M1G

M₁G

Names
IUPAC name Pyrimido[1,2-a]purin-10(3H)-one
Identifiers
CAS Number	103408-45-3 Y
3D model (JSmol)	Interactive image
ChemSpider	110673 N
MeSH	C107643
PubChem CID	124218
UNII	M1G1G9A3TZ N
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) N Key: ZREGNVKUSNORFO-UHFFFAOYSA-N 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). N verify (what is YN ?) 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) or acrolein. If not repaired, these adducts are mutagenic and carcinogenic.

Malondialdehyde is an end product of lipid peroxidation while acrolein is a result of DNA peroxidation.

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 10⁸nucleotides. 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.

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)