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Literature DB >> 6719117

Reactive metabolites from the bioactivation of toxic methylfurans.

Abstract

An important mechanism of toxicity of furans involves the cytochrome P-450 monooxygenase-catalyzed bioactivation of the compound in situ directly within the target tissues to highly reactive electrophilic products. The unsaturated aldehydes acetylacrolein and methylbutenedial have been identified as the principal reactive intermediates of 2- and 3-methylfuran, respectively, that are produced and bound covalently to tissue macromolecules in hepatic and pulmonary microsomal systems in vitro.

Entities: Chemical Disease Gene

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Year: 1984 PMID： 6719117 DOI： 10.1126/science.6719117

Source DB: PubMed Journal: Science ISSN： 0036-8075 Impact factor: 47.728

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Cited

15 in total

1. Formation and emission of large furans and oxygenated hydrocarbons from flames.

Authors: K Olof Johansson; Tyler Dillstrom; Matteo Monti; Farid El Gabaly; Matthew F Campbell; Paul E Schrader; Denisia M Popolan-Vaida; Nicole K Richards-Henderson; Kevin R Wilson; Angela Violi; Hope A Michelsen
Journal: Proc Natl Acad Sci U S A Date: 2016-07-07 Impact factor: 11.205

2. Comparison of the in vitro replication of the 7-(2-oxoheptyl)-1,N2-etheno-2'-deoxyguanosine and 1,N2-etheno-2'-deoxyguanosine lesions by Sulfolobus solfataricus P2 DNA polymerase IV (Dpo4).

Authors: Plamen P Christov; Katya V Petrova; Ganesh Shanmugam; Ivan D Kozekov; Albena Kozekova; F Peter Guengerich; Michael P Stone; Carmelo J Rizzo
Journal: Chem Res Toxicol Date: 2010-08-16 Impact factor: 3.739

3. Phase II study of 4-ipomeanol, a naturally occurring alkylating furan, in patients with advanced hepatocellular carcinoma.

Authors: S Lakhanpal; R C Donehower; E K Rowinsky
Journal: Invest New Drugs Date: 2001 Impact factor: 3.850

4. Scientific Opinion on Flavouring Group Evaluation 67, Revision 3 (FGE.67Rev3): consideration of 23 furan-substituted compounds evaluated by JECFA at the 55th, 65th, 69th and 86th meetings.

Authors: Maged Younes; Gabriele Aquilina; Laurence Castle; Karl-Heinz Engel; Paul Fowler; Maria Jose Frutos Fernandez; Peter Fürst; Ursula Gundert-Remy; Rainer Gürtler; Trine Husøy; Melania Manco; Peter Moldeus; Sabina Passamonti; Romina Shah; Ine Waalkens-Berendsen; Detlef Wölfle; Matthew Wright; Romualdo Benigni; Claudia Bolognesi; Kevin Chipman; Eugenia Cordelli; Gisela Degen; Daniel Marzin; Camilla Svendsen; Maria Carfì; Giorgia Vianello; Wim Mennes
Journal: EFSA J Date: 2021-02-03

5. Scientific Opinion on Flavouring Group Evaluation 13 Revision 3 (FGE.13Rev3): furfuryl and furan derivatives with and without additional side-chain substituents and heteroatoms from chemical group 14.

Reactive metabolites from the bioactivation of toxic methylfurans.

1. Formation and emission of large furans and oxygenated hydrocarbons from flames.

2. Comparison of the in vitro replication of the 7-(2-oxoheptyl)-1,N2-etheno-2'-deoxyguanosine and 1,N2-etheno-2'-deoxyguanosine lesions by Sulfolobus solfataricus P2 DNA polymerase IV (Dpo4).

3. Phase II study of 4-ipomeanol, a naturally occurring alkylating furan, in patients with advanced hepatocellular carcinoma.

4. Scientific Opinion on Flavouring Group Evaluation 67, Revision 3 (FGE.67Rev3): consideration of 23 furan-substituted compounds evaluated by JECFA at the 55th, 65th, 69th and 86th meetings.

5. Scientific Opinion on Flavouring Group Evaluation 13 Revision 3 (FGE.13Rev3): furfuryl and furan derivatives with and without additional side-chain substituents and heteroatoms from chemical group 14.

6. Metabolism and toxicity of menthofuran in rat liver slices and in rats.

Review 7. Metabolic Activation and DNA Interactions of Carcinogenic N-Nitrosamines to Which Humans Are Commonly Exposed.

Review 8. Reactive metabolites in the biotransformation of molecules containing a furan ring.

9. Synthesis and evaluation of a 18F-labeled 4-ipomeanol as an imaging agent for CYP4B1 gene prodrug activation therapy.

10. Chlorination of Phenols Revisited: Unexpected Formation of α,β-Unsaturated C₄-Dicarbonyl Ring Cleavage Products.