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Research Article

Hydroxylation of Deoxyguanosine at 5′ Site of GG and GGG Sequences in Double-stranded DNA Induced by Carbamoyl Radicals

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Pages 667-675 | Published online: 07 Jul 2009

  • Loeb, K.R. and Loeb, L.A. (2000) "Significance of multiple mutations in cancer", Carcinogenesis 21, 379-385.
  • Bechman, K.B. and Ames, B.N. (1998) "The free radical theory of aging matures", Physiol. Rev. 78, 547-581.
  • Kawanishi, S., Hiraku, Y. and Oikawa, S. (2000) "Mechanism of guanine-specific DNA damage by oxidative stress and its role in carcinogenesis and aging", Mutât. Res. 488, 65-76.
  • Anson, R.M., Senturker, S., Dizdaroglu, M. and Bohr, VA. (1999) "Measurement of oxidatively induced base lesions in liver from Wistar rats of different ages", Free Radic. Biol. Med. 27, 456-462.
  • Melov, S., Coskun, P., Patel, M., Tuinstra, R., Cottrell, B., Jun, A.S., Zastawny, T.H., Dizdaroglu, M., Goodman, S.I., Huang, T.T., Miziorko, H., Epstein, CJ. and Wallace, D.C. (1999) "Mitochondrial disease in Superoxide dismutase 2 mutant mice", Prac. Natl Acad. Sci. USA 96, 846-851.
  • Niki, E. (2000) "Oxidative stress and aging", Intern. Med. 39, 324-326.
  • Kondo, S., Toyokuni, S., Tanaka, T., Hiai, H., Onodera, H., Kasai, H. and Imamura, M. (2000) "Overexpression of the hOGGl gene and high 8-hydroxy-2'-deoxyguanosine (8OHdG) lyase activity in human colorectal carcinoma: regulation mechanism of the 8-OHdG level in DNA", CHn. Cancer Res. 6, 1394-1400.
  • Kasai, H. (1997) "Analysis of a form of oxidative DNA damage, 8-hydroxy-2'-deoxyguanosine, as a marker of cellular oxidative stress during carcinogenesis", Mutât. Res. 387, 147-163.
  • Vineis, P., Malats, N., Porta, M. and Real, EX. (1999) "Human cancer, carcinogenic exposures and mutation spectra", Mutat. Res. 436, 185-194.
  • Halliwell, B. (1998) "Can oxidative DNA damage be used as a biomarker of cancer risk in humans? Problems, resolutions and preliminary results from nutritional supplementation studies", Free Radie. Res. 29, 469-486.
  • Wang, D., Kreutzer, D.A. and Essigmann, J.M. (1998) "Mutagenicity and repair of oxidative DNA damage: insights from studies using defined lesions", Mutât. Res. 400, 99-115.
  • Poulsen, H.E., Prieme, H. and Loft, S. (1998) "Role of oxidative DNA damage in cancer initiation and promotion", Eur. J. Cancer Prev. 7, 9-16.
  • Hanrahan, C.J., Bacolod, M.D., Vyas, R.R., Liu, T., Geacintov, N.B., Loechler, E.L. and Basu, A.K. (1997) "Sequence specific mutagenesis of the major (+)-anti-benzo [a]pyrene diol epoxide-DNA adduct at a mutational hot spot in vitro and in Escherichia coli cells", Chem. Res. Toxicol. 10, 369-377.
  • Geländer, D.W. and Cech, T.R. (1990) "Iron(II)-ethylenediaminetetraacetic acid catalyzed cleavage of RNA and DNA oligonucleotides: similar reactivity toward single-and double-stranded forms", Biochemistry 29, 1355-1361.
  • Inoue, S. and Kawanishi, S. (1987) "Hydroxyl radical production and human DNA damage induced by ferric nitrilotriacetate and hydrogen peroxide", Cancer Res. 47, 6522-6527.
  • Kawanishi, S., Inoue, S. and Sano, S. (1986) "Mechanism of DNA cleavage induced by sodium chromate (VI) in the presence of hydrogen peroxide", /. Biol. Chem. 261, 5952-5958.
  • Kawanishi, S., Yamamoto, K. and Inoue, S. (1989) "Sitespecific DNA damage induced by sulfite in the presence of cobalt(II) ion. Role of sulfate radical", Biochem. Pharmacol. 38, 3491-3496.
  • Kawanishi, S., Oikawa, S., Murata, M., Tsukitome, H. and Saito, I. (1999) "Site-specific oxidation at GG and GGG sequences in double-stranded DNA by benzoyl peroxide as a tumor promoter", Biochemistry 38, 16733-16739.
  • Nikolic, D. and van Breemen, R.B. (2001) "DNA oxidation induced by cyclooxygenase-2", Chem. Res. Toxicol. 14, 351-354.
  • Kikugawa, K., Hiramoto, K., Kato, T. and Ysnagawa, H.(2000) "Effect of food reductones on the generation of thepyrazine cation radical and on the formation of the mutagensin the reaction of glucose, glycine and creatinine", Mutât. Res.465, 183-190.
  • Kagan, VE. and Tyurina, YY. (1998) "Recycling and redoxcycling of pnenolic antioxidants", Ann. N. Y. Acad. Sci. 854, 425-434.
  • Capon, D.J., Chen, E.Y, Levinson, A.D., Seeburg, P.H. andGoeddel, D.V. (1983) "Complete nucleotide sequences of theT24 human bladder carcinoma oncogene and its normalhomologue", Nature 302, 33-37.
  • Yamashita, N., Murata, M., Inoue, S., Hiraku, Y, Yoshinaga, T.and Kawanishi, S. (1998) "Superoxide formation and DNAdamage induced by a fragrant furanone in the presence ofcopper (II)", Mutât. Res. 397, 191-201.
  • Yamamoto, K. and Kawanishi, S. (1991) "Site-specific DNAdamage induced by hydrazine in the presence of manganeseand copper ions; the role of hydroxyl radical and hydrogenatom", /. Biol. Chem. 266, 1509-1515.
  • Oikawa, S. and Kawanishi, S. (1996) "Copper-mediated DNAdamage by metabolites of p-dichlorobenzene", Carcinogenesis 17, 2733-2739.
  • Yamamoto, K. and Kawanishi, S. (1989) "Hydroxyl freeradical is not the main active species in site-specific DNAdamage induced by copper(II) ion and hydrogen peroxide", /. Biol. Chem. 264, 15435-15440.
  • Maxam, A.M. and Gilbert, W. (1980) "Sequencing end-labeledDNA with base-specific chemical cleavages", Meth. Enzymol.65, 499-560.
  • Ito, K., Inoue, S., Yamamoto, K. and Kawanishi, S. (1993) "8-Hydroxy-deoxyguanosine formation at the 5' site of 5'-GG-3'sequences in double-stranded DNA by UV radiation withriboflavin", /. Biol. Chem. 268, 13221-13227.
  • Pryor, W.A. and Tang, R.H. (1978) "Ethylene formation frommethional", Biochem. Biophys. Res. Commun. 81, 498-503.
  • David-Cordonnier, M.H., Lavai, J. and O7NeUl, P. (2000) "Clustered DNA damage, influence on damage excision by XRS5 nuclear extracts and Esherichia coH Nth and Fpg proteins", /. Biol. Chem. 275, 11865-11873.
  • Minisci, E, Citterio, A. and Vismara, E. (1985) "Polar effects in free-radical reactions. New synthetic developments in the functionalization of heteroaromatic bases by nucleophlic radicals", Tetrahedron 41, 4157-4170.
  • Oikawa, S. and Kawanishi, S. (1998) "Distinct mechanisms of site-specific DNA damage induced by endogenous reductants in the presence of iron(III) and copper(II)", Biochem. Biophy. Acta 1399, 19-30.
  • Casey, J. and Davidson, N. (1977) "Rate of formation and thermal stabilities of RNA:DNA and DNA:DNA duplexes at high concentrations of formamide", Nuclic Acids Res. 4, 1539-1552.
  • McConaughy, B.L., Laird, C.D. and MaCarthy, BJ. (1969) "Nucleic acid reassociation in formamide", Biochemistry 8, 3289-3295.
  • Burrows, CJ. and Muller, J.G. (1998) "Oxidative nucleobase modifications leading to strand scission", Chem. ReO. 98, 1109-1151.
  • Steenken, S. and Jovanovic, S. (1997) "How easily oxidizable is DNA? One-electron reduction potentials of adenosine and guanosine radicals in aqueous solution", J. Am. Chem. Soc. 119, 617-618.
  • Sugiyama, H. and Saito, I. (1996) "Theoretical studies of GGspecific 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. 118, 7063-7068.
  • Wayner, D.D.M., McPhee, DJ. and Griller, D. (1988) "Oxidation and reduction potentials of transient free radicals", J. Am. Chem. Soc. 110, 132-137.
  • Yoshioka, Y, Kitagawa, Y, Takano, Y, Yamaguchi, K., Nakamura, T. and Saito, I. (1999) "Experimental and theoretical studies on the selectivity of GGG triplets toward one-electron oxidation in B-form DNA", J. Am. Chem. Soc. 121, 8712-8719.

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