DNAmod: 8-oxoguanine

Description

An oxopurine that is guanine which is substituted by an oxo group at position 8.

Chemical properties

Chemical formula	Net charge	Average mass
C5H3N5O2	0	165.10960

Recommended notation

Name	8-oxoguanine
Abbreviation	8oxoG
Symbol	o

Nomenclature

IUPAC	SMILES	InChI	InChIKey
2-amino-1H-purine-6,8-dione	Nc1nc2=NC(=O)N=c2c(=O)[nH]1	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)	UBKVUFQGVWHZIR-UHFFFAOYSA-N

Mapping techniques

Method	Method detail	Resolution	Qualifier	References
SMRT	direct detection	single-base	target sequences	Clark, TA, et al. 2011. Direct detection and sequencing of damaged DNA bases. Genome Integrity. 2.
array-based profiling	affinity-based	low	target sequences	Yoshihara, M, et al. 2014. Genome-wide profiling of 8-oxoguanine reveals its association with spatial positioning in nucleus. DNA Research : An International Journal For Rapid Publication of Reports On Genes and Genomes. 21(6).
fluorescence in situ hybridization	affinity-based	low	target sequences	Ohno, M, et al. 2006. A genome-wide distribution of 8-oxoguanine correlates with the preferred regions for recombination and single nucleotide polymorphism in the human genome. Genome Research. 16(5).
gap ligation	excision repair enzyme-based	high	target sequences	Riedl, J, et al. 2016. Sequencing of DNA Lesions Facilitated by Site-Specific Excision via Base Excision Repair DNA Glycosylases Yielding Ligatable Gaps. Journal of the American Chemical Society. 138(2).
immunoprecipitation	affinity-based	low	target sequences	Akatsuka, S, et al. 2006. Contrasting genome-wide distribution of 8-hydroxyguanine and acrolein-modified adenine during oxidative stress-induced renal carcinogenesis. The American Journal of Pathology. 169(4).
nanopore	direct detection	single-base	target sequences	An, N, et al. 2015. Nanopore detection of 8-oxoguanine in the human telomere repeat sequence. ACS Nano. 9(4). Wang, F, et al. 2017. Solid-State Nanopore Analysis of Diverse DNA Base Modifications Using a Modular Enzymatic Labeling Process. Nano Letters. 17(11).

Nature

Origin	Function	Functional detail	Organisms	References
natural	damage and epigenetic mark	reactive oxygen species	Homo sapiens	Shigenaga, MK, et al. 1989. Urinary 8-hydroxy-2'-deoxyguanosine as a biological marker of in vivo oxidative DNA damage. Proceedings of the National Academy of Sciences of the United States of America. 86(24). Ravanat, JL, et al. 1999. Simultaneous determination of five oxidative DNA lesions in human urine. Chemical Research in Toxicology. 12(9). Fleming, AM, et al. 2017. 8-Oxo-7,8-dihydroguanine, friend and foe: Epigenetic-like regulator versus initiator of mutagenesis. DNA Repair. 56.

Database references:

CHEBI:44605

Citations

Akatsuka, S, et al. 2006. Contrasting genome-wide distribution of 8-hydroxyguanine and acrolein-modified adenine during oxidative stress-induced renal carcinogenesis. The American Journal of Pathology. 169(4).
An, N, et al. 2015. Nanopore detection of 8-oxoguanine in the human telomere repeat sequence. ACS Nano. 9(4).
Clark, TA, et al. 2011. Direct detection and sequencing of damaged DNA bases. Genome Integrity. 2.
Fleming, AM, et al. 2017. 8-Oxo-7,8-dihydroguanine, friend and foe: Epigenetic-like regulator versus initiator of mutagenesis. DNA Repair. 56.
Ohno, M, et al. 2006. A genome-wide distribution of 8-oxoguanine correlates with the preferred regions for recombination and single nucleotide polymorphism in the human genome. Genome Research. 16(5).
Ravanat, JL, et al. 1999. Simultaneous determination of five oxidative DNA lesions in human urine. Chemical Research in Toxicology. 12(9).
Riedl, J, et al. 2016. Sequencing of DNA Lesions Facilitated by Site-Specific Excision via Base Excision Repair DNA Glycosylases Yielding Ligatable Gaps. Journal of the American Chemical Society. 138(2).
Shigenaga, MK, et al. 1989. Urinary 8-hydroxy-2'-deoxyguanosine as a biological marker of in vivo oxidative DNA damage. Proceedings of the National Academy of Sciences of the United States of America. 86(24).
Wang, F, et al. 2017. Solid-State Nanopore Analysis of Diverse DNA Base Modifications Using a Modular Enzymatic Labeling Process. Nano Letters. 17(11).
Yoshihara, M, et al. 2014. Genome-wide profiling of 8-oxoguanine reveals its association with spatial positioning in nucleus. DNA Research : An International Journal For Rapid Publication of Reports On Genes and Genomes. 21(6).