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Chemical Compound Review

SureCN1914     1-methylpurin-6-amine

Synonyms: SureCN1915, CHEMBL304483, CHEBI:18083, HMDB11599, NSC-70896, ...
 
 
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Disease relevance of NSC 70896

 

High impact information on NSC 70896

  • In starfish oocytes, the hormone 1-methyladenine triggers synchronous meiotic divisions that are accompanied by a rapid 30-fold stimulation of H1K activity [4].
  • Here we show that AlkB from Escherichia coli is indeed a 2-oxoglutarate-dependent and iron-dependent DNA repair enzyme that releases replication blocks in alkylated DNA by a mechanism involving oxidative demethylation of 1-methyladenine residues [5].
  • Two human homologs of the Escherichia coli AlkB protein, denoted hABH2 and hABH3, were recently shown to directly reverse 1-methyladenine (1meA) and 3-methylcytosine (3meC) damages in DNA [6].
  • Furthermore, embryonal fibroblasts from mABH2-deficient mice are unable to remove methyl methane sulfate (MMS)-induced 1meA from genomic DNA and display increased cytotoxicity after MMS exposure [6].
  • However, in the absence of any exogenous exposure to methylating agents, mice lacking mABH2, but not mABH3 defective mice, accumulate significant levels of 1meA in the genome, suggesting the presence of a biologically relevant endogenous source of methylating agent [6].
 

Chemical compound and disease context of NSC 70896

 

Biological context of NSC 70896

 

Anatomical context of NSC 70896

 

Associations of NSC 70896 with other chemical compounds

  • In agreement with these results, we found that in vitro repair of 1meA and 3meC in double-stranded DNA by nuclear extracts depended primarily, if not solely, on mABH2 [6].
  • The stimulation of oocyte maturation by 1-methyladenine in starfish, and by a steroid in frogs, has been proposed to involve G-protein-coupled receptors [18].
  • Inhibition of subsite-substituted leupeptin analogs, potent trypsin inhibitors, on 1-methyladenine-induced germinal vesicle breakdown was investigated in a starfish, Asterina pectinifera [19].
  • In response to the maturation-inducing hormone 1-methyladenine, starfish oocytes acquire increased sensitivity to sperm and inositol trisphosphate (InsP3), stimuli that cause a release of calcium from intracellular stores and a rise in intracellular free calcium [20].
  • Although MGBG is required during a slightly longer period than the natural hormone 1-methyladenine (1-MeAde), the maturation kinetics are identical [21].
 

Gene context of NSC 70896

  • Significantly, PRK2 is phosphorylated in vivo in response to 1-methyladenine which precedes MPF activation, making PRK2 a candidate regulator of early signaling events of meiotic maturation [22].
  • The Escherichia coli AlkB protein encoded by alkB gene was recently found to repair cytotoxic DNA lesions 1-methyladenine (1-meA) and 3-methylcytosine (3-meC) by using a novel iron-catalysed oxidative demethylation mechanism that protects the cell from the toxic effects of methylating agents [23].
  • These results suggest that beta gamma dissociates from alpha-subunit by the stimulation of 1-methyladenine and interacts with a cytoplasmic effector, which results in formation of active cdc2 kinase [24].
  • Components of the signaling pathway linking the 1-methyladenine receptor to MPF activation and maturation in starfish oocytes [25].
  • In starfish oocytes, the beta gamma subunit of G protein mediates 1-methyladenine stimulation of oocyte maturation [26].
 

Analytical, diagnostic and therapeutic context of NSC 70896

References

  1. Human and bacterial oxidative demethylases repair alkylation damage in both RNA and DNA. Aas, P.A., Otterlei, M., Falnes, P.O., Vågbø, C.B., Skorpen, F., Akbari, M., Sundheim, O., Bjørås, M., Slupphaug, G., Seeberg, E., Krokan, H.E. Nature (2003) [Pubmed]
  2. Methyl-accepting RNA in 13762 mammary adenocarcinoma correlated with low adenine methyltransferase levels. Salas, C.E., Uschmann, B.D., Leboy, P.S. Cancer Res. (1982) [Pubmed]
  3. Pertussis toxin inhibits 1-methyladenine-induced maturation in starfish oocytes. Shilling, F., Chiba, K., Hoshi, M., Kishimoto, T., Jaffe, L.A. Dev. Biol. (1989) [Pubmed]
  4. cdc2 is a component of the M phase-specific histone H1 kinase: evidence for identity with MPF. Arion, D., Meijer, L., Brizuela, L., Beach, D. Cell (1988) [Pubmed]
  5. AlkB-mediated oxidative demethylation reverses DNA damage in Escherichia coli. Falnes, P.Ø., Johansen, R.F., Seeberg, E. Nature (2002) [Pubmed]
  6. Repair deficient mice reveal mABH2 as the primary oxidative demethylase for repairing 1meA and 3meC lesions in DNA. Ringvoll, J., Nordstrand, L.M., Vågbø, C.B., Talstad, V., Reite, K., Aas, P.A., Lauritzen, K.H., Liabakk, N.B., Bjørk, A., Doughty, R.W., Falnes, P.Ø., Krokan, H.E., Klungland, A. EMBO J. (2006) [Pubmed]
  7. Mutagenesis, genotoxicity, and repair of 1-methyladenine, 3-alkylcytosines, 1-methylguanine, and 3-methylthymine in alkB Escherichia coli. Delaney, J.C., Essigmann, J.M. Proc. Natl. Acad. Sci. U.S.A. (2004) [Pubmed]
  8. Membrane response to 1-methyladenine requires the presence of the nucleus. Dale, B., de Santis, A., Hoshi, M. Nature (1979) [Pubmed]
  9. Metaphase I arrest of starfish oocytes induced via the MAP kinase pathway is released by an increase of intracellular pH. Harada, K., Oita, E., Chiba, K. Development (2003) [Pubmed]
  10. Stereospecific induction of starfish oocyte maturation by (8R)-hydroxyeicosatetraenoic acid. Meijer, L., Brash, A.R., Bryant, R.W., Ng, K., Maclouf, J., Sprecher, H. J. Biol. Chem. (1986) [Pubmed]
  11. Degradation of polyubiquitinated cyclin B is blocked by the MAPK pathway at the metaphase I arrest in starfish oocytes. Oita, E., Harada, K., Chiba, K. J. Biol. Chem. (2004) [Pubmed]
  12. Reverse transcription of tRNA. Wittig, B., Wittig, S. Nucleic Acids Res. (1978) [Pubmed]
  13. Hormonal control of meiosis: specificity of the 1-methyladenine receptors in starfish oocytes. Dorée, M., Guerrier, P., Leonard, N.J. Proc. Natl. Acad. Sci. U.S.A. (1976) [Pubmed]
  14. Involvement of G-proteins and adenylate cyclase in the action of gonad-stimulating substance on starfish ovarian follicle cells. Mita, M., Nagahama, Y. Dev. Biol. (1991) [Pubmed]
  15. Breakdown of cytoskeletal proteins during meiosis of starfish oocytes and proteolysis induced by calpain. Santella, L., Kyozuka, K., Hoving, S., Munchbach, M., Quadroni, M., Dainese, P., Zamparelli, C., James, P., Carafoli, E. Exp. Cell Res. (2000) [Pubmed]
  16. 1-Methyladenine-producing cell in starfish testis. Kubota, J., Nakao, K., Shirai, H., Kanatani, H. Exp. Cell Res. (1977) [Pubmed]
  17. Microtubule arrays in the cortex and near the germinal vesicle of immature starfish oocytes. Otto, J.J., Schroeder, T.E. Dev. Biol. (1984) [Pubmed]
  18. A receptor linked to a Gi-family G-protein functions in initiating oocyte maturation in starfish but not frogs. Kalinowski, R.R., Jaffe, L.A., Foltz, K.R., Giusti, A.F. Dev. Biol. (2003) [Pubmed]
  19. Inhibition of starfish oocyte maturation by leupeptin analogs, potent trypsin inhibitors. Sawada, M.T., Someno, T., Hoshi, M., Sawada, H. Dev. Biol. (1989) [Pubmed]
  20. Development of calcium release mechanisms during starfish oocyte maturation. Chiba, K., Kado, R.T., Jaffe, L.A. Dev. Biol. (1990) [Pubmed]
  21. Immobilized methylglyoxal-bis(guanylhydrazone) induces starfish oocyte maturation. Meijer, L., Guerrier, P. Dev. Biol. (1983) [Pubmed]
  22. Phosphorylation of protein kinase C-related kinase PRK2 during meiotic maturation of starfish oocytes. Stapleton, G., Nguyen, C.P., Lease, K.A., Hille, M.B. Dev. Biol. (1998) [Pubmed]
  23. Mutator specificity of Escherichia coli alkB117 allele. Nieminuszczy, J., Janion, C., Grzesiuk, E. Acta Biochim. Pol. (2006) [Pubmed]
  24. Induction of starfish oocyte maturation by the beta gamma subunit of starfish G protein and possible existence of the subsequent effector in cytoplasm. Chiba, K., Kontani, K., Tadenuma, H., Katada, T., Hoshi, M. Mol. Biol. Cell (1993) [Pubmed]
  25. Components of the signaling pathway linking the 1-methyladenine receptor to MPF activation and maturation in starfish oocytes. Sadler, K.C., Ruderman, J.V. Dev. Biol. (1998) [Pubmed]
  26. A periodic network of G protein beta gamma subunit coexisting with cytokeratin filament in starfish oocytes. Chiba, K., Longo, F.J., Kontani, K., Katada, T., Hoshi, M. Dev. Biol. (1995) [Pubmed]
  27. Is calcium the second messenger of 1-methyladenine in meiosis reinitiation of starfish oocytes? Picard, A., Dorée, M. Exp. Cell Res. (1983) [Pubmed]
  28. Extraction and preliminary characterization of maturation-promoting factor from starfish oocytes. Kishimoto, T., Kondo, H. Exp. Cell Res. (1986) [Pubmed]
  29. 1-Methyladenine can consistently induce a fura-detectable transient calcium increase which is neither necessary nor sufficient for maturation in oocytes of the starfish Asterina miniata. Witchel, H.J., Steinhardt, R.A. Dev. Biol. (1990) [Pubmed]
  30. Separate activation of the cytoplasmic and nuclear calcium pools in maturing starfish oocytes. Santella, L., De Riso, L., Gragnaniello, G., Kyozuka, K. Biochem. Biophys. Res. Commun. (1998) [Pubmed]
  31. The starfish (Patiria and Pisaster) oocyte: a model system for the study of hormone-surface interaction in oogenesis. Lee, H.H., Rosenberg, M.P., Hoesch, R. Lab. Anim. Sci. (1977) [Pubmed]
 
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