M1G

From Wikipedia, the free encyclopedia
Jump to: navigation, search
M1G
DNA-adduct M1G.png
Identifiers
CAS number 103408-45-3 YesY
PubChem 124218
ChemSpider 110673
MeSH C107643
Jmol-3D images Image 1
Properties
Molecular formula C8H5N5O
Molar mass 187.1582
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
 YesY (verify) (what is: YesY/N?)
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[1] or base propenal.[2] If not repaired, these adducts are mutagenic and carcinogenic.

Malondialdehyde is an end product of lipid peroxidation[2] while base propenal 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[edit]

  1. ^ a b c 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. ^ 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. 
  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. 

External links[edit]