Description
A nucleobase analogue obtained by addition of an etheno group across positions N2 and 3 of guanine.
Chemical properties
| Chemical formula | Net charge | Average mass |
|---|---|---|
| C7H5N5O | 0 | 175.148 |
,3-ethenoguanine.svg)
Recommended notation
| Name | N2,3-ethenoguanine |
|---|---|
| Abbreviation | N(2),3-ɛG |
Nomenclature
| IUPAC | SMILES | InChI | InChIKey | Synonyms |
|---|---|---|---|---|
| 1H-imidazo(2,1-b)purin-4(5H)-one | O=C1NC=2N(C=3NC=NC31)C=CN2 | InChI=1S/C7H5N5O/c13-6-4-5(10-3-9-4)12-2-1-8-7(12)11-6/h1-3H,(H,9,10)(H,8,11,13) | OSXKHFTZRHDUJN-UHFFFAOYSA-N |
|
Nature
| Origin | Function | Functional detail |
Organisms
|
References |
|---|---|---|---|---|
| natural | damage | mutagenic | Homo sapiens |
|
Citations
- Chang, SC, et al. 2015. Next-generation sequencing reveals the biological significance of the N(2),3-ethenoguanine lesion in vivo. Nucleic Acids Research. 43(11).
- Choi, JH, et al. 2004. DNA damage and mutations produced by chloroacetaldehyde in a CpG-methylated target gene. Mutation Research. 568(2).
- Gros, L, et al. 2003. Enzymology of repair of etheno-adducts. Mutation Research. 531(1-2).
- Ham, AJ, et al. 1999. Immunoaffinity/gas chromatography/high-resolution mass spectrometry method for the detection of N(2),3-ethenoguanine. Chemical Research in Toxicology. 12(12).
- Ham, AJ, et al. 2000. 4-Hydroxy-2-nonenal and ethyl linoleate form N(2),3-ethenoguanine under peroxidizing conditions. Chemical Research in Toxicology. 13(12).
- Morinello, EJ, et al. 2001. Simultaneous quantitation of N(2),3-ethenoguanine and 1,N(2)-ethenoguanine with an immunoaffinity/gas chromatography/high-resolution mass spectrometry assay. Chemical Research in Toxicology. 14(3).
- Morinello, EJ, et al. 2002. Differential induction of N(2),3-ethenoguanine in rat brain and liver after exposure to vinyl chloride. Cancer Research. 62(18).
- Morinello, EJ, et al. 2002. Molecular dosimetry and repair of N(2),3-ethenoguanine in rats exposed to vinyl chloride. Cancer Research. 62(18).
- Mutlu, E, et al. 2010. Development and application of an LC-MS/MS method for the detection of the vinyl chloride-induced DNA adduct N(2),3-ethenoguanine in tissues of adult and weanling rats following exposure to [(13)C(2)]-VC. Chemical Research in Toxicology. 23(9).
- Mutlu, E, et al. 2016. Polychlorinated Biphenyls Induce Oxidative DNA Adducts in Female Sprague-Dawley Rats. Chemical Research in Toxicology. 29(8).
- Srinivasadesikan, V, et al. 2011. Model calculations for the misincorporation of nucleotides opposite five-membered exocyclic DNA adduct: N(2),3-ethenoguanine. The Journal of Physical Chemistry. B. 115(35).
- Swenberg, JA, et al. 2010. Endogenous versus exogenous DNA adducts: their role in carcinogenesis, epidemiology, and risk assessment. Toxicological Sciences : An Official Journal of the Society of Toxicology. 120 Suppl 1.
- Zhao, L, et al. 2012. Basis of miscoding of the DNA adduct N2,3-ethenoguanine by human Y-family DNA polymerases. The Journal of Biological Chemistry. 287(42).