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Chemical Compound Review:

Benzyloxirane 2-benzyloxirane

Synonyms: NSC-4327, CCRIS 1134, AG-F-55718, ACMC-20lue5, NSC4327, ...

El-Tantawy, M.A. et al., Harder, A. et al., Qato, M.K. et al., Labuschagne, M. et al.

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Disease relevance of NSC4327

Comparison of toxicity observed in those strains suggests three clearly distinguishable modes of toxic action for electrophilic chemicals: "DNA damage", "GSH depletion-related toxicity", and "unspecific reactivity". The class of chemicals causing DNA damage includes the epoxides 1,2-epoxybutane, (2,3-epoxypropyl)benzene, and styrene oxide [1].
7 epoxide-containing compounds: allylbenzene oxide, styrene oxide, trans-beta-methylstyrene oxide, 4-chlorophenyl glycidyl ether, vinylcyclohexene dioxide, octene dioxide and hexene dioxide were evaluated for mutagenic activity in 4 histidine-requiring strains of Salmonella typhimurium, namely: TA1535, TA100, TA1537 and TA98 [2].

High impact information on NSC4327

Whole-cell biotransformation of (2,3-epoxypropyl)benzene, using the recombinant EH, revealed activity and selectivity far superior to any other activity and selectivity reported in literature using wild-type organisms [3].
Both the cytosolic (100000 g soluble) and/or microsomal (100000 g pellet) fractions derived from noninduced mouse, guinea pig, and/or rat consistently decreased the mutagenic activity of the 3 most active mutagens: allylbenzene oxide, styrene oxide and 4-chlorophenyl glycidyl ether [2].
We also demonstrate that adducts with similar mobility to the major safrole 2',3'-oxide-DNA adduct are formed in vitro between safrole 2',3'-oxide and deoxyguanosine, and also between its chemical analogs allylbenzene 2',3'-oxide or estragole 2',3'-oxide and DNA [4].

References

Evaluation of bioanalytical assays for toxicity assessment and mode of toxic action classification of reactive chemicals. Harder, A., Escher, B.I., Landini, P., Tobler, N.B., Schwarzenbach, R.P. Environ. Sci. Technol. (2003) [Pubmed]
The effect of hepatic microsomal and cytosolic subcellular fractions on the mutagenic activity of epoxide-containing compounds in the Salmonella assay. El-Tantawy, M.A., Hammock, B.D. Mutat. Res. (1980) [Pubmed]
Cloning of an epoxide hydrolase-encoding gene from Rhodotorula mucilaginosa and functional expression in Yarrowia lipolytica. Labuschagne, M., Albertyn, J. Yeast (2007) [Pubmed]
32P-postlabeling analysis of adducts formed between DNA and safrole 2',3'-epoxide: absence of adduct formation in vivo. Qato, M.K., Guenthner, T.M. Toxicol. Lett. (1995) [Pubmed]

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