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Chemical Compound Review

Epiguanine     2-amino-7-methyl-3H-purin-6- one

Synonyms: SureCN25547, AG-G-04617, SureCN7617554, SureCN7617558, CHEBI:28664, ...
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Disease relevance of NSC19647


Psychiatry related information on NSC19647


High impact information on NSC19647


Chemical compound and disease context of NSC19647


Biological context of NSC19647

  • In contrast, there was no difference between the human and rat liver extracts in catalyzing the loss of another methylation product, 7-methylguanine, from alkylated DNA [17].
  • As MMS produces less methylation at the O6 position of guanine and more methylation at the N7 position in comparison to MNNG, the results suggest that: (i) N7-methylguanine is not implicated in the adaptive response and (ii) adaptation to mutagenesis can be correlated with the amount of O6-methylguanine induced during the pretreatment [18].
  • The cloned cDNA, expressed from the pBR322 beta-lactamase promoter, contains an 894-base-pair open reading frame encoding a 32,894-Da protein able to release 3-MeAde, but not 7-methylguanine, from alkylated DNA [19].
  • A characteristic feature of gene expression in eukaryotes is the addition of a 5'-terminal 7-methylguanine cap (m7GpppN) to nascent pre-mRNAs in the nucleus catalyzed by capping enzyme and cap methyltransferase [20].
  • In addition, the repair of N7-methylguanine in the overall genome was assessed by use of a 32P end-labeling technique [21].

Anatomical context of NSC19647


Associations of NSC19647 with other chemical compounds


Gene context of NSC19647

  • Evidence is also provided that the BER intermediates resulting from excision of 7-methylguanine by wild-type AAG contributes to the mutagenicity and cytotoxicity of alkylating agents [31].
  • As this mutagenic event occurs during the growth of adenomas, both biomarkers of exposure (N7-methylguanine levels in DNA) and susceptibility (MGMT activity) were measured in biopsy samples obtained from normal and adenomatous tissue from 34 patients with large adenomas (>10 mm in size) [32].
  • Then, we determined DNA strand breaks and the level of 7-methylguanine (7-mGua), a product of NNK metabolism by cytochrome P450 (CYP) [33].
  • We also investigated the in vivo repair kinetics of another Aag substrate, 7-methylguanine [34].
  • Nuclear DNAs of tissue culture cells treated with 0, 0.01 and 0.1 mM N-methyl-N'-nitro-N-nitrosoguanidine contained 0.18, 31 and 320 mumol, respectively, of 7-methylguanine adducts per mol of nucleotides [35].

Analytical, diagnostic and therapeutic context of NSC19647


  1. Di-and trimethylated congeners of 7-methylguanine in Sindbis virus mRNA. HsuChen, C.C., Dubin, D.T. Nature (1976) [Pubmed]
  2. Cloning and expression in Escherichia coli of a gene for an alkylbase DNA glycosylase from Saccharomyces cerevisiae; a homologue to the bacterial alkA gene. Berdal, K.G., Bjørås, M., Bjelland, S., Seeberg, E. EMBO J. (1990) [Pubmed]
  3. Release of 7-methylguanine residues from alkylated DNA by extracts of Micrococcus luteus and Escherichia coli. Laval, J., Pierre, J., Laval, F. Proc. Natl. Acad. Sci. U.S.A. (1981) [Pubmed]
  4. DNA alkylation in the hamster induced by two pancreatic carcinogens. Kokkinakis, D.M., Scarpelli, D.G. Cancer Res. (1989) [Pubmed]
  5. Altered growth properties of Chinese hamster cells exposed to 1-methylguanine and 7-methylguanine. Trewyn, R.W., Kerr, S.J. Cancer Res. (1978) [Pubmed]
  6. Decreasing urinary PAH metabolites and 7-methylguanine after smoking cessation. Ichiba, M., Matsumoto, A., Kondoh, T., Horita, M., Tomokuni, K. International archives of occupational and environmental health. (2006) [Pubmed]
  7. Differential repair of O(6)-methylguanine in DNA of rat hepatocytes and nonparenchymal cells. Lewis, J.G., Swenberg, J.A. Nature (1980) [Pubmed]
  8. DNA alkylation and tumor induction in regenerating rat liver after cell cycle-related continuous N-nitrosodimethylamine infusion. Rabes, H.M., Kerler, R., Wilhelm, R. J. Natl. Cancer Inst. (1983) [Pubmed]
  9. Alkylation of rat liver DNA by dimethylnitrosamine: effect of dosage on O6-methylguanine levels. Pegg, A.E. J. Natl. Cancer Inst. (1977) [Pubmed]
  10. Isolation and structure of a cDNA expressing a mammalian 3-methyladenine-DNA glycosylase. O'Connor, T.R., Laval, F. EMBO J. (1990) [Pubmed]
  11. Function of the p86 subunit of eukaryotic initiation factor (iso)4F as a microtubule-associated protein in plant cells. Bokros, C.L., Hugdahl, J.D., Kim, H.H., Hanesworth, V.R., van Heerden, A., Browning, K.S., Morejohn, L.C. Proc. Natl. Acad. Sci. U.S.A. (1995) [Pubmed]
  12. Biological properties of imidazole ring-opened N7-methylguanine in M13mp18 phage DNA. Tudek, B., Boiteux, S., Laval, J. Nucleic Acids Res. (1992) [Pubmed]
  13. O6-methylguanine, but not N7-methylguanine or N3-methyladenine, induces gene mutations, sister-chromatid exchanges and chromosomal aberrations in Chinese hamster cells. Kaina, B., Heindorff, K., Aurich, O. Mutat. Res. (1983) [Pubmed]
  14. Identification of N5-methyl-N5-formyl-2,5,6-triamino-4-hydroxypyrimidine as a major adduct in rat liver DNA after treatment with the carcinogens, N,N-dimethylnitrosamine or 1,2-dimethylhydrazine. Beranek, D.T., Weis, C.C., Evans, F.E., Chetsanga, C.J., Kadlubar, F.F. Biochem. Biophys. Res. Commun. (1983) [Pubmed]
  15. Metabolism of N-nitrosodimethylamine and N-nitrosomethylbenzylamine in domestic fowls: DNA alkylation and potential target sites for carcinogenicity. Schmerold, I., Kleihues, P., Wiestler, O., O'Neill, C. Anticancer Res. (1986) [Pubmed]
  16. Methylation patterns of tRNA at different concentrations of dimethylsulphate. Kanduc, D. Boll. Soc. Ital. Biol. Sper. (1979) [Pubmed]
  17. Removal of O6-methylguanine from DNA by human liver fractions. Pegg, A.E., Roberfroid, M., von Bahr, C., Foote, R.S., Mitra, S., Bresil, H., Likhachev, A., Montesano, R. Proc. Natl. Acad. Sci. U.S.A. (1982) [Pubmed]
  18. Adaptive response in mammalian cells: crossreactivity of different pretreatments on cytotoxicity as contrasted to mutagenicity. Laval, F., Laval, J. Proc. Natl. Acad. Sci. U.S.A. (1984) [Pubmed]
  19. Cloning and characterization of a 3-methyladenine DNA glycosylase cDNA from human cells whose gene maps to chromosome 16. Samson, L., Derfler, B., Boosalis, M., Call, K. Proc. Natl. Acad. Sci. U.S.A. (1991) [Pubmed]
  20. Human mRNA cap methyltransferase: alternative nuclear localization signal motifs ensure nuclear localization required for viability. Shafer, B., Chu, C., Shatkin, A.J. Mol. Cell. Biol. (2005) [Pubmed]
  21. Heterogeneous repair of methylnitrosourea-induced alkali-labile sites in different DNA sequences. LeDoux, S.P., Thangada, M., Bohr, V.A., Wilson, G.L. Cancer Res. (1991) [Pubmed]
  22. Alkylpurine-DNA-N-glycosylase knockout mice show increased susceptibility to induction of mutations by methyl methanesulfonate. Elder, R.H., Jansen, J.G., Weeks, R.J., Willington, M.A., Deans, B., Watson, A.J., Mynett, K.J., Bailey, J.A., Cooper, D.P., Rafferty, J.A., Heeran, M.C., Wijnhoven, S.W., van Zeeland, A.A., Margison, G.P. Mol. Cell. Biol. (1998) [Pubmed]
  23. Organ and cell specificity of DNA methylation by N-nitrosomethylamylamine in rats. Koenigsmann, M., Schmerold, I., Jeltsch, W., Ludeke, B., Kleihues, P., Wiessler, M. Cancer Res. (1988) [Pubmed]
  24. Carcinogenicity of N-nitrosomethyl(2-oxopropyl)amine in Syrian hamsters. Pour, P., Gingell, R., Langenbach, R., Nagel, D., Grandjean, C., Lawson, T., Salmasi, S. Cancer Res. (1980) [Pubmed]
  25. Methylation versus ethylation of DNA in target and nontarget tissues of Fischer 344 rats treated with N-nitrosomethylethylamine. von Hofe, E., Grahmann, F., Keefer, L.K., Lijinsky, W., Nelson, V., Kleihues, P. Cancer Res. (1986) [Pubmed]
  26. Interaction of the carcinogen 3,3-dimethyl-1-phenyltriazene with nucleic acids of various rat tissues and the effect of a protein-free diet. Kleihues, P., Kolar, G.F., Margison, G.P. Cancer Res. (1976) [Pubmed]
  27. Inhibition of N-methyl-N-nitrosourea-induced mutagenicity and DNA methylation by ellagic acid. Dixit, R., Gold, B. Proc. Natl. Acad. Sci. U.S.A. (1986) [Pubmed]
  28. Enhancement of the chemical transformation of Chinese hamster embryo cells in vitro by 7-methylguanine. Muralidhar, G., Trewyn, R.W. Cancer Res. (1987) [Pubmed]
  29. Preferential DNA repair of alkali-labile sites within the active insulin gene. LeDoux, S.P., Patton, N.J., Nelson, J.W., Bohr, W.A., Wilson, G.L. J. Biol. Chem. (1990) [Pubmed]
  30. Some effects of treatment of hen erythrocytes in vitro with N-methyl-N-nitrosourea. Ward, T.H., Itzhaki, R.F. J. Cell. Sci. (1981) [Pubmed]
  31. Effects of substrate specificity on initiating the base excision repair of N-methylpurines by variant human 3-methyladenine DNA glycosylases. Connor, E.E., Wilson, J.J., Wyatt, M.D. Chem. Res. Toxicol. (2005) [Pubmed]
  32. Reduced MGMT activity in human colorectal adenomas is associated with K-ras GC->AT transition mutations in a population exposed to methylating agents. Lees, N.P., Harrison, K.L., Hall, C.N., Margison, G.P., Povey, A.C. Carcinogenesis (2004) [Pubmed]
  33. Flavonoids suppresses the enhancing effect of beta-carotene on DNA damage induced by 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone (NNK) in A549 cells. Yeh, S.L., Wang, W.Y., Huang, C.S., Hu, M.L. Chem. Biol. Interact. (2006) [Pubmed]
  34. In vivo repair of methylation damage in Aag 3-methyladenine DNA glycosylase null mouse cells. Smith, S.A., Engelward, B.P. Nucleic Acids Res. (2000) [Pubmed]
  35. High avidity monoclonal antibody to imidazole ring-opened 7-methylguanine. Stein, A.M., Gratzner, H.G., Stein, J.H., McCabe, M.M. Carcinogenesis (1989) [Pubmed]
  36. 7-Methylguanine adducts in DNA are normally present at high levels and increase on aging: analysis by HPLC with electrochemical detection. Park, J.W., Ames, B.N. Proc. Natl. Acad. Sci. U.S.A. (1988) [Pubmed]
  37. Specific protein recognition of an mRNA cap through its alkylated base. Hodel, A.E., Gershon, P.D., Shi, X., Wang, S.M., Quiocho, F.A. Nat. Struct. Biol. (1997) [Pubmed]
  38. 7-Methylguanine specific tRNA-methyltransferase from Escherichia coli. Aschhoff, H.J., Elten, H., Arnold, H.H., Mahal, G., Kersten, W., Kersten, H. Nucleic Acids Res. (1976) [Pubmed]
  39. Separation of 7-methyl- and 7-(2-hydroxyethyl)-guanine adducts in human DNA samples using a combination of TLC and HPLC. Kumar, R., Hemminki, K. Carcinogenesis (1996) [Pubmed]
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