| Revision as of 10:40, 17 February 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{chembox}} taken from revid 464810689 of page 7-Methylguanosine for the Chem/Drugbox validation project (updated: 'ChEBI', 'CASNo'). |
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{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}} |
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{{Chembox |
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{{Chembox |
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| ImageFile = 7-Methylguanosine.svg |
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| verifiedrevid = 477346139 |
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| ImageFile = 7methylguanine.png |
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| ImageSize = 180px |
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| ImageSize = 180px |
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| ImageFile1 = |
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| IUPACName = 7-Methylguanosine |
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| ImageSize1 = 180px |
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| OtherNames = N7-Methylguanosine; 2-Amino-1,6-dihydro-7-methyl-6-oxo-9-β-<small>D</small>-ribofuranosylpurinium |
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| IUPACName = 7-Methylguanine |
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| Section1 = {{Chembox Identifiers |
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| PIN = 2-Amino-7-methyl-1,7-dihydro-6''H''-purin-6-one |
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| Abbreviations = m7G; m<sup>7</sup>G |
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| OtherNames = N7-Methylguanine; Epiguanine |
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| CASNo = <!-- blanked - oldvalue: 20244-86-4 --> |
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|Section1={{Chembox Identifiers |
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| CASNo_Ref = {{cascite|correct|}} |
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| ChEBI = 20794 |
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| Abbreviations = |
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| PubChem = 445404 |
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| CASNo = 578-76-7 |
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| CASNo_Ref = {{cascite|correct|Pubchem}} |
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| ChemSpiderID = 393054 |
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| ChEBI_Ref = {{ebicite|correct|EBI}} |
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| SMILES = O=C3/N=C(/N)Nc1c3n(c12O((O)2O)CO)C |
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| ChEBI = 2274 |
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| InChI = 1/C11H15N5O5/c1-15-3-16(8-5(15)9(20)14-11(12)13-8)10-7(19)6(18)4(2-17)21-10/h3-4,6-7,10,17-19H,2H2,1H3,(H2-,12,13,14,20)/p+1/t4-,6-,7-,10-/m1/s1 |
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| PubChem = 135398679 |
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| InChIKey = OGHAROSJZRTIOK-UJMNIJGGBX |
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| Beilstein = 174245 |
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| StdInChI = 1S/C11H15N5O5/c1-15-3-16(8-5(15)9(20)14-11(12)13-8)10-7(19)6(18)4(2-17)21-10/h3-4,6-7,10,17-19H,2H2,1H3,(H2-,12,13,14,20)/p+1/t4-,6-,7-,10-/m1/s1 |
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| KEGG = C02242 |
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| StdInChIKey = OGHAROSJZRTIOK-KQYNXXCUSA-O |
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| EC_number = 209-431-0 |
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| UNII = 661J4K04NB |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 10883 |
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| SMILES = CN1C=NC2=C1C(=O)N=C(N2)N |
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| StdInChI = 1S/C6H7N5O/c1-11-2-8-4-3(11)5(12)10-6(7)9-4/h2H,1H3,(H3,7,9,10,12) |
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| StdInChIKey = FZWGECJQACGGTI-UHFFFAOYSA-N |
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| Section2 = {{Chembox Properties |
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|Section2={{Chembox Properties |
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| C=11|H=16|N=5|O=5 |
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| C=6 | H=7 | N=5 | O=1 |
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| Section3 = {{Chembox Hazards |
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| MainHazards = |
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'''7-Methylguanine''' is a modified ] ]. It is a ] version of ]. The 7-methylguanine ] is called ]. However, the free 7-methylguanine base is not involved in the synthesis of nucleotides and not incorporated directly into nucleic acids.<ref>{{cite journal | pmid = 5669851 | year = 1968 | last1 = Craddock | first1 = VM | last2 = Mattocks | first2 = AR | last3 = Magee | first3 = PN | title = The fate of 7-methylguanine after administration to the rat | volume = 109 | pages = 75–78 | journal = Biochem. J. | issue = 1 | doi=10.1042/bj1090075| pmc = 1186754 }}</ref><ref>{{cite journal | pmid = 6835224 | year = 1983 | last1 = Kaina | first1 = B | last2 = Heindorff | first2 = K | last3 = Aurich | first3 = O | title = O6-methylguanine, but not N7-methylguanine or N3-methyladenine, induces gene mutations, sister-chromatid exchanges and chromosomal aberrations in Chinese hamster cells | volume = 108 | pages = 279–292 | journal = Mutat. Res. | issue = 1–3 | doi=10.1016/0027-5107(83)90126-4}}</ref> 7-Methylguanine is a natural inhibitor of ] (PARP) and tRNA guanine transglycosylase (TGT) - and thus may exert anticancer activity.<ref>{{cite journal | pmid = 32245127 | year = 2020 | last1 = Nilov | first1 = D | last2 = Maluchenko | first2 = N | last3 = Kurgina | first3 = T | last4 = Pushkarev | first4 = S | last5 = Lys | first5 = A | last6 = Kutuzov | first6 = M | last7 = Gerasimova | first7 = N | last8 = Feofanov | first8 = A | last9 = Švedas | first9 = V | last10 = Lavrik | first10 = O | last11 = Studitsky | first11 = VM | title = Inhibition of poly(ADP-ribose) polymerase by nucleic acid metabolite 7-methylguanine | volume = 21 | pages = 2159 | journal = Int. J. Mol. Sci. | issue = 6 | doi=10.3390/ijms21062159| pmc = 7139824 | doi-access = free }}</ref><ref>{{cite journal | pmid = 33801950 | year = 2021 | last1 = Manasaryan | first1 = G | last2 = Suplatov | first2 = D | last3 = Pushkarev | first3 = S | last4 = Drobot | first4 = V | last5 = Kuimov | first5 = A | last6 = Švedas | first6 = V | last7 = Nilov | first7 = D | title = Bioinformatic analysis of the nicotinamide binding site in poly(ADP-ribose) polymerase family proteins | volume = 13 | pages = 1201 | journal = Cancers | issue = 6 | doi=10.3390/cancers13061201| pmc = 8002165 | doi-access = free }}</ref><ref>{{cite journal | pmid = 6696916 | year = 1984 | last1 = Farkas | first1 = WR | last2 = Jacobson | first2 = KB | last3 = Katze | first3 = JR | title = Substrate and inhibitor specificity of tRNA-guanine ribosyltransferase | volume = 781 | pages = 64–75 | journal = Biochim. Biophys. Acta | issue = 1–2 | doi=10.1016/0167-4781(84)90124-6}}</ref> For example, it was demonstrated that 7-methylguanine could accelerate apoptotic death of BRCA1-deficient breast cancer cells induced by cisplatin and doxorubicin.<ref>{{cite journal | pmid = 27437145 | year = 2016 | last1 = Nilov | first1 = DK | last2 = Tararov | first2 = VI | last3 = Kulikov | first3 = AV | last4 = Zakharenko | first4 = AL | last5 = Gushchina | first5 = IV | last6 = Mikhailov | first6 = SN | last7 = Lavrik | first7 = OI | last8 = Švedas | first8 = VK | title = Inhibition of poly(ADP-ribose) polymerase by nucleic acid metabolite 7-methylguanine | volume = 8 | pages = 108–115 | journal = Acta Naturae| issue = 2 | doi = 10.32607/20758251-2016-8-2-108-115 | pmc = 4947994 }}</ref> |
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==References== |
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{{reflist}} |
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{{DEFAULTSORT:Methylguanine, 7-}} |
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{{organic-compound-stub}} |