7-Methylguanine
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| 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 |
| EC Number |
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| KEGG | |
PubChem CID | |
| UNII | |
CompTox Dashboard (EPA) | |
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| 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). | |
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[edit]
- ^ 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.
- ^ 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; 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.
- ^ 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.
- ^ 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. PMC 4947994. PMID 27437145.
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