7-Methylguanine

Last updated
7-Methylguanine
7methylguanine.svg
Names
IUPAC name
7-Methylguanine
Preferred IUPAC name
2-Amino-7-methyl-1,7-dihydro-6H-purin-6-one
Other names
N7-Methylguanine; Epiguanine
Identifiers
3D model (JSmol)
174245
ChEBI
ChemSpider
ECHA InfoCard 100.008.575 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 209-431-0
KEGG
PubChem CID
UNII
  • InChI=1S/C6H7N5O/c1-11-2-8-4-3(11)5(12)10-6(7)9-4/h2H,1H3,(H3,7,9,10,12)
    Key: FZWGECJQACGGTI-UHFFFAOYSA-N
  • CN1C=NC2=C1C(=O)N=C(N2)N
Properties
C6H7N5O
Molar mass 165.156 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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7-Methylguanine is a modified purine nucleobase. It is a methylated version of guanine. The 7-methylguanine nucleoside is called 7-methylguanosine. However, the free 7-methylguanine base is not involved in the synthesis of nucleotides and not incorporated directly into nucleic acids. [1] [2] 7-Methylguanine is a natural inhibitor of poly (ADP-ribose) polymerase (PARP) and tRNA guanine transglycosylase (TGT) - and thus may exert anticancer activity. [3] [4] [5] For example, it was demonstrated that 7-methylguanine could accelerate apoptotic death of BRCA1-deficient breast cancer cells induced by cisplatin and doxorubicin. [6]

References

  1. ↑ Craddock, VM; Mattocks, AR; Magee, PN (1968). "The fate of 7[14C]-methylguanine after administration to the rat". Biochem. J. 109 (1): 75–78. doi:10.1042/bj1090075. PMC   1186754 . PMID   5669851.
  2. ↑ Kaina, B; Heindorff, K; Aurich, O (1983). "O6-methylguanine, but not N7-methylguanine or N3-methyladenine, induces gene mutations, sister-chromatid exchanges and chromosomal aberrations in Chinese hamster cells". Mutat. Res. 108 (1–3): 279–292. doi:10.1016/0027-5107(83)90126-4. PMID   6835224.
  3. ↑ Nilov, D; Maluchenko, N; Kurgina, T; Pushkarev, S; Lys, A; Kutuzov, M; Gerasimova, N; Feofanov, A; Švedas, V; Lavrik, O; Studitsky, VM (2020). "Inhibition of poly(ADP-ribose) polymerase by nucleic acid metabolite 7-methylguanine". Int. J. Mol. Sci. 21 (6): 2159. doi: 10.3390/ijms21062159 . PMC   7139824 . PMID   32245127.
  4. ↑ Manasaryan, G; Suplatov, D; Pushkarev, S; Drobot, V; Kuimov, A; Švedas, V; Nilov, D (2021). "Bioinformatic analysis of the nicotinamide binding site in poly(ADP-ribose) polymerase family proteins". Cancers. 13 (6): 1201. doi: 10.3390/cancers13061201 . PMC   8002165 . PMID   33801950.
  5. ↑ Farkas, WR; Jacobson, KB; Katze, JR (1984). "Substrate and inhibitor specificity of tRNA-guanine ribosyltransferase". Biochim. Biophys. Acta. 781 (1–2): 64–75. doi:10.1016/0167-4781(84)90124-6. PMID   6696916.
  6. ↑ Nilov, DK; Tararov, VI; Kulikov, AV; Zakharenko, AL; Gushchina, IV; Mikhailov, SN; Lavrik, OI; Švedas, VK (2016). "Inhibition of poly(ADP-ribose) polymerase by nucleic acid metabolite 7-methylguanine". Acta Naturae. 8 (2): 108–115. doi:10.32607/20758251-2016-8-2-108-115. PMC   4947994 . PMID   27437145.
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