Abstract
1,2-Dibromoethane (DBE) is widely used as an insecticide, fungicide and gasoline additive.1 A number of adverse effects of this compound have been reported, notably its mutagenicity towards bacteria2 and carcinogenicity towards rats and mice.3 Apart from its direct alkylating ability, two mechanisms for these toxic actions can be envisaged, both of which involve biotransformation. The first one consists of oxidation, followed by loss of hydrogen bromide, leading to bromoacetaldehyde, a highly reactive substance which can bind covalently to macromolecules.4, 5 However, bromoacetaldehyde has been reported to be non-mutagenic.6 The second possible mechanism involves conjugation to glutathione (GSH). As has been shown for 1,2-dichloroethane7 and cis-1,2-dichlorocyclohexane,8 the 2-halogenothioether resulting from substitution of one of the halogen atoms by glutathione is responsible for enhanced mutagenic activity of these compounds in the presence of GSH and GSH-S-transferases (see Fig. 1).
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van Bladeren, P.J. et al. (1982). The Activating Role of Glutathione in the Mutagenicity of 1,2-Dibromoethane. In: Snyder, R., et al. Biological Reactive Intermediates—II. Advances in Experimental Medicine and Biology, vol 136. Springer, New York, NY. https://doi.org/10.1007/978-1-4757-0674-1_63
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DOI: https://doi.org/10.1007/978-1-4757-0674-1_63
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