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 ;
	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).
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	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

↑ ^1.0 ^1.1 ^1.2 Marnett LJ (1999). "Lipid peroxidation-DNA damage by malondialdehyde". Mutat. Res. 424 (1–2): 83–95. doi:10.1016/S0027-5107(99)00010-X. PMID 10064852.
↑ ^2.0 ^2.1 "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. 1983. doi:10.1246/bcsj.56.1799.
↑ "Metabolism in vitro and in vivo of the DNA base adduct, M1G". Chem. Res. Toxicol. 20 (3): 550–7. March 2007. doi:10.1021/tx600334x. PMID 17311424.

External links

pyrimido(1,2-a)purin-10(3H)-one at the US 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 US National Library of Medicine Medical Subject Headings (MeSH)

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[martnett-1] 1.0 ^1.1 ^1.2 Marnett LJ (1999). "Lipid peroxidation-DNA damage by malondialdehyde". Mutat. Res. 424 (1–2): 83–95. doi:10.1016/S0027-5107(99)00010-X. PMID 10064852.

[seto-2] 2.0 ^2.1 "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. 1983. doi:10.1246/bcsj.56.1799.

[pmid17311424-3] "Metabolism in vitro and in vivo of the DNA base adduct, M1G". Chem. Res. Toxicol. 20 (3): 550–7. March 2007. doi:10.1021/tx600334x. PMID 17311424.

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M1G

Topic: Chemistry

References

External links