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7-Methylguanine Sale

(Synonyms: 7-甲基鸟嘌呤) 目录号 : GC33616

A nucleotide metabolite

7-Methylguanine Chemical Structure

Cas No.:578-76-7

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5mg
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产品描述

7-Methylguanine is a metabolite of the natural purine base whose N9 position is available for chemical modifications.1 This genotoxic adduct can be generated by DNA methylation and has been used as a probe of protein-DNA interactions and for DNA sequencing methods.2 It is also considered to be a carcinogenic biomarker for cigarette smoking that is detectable in urine.3

1.Kozma, A., Ibá?ez, S., Silaghi-Dumitrescu, R., et al.7-Methylguanine: Protonation, formation of linkage isomers with trans-(NH3)2Pt(II), and base pairing propertiesDalton Trans.416094-6103(2012) 2.Lee, S., Bowman, B.R., Ueno, Y., et al.Synthesis and structure of duplex DNA containing the genotoxic nucleobase lesion N7-methylguanineJ. Am. Chem. Soc.130(35)11570-11571(2008) 3.Lee, H.L., Hsueh, Y.M., Chung, C.J., et al.Correlation between the urine profile of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone metabolites and N7-methylguanine in urothelial carcinoma patientsCancer Epigemiol. Biomarkers Prev.17(12)3390-3395(2008)

Chemical Properties

Cas No. 578-76-7 SDF
别名 7-甲基鸟嘌呤
Canonical SMILES O=C1NC(N)=NC2=C1N(C)C=N2
分子式 C6H7N5O 分子量 165.15
溶解度 1 M NaOH: 50 mg/ml 储存条件 Store at -20°C
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1 mM 6.0551 mL 30.2755 mL 60.551 mL
5 mM 1.211 mL 6.0551 mL 12.1102 mL
10 mM 0.6055 mL 3.0276 mL 6.0551 mL
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Research Update

Toxicological Properties of 7-Methylguanine, and Preliminary Data on its Anticancer Activity

Front Pharmacol 2022 Jul 6;13:842316.PMID:35873588DOI:10.3389/fphar.2022.842316.

7-Methylguanine (7-MG) competitively inhibits the DNA repair enzyme poly(ADP-ribose) polymerase (PARP) and RNA-modifying enzyme tRNA-guanine transglycosylase (TGT) and represents a potential anticancer drug candidate. Furthermore, as a natural compound, it could escape the serious side effects characteristic for approved synthetic PARP inhibitors. Here we present a comprehensive study of toxicological and carcinogenic properties of 7-MG. It was demonstrated that 7-MG does not induce mutations or structural chromosomal abnormalities, and has no blastomogenic activity. A treatment regimen with 7-MG has been established in mice (50 mg/kg per os, 3 times per week), exerting no adverse effects or changes in morphology. Preliminary data on the 7-MG anticancer activity obtained on transplantable tumor models support our conclusions that 7-MG can become a promising new component of chemotherapy.

Molecular Mechanisms of PARP-1 Inhibitor 7-Methylguanine

Int J Mol Sci 2020 Mar 20;21(6):2159.PMID:32245127DOI:10.3390/ijms21062159.

7-Methylguanine (7-MG), a natural compound that inhibits DNA repair enzyme poly(ADP-ribose) polymerase 1 (PARP-1), can be considered as a potential anticancer drug candidate. Here we describe a study of 7-MG inhibition mechanism using molecular dynamics, fluorescence anisotropy and single-particle Förster resonance energy transfer (spFRET) microscopy approaches to elucidate intermolecular interactions between 7-MG, PARP-1 and nucleosomal DNA. It is shown that 7-MG competes with substrate NAD+ and its binding in the PARP-1 active site is mediated by hydrogen bonds and nonpolar interactions with the Gly863, Ala898, Ser904, and Tyr907 residues. 7-MG promotes formation of the PARP-1-nucleosome complexes and suppresses DNA-dependent PARP-1 automodification. This results in nonproductive trapping of PARP-1 on nucleosomes and likely prevents the removal of genotoxic DNA lesions.

Inhibitory Effects of 7-Methylguanine and Its Metabolite 8-Hydroxy-7-Methylguanine on Human Poly(ADP-Ribose) Polymerase 1

Biochemistry (Mosc) 2022 Aug;87(8):823-831.PMID:36171646DOI:10.1134/S0006297922080132.

Previously, we have found that a nucleic acid metabolite, 7-Methylguanine (7mGua), produced in the body can have an inhibitory effect on the poly(ADP-ribose) polymerase 1 (PARP1) enzyme, an important pharmacological target in anticancer therapy. In this work, using an original method of analysis of PARP1 activity based on monitoring fluorescence anisotropy, we studied inhibitory properties of 7mGua and its metabolite, 8-hydroxy-7-methylguanine (8h7mGua). Both compounds inhibited PARP1 enzymatic activity in a dose-dependent manner, however, 8h7mGua was shown to be a stronger inhibitor. The IC50 values for 8h7mGua at different concentrations of the NAD+ substrate were found to be 4 times lower, on average, than those for 7mGua. The more efficient binding of 8h7mGua in the PARP1 active site is explained by the presence of an additional hydrogen bond with the Glu988 catalytic residue. Experimental and computational studies did not reveal the effect of 7mGua and 8h7mGua on the activity of other DNA repair enzymes, indicating selectivity of their inhibitory action.

7-Methylguanine: protonation, formation of linkage isomers with trans-(NH3)2Pt(II), and base pairing properties

Dalton Trans 2012 May 28;41(20):6094-103.PMID:22354137DOI:10.1039/c2dt12228f.

Three protonated forms of 7-Methylguanine (7-MeGH, 1) with different counter ions, [7-MeGH(2)]X (X = NO(3), 1a; ClO(4), 1b; BF(4), 1c) and two Pt(II) complexes, trans-[Pt(NH(3))(2)(7-MeGH-N9)(2)](ClO(4))(2) (4) and trans-[Pt(NH(3))(2)(7-MeGH-N9)(7-MeGH-N3)](ClO(4))(2)·3H(2)O (5) are described and their X-ray crystal structures are reported. 1a-1c form infinite ribbons via pairs of intermolecular hydrogen bonds between N1H···O6 and N3···N2H(2) sites, with anions connecting individual ribbons, thereby generating extended sheets. 4 and 5 do not display unusual features, except that 5 represents a rare case of a bis(nucleobase) complex of Pt(II) in which linkage isomers occur. Unlike in a previously reported compound, [Pt(dien)(7-MeGH-N9)](NO(3))(ClO(4)), the Pt coordination planes and the 7-MeGH planes are not coplanar in 4 and 5. The hydrogen bonding behaviour of 7-MeGH, free and when platinated at N9 (complex 4), was studied in Me(2)SO-d(6). It revealed the following: (i) there is no detectable self-association of 1 in Me(2)SO solution. (ii) 1 and 1-methylcytosine (1-MeC) form Watson-Crick pairs. (iii) 4 does not self-associate. (iv) 4 associates with 1-MeC in the Watson-Crick fashion. (v) 4 and 1 interact in solution, but no model can be proposed at present. (vi) Remarkable interaction shifts between 4 and 1 occur when NH(3) is liberated from trans-(NH(3))(2)Pt(II) to give NH(4)(+) in Me(2)SO-d(6). Feasible models, which imply the presence of deprotonated 7-MeG(-) species are proposed. Finally, DFT calculations were carried out to qualitatively estimate the effect of 7-MeGH acidity in [Pt(dien)(7-MeGH-N9)](2+) in dependence of the dihedral angle between the Pt coordination plane and the nucleobase.

Evaluation of carboxyfluorescein-labeled 7-Methylguanine nucleotides as probes for studying cap-binding proteins by fluorescence anisotropy

Sci Rep 2021 Apr 8;11(1):7687.PMID:33833335DOI:10.1038/s41598-021-87306-8.

Fluorescence anisotropy (FA) is a powerful technique for the discovery of protein inhibitors in a high-throughput manner. In this study, we sought to develop new universal FA-based assays for the evaluation of compounds targeting mRNA 5' cap-binding proteins of therapeutic interest, including eukaryotic translation initiation factor 4E and scavenger decapping enzyme. For this purpose, a library of 19 carboxyfluorescein probes based on 7-Methylguanine nucleotides was evaluated as FA probes for these proteins. Optimal probe:protein systems were further investigated in competitive binding experiments and adapted for high-throughput screening. Using a small in-house library of compounds, we verified and confirmed the accuracy of the developed FA assay to study cap-binding protein binders. The applications of the most promising probes were then extended to include evaluation of allosteric inhibitors as well as RNA ligands. From this analysis, we confirmed the utility of the method to study small molecule ligands and evaluate differently 5' capped RNAs.