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Article

Excision by the human methylpurine DNA N‐glycosylase of cyanuric acid, a stable and mutagenic oxidation product of 8‐oxo‐7,8‐dihydroguanine

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Pages 21-27 | Received 03 Jun 2003, Accepted 24 Sep 2003, Published online: 03 Jul 2009

References

  • ALSETH, I., EIDE, L., PIROVANO, M., ROGNES, T., SEEBERG, E. and BJORAS, M., 1999, The Saccharomyces cerevisiae homologues of endonuclease III from Escherichia coli, Ntg 1 and Ntg2, are both required for efficient repair of spontaneous and induced oxidative DNA damage in yeast. Molecular and Cellular Biology, 19, 3779–3787.
  • AUDEBERT, M., RADICELLA, J. P. and DIZDAROGLU, M., 2000, Effect of single mutation in the OGG1 gene found in human tumors on the substrate specificity of the Oggl protein. Nucleic Acids Research, 28, 2672–2678.
  • AUGERI, L., LEE, Y. M., BARTON, A. B. and DOETSCH, P. W., 1997, Purification, characterization, gene cloning and expression of Saccharomyces cerevisiae redoxyendonuclease, a homolog of Eschefichia coli endonuclease III. Biochemistry, 36, 721–729.
  • BECKMAN, K. B. and AMES, B. N., 1997, Oxidative decay of DNA. Journal of Biological Chemistry, 272, 19 633–19 636.
  • BERDAL, K. G., JOHANSEN, R. F. and SEEBERG, E., 1998, Release of normal bases from intact DNA by a native DNA repair enzyme. EMBO Journal, 17, 363–367.
  • BJELLAND, S., KIRKELAND, N. K., BENNECHE, T., VOLDEN, G. and SEEBERG, E., 1994, DNA glycosylase activities for thymine residues oxidized in the methyl group are functions of the AlkA enzyme in Escherichia coli. Journal of Biological Chemistry, 269, 30 489–30 495.
  • BorrEux, S., 1993, Properties and biological functions of the Nth and Fpg proteins of Escherichia coli: two DNA glycosylases that repair oxidative damage in DNA. Journal of Photochemistry Photobiology B: Biology, 19, 87–96.
  • BorrEux, S., BEITYNEY, J., ROQUES, B. P. and LAVAL, J., 1984, Two rotameric forms of open ring 7-methylguanine are present in alkylated polynucleotides. Nucleic Acids Research, 12, 5429–5439.
  • BOITEUX, S., GAJEWSKI, E., LAVAL, J. and DIZDAROGLU, M., 1992, Substrate specificity of Escherichia coli Fpg protein: excision of purine lesions in DNA produced by ionizing radiation and photosensitization. Biochemistry, 31, 106–110.
  • BOITEUX, S., GELLON, L. and GUIBOURT, N., 2002, Repair of 8-oxoguanine in Saccharomyces cerevisiae: interplay of DNA repair and replication mechanisms. Free Radicals in Biology and Medicine, 32, 1244–1253.
  • BOITEUX, S., O'CONNOR, T. R., LEDERER, F., GOUYETTE, A. and LAVAL, J., 1990, Homogeneous Fpg protein of Escherichia coli: a DNA glycosylase, which excises imidazole-ring opened purines and nicks DNA at abasic sites. Journal of Biological Chemistry, 265, 3916–3922.
  • BorrEux, S. and RADICELLA, J. P., 2000, The human OGGI gene: structure, functions and its implication in the process of carcinogenesis. Archives of Biochemistry and Biophysics, 377, 1–8.
  • CADET, J., BERGER, M., DOUKI, T. and RAVANAT, J.-L., 1997, Oxidative damage to DNA: formation, measurement, and biological significance. Reviews Physiological Biochemistry and Pharmacology, 131, 1–87.
  • D'HAm, C., ROMIEU, A., JAQumron, M., GASPARITITO, D. and CADET, J., 1999, Excision of 5,6-clihyclrothymine and 5-hydroxycytosine from defined sequence oligonucleotides by Escherichia coli endonuclease III and Fpg protein: kinetic and mechanistic aspects. Biochemistry, 38, 3335–3344.
  • DIZDAROGLU, M., LAVAL, J. and BOITEUX, S., 1993, Substrate specificity of E. coli endonuclease III: Excision of thymine and cytosine derived lesions in DNA produced by radiation-generated free radicals. Biochemistry, 32, 12105–12111.
  • DUARTE, V., GASPARUTIO, D., JAQUINOD, M. and CADET, J., 2000a, In vitro synthesis opposite oxazolone and repair of this damage using modified oligonucleotides. Nucleic Acids Research, 28, 1555–1563.
  • DUARTE, V., GASPARUTTO, D., JAQUINOD, M., RAVANAT, J.-L. and CADET, J., 2001, Repair and mutagenic potential of oxaluric acid, a major product of singlet oxygen-mediated oxidation of 8-oxo-7,8-clihydroguanine. Chemical Research in Toxicology, 14, 46–53.
  • DUARTE, V., GASPARUTIO, D., YAMAGUCHI, L. F., RAVANAT, J.-L., MARTINEZ, G. R., MEDEIROS, M. H. G., Di MASCIO, P. and CADET, J., 2000b, Oxaluric acid as the major product of singlet oxygen-mediated oxidation of 8-oxo-7.8-dihydroguanine in DNA. Journal of the American Chemical Society, 122, 12 622–12 628.
  • DUARTE, V., MULLER," G. and BURROWS, C. J., 1999, Insertion of d.GMP and d.AMP during in vitro DNA synthesis opposite an oxidized form of 7,8-clihydro-8-oxoguanine. Nucleic Acids Research, 27, 496–502.
  • FINKEL, T. and HOLBROOK, N. J., 2000, Oxidants, oxidative stress and the biology of ageing. Nature, 408, 239–247.
  • FLoYD, R. A., 1999, Neuroinflammatory processes are important in neurodegenerative diseases: an hypothesis to explain the increased formation of reactive oxygen and nitrogen species as major factors involved in neurodegenerative disease development. Free Radicals in Biology and Medicine, 26, 1346–1355.
  • GASPARUTTO, D., DA CRUZ, S., BOURDAT, A. G., JAQUINTOT, M. and CADET, J., 1999, Synthesis and biochemical properties of cyanuric acid nucleoside-containing oligomers. Chemical Research in Toxicology, 12, 630–638.
  • GASPARUTTO, D., Dutkmr, C., BOITEUX, S. and CADET, J., 2002, Excision of 8-methylguanine site-specifically incorporated into oligonucleotides substrates by the AlkA protein of Escherichia coli. DNA Repair, 1, 437–447.
  • GIRARD, P.M., D'HAm, C., CADET, J. and BorrEux, S., 1998, Opposite base-dependent excision of 7,8-dihyclro-8-oxoguanine by the Oggl protein of Saccharomyces cerevisiae. Carcinogenesis, 19, 1299–1305.
  • GIRARD, P. M., GUIBOURT, N. and BorrEux, S., 1997, The Ogg 1 protein of Saccharomyces cerevisiae: a 7,8-clihyclro-8-oxoguanine DNA glycosylase/AP lyase whose lysine 241 is a critical residue for catalytic activity. Nucleic Acids Research, 25, 3404–3411.
  • GROLLMAN, A. P. and MORIYA, M., 1993, Mutagenesis by 8-hydroxyguanine: an enemy within. Trends in Genetics, 9, 246–249.
  • HAZRA, T. K., MULLER, J. G., MANUEL, R. C., BURROWS, C. J., LroyD, R. S. and MITRA, S., 2001, Repair of hydantoins, one electron oxidation product of 8-oxoguanine, by DNA glycosylases of Escherichia coli. Nucleic Acids Research, 29, 1967–1974.
  • HENDERSON, P. T., DELANEY," C., Gu, F., TANNENBAUM, S. R. and ESSIGMANN, J. M., 2002, Oxidation of 7.8-dihydro-8-oxoguanine affords lesions that are potent sources of replication errors in vivo. Biochemistry, 41, 914–921.
  • Hru,, J. W., HAZRA, T. K., Izumr, T. and MITRA, S., 2001, Stimulation of human 8-oxoguanine DNA glycosylase by AP-endonuclease: potential coordination of the initial steps in base excision repair. Nucleic Acids Research, 29, 430–438.
  • HOEIJMAKERS, J. H. J., 2001, Genome maintenance mechanisms for preventing cancer. Nature, 411, 366–374.
  • IKEDA, S., BISWAS, T., ROY, R., Izumi, T., BOLDOGH, I., KUROSKI, A., SARKER, A. H., SEKI, S. and MITRA, S., 1998, Purification and characterization of human NTH1, a homolog of Escherichia coli endonuclease III. Journal of Biological Chemistry, 273, 21 585–21 593.
  • KARADArm, B., GIRARD, P. M., BorrEux, S. and DIZDAROGLU, M., 1998, Substrate specificity of the Oggl protein of Saccharomyces cerevisiae: excision of purine lesions produced in DNA by ionizing radiation-or hydrogen peroxide/ metal ion-generated free radicals. Nucleic Acids Research, 26, 1228–1232.
  • KORNYUSHYNA, 0., BERGES, A. M., MULLER, J. G. and BURROWS, C. J., 2002, In vitro nucleotide misinsertion opposite the oxidized guanosine lesions spiroiminodihydantoin and guanidinohydantoin and DNA synthesis past the lesions using Escherichia coli DNA polymerase I. Biochemistry, 41, 15 304–15 314.
  • KROKAN, H. E., STANDAL, R. and SLUPPHAU GG., 1997, DNA glycosylases in the base excision repair of DNA. Biochemical Journal, 325, 1–16.
  • LEIPOLD, M. D., MULLER, J. G., BuRRows, C. J. and DAVID, S. S., 2000, Removal of hyclantoin products of 8-oxoguanine oxidation by the Escherichia coli DNA repair enzyme, FPG. Biochemistry, 39, 14 984–14 992.
  • Luo, W., MULLER, J. G., RACHLIN, E. M. and BuRRows, C. J., 2000, Characterization of spiroiminodihydantoin as a product of one-electron oxidation of 8-oxo-7.8-clihydroguanosine. Organic Letters, 2, 613–616.
  • Luo, W., MULLER, J. G., RACHLIN, E. M. and BuRRows, C. J., 2001, Characterization of hydantoin products from one-electron oxidation of 8-oxo-7,8-clihydroguanosine in a nucleoside model. Chemical Research in Toxicology, 4, 927–938.
  • MARNETT, L. J., 2000, Oxyradicals and DNA damage. Carcinogenesis, 21, 361–370.
  • MIAO, F., BOUZIANE, M. and O'CONNOR, T. R., 1998, Interaction of the recombinant human methylpurine DNA glycosylase (MPG protein) with oligodeoxyribonucleotides containing either hypoxanthine or abasic sites. Nucleic Acids Research, 26, 4034–4041.
  • MICHAELS, M. L. and MILLER, J. H., 1992, The GO system protects organisms from the mutagenic effect of spontaneous lesion 8-hydroxyguanine (7,8-dihydro-8-oxoguanine). Journal of Bacteriology, 174, 6321–6325.
  • NAKABEPPU, Y., KONDO, H. and SEKIGUCHI, M., 1984, Cloning and characterization of the alkA gene of Escherichia coli that encodes 3-methyladenine DNA glycosylase II. Journal of Biological Chemistry, 259, 13 723–13 729.
  • NILES, J. C., WISHNOK, J. S. and TANNENBAUM, S. R., 2001, Spiroiminodihydantoin is the major product of 8-oxo-7.8-dihydroguanosine reaction with peroxynitrite in the presence of thiols and guanosine photooxiclation by methylene blue. Organic Letters, 3, 963–966.
  • NnsEN, H., HAUSHALTER, K. A., ROBINS, P., BARNES, D. E., VERDINE, G. L. and LINDAHL, T., 2001, Excision of deaminated cytosine from the vertebrate genome: role of the Smugl uracil DNA glycosylase. EMBO Journal, 20, 4278–4286.
  • O'CONNOR, T. R., 1993, Purification and characterization of human 3-methyladenine DNA glycosylase. Nucleic Acids Research, 21, 5561–5569.
  • O'CONNOR, T. R. and LAVAL, F., 1990, Isolation and structure of a cDNA expressing a mammalian 3-methyladenine DNA glycosylase. EMBO Journal, 9, 3337–3342.
  • RAOUL, S. and CADET, J., 1996, Photosensitized recation of 8-oxo-7.8-clihydro-2'-deoxyguanosine: identification of 1-(2-deoxy-fl-D-egthro-pentofuranosyl)-cyanuric acid as the major singlet oxygen oxidation product. Journal of the American Chemical Society, 118, 1892–1898.
  • SAPARBAEV, M., Krum, K. and LAVAL, J., 1995, Escherichia coli, Saccharomyces cerevisiae, rat and human 3-methyladenine DNA glycosylases repair 1, N6-ethenoadenine when present in DNA. Nucleic Acids Research, 23, 3750–3755.
  • SAPARBAEV, M. and LAVAL, J., 1994, Excision of hypoxanthine from DNA containing dIMP residues by the Escherichia coli, yeast, rat and human alkylpurine DNA glycosylases. Proceedings of the National Academy of Sciences, USA, 91, 5873–5877.
  • SCHARER, 0. and JnucNY, J., 2001, Recent progress in the biology, chemistry and structural biology of DNA glycosylases. BioEssays, 23, 270–281.
  • SENTURKER, S., AUFFRET VAN DER KEMP, P., You, H.-J., DOETSCH, P. W., DIZDAROGLU, M. and BorrEux, S., 1998, Substrate specificity of the Ntgl and Ntg2 proteins of Saccharomyces cerevisiae for modified bases in oxiclatively damaged DNA. Nucleic Acids Research, 26, 5270–5276.
  • SUZUKI, T., MASUDA, M., FRIESEN, M. D. and OHSHIMA, H., 2001, Formation of spiroiminodihydantoin nucleoside by reaction of 8-oxo-7,8-dihydro-2'-deoxyguanosine with hypochlorous acid or a myeloperoxiclase-H202-Cr system. Chemical Research in Toxicology, 14, 1163–1169.
  • TRETYAKOVA, N., NILES, J., BURNEY, S., WISHNOK, J. S. and TANNENBAUM, R. S., 1999, Peroxinitrite-induced reactions of oligonucleotides containing 8-oxoguanine. Chemical Research in Toxicology, 12, 459–466.
  • TRETYAKOVA, N. Y., WisDNoK, J. S. and TANNENBAUM, S. R., 2000, Peroxinitrite-induced secondary oxidative lesions at guanine nucleobases: chemical stability and recognition by the Fpg DNA repair enzyme. Chemical Research in Toxicology, 13, 658–664.
  • UPPU, R. M., CUETO, R., SQUADRITO, G. L., SALGO, M. G. and PRYOR, W. A., 1996, Competitive reactions of peroxinitrite with2'-deoxyguanosineand deoxyguanosine (8-oxodG): relevance to the formation of 8-oxodG in DNA exposed to peroxinitrite. Free Radicals in Biology and Medicine, 21, 407–411.
  • VIDAL, A. E., HICKSON, I. D., BorrEux, S. and RADICELLA, J. P., 2001, Mechanism of stimulation of the DNA glycosylase activity of hOGG1 by the major human AP endonuclease: bypass of the AP lyase step. Nucleic Acids Research, 29, 1285–1292.
  • ZHARKOV, D. 0., SHOHAM, G. and GROLLMAN, A. P., 2003, Structural characterization of the Fpg family of DNA glycosylases. DNA Repair, 2, 839–862.

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