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

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) [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. ↑ 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. ↑ 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.
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.

## 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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*[CID]: Compound ID