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 Y

3D model (JSmol)

* Interactive image
* Interactive image

ChEBI |

* CHEBI:44605 Y

ChemSpider |

* 106574 Y

MeSH | 8-hydroxyguanine

PubChem CID

* 119315

UNII |

* V5WDN6HY4L Y

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) Y

Key: UBKVUFQGVWHZIR-UHFFFAOYSA-N Y

* 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 | 167.128 g·mol−1

Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Y verify (what is YN ?)
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] modifying guanine, 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]

## Cancer, aging, infertility

The role of the deoxyriboside form of 8-oxoguanine, 8-oxo-2'-deoxyguanosine (abbreviated 8-oxo-dG or 8-OHdG) in cancer and aging also applies to 8-oxoguanine. Oxoguanine glycosylase is employed in the removal of 8-oxoguanine from DNA by the process of base excision repair. As described in oxoguanine glycosylase, deficient expression of this enzyme causes 8-oxoguanine to accumulate in DNA. This accumulation may then lead upon replication of DNA to mutations including some that contribute to carcinogenesis. 8-oxoguanine is usually formed by the interaction of reactive oxygen species (ROS) with the guanine base in DNA under conditions of oxidative stress; as noted in the article about them, such species may have a role in aging and male infertility, and 8-oxoguanine can be used to measure such stress.

## References

1. ↑ 8-hydroxyguanine - Compound Summary, PubChem
2. ↑ Kanvah, S. (2010). "Oxidation of DNA: Damage to Nucleobases". Acc. Chem. Res. 43 (2): 280–287. doi:10.1021/ar900175a. PMID 19938827.
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. doi:10.1016/S0021-9258(18)48474-8. 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 et al. (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.

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Nucleic acid constituents

Nucleobase|

* Purine
* Adenine
* Guanine
* Hypoxanthine
* Xanthine
* Purine analogue
* Pyrimidine
* Uracil
* Thymine
* Cytosine
* Pyrimidine analogue
* Unnatural base pair (UBP)

Nucleoside|

| Ribonucleoside|

* Adenosine
* Guanosine
* 5-Methyluridine
* Uridine
* 5-Methylcytidine
* Cytidine
* Pseudouridine
* Inosine
* N6-Methyladenosine
* Xanthosine
* Wybutosine

|

Deoxyribonucleoside|

* Deoxyadenosine
* Deoxyguanosine
* Thymidine
* Deoxyuridine
* Deoxycytidine
* Deoxyinosine
* Deoxyxanthosine

Nucleotide
(Nucleoside monophosphate)|

| Ribonucleotide|

* AMP
* GMP
* m5UMP
* UMP
* CMP
* IMP
* XMP

|

Deoxyribonucleotide|

* dAMP
* dGMP
* dTMP
* dUMP
* dCMP
* dIMP
* dXMP

Cyclic nucleotide|

* cAMP
* cGMP
* c-di-GMP
* c-di-AMP
* cADPR

Nucleoside diphosphate|

* ADP
* GDP
* m5UDP
* UDP
* CDP

* dADP
* dGDP
* dTDP
* dUDP
* dCDP

Nucleoside triphosphate|

* ATP
* GTP
* m5UTP
* UTP
* CTP
* ITP
* XTP

* dATP
* dGTP
* dTTP
* dUTP
* dCTP
* dITP
* dXTP

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DNA repair

Excision repair|

* Base excision repair/AP site
* DNA glycosylase
* Uracil-DNA glycosylase
* Poly ADP ribose polymerase
* Nucleotide excision repair/ERCC
* XPA
* XPB
* XPC
* XPD/ERCC2
* XPE/DDB1
* XPF/DDB1
* XPG/ERCC5
* ERCC1
* RPA
* RAD23A
* RAD23B
* Excinuclease
* DNA mismatch repair
* MLH1
* MSH2

Other forms of repair|

* Transcription-coupled repair
* ERCC6
* ERCC8
* Homology directed repair
* Non-homologous end joining
* Ku
* Microhomology-mediated end joining
* Postreplication repair
* Photolyase
* CRY1
* CRY2

Other/ungrouped proteins|

* Ogt
* PcrA
* Proliferating Cell Nuclear Antigen
* Homologous recombination
* RecA/RAD51
* Sgs1
* Slx4

Regulation|

* SOS box
* SOS response

Other/ungrouped|

* 8-Oxoguanine
* Adaptive response
* Meiotic recombination checkpoint
* RecF pathway

* DNA helicase: BLM
* WRN

* FANC proteins: core protein complex
* FANCA
* FANCB
* FANCC
* FANCE
* FANCF
* FANCG
* FANCL
* FANCM
* FANCD1
* FANCD2
* FANCI
* FANCJ
* FANCN

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