ArticleChemical research in toxicology2014
Covalent modification of cytochrome c by reactive metabolites of furan.
Article in Chemical research in toxicology, 2014. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 8 papers.
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Who cites it
8 citing papers in PubMed, 41 citations in OpenAlex.
- Analytical Identification of Novel Furan Metabolites in Human Hepatocytes and Urine: Implications for Liver and Respiratory Disease Research.Chemical research in toxicology · 2026Article
- Glycerolphosphorylethanolamine and Several Other Biochemical Amines Are Targets of Furan's Reactive Metabolite in Rodents.Chemical research in toxicology · 2026Article
- Article
- Gold(III)-Catalyzed Propargylic Substitution Reaction Followed by Cycloisomerization for Synthesis of Poly-Substituted Furans fromMolecules (Basel, Switzerland) · 2024Article
- Article
- Risks for public health related to the presence of furan and methylfurans in food.EFSA journal. European Food Safety Authority · 2017Article
- Chemical Identity of Interaction of Protein with Reactive Metabolite of Diosbulbin B In Vitro and In Vivo.Toxins · 2017Article
- Comparative metabolism of furan in rodent and human cryopreserved hepatocytes.Drug metabolism and disposition: the biological fate of chemicals · 2014Article
Corrections and comments
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Authors and funding
4 authors at 1 institution in 1 country.
Funding
Abstract
Metabolism of the hepatotoxicant furan leads to protein adduct formation in the target organ. The initial bioactivation step involves cytochrome P450-catalyzed oxidation of furan, generating cis-2-butene-1,4-dial (BDA). BDA reacts with lysine to form pyrrolin-2-one adducts. Metabolic studies indicate that BDA also reacts with glutathione (GSH) to generate 2-(S-glutathionyl)butanedial (GSH-BDA), which then reacts with lysine to form GSH-BDA-lysine cross-links. To explore the relative reactivity of these two reactive intermediates, cytochrome c was reacted with BDA in the presence and absence of GSH. As judged by MALDI-TOF mass spectrometry, BDA reacts extensively with cytochrome c to form adducts that add 66 Da to the protein, consistent with the formation of pyrrolinone adducts. Addition of GSH to the reaction mixture reduced the overall extent of adduct formation. The mass of the adducted protein was shifted by 355 Da as expected for GSH-BDA-protein cross-link formation. LC-MS/MS analysis of the tryptic digests of the alkylated protein indicated that the majority of adducts occurred on lysine residues, with BDA reacting less selectively than GSH-BDA. Both types of adducts may contribute to the toxic effects of furan.
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Registered trials
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