Electrophilic intermediates produced by bioactivation of furan

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Abstract

The industrial and environmental chemical, furan, is a liver toxicant and carcinogen in laboratory animals. It has been classified as a possible human carcinogen. The mechanism of tumor induction is unknown. However, toxicity is initiated by cytochrome P450 catalyzed oxidation of furan to an α,β-unsaturated dialdehyde, cis-2-butene-1,4-dial. This metabolite reacts readily with protein and DNA nucleophiles and is a bacterial mutagen in Ames assay strain TA104. Metabolism studies indicate that this reactive metabolite is formed in vivo. It is also an intermediate leading to other metabolites whose role in furan-derived toxicities has yet to be explored.

Original languageEnglish (US)
Pages (from-to)615-626
Number of pages12
JournalDrug Metabolism Reviews
Volume38
Issue number4
DOIs
StatePublished - Jul 1 2006

Keywords

  • α,β-Unsaturated aldehyde
  • Carcinogenesis
  • Furan
  • Glutathione conjugates
  • Metabolism
  • Stable isotope methods
  • Toxicity

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