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Chemical Compound Review

SureCN102725     6-amino-1-methyl-pyrimidin-2- one

Synonyms: CHEBI:39992, HMDB11601, CTK0H6520, ZINC02047226, AKOS006347212, ...
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Disease relevance of 3MC

  • 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 [1].
  • Salmonella bacteria were detected by both cultivation and PCR-hybridization in 68% (17 of 25) of the positive samples that were preenriched in TSB, in 73% (11 of 15) of the positive samples preenriched in 3MC broth, and in 24% (6 of 25) of the positive samples enriched in RV10 [2].
  • The effectiveness of combined chemoimmunotherapy with ifosfamide derivative CBM-4A and granulocyte-macrophage colony-stimulating factor (GM-CSF) was investigated in two experimental tumor models, 3MC-induced MHC class I+ sarcoma Mc12 and HPV16 E6/E7 oncogene-induced MHC class I- carcinoma MK16, transplanted in syngeneic mice [3].

High impact information on 3MC


Chemical compound and disease context of 3MC


Biological context of 3MC


Anatomical context of 3MC

  • We showed in Caco-2 cells that addition of RA significantly decreased 3MC-induced CYP1A1 expression by -55% for mRNA level and -30% for promoter and enzymatic activities [8].
  • Eleven P-450s, 3MC and PB microsomes preferentially formed 1R,2R-diol enantiomer (80-96%) [12].
  • Rat liver epithelial cells resistant to the chemical carcinogen 3MC, termed F258/3MC cells and generated by long-term exposure of parental F258 cells to the PAH, were characterized, especially with respect to expression of multidrug resistance transporters such as P-glycoprotein, MRP1 and MRP2 [13].
  • Benzo(a)pyrene hydroxylase activity was found in the bone marrow of control and 3MC-induced New Zealand white rabbits [14].

Associations of 3MC with other chemical compounds

  • F258/3MC cells were found to be cross-resistant to other PAHs such as BP and dimethylbenz(a)anthracene but remained sensitive to known substrates of multidrug resistance efflux pumps such as doxorubicin and vincristine [13].

Gene context of 3MC

  • 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 [15].
  • The benzyloxyresorufin-O-deethylase (BROD) activity was decreased after incubation with 3MC but increased with beta N [16].
  • Induction of AHH activity of female rats administered 3MC was higher than that of male rats [17].
  • In addition, P-glycoprotein and MRP2 mRNA levels were not, or only barely detected, in F258/3MC cells and in their parental counterparts whereas these PAH-resistant and sensitive cells showed closed levels of MRP1 mRNAs and activity [13].
  • The alkoxyresorufin-O-dealkylase activity was measured in the S9 fraction of lung slices incubated for 24 h with 10(6) mol/L 20-methylcholanthrene (3MC) or beta-naphthoflavone (beta N) [16].

Analytical, diagnostic and therapeutic context of 3MC

  • R/S enantiomer ratios of 1-OH-3MC formed in the metabolism of 3MC by three rat liver microsomal preparations were determined by CSP HPLC: 35:65 (control), 39:61 (PB treated) and 46:54 (3MC treated) respectively [6].
  • At the maximum of the induction effect after pretreatment with the highest dose of 3MC no morphological alterations in the liver could be observed by light and electron microscopy [18].


  1. 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]
  2. Comparison of cultivation and PCR-hybridization for detection of Salmonella in porcine fecal and water samples. Feder, I., Nietfeld, J.C., Galland, J., Yeary, T., Sargeant, J.M., Oberst, R., Tamplin, M.L., Luchansky, J.B. J. Clin. Microbiol. (2001) [Pubmed]
  3. Chemoimmunotherapy of cancer: potentiated effectiveness of granulocyte-macrophage colony-stimulating factor and ifosfamide derivative CBM-4A. Indrová, M., Bubeník, J., Símová, J., Bieblová, J., Jandlová, T., Smahel, M., Vonka, V., Glazman-Kusnierczyk, H., Pajtasz-Piasecka, E., Radzikowski, C., Mikysková, R. Oncol. Rep. (2001) [Pubmed]
  4. Demethylation of 3-methylthymine in DNA by bacterial and human DNA dioxygenases. Koivisto, P., Robins, P., Lindahl, T., Sedgwick, B. J. Biol. Chem. (2004) [Pubmed]
  5. DNA repair: bioinformatics helps reverse methylation damage. Jiricny, J. Curr. Biol. (2002) [Pubmed]
  6. 1-Hydroxy- and 2-hydroxy-3-methylcholanthrene: regioselective and stereoselective formations in the metabolism of 3-methylcholanthrene and enantioselective disposition in rat liver microsomes. Shou, M., Yang, S.K. Carcinogenesis (1990) [Pubmed]
  7. Testosterone metabolite profiles reveal differences in the spectrum of cytochrome P-450 isozymes induced by phenobarbitone, 2-acetylaminofluorene and 3-methylcholanthrene in the chick embryo liver. Darby, N.J., Lodola, A., Burnet, F. Biochem. Pharmacol. (1986) [Pubmed]
  8. Retinoids repress Ah receptor CYP1A1 induction pathway through the SMRT corepressor. Fallone, F., Villard, P.H., Sérée, E., Rimet, O., Nguyen, Q.B., Bourgarel-Rey, V., Fouchier, F., Barra, Y., Durand, A., Lacarelle, B. Biochem. Biophys. Res. Commun. (2004) [Pubmed]
  9. Aberrant activity of the DNA repair enzyme AlkB. Henshaw, T.F., Feig, M., Hausinger, R.P. J. Inorg. Biochem. (2004) [Pubmed]
  10. Mutagenesis by alkylating agents: coding properties for DNA polymerase of poly (dC) template containing 3-methylcytosine. Boiteux, S., Laval, J. Biochimie (1982) [Pubmed]
  11. In vitro methylation of rat liver tRNA-synthesis of 3-methylcytosine and 1-methylhypoxantheine. Friedman, S. Biochem. Biophys. Res. Commun. (1977) [Pubmed]
  12. Regio- and stereo-selective metabolism of phenanthrene by twelve cDNA-expressed human, rodent, and rabbit cytochromes P-450. Shou, M., Korzekwa, K.R., Krausz, K.W., Crespi, C.L., Gonzalez, F.J., Gelboin, H.V. Cancer Lett. (1994) [Pubmed]
  13. Unaltered expression of multidrug resistance transporters in polycyclic aromatic hydrocarbon-resistant rat liver cells. Payen, L., Courtois, A., Langouët, S., Guillouzo, A., Fardel, O. Toxicology (2001) [Pubmed]
  14. Characterization and induction of aryl hydrocarbon (benzo(a)pyrene) hydroxylase in rabbit bone marrow. Andrews, L.S., Sonawane, B.R., Yaffe, S.J. Res. Commun. Chem. Pathol. Pharmacol. (1976) [Pubmed]
  15. Mutator specificity of Escherichia coli alkB117 allele. Nieminuszczy, J., Janion, C., Grzesiuk, E. Acta Biochim. Pol. (2006) [Pubmed]
  16. In vitro modulation of the P450 activities of hamster and human lung slices. Hoet, P.H., Demedts, M., Nemery, B. Cell Biol. Toxicol. (1997) [Pubmed]
  17. Relationship between survival times of rats exposed to lethal level of nitrogen dioxide and arylhydrocarbon hydroxylase activity in lungs. Sagai, M., Suzuki, S., Ichinose, T. Toxicol. Lett. (1983) [Pubmed]
  18. On the selectivity of aryl hydrocarbon hydroxylase induction after 3-methylcholanthrene pretreatment. Kleeberg, U., Barth, A., Roth, J., Klinger, W., Karge, E. Acta Biol. Med. Ger. (1975) [Pubmed]
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