The biotransformation of isoprene and the two isoprene monoepoxides by human cytochrome P450 enzymes, compared to mouse and rat liver microsomes
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Cited by (33)
Measuring urinary N-acetyl-S-(4-hydroxy-2-methyl-2-buten-1-yl)-L-cysteine (IPMA3) as a potential biomarker of isoprene exposure
2016, Analytica Chimica ActaCitation Excerpt :While isoprene appears to be ubiquitous in exhaled human breath, breath isoprene has not been shown to increase in people with increased isoprene exposure [13]. Isoprene has been studied extensively to characterize metabolism and mutagenicity [14]; biotransformation of isoprene and isoprene mono-epoxides by human cytochrome P450 enzymes [15]; stereo-chemical and kinetic comparisons of mono- and di-epoxide formation in vitro, in rats, mice, and humans [16–18]; and conjugation of isoprene mono-epoxides with glutathione by glutathione S-transferases of rats and humans [19]. Despite the extensive past work on isoprene, no methods have been published for biomonitoring of isoprene exposure in humans for large scale studies.
Concentration- and time-dependent genotoxicity profiles of isoprene monoepoxides and diepoxide, and the cross-linking potential of isoprene diepoxide in cells
2014, Toxicology ReportsCitation Excerpt :It is ranked third (after 1,3-butadiene and acetaldehyde) with respect to cancer hazards stemming from smoking by the World Health Organization on the basis of its abundance in cigarette smoke and its animal carcinogenicity [15]. Similarly to 1,3-butadiene, isoprene undergoes oxidative metabolism, which is primarily mediated by cytochrome P450 2E1, followed by P450 2B6 [16], to produce two isomeric monoepoxides, 2-ethenyl-2-methyloxirane (i.e., isoprene-1,2-oxide, IP-1,2-O) and 2-(1-methylethenyl)oxirane (i.e., isoprene-3,4-oxide, IP-3,4-O). Both monoepoxides can be further metabolized to the diepoxide, 2-methyl-2,2′-bioxirane (MBO) (Fig. 1) [16–19].
DNA-damaging ability of isoprene and isoprene mono-epoxide (EPOX I) in human cells evaluated with the comet assay
2007, Mutation Research - Genetic Toxicology and Environmental MutagenesisEffect of ethanol on the tumorigenicity of urethane (ethyl carbamate) in B6C3F<inf>1</inf> mice
2005, Food and Chemical ToxicologyPrediction of isoprene diepoxide levels in vivo in mouse, rat and man using enzyme kinetic data in vitro and physiologically-based pharmacokinetic modelling
2001, Chemico-Biological InteractionsCitation Excerpt :3,4-Epoxy-3-methyl-1-butene (EPOX-I) (purity 95%) was obtained from Aldrich (Bornem, Belgium). 3,4-Epoxy-2-methyl-1-butene (EPOX-II) (purity≥99%) and 2-methyl-1,2:3,4-diepoxybutane (purity≥99%), the diepoxide of isoprene, were synthesized as described before [6]. The purity of EPOX-II and isoprene diepoxide were determined by GC and NMR analysis as described before [6].
Metabolism and molecular toxicology of isoprene
2001, Chemico-Biological Interactions