8-Oxoguanine

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8-Oxoguanine[1]
8-Oxoguanine.png
Names
IUPAC name
2-Amino-7,9-dihydro-1H-purine-6,8-dione
Other names
8-Oxo-7,8-dihydroguanine
Identifiers
5614-64-2 YesY
ChEBI CHEBI:44605 YesY
ChemSpider 106574 YesY
Jmol-3D images Image
Image
MeSH 8-hydroxyguanine
PubChem 119315
Properties
C5H5N5O2
Molar mass 167.13 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

8-Oxoguanine (8-hydroxyguanine, 8-oxo-Gua, or OH8Gua) is one of the most common DNA lesions resulting from reactive oxygen species [2] and can result in a mismatched pairing with Adenine resulting in G to T and C to A substitutions in the genome.[3] In humans, it is primarily repaired by the DNA glycosylase OGG1. It can be caused by ionizing radiation, in connection with oxidative metabolism.

8-oxoG (syn) in a Hoogsteen base pair with dA (anti)
For comparison here is a standard (non-mutagenic) GC base pair with both bases in the anti configuration of the bond between base and sugar.

8- Oxoguanine in Body fluids[edit]

Increased concentrations of 8-oxoguanine in body fluids have been found to be associated with increased risk of mutagenesis and carcinogenesis. [4][5]

Care must be taken in the assay of 8-oxoguanine due to the ease with which it can be oxidised during extraction and the assay procedure.[6]

References[edit]

  1. ^ 8-hydroxyguanine - Compound Summary, PubChem
  2. ^ S. Kanvah, et al., Oxidation of DNA: Damage to Nucleobases; Acc. Chem. Res. 2010, 43(2), 280-287
  3. ^ Cheng KC, Cahill DS, Kasai H, Nishimura S, Loeb LA (Jan 5, 1992). "8-Hydroxyguanine, an abundant form of oxidative DNA damage, causes G→T and C→A substitutions.". J Biol Chem. 267 (1): 166–72. PMID 1730583. 
  4. ^ Kasai, H (December 1997). "Analysis of a form of oxidative DNA damage, 8-hydroxy-2'-deoxyguanosine, as a marker of cellular oxidative stress during carcinogenesis.". Mutation research 387 (3): 147–63. doi:10.1016/s1383-5742(97)00035-5. PMID 9439711. 
  5. ^ Halliwell, B (December 1998). "Can oxidative DNA damage be used as a biomarker of cancer risk in humans? Problems, resolutions and preliminary results from nutritional supplementation studies.". Free radical research 29 (6): 469–86. doi:10.1080/10715769800300531. PMID 10098453. 
  6. ^ Ravanat, JL; Douki, T; Duez, P; Gremaud, E; Herbert, K; Hofer, T; Lasserre, L; Saint-Pierre, C; Favier, A; Cadet, J (November 2002). "Cellular background level of 8-oxo-7,8-dihydro-2'-deoxyguanosine: an isotope based method to evaluate artefactual oxidation of DNA during its extraction and subsequent work-up.". Carcinogenesis 23 (11): 1911–8. doi:10.1093/carcin/23.11.1911. PMID 12419840.