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Chemical Compound Review:

Cyanooxirane oxirane-2-carbonitrile

Synonyms: GLYCIDONITRILE, CCRIS 6496, AG-F-57805, AC1L2GQR, LS-72154, ...

Kodama, Y. et al., Hogy, L.L. et al., Kirman, C.R. et al., Recio, L. et al., Geiger, L.E. et al., et al.

Kirman, Gargas, Marsh, Strother, Klaunig, Collins, Deskin,

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Disease relevance of Cyanoethylene oxide

While glycidonitrile-induced strand breaks in SV40 phage DNA in vitro, acrylonitrile did not [1].
The proportion of the dose metabolized via CEO may be an important determinant of the toxicity and carcinogenicity of acrylonitrile [2].

High impact information on Cyanoethylene oxide

No 1,N6-ethenoadenosine or 1,N6-ethenodeoxyadenosine was found in liver nucleic acids after administration of either acrylonitrile or 2-cyanoethylene oxide to rats, with the limits of detection being 0.3 alkylations per 10(6) RNA bases and 1 alkylation per 10(6) DNA bases [3].
2-Cyanoethylene oxide accumulated in the hepatocyte incubations but did not appear to contribute extensively to alkylation of GSH or protein [4].
Molecular analysis of hprt mutants induced by 2-cyanoethylene oxide in human lymphoblastoid cells [5].
Cytogenetic analysis of spontaneous and 2-cyanoethylene oxide-induced tk-/- mutants in TK6 human lymphoblastoid cultures [6].
Complete karyotypes of metaphase chromosomes were prepared and analyzed from 16 tks mutants (eight spontaneous and eight 2-cyanoethylene oxide [CNEtO]-induced), two spontaneous tkn mutants, and the parental TK6 cell line [6].

Biological context of Cyanoethylene oxide

Mechanistic studies implicate the involvement of oxidative stress in rat brain due to a metabolite (2-cyanoethylene oxide or CEO, cyanide), but do not conclusively rule out a potential role for the direct genotoxicity of CEO [7].

Anatomical context of Cyanoethylene oxide

Metabolism of acrylonitrile to 2-cyanoethylene oxide in F-344 rat liver microsomes, lung microsomes, and lung cells [8].
In vitro reactions of 2-cyanoethylene oxide with calf thymus DNA [9].

Gene context of Cyanoethylene oxide

The mutagenicity of the rat carcinogen acrylonitrile (ACN) and its metabolite 2-cyanoethylene oxide (CNEtO) was assessed in vitro in human lymphoblasts using the heterozygous thymidine kinase (tk) locus as a genetic marker [10].

References

A note on synthesis and reactivity towards DNA of glycidonitrile, the epoxide of acrylonitrile. Peter, H., Schwarz, M., Mathiasch, B., Appel, K.E., Bolt, H.M. Carcinogenesis (1983) [Pubmed]
Urinary metabolites of [1,2,3-13C]acrylonitrile in rats and mice detected by 13C nuclear magnetic resonance spectroscopy. Fennell, T.R., Kedderis, G.L., Sumner, S.C. Chem. Res. Toxicol. (1991) [Pubmed]
In vivo interaction of acrylonitrile and 2-cyanoethylene oxide with DNA in rats. Hogy, L.L., Guengerich, F.P. Cancer Res. (1986) [Pubmed]
Metabolism of acrylonitrile by isolated rat hepatocytes. Geiger, L.E., Hogy, L.L., Guengerich, F.P. Cancer Res. (1983) [Pubmed]
Molecular analysis of hprt mutants induced by 2-cyanoethylene oxide in human lymphoblastoid cells. Recio, L., Simpson, D., Cochrane, J., Liber, H., Skopek, T.R. Mutat. Res. (1990) [Pubmed]
Cytogenetic analysis of spontaneous and 2-cyanoethylene oxide-induced tk-/- mutants in TK6 human lymphoblastoid cultures. Kodama, Y., Boreiko, C.J., Skopek, T.R., Recio, L. Environ. Mol. Mutagen. (1989) [Pubmed]
Cancer dose--response assessment for acrylonitrile based upon rodent brain tumor incidence: use of epidemiologic, mechanistic, and pharmacokinetic support for nonlinearity. Kirman, C.R., Gargas, M.L., Marsh, G.M., Strother, D.E., Klaunig, J.E., Collins, J.J., Deskin, R. Regulatory toxicology and pharmacology : RTP. (2005) [Pubmed]
Metabolism of acrylonitrile to 2-cyanoethylene oxide in F-344 rat liver microsomes, lung microsomes, and lung cells. Roberts, A.E., Lacy, S.A., Pilon, D., Turner, M.J., Rickert, D.E. Drug Metab. Dispos. (1989) [Pubmed]
In vitro reactions of 2-cyanoethylene oxide with calf thymus DNA. Solomon, J.J., Singh, U.S., Segal, A. Chem. Biol. Interact. (1993) [Pubmed]
Mutagenicity of acrylonitrile and its metabolite 2-cyanoethylene oxide in human lymphoblasts in vitro. Recio, L., Skopek, T.R. Mutat. Res. (1988) [Pubmed]

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