Forsythe DB. Effects of the dietary phytoes-trogens daidzein and genistein on the incidence of vulvar carcinomas in 129/J mice. Cancer Detect Prev. 2001; 25: 527-32.
91. Allred CD, Allred KF, Ju YH, Virant SM, Helferich WG. Soy diets containing varying amounts of genistein stimulate growth of estrogen-dependent (MCF-7) tumors in a dose-dependent manner. Cancer Res. 2001; 61: 5045-50.
92. Rao CV, Wang CX, Simi B, Lubet R, Kelloff G, Steele V, Reddy BS. Enhancement of experimental colon cancer by genistein. Cancer Res. 1997; 57: 3717-22.
93. Murata M, Midorikawa K, Koh M, Umezawa K, Kawanishi S. Genistein and daidzein induce cell proliferation and their metabolites cause oxidative DNA damage in relation to isoflavone-induced cancer of estrogen-sensitive organs. Biochemistry. 2004; 43: 2569-77.
94. Soto AM, Sonnenschein C, Chung KL, Fernandez MF, Olea N, Serrano FO. The E-SCREEN assay as a tool to identify estrogens: an update on estrogenic environmental pollutants. Environ Health Perspect. 1995; 103 Suppl 7: 113-22.
95. Hiraku Y, Yamashita N, Nishiguchi M, Kawanishi S. Catechol estrogens induce oxidative DNA damage and estradiol enhances cell proliferation. Int J Cancer. 2001; 92: 333-7.
96. Oikawa S, Ito T, Iwayama M, Kawanishi S. Radical production and DNA damage induced by carcinogenic 4-hydrazinobenzoic acid, an ingredient of mushroom Agaricus bisporus. Free Radic Res. 2006; 40: 31-9.
97. Tajima K, Tominaga S. Dietary habits and gastro-intes-tinal cancers: a comparative case-control study of stomach and large intestinal cancers in Nagoya, Japan. Jpn J Cancer Res. 1985; 76: 705-16.
98. Buiatti E, Palli D, Decarli A, Amadori D, Avellini C, Bianchi S, Biserni R, Cipriani F, Cocco P, Giacosa A, et al. A case-control study of gastric cancer and diet in Italy. Int J Cancer. 1989; 44: 611-6.
99. Alpha-Tocopherol Beta Carotene Cancer 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. 1994; 330: 1029-35.
100. Omenn GS, Goodman GE, Thornquist MD, Balmes J, Cullen MR, Glass A, Keogh JP, Meyskens FL, Valanis B, Williams JH, Barnhart S, Hammar S. Effects of a combination of beta carotene and vitamin A on lung cancer and cardiovascular disease. N Engl J Med. 1996; 334: 1150-5.
101. Kawanishi S, Oikawa S, Murata M. Evaluation for safety of antioxidant chemopreventive agents. Antioxid Redox Signal. 2005; 7: 1728-39.
102. Murata M, Kawanishi S. Oxidative DNA damage by vitamin A and its derivative via superoxide generation. J Biol Chem. 2000; 275: 2003-8.
103. Yamashita N, Murata M, Inoue S, Burkitt MJ, Milne L, Kawanishi S. Alpha-tocopherol induces oxidative damage to DNA in the presence of copper(II) ions. Chem Res Toxicol. 1998; 11: 855-62.
104. Inoue S, Ito K, Yamamoto K, Kawanishi S. Caffeic acid causes metal-dependent damage to cellular and isolated DNA through H2O2 formation. Carcinogenesis. 1992; 13: 1497-502.
105. Zhang Y, Talalay P. Anticarcinogenic activities of organic isothiocyanates: chemistry and mechanisms. Cancer Res. 1994; 54: 1976s-81s.
106. Staretz ME, Foiles PG, Miglietta LM, Hecht SS. Evidence for an important role of DNA pyridyloxobutyla-tion in rat lung carcinogenesis by 4-(methyl-nitrosamino)-1-(3-pyridyl)-1-butanone: effects of dose and phenethyl isothiocyanate. Cancer Res. 1997; 57: 259-66.
107. Sugie S, Yoshimi N, Okumara A, Tanaka T, Mori H. Modifying effects of benzyl isothiocyanate and benzyl thiocyanate on DNA synthesis in primary cultures of rat hepatocytes. Carcinogenesis. 1993; 14: 281-3.
108. Zhang Y, Kensler TW, Cho CG, Posner GH, Talalay P. Anticarcinogenic activities of sulforaphane and structurally related synthetic norbornyl isothiocyanates. Proc Natl Acad Sci USA. 1994; 91: 3147-50.
109. Hirose M, Yamaguchi T, Kimoto N, Ogawa K, Futakuchi M, Sano M, Shirai T. Strong promoting activity of phenylethyl isothiocyanate and benzyl isothioc-yanate on urinary bladder carcinogenesis in F344 male rats. Int J Cancer. 1998; 77: 773-7.
110. Lubet RA, Steele VE, Eto I, Juliana MM, Kelloff GJ, Grubbs CJ. Chemopreventive efficacy of anethole trithione, N-acetyl-L-cysteine, miconazole and phenethylisothiocyanate in the DMBA-induced rat mammary cancer model. Int J Cancer. 1997; 72: 95-101.
111. Murata M, Yamashita N, Inoue S, Kawanishi S. Mechanism of oxidative DNA damage induced by carcinogenic allyl isothiocyanate. Free Radic Biol Med. 2000; 28: 797-805.
112. Morimitsu Y, Nakagawa Y, Hayashi K, Fujii H, Kumagai T, Nakamura Y, Osawa T, Horio F, Itoh K, Iida K, Yamamoto M, Uchida K. A sulforaphane analogue that potently activates the Nrf2-dependent detoxification pathway. J Biol Chem. 2002; 277: 3456-63.
113. McWalter GK, Higgins LG, McLellan LI, Henderson CJ, Song L, Thornalley PJ, Itoh K, Yamamoto M, Hayes JD. Transcription factor Nrf2 is essential for induction of NAD(P)H:quinone oxidoreductase 1, glutathione S-transferases, and glutamate cysteine ligase by broccoli seeds and isothiocyanates. J Nutr. 2004; 134: 3499S-506S.
114. Kurokawa Y, Hayashi Y, Maekawa A, Takahashi M, Kokubo T, Odashima S. Carcinogenicity of potassium bromate administered orally to F344 rats. J Natl Cancer Inst. 1983; 71: 965-72.
115. Murata M, Bansho Y, Inoue S, Ito K, Ohnishi S, Midorikawa K, Kawanishi S. Requirement of glutathione and cysteine in guanine-specific oxidation of DNA by carcinogenic potassium bromate. Chem Res Toxicol. 2001; 14: 678-85.
116. Kawanishi S, Oikawa S, Murata M, Tsukitome H, Saito I. Site-specific oxidation at GG and GGG sequences in double-stranded DNA by benzoyl peroxide as a tumor promoter. Biochemistry. 1999; 38: 16733-9.
117. Hussain SP, Hofseth LJ, Harris CC. Radical causes of cancer. Nat Rev Cancer. 2003; 3: 276-85.
118. Evans MD, Dizdaroglu M, Cooke MS. Oxidative DNA damage and disease: induction, repair and significance. Mutat Res. 2004; 567: 1-61.
119. Kawanishi S, Hiraku Y, Oikawa S. Mechanism of guanine-specific DNA damage by oxidative stress and its role in carcinogenesis and aging. Mutat Res. 2001; 488: 65-76.
120. Burrows CJ, Muller JG. Oxidative nucleobase modifications leading to strand scission. Chem Rev. 1998; 98: 1109-51.
121. Wiseman H, Halliwell B. Damage to DNA by reactive oxygen and nitrogen species: role in inflammatory disease and progression to cancer. Biochem J. 1996; 313 (Pt 1): 17-29.
122. Steenken S, Jovanovic S. How easily oxidizable is DNA? One-electron reduction potentials of adenosine and guanosine radicals in aqueous solution. J Am Chem Soc. 1997; 119: 617-8.
123. Shibutani S, Takeshita M, Grollman AP. Insertion of specific bases during DNA synthesis past the oxidation-damaged base 8-oxodG. Nature. 1991; 349: 431-4.
124. Bruner SD, Norman DP, Verdine GL. Structural basis for recognition and repair of the endogenous mutagen 8-oxoguanine in DNA. Nature. 2000; 403: 859-66.
125. Hender son PT, Delaney JC, Gu F, Tannenbaum SR, Essigmann JM. Oxidation of 7,8-dihydro-8-oxoguanine affords lesions that are potent sources of replication errors in vivo. Biochemistry. 2002; 41: 914-21.
126. Neeley WL, Delaney JC, Henderson PT, Essigmann JM. In vivo bypass efficiencies and mutational signatures of the guanine oxidation products 2-aminoi-midazolone and 5-guanidino-4-nitroimidazole. J Biol Chem. 2004; 279: 43568-73.
127. Kino K, Saito I, Sugiyama H. Product analysis of GG-specific photooxidation of DNA via electron transfer: 2-aminoimidazolone as a major guanine oxidation product. J Am Chem Soc. 1998; 120: 7373-4.
128. Singh R, Farmer PB. Liquid chromatography-elec-trospray ionization-mass spectrometry: the future of DNA adduct detection. Carcinogenesis. 2006; 27: 178-96.