8-Oxoguanine

8-Oxoguanine^[1]

Names
IUPAC name 2-Amino-7,9-dihydro-1H-purine-6,8-dione
Other names 7,8-Dihydro-8-oxoguanine; 8-Oxo-7,8-dihydroguanine
Identifiers
CAS Number	5614-64-2
3D model (Jmol)	Interactive image Interactive image
ChEBI	CHEBI:44605
ChemSpider	106574
ECHA InfoCard	100.024.578
MeSH	8-hydroxyguanine
PubChem	119315
InChI InChI=1S/C5H3N5O2/c6-4-8-2-1(3(11)10-4)7-5(12)9-2/h(H3,6,8,9,10,11,12) Key: UBKVUFQGVWHZIR-UHFFFAOYSA-N InChI=1/C5H5N5O2/c6-4-8-2-1(3(11)10-4)7-5(12)9-2/h(H5,6,7,8,9,10,11,12) Key: CLGFIVUFZRGQRP-UHFFFAOYAZ InChI=1/C5H3N5O2/c6-4-8-2-1(3(11)10-4)7-5(12)9-2/h(H3,6,8,9,10,11,12) Key: UBKVUFQGVWHZIR-UHFFFAOYAW
SMILES O=C2NC=1N\C(=N/C(=O)C=1N2)N c12=NC(=O)N=c1[nH]c(nc2=O)N
Properties
Chemical formula	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 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.

In body fluids

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]

See also

• 8-Oxo-2'-deoxyguanosine

References

1. 8-hydroxyguanine - Compound Summary, PubChem
2. Kanvah, S.; et al. (2010). ", Oxidation of DNA: Damage to Nucleobases". Acc. Chem. Res. 43 (2): 280–287. doi:10.1021/ar900175a.
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.