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 Y[Pubchem]

3D model (JSmol)

* Interactive image

Beilstein Reference

| 174245
ChEBI |

* CHEBI:2274 Y

ChemSpider |

* 10883 Y

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).

N verify (what is YN ?)
Infobox references

Tracking categories (test):

* SizeSet

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. 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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*[CID]: Compound ID