Interspecies differences in metabolism and kinetics of 1,3-butadiene, isobutene and styrene. 1993

H M Bolt
Institut für Arbeitsphysiologie, Universität Dortmund, Germany.

Investigations on the pharmacokinetics of inhalation of 1,3-butadiene and its primary reactive intermediate, epoxybutene, in mice and rats have demonstrated reasonably clearly that the species differences observed in the carcinogenicity of butadiene are accompanied by species differences in its metabolism. Mice metabolize butadiene to epoxybutene faster than rats but have a limited capacity for detoxification and accumulation of the reactive epoxide intermediate; these characteristics are viewed as major determinants of the greater susceptibility of mice to butadiene. The detection of alkylation products of epoxybutene and diepoxybutane with guanine residues in DNA of livers of mice exposed to butadiene indicate that eposybutene is further biotransformed to diepoxybutane in this species. This assumption is supported by the finding that butadiene induces cross-linking between DNA and proteins in mice, which can be attributed to the bifunctional alkylating diepoxybutane. Quantitative differences between rats and mice in butadiene metabolism and in the biological effectiveness of the reactive epoxide intermediates reflect the activities of different enzymes in butadiene metabolism. Epoxybutene is metabolized primarily via glutathione S-transferase-mediated pathways, resulting in glutathione depletion, increased toxicity at higher doses and covalent binding of reactive butadiene intermediates. A drastic depletion of non-protein sulfhydryl is observed in the tissues of mice but not of rats after acute exposure to butadiene. Isobutene (2-methylpropene) is converted by hepatic monooxygenase(s) to the epoxide, 2,2-dimethyloxirane. This epoxide, when appropriately tested, was mutagenic to Salmonellatyphimurium strains TA100 and TA1535. Addition of an exogenous metabolic system diminished the mutagenicity of 2,2-dimethyloxirane.(ABSTRACT TRUNCATED AT 250 WORDS)

UI MeSH Term Description Entries
D008815 Mice, Inbred Strains Genetically identical individuals developed from brother and sister matings which have been carried out for twenty or more generations, or by parent x offspring matings carried out with certain restrictions. All animals within an inbred strain trace back to a common ancestor in the twentieth generation. Inbred Mouse Strains,Inbred Strain of Mice,Inbred Strain of Mouse,Inbred Strains of Mice,Mouse, Inbred Strain,Inbred Mouse Strain,Mouse Inbred Strain,Mouse Inbred Strains,Mouse Strain, Inbred,Mouse Strains, Inbred,Strain, Inbred Mouse,Strains, Inbred Mouse
D009153 Mutagens Chemical agents that increase the rate of genetic mutation by interfering with the function of nucleic acids. A clastogen is a specific mutagen that causes breaks in chromosomes. Clastogen,Clastogens,Genotoxin,Genotoxins,Mutagen
D002070 Butadienes Four carbon unsaturated hydrocarbons containing two double bonds. Butadiene Derivative,Butadiene Derivatives,Derivative, Butadiene,Derivatives, Butadiene
D004852 Epoxy Compounds Organic compounds that include a cyclic ether with three ring atoms in their structure. They are commonly used as precursors for POLYMERS such as EPOXY RESINS. Epoxide,Epoxides,Epoxy Compound,Oxiranes,Compound, Epoxy,Compounds, Epoxy
D006801 Humans Members of the species Homo sapiens. Homo sapiens,Man (Taxonomy),Human,Man, Modern,Modern Man
D000475 Alkenes Unsaturated hydrocarbons of the type Cn-H2n, indicated by the suffix -ene. (Grant & Hackh's Chemical Dictionary, 5th ed, p408) Alkene,Olefin,Olefins,Pentene,Pentenes
D000478 Alkylation The covalent bonding of an alkyl group to an organic compound. It can occur by a simple addition reaction or by substitution of another functional group. Alkylations
D000818 Animals Unicellular or multicellular, heterotrophic organisms, that have sensation and the power of voluntary movement. Under the older five kingdom paradigm, Animalia was one of the kingdoms. Under the modern three domain model, Animalia represents one of the many groups in the domain EUKARYOTA. Animal,Metazoa,Animalia
D013045 Species Specificity The restriction of a characteristic behavior, anatomical structure or physical system, such as immune response; metabolic response, or gene or gene variant to the members of one species. It refers to that property which differentiates one species from another but it is also used for phylogenetic levels higher or lower than the species. Species Specificities,Specificities, Species,Specificity, Species
D013343 Styrenes Derivatives and polymers of styrene. They are used in the manufacturing of synthetic rubber, plastics, and resins. Some of the polymers form the skeletal structures for ion exchange resin beads.

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