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Original Article

Alkylation of the O6 of Guanine is Only One of Many Chemical Events that May Initiate Carcinogenesis

Pages 233-238 | Published online: 11 Jun 2009

References

  • Magee PN, Farber, E: Toxic liver injury and carcinogenesis. Methylation of rat-li ver nucleic acids by dimethylnitrosamine in vivo. Biochem J 83: 114-124, 1962.
  • Singer B: Chemical effects of nucleic acid alkylation and their relation to mutagenesis and carcinogenesis. Prog Nucleic Acid Res Mol Biol 15:219–284, 1975; 15:330-332, 1975.
  • Swann PE, Magee PN: Nitrosamine-induced carcinogenesis. The alkylation of N-7 of guanine of nucleic acids of the rat by diethylnitrosamine, N-ethyl-N-nitrosourea and ethyi methanesulphonate. Biochem J 125: 841-847, 1971.
  • Loveless A: Possible relevance of 0-6 alkylation of deoxyguanosine to the mutagenicity and carcinogenicity of nitrosamines and nitrosamides. Nature (London) 223:206–207, 1969.
  • O'Connor PJ, Capps MJ, Craig AW: Comparative studies of the hepatocarcinogen N,N-dimethylnitrosamine in vivo: Reaction sites in rat liver DNA and the significance of their relative stabilities. Br J Cancer 27: 153–167, 1973.
  • Goth R, Rajewsky MF: Molecular and cellular mechanisms associated with pulse-carcinogenesis in the rat nervous system by ethylnitrosourea: Ethylation of nucleic acids and elimination rates of ethylated bases from the DNA of different tissues. Z Krebsforsch 82:37–64, 1974.
  • Pegg AE: Alkylation and subsequent repair of DNA after exposure to dimethylnitrosamine and related carcinogens. In Reviews in Biochemical Toxicology, Hodgson E, Bend JR, Philpot RM, Eds: Elsevier, New York, 1983, pp 83–133.
  • Singer B: Correlations between sites of chemical modification of DNA, repair and carcinogenesis. In Primary and Tertiary Structure of Nucleic Acids and Cancer Research, Miwa M, Nishimura S, Rich A, Soli DG, Sugimura T, Eds: Japan Science Society Press, Tokyo, 1982, pp 117–137.
  • Gerchman LL, Ludlum DB: The Properties of O”-methylguanine in templates for RNA polymerase. Biochim Biophys Acta 308:310–316, 1982.
  • Mehta JR, Ludlum DB: Synthesis and properties of 06-methyldeoxyguanylic acid and its copolymers with deoxycytidylic acid. Biochim Biophys Acta 521:770–778, 1978.
  • Ludlum DB: The properties of 7-methylguanine-containing templates for ribonucleic acid polymers. J Biol Chem 245:477–482, 1970.
  • Kunkel TA, Shearman CW, Loeb LA: Mutagenesis in vitro by depurination of cP X174 DNA. Nature (London) 291:349–351, 1981.
  • Buecheler J, Kleihues P: Excision of O”-methylguanine from DNA of various mouse tissues following a single injection of N-methyl-N-nitrosourea. Chem Biol Interact 16:326–333, 1977.
  • Rogers KJ, Pegg AE: Formation of O”-methylguanine by alkylation of rat liver, colon, and kidney DNA following administration of 1,2-dimethylhydrazine. Cancer Res 37:4082–4084, 1977.
  • Hodgson R, Swann P, Clothier R, Balls M: The persistence in Xenopus laevis DNA of O”-methylguanine produced by exposure to N-nitrosourea. Eur J Cancer 16:381–486, 1980.
  • Kleihues P, Bamborschke S, Gerhard D: Persistence of aJkylated DNA bases in the Mongolian gerbil (Meriones unguiculatus) following a single dose of methylnitrosourea. Carcinogenesis 1:111–113, 1980.
  • Likhachev AJ, Ivanov MN, Bresil H, Planche-Martel G, Montesano R, Margison GP: Carcinogenicity of single doses of Nnitroso-N-methylurea and N-nitroso-N-ethylurea in Syrian golden hamsters and the persistence of alkylated purines in the DNA of various tissues. Cancer Res 43:829–833, 1983.
  • Margison GP, Margison JM, Montesano R: Accumulation of O-methylguanine in non-target-tissue deoxyribonucleic acid during chronic administration of dimethylnitrosamine. Biochem J 165: 463–468, 1977.
  • Kleihues P, Veit C, Wiessler M, Hodgson RM: DNA methylation by N-nitrosomethylbenzylamine in target and non-target tissues of NMRI mice. Carcinogenesis 2:897–899, 1981.
  • Hodgson RM, Schweinsberg F, Weissler M, Kleihues P: Mechanism of esophageal tumor induction in rats by N-nitrosomethylbenzylamine and its ring-methylated analog Nnitrosomethyl (4-methyl-benzyl)amine. Cancer Res 42:2836–2840, 1982.
  • Herron D, Shank RC: DNA methylation during chronic administration of 1,2-methylhydrazine in a carcinogenic regimen. Carcinogenesis 3:857–860, 1982.
  • Bosan WS, Shank RC: Methylation of liver DNA guanine in hamster given hydrazine. Toxicol Appl Pharacol, in press.
  • Pegg AE, Wiest L, Foote RE, Mitra S, Perry W: Purification and properties of O”-methylguanine-DNA transmethylase from rat liver. J Biol Chem 258:2327–2333, 1983.
  • Bamborschke S, O'Connor PJ, Margison GP, Kleihues P, Maru GB: DNA methylation by dimethylnitrosamine in the Mongolian gerbil (Meriones unguiculatus): Indications of a deficient, noninducible hepatic repair system for 06-methylguanine. Cancer Res 43:1306-1311, 1983.
  • Kleihues P, Bucheler J, Riede UN: Selective induction of melanomas in gerbils (Meriones unguiculatus) following postnasal administration of N-ethyl-N-nitrosourea. J Natl Cancer Inst 61:859–863, 1978.
  • Singer B: All oxygens in nucleic acids react with carcinogenic ethylating agents. Nature (London) 264:333–339, 1976.
  • Singer B, Bodell WJ, Cleaver JE, Thomas GH, Rajewsky MF, Thon W: Oxygens in DNA are main targets for ethylnitrosourea in normal and Xeroderma pigmentosum fibroblasts and fetal rat brain cells. Nature (London) 276: 85–88, 1978.
  • Singer B, Spengler S, Bodell WJ: Tissue-dependent enzymemediated repair or removal of O-ethyl pyrimidines and ethyl purines in carcinogen-treated rats. Carcinogenesis 2:1069–1073, 1981.
  • Singer B, Fraenkel-Conrat H, Kusmierek JT: Preparation and template activities of polynucleotides containing Q2-and 04alkyluridine. Proc Natl Acad Sci USA 75: 1722–1726, 1978.
  • Singer B, Pergolizzi RG. Grunberger 0: Synthesis and coding properties of dinucleoside diphosphates containing alkyl pyrimidines which are formed by the action of carcinogens on nucleic acids. Nucleic Acids Res 6:1709–1719, 1979.
  • Singer B, Krôger M: Participation of modified nucleosides in translation and transcription. Prog Nucleic Res Mol Biol 23:151–194, 1979.
  • Singer B, Kusmierek JT, Fraenkel-Conrat H: In vitro discrimination of replicases acting on carcinogen-modified polynucleotide templates. Proc Natl Acad Sei USA 80:969–972, 1983.
  • Singer B, Sagi J, Kusmierek JT: Escherichia coli polymerase 1 can use Oê-methyldeoxythyrnidine or 04-methyldeoxythymidine in place of deoxythymidine in primed poly(dA-dT) poly(dA-dT) synthesis. Proc Natl Acad Sci USA 80:4884-4888. 1983.
  • Frei JV, Swenson DH, Warren W, Lawley P: Alkylation of deoxyribonucleic acid in vivo in various organs of C57BL mice by the carcinogens N-methyl-N-nitrosourea, N-ethyl-N-nitrosourea and ethyl methanesulphonate in relation to induction of thymie lymphoma. Sorne applications of high-pressure liquid chromatography. Biochem J 174:1031-1044, 1978.
  • Steward AP, Scherer E, Emmelot P: Formation of relatively persistent Oê-cthylthymidine by diethylnitrosamine in rat liver DNA. FEBS Lett 100:191–194, 1979.
  • Scherer AP, Timmer AP, Emmelot P: Formation by diethylnitrosamine and persistence of O”-ethylthymidine in rat liver DNA in vivo. Cancer Lett 10:1–6.
  • Lewis JG, Swenberg JA: DifferentiaI repair of O”-methylguanine in DNA of rat hepatocytes and nonparenchymal cells. Nature (London) 228:185–187, 1980.
  • Bedell MA, Lewis JO, Billings KC, Swenberg JA: Cell specificity in hepatocarcinogenesis: Preferential accumulation of 06-methylguanine in target cell DNA during continuo us exposure of rats to 1,2-dimethylhydrazine. Cancer Res 42:3079–3083, 1982.
  • Swenberg JA, Bedell MA, BiIlings KC, Umbenhauer DR, Pegg AE: Cell-specific differences in O6-alkylguanine DNA repair activity during continuous exposure to carcinogen. Proc Natl Acad Sei USA 79:5499–5502, 1982.
  • Swenberg JA, Bedell MA, BiIlings KC, Huh N, Kurstein U, Rajewsky MF: O”-Ethylthymidine accumulates in DNA of hepatocytes exposed continuously to diethylnitrosamine (DEN). Proc Assoc Cancer Res 24:268, 1983.
  • Heyting C, Van Der Laken 0, van Raarnsdonk W, Pool CW: Immunohistochemical detection of O6-ethyldeoxyguanosine in the rat brain after in vivo applications of N-ethyl-N-nitrosourea. Cancer Res 43:2935-2941, 1983.
  • Singer B, Kusmierek JT: Chemical mutagenesis. Ann Rev Biochem 51:655–693, 1982

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