Metabolic activation of 2-methylfuran by rat microsomal systems
References (15)
- et al.
The reaction of cysteine with α,β-unsaturated aldehydes
Tetrahedron
(1976) - et al.
Studies of the mechanism of denaturation of cytochrome P-450 by cyclophosphamide and its metabolites
J. Biol. Chem.
(1981) - et al.
In vitro studies on the metabolic activation of the pulmonary toxin, 4-ipomeanol, by rat lung and liver microsomes
J. Pharmacol. Exp. Ther.
(1978) - et al.
In vivo studies on the relationship between target organ alkylation and the pulmonary toxicity of a chemically reactive metabolite of 4-ipomeanol
J. Pharmacol. Exp. Ther.
(1978) Biochemical mechanisms in pulmonary toxicity of furan derivatives
On the evaluation of the constants Vmax and Km in enzyme reactions
Science (Washington, D.C.)
(1952)- et al.
Reaction of glutathione with conjugated carbonyls
Z. Naturforsch.
(1975)
Cited by (49)
Green toxicological investigation for biofuel candidates
2021, Science of the Total EnvironmentCitation Excerpt :Among four furan-based biofuel candidates (2-MF, 2-MTHF, 3-MTHF and 2-BTHF), 2-MF showed the highest toxicity on Daphnia magna, and the reason may be due to the metabolic activation of 2-MF by microsomal systems. Both in vitro and in vivo studies proved that 2-MF could be metabolically activated by mixed-function oxidases to acetyl acrolein, a highly reactive metabolite that binds covalently to microsomal protein and DNA (Ravindranath and Boyd, 1985; Ravindranath et al., 1984; Ravindranath et al., 1986), thereby causing damage to the adjacent cells (Arai et al., 2014). Compared to 2-MF, 2-MTHF showed not only much lower acute toxicity on Daphnia magna, but also lower cytotoxicity on fish liver cell line RTL-W1 (Oncorhynchus mykiss) (Heger et al., 2016), lower acute toxicity on zebrafish embryo (Bluhm et al., 2016), lower genotoxicity on Chinese hamster (Cricetulus griseus) V79 cells (Bluhm et al., 2018).
Genotoxicity of three biofuel candidates compared to reference fuels
2018, Environmental Toxicology and PharmacologyCitation Excerpt :Furans are known to be metabolized by cytochrome P450 monooxygenases and bio-activated to unsaturated aldehydes as their main intermediate products (Ravindranath et al., 1984; Kobayashi et al., 1987; Peterson et al., 2006). These metabolites are suspected to readily react with DNA (Peterson et al., 2006) or covalently bind to microsomal protein (Ravindranath and Boyd, 1985). Thus, the metabolites are supposed to contribute to the toxic effects of furans (Bakhiya and Appel, 2010).
Furan and alkylfurans: Occurrence and risk assessment
2018, Encyclopedia of Food ChemistryHeat-Generated Toxicants in Foods (Acrylamide, MCPD Esters, Glycidyl Esters, Furan, and Related Compounds)
2017, Chemical Contaminants and Residues in Food: Second EditionSimultaneous determination of furan and 2-alkylfurans in heat-processed foods by automated static headspace gas chromatography-mass spectrometry
2016, LWTCitation Excerpt :In contrast to furan, little attention has been paid to the presence of 2-methylfuran in heat-processed foods. 2-Methylfuran has been found to cause liver damage as well as pulmonary bronchiolar lesions in mice (Ravindranath & Boyd, 1985). In a previous pilot study on the oral toxicity of 2-methylfuran, histological lesions were observed in Fischer 344 rats starting at the 1.5 mg/kg bw/day dose group (Gill et al., 2014).
2-Methylfuran: Toxicity and genotoxicity in male Sprague-Dawley rats
2020, Mutation Research - Genetic Toxicology and Environmental MutagenesisCitation Excerpt :Equivocal results were reported by Zeiger et al. [16] for strain TA104. In another report, an increase in chromosomal aberrations was observed in CHO cells exposed to 2-MF in the absence of S9, which was unexpected, because metabolic activation is required for the chemical reactivity of methylfurans [51]. In this study, 2-MF has been evaluated for genotoxicity in different tissues (liver, blood, and bone marrow) and in different endpoints (Pig-a assay, comet assay, and MN test) in vivo with repeated dosing.