M₁G

M₁G
Names
	IUPAC name Pyrimido[1,2-a]purin-10(3H)-one
Identifiers
CAS Number	103408-45-3 ;
3D model (JSmol)	Interactive image;
ChemSpider	110673 ;
MeSH	C107643
PubChem CID	124218;
UNII	M1G1G9A3TZ ;
CompTox Dashboard (EPA)	DTXSID60145820 ;
	InChI InChI=1S/C8H5N5O/c14-7-5-6(11-4-10-5)12-8-9-2-1-3-13(7)8/h1-4H,(H,10,11) Key: ZREGNVKUSNORFO-UHFFFAOYSA-N ; 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) Key: ZREGNVKUSNORFO-UHFFFAOYAI;
	SMILES C1=CN2C(=O)C3=C(N=CN3)N=C2N=C1;
Properties
Chemical formula	C8H5N5O
Molar mass	187.162 g·mol−1
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

M₁G (pyrimido[1,2-a]purin-10(3H)-one) is a heterocyclic compound which is a by-product of base excision repair (BER) of a specific type of DNA adduct called M₁dG. The M₁dG adduct in turn is formed by a condensation reaction between guanosine nucleotides in DNA and either malondialdehyde (propanedial) ^[1] or acrolein.^[2] If not repaired, these adducts are mutagenic and carcinogenic.

Malondialdehyde is an end product of lipid peroxidation^[2] while acrolein is a result of DNA peroxidation.^[3]

M₁dG is the major endogenous DNA adduct in humans. M₁dG adducts have been detected in cell DNA in liver, leucocytes, pancreas and breast in concentrations of 1-120 per 10⁸ nucleotides.^[1] Detection and quantification of M₁dG adducts in the body as measured by free M₁G is a tool for detecting DNA damage that may lead to cancer. Free M₁G is also biomarker for oxidative stress.^[1]

References

^ ^a ^b ^c Marnett LJ (1999). "Lipid peroxidation-DNA damage by malondialdehyde". Mutat. Res. 424 (1–2): 83–95. Bibcode:1999MRFMM.424...83M. doi:10.1016/S0027-5107(99)00010-X. PMID 10064852.
^ ^a ^b Seto H, Okuda T, Takesue T, Ikemura T (1983). "Reaction of Malonaldehyde with Nucleic Acid. I. Formation of Fluorescent Pyrimido[1,2-a]purin-10(3H)-one Nucleosides". Bulletin of the Chemical Society of Japan. 56 (6): 1799–1802. doi:10.1246/bcsj.56.1799.
^ Knutson CG, Akingbade D, Crews BC, Voehler M, Stec DF, Marnett LJ (March 2007). "Metabolism in vitro and in vivo of the DNA base adduct, M1G". Chem. Res. Toxicol. 20 (3): 550–7. doi:10.1021/tx600334x. PMID 17311424.

External links

pyrimido(1,2-a)purin-10(3H)-one at the U.S. National Library of Medicine Medical Subject Headings (MeSH)
3-(2'-deoxy-beta-D-erythro-pentofuranosyl)pyrimido(1,2-alpha)purin-10(3H)-one at the U.S. National Library of Medicine Medical Subject Headings (MeSH)

[martnett-1] Marnett LJ (1999). "Lipid peroxidation-DNA damage by malondialdehyde". Mutat. Res. 424 (1–2): 83–95. Bibcode:1999MRFMM.424...83M. doi:10.1016/S0027-5107(99)00010-X. PMID 10064852.

[seto-2] Seto H, Okuda T, Takesue T, Ikemura T (1983). "Reaction of Malonaldehyde with Nucleic Acid. I. Formation of Fluorescent Pyrimido[1,2-a]purin-10(3H)-one Nucleosides". Bulletin of the Chemical Society of Japan. 56 (6): 1799–1802. doi:10.1246/bcsj.56.1799.

[pmid17311424-3] Knutson CG, Akingbade D, Crews BC, Voehler M, Stec DF, Marnett LJ (March 2007). "Metabolism in vitro and in vivo of the DNA base adduct, M1G". Chem. Res. Toxicol. 20 (3): 550–7. doi:10.1021/tx600334x. PMID 17311424.

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