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{{DISPLAYTITLE:M<sub>1</sub>G}} |
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{{DISPLAYTITLE:M<sub>1</sub>G}} |
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{{chembox |
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{{chembox |
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| Name = M<sub>1</sub>G |
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| verifiedrevid = 373444032 |
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| ImageFile = DNA-adduct M1G.png |
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| verifiedrevid = 442286189 |
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| IUPACName = pyrimidopurin-10(''3H'')-one |
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| ImageFile = File:M1G V2.png |
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| OtherNames = |
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| IUPACName = Pyrimidopurin-10(''3H'')-one |
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| Section1 = {{Chembox Identifiers |
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|Section1={{Chembox Identifiers |
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| CASNo=103408-45-3 |
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| CASNo_Ref = {{cascite|correct|??}} |
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| PubChem=124218 |
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| CASNo=103408-45-3 |
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| SMILES=C1=CN2C(=O)C3=C(N=CN3)N=C2N=C1 |
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| UNII_Ref = {{fdacite|changed|FDA}} |
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| UNII = M1G1G9A3TZ |
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| PubChem=124218 |
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| SMILES=C1=CN2C(=O)C3=C(N=CN3)N=C2N=C1 |
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| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}} |
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| ChemSpiderID = 110673 |
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| InChI = 1/C8H5N5O/c14-7-5-6(11-4-10-5)12-8-9-2-1-3-13(7)8/h1-4H,(H,10,11) |
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| InChIKey = ZREGNVKUSNORFO-UHFFFAOYAI |
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| StdInChI_Ref = {{stdinchicite|changed|chemspider}} |
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| StdInChI = 1S/C8H5N5O/c14-7-5-6(11-4-10-5)12-8-9-2-1-3-13(7)8/h1-4H,(H,10,11) |
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| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} |
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| StdInChIKey = ZREGNVKUSNORFO-UHFFFAOYSA-N |
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| RTECS = |
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| MeSHName = C107643 |
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}} |
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| Section2 = {{Chembox Properties |
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|Section2={{Chembox Properties |
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| C=8 | H=5 | N=5 | O=1 |
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| Formula=C<sub>8</sub>H<sub>5</sub>N<sub>5</sub>O |
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| MolarMass=187.1582 |
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| Section3 = {{Chembox Hazards |
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|Section3={{Chembox Hazards |
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| FlashPt= |
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'''M<sub>1</sub>G''' (pyrimido<nowiki></nowiki>purin-10(''3H'')-one) is a ] which is a ] of ] (BER) of a specific type of ] called M<sub>1</sub>dG. The M<sub>1</sub>dG adduct in turn is formed by a ] between ] nucleotides in DNA and either ]<ref name="martnett">{{cite journal | author = Marnett LJ | title = Lipid peroxidation-DNA damage by malondialdehyde | journal = Mutat. Res. | volume = 424 | issue = 1-2 | pages = 83–95 | year = 1999 | pmid = 10064852 | doi = 10.1016/S0027-5107(99)00010-X | url = | issn = }}</ref> or base ].<ref name="seto">{{cite journal | author = Seto H, Okuda T, Takesue T, Ikemura T | title = Reaction of Malonaldehyde with Nucleic Acid. I. Formation of Fluorescent Pyrimidopurin-10(3H)-one Nucleosides | journal = Bulletin of the Chemical Society of Japan | volume = 56 | issue = 6 | pages = 1799–1802 | year = 1983 | pmid = | doi = 10.1246/bcsj.56.1799 | url = | issn = }}</ref> If not repaired, these adducts are ] and ]. |
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'''M<sub>1</sub>G''' ('''pyrimidopurin-10(''3H'')-one''') is a ] which is a ] of ] (BER) of a specific type of ] called M<sub>1</sub>dG. The M<sub>1</sub>dG adduct in turn is formed by a ] between ] nucleotides in ] and either ] (propanedial) <ref name="martnett">{{cite journal | author = Marnett LJ | title = Lipid peroxidation-DNA damage by malondialdehyde | journal = Mutat. Res. | volume = 424 | issue = 1–2 | pages = 83–95 | year = 1999 | pmid = 10064852 | doi = 10.1016/S0027-5107(99)00010-X | bibcode = 1999MRFMM.424...83M }}</ref> or ].<ref name="seto">{{cite journal |vauthors=Seto H, Okuda T, Takesue T, Ikemura T | title = Reaction of Malonaldehyde with Nucleic Acid. I. Formation of Fluorescent Pyrimidopurin-10(3H)-one Nucleosides | journal = Bulletin of the Chemical Society of Japan | volume = 56 | issue = 6 | pages = 1799–1802 | year = 1983 | doi = 10.1246/bcsj.56.1799 | doi-access = free }}</ref> If not repaired, these adducts are ]ic and ]ic. |
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Malondialdehyde is an end product of ]<ref name="seto"/> while base propenal is a result of DNA peroxidation.<ref name="pmid17311424">{{cite journal | author = Knutson CG, Akingbade D, Crews BC, Voehler M, Stec DF, Marnett LJ | title = Metabolism in vitro and in vivo of the DNA base adduct, M1G | journal = Chem. Res. Toxicol. | volume = 20 | issue = 3 | pages = 550–7 | year = 2007 | month = March | pmid = 17311424 | doi = 10.1021/tx600334x | url = | issn = }}</ref> |
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Malondialdehyde is an end product of ]<ref name="seto"/> while ] is a result of DNA peroxidation.<ref name="pmid17311424">{{cite journal |vauthors=Knutson CG, Akingbade D, Crews BC, Voehler M, Stec DF, Marnett LJ | title = Metabolism in vitro and in vivo of the DNA base adduct, M1G | journal = Chem. Res. Toxicol. | volume = 20 | issue = 3 | pages = 550–7 |date=March 2007 | pmid = 17311424 | doi = 10.1021/tx600334x | doi-access = free }}</ref> |
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M<sub>1</sub>dG is the major ] DNA adduct in humans. M<sub>1</sub>dG adducts have been detected in cell DNA in ], ], ] and ] in concentrations of 1-120 per 10<sup>8</sup> ].<ref name="martnett"/> Detection and quantification of M<sub>1</sub>dG adducts in the body as measured by free M<sub>1</sub>G is a tool for detecting DNA damage that may lead to cancer. Free M<sub>1</sub>G is also ] for ].<ref name="martnett"/> |
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M<sub>1</sub>dG is the major ] DNA adduct in humans. M<sub>1</sub>dG adducts have been detected in cell DNA in ], ], ] and ] in concentrations of 1-120 per 10<sup>8</sup> ].<ref name="martnett"/> Detection and quantification of M<sub>1</sub>dG adducts in the body as measured by free M<sub>1</sub>G is a tool for detecting DNA damage that may lead to cancer. Free M<sub>1</sub>G is also ] for ].<ref name="martnett"/> |
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==References== |
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==References== |
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* {{MeshName|pyrimido(1,2-a)purin-10(3H)-one}} |
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* {{MeshName|pyrimido(1,2-a)purin-10(3H)-one}} |
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* {{MeshName|3-(2'-deoxy-beta-D-erythro-pentofuranosyl)pyrimido(1,2-alpha)purin-10(3H)-one}} |
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* {{MeshName|3-(2'-deoxy-beta-D-erythro-pentofuranosyl)pyrimido(1,2-alpha)purin-10(3H)-one}} |
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{{biochemistry-stub}} |
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