Electrophilic Intermediates Produced by Bioactivation of Furan
- 1 January 2006
- journal article
- review article
- Published by Taylor & Francis Ltd in Drug Metabolism Reviews
- Vol. 38 (4), 615-626
- https://doi.org/10.1080/03602530600959417
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 alpha,beta-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.Keywords
This publication has 28 references indexed in Scilit:
- Detection of DNA Adducts Derived from the Reactive Metabolite of Furan, cis-2-Butene-1,4-dialChemical Research in Toxicology, 2006
- The Formation of Substituted 1,N6-Etheno-2‘-deoxyadenosine and 1,N2-Etheno-2‘-deoxyguanosine Adducts by cis-2-Butene-1,4-dial, a Reactive Metabolite of FuranChemical Research in Toxicology, 2004
- Characterization of Nucleoside Adducts of cis-2-Butene-1,4-dial, a Reactive Metabolite of FuranChemical Research in Toxicology, 2002
- Mutation spectra in Salmonella of analogues of MX: implications of chemical structure for mutational mechanismsMutation Research - Reviews in Mutation Research, 2000
- Characterization of Amino Acid and Glutathione Adducts ofcis-2-Butene-1,4-dial, a Reactive Metabolite of FuranChemical Research in Toxicology, 1997
- Identification of cis-2-Butene-1,4-dial as a Microsomal Metabolite of FuranChemical Research in Toxicology, 1995
- Furan-Induced Cytolethality in Isolated Rat Hepatocytes: Correspondence with in Vivo DosimetryToxicology and Applied Pharmacology, 1993
- Oxidation of furans with dimethyldioxirane. Interception of malealdehyde and related aldehydes via Wittig reactionsJournal of the Chemical Society, Chemical Communications, 1993
- Disposition of [14C]furan in the male F344 ratJournal of Toxicology and Environmental Health, 1991
- Effects of Exposure to Solvents Caused by Air Pollution with Special Reference to CCl4and Its Distribution in AirClinical Toxicology, 1973