7-Methylguanine

7-Methylguanine
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
CAS Number	578-76-7 [Pubchem];
3D model (JSmol)	Interactive image;
Beilstein Reference	174245
ChEBI	CHEBI:2274 ;
ChemSpider	10883 ;
EC Number	209-431-0;
KEGG	C02242;
PubChem CID	135398679;
UNII	661J4K04NB;
	InChI 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;
	SMILES CN1C=NC2=C1C(=O)N=C(N2)N;
Properties
Chemical formula	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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	Infobox references

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

↑ 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. PMID 5669851.
↑ 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.
↑ Nilov, D; Maluchenko, N; Kurgina, T; Pushkarev, S; Lys, A; Kutuzov, M; Gerasimova, N; Feofanov, A et al. (2020). "Inhibition of poly(ADP-ribose) polymerase by nucleic acid metabolite 7-methylguanine". Int. J. Mol. Sci. 21 (6): 2159. doi:10.3390/ijms21062159. PMID 32245127.
↑ 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. PMID 33801950.
↑ 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.
↑ 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. PMID 27437145.

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[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. 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 et al. (2020). "Inhibition of poly(ADP-ribose) polymerase by nucleic acid metabolite 7-methylguanine". Int. J. Mol. Sci. 21 (6): 2159. doi:10.3390/ijms21062159. 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. 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. PMID 27437145.

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7-Methylguanine

Topic: Chemistry

References