Muconaldehyde formation from 14C-benzene in a hydroxyl radical generating system
It has recently been proposed that muconaldehyde, a six carbon, alpha, beta-unsaturated dialdehyde, may be a hematotoxic metabolite of benzene. The present studies indicate that trans, trans-muconaldehyde is formed from benzene in vitro in a hydroxyl radical (.OH) generating system containing ascorbate, ferrous sulfate and EDTA in phosphate buffer, pH 6.7. Muconaldehyde formed from benzene in the .OH generating system was identified by trapping it with thiobarbituric acid (TBA), which results in the formation of an adduct with a 495 nm absorption maximum and a 510 nm fluorescence emission maximum. These maxima were identical to those observed after reacting authentic trans, trans-muconaldehyde with TBA. This finding was supported by thin layer chromatography and solid phase extraction studies. In those studies benzene-derived muconaldehyde cochromatographed with the muconaldehyde/TBA standard. Analyses of the products from the .OH generating system using high performance liquid chromatography (HPLC) confirm that trans, trans-muconaldehyde is a product of benzene ring fission. Regardless of whether or not TBA was used for trapping, samples from the .OH system incubated with benzene contained a peak which cochromatographed with the muconaldehyde standard. The radioactivity profile of fractions collected during HPLC analysis demonstrates 14C-benzene to be the source of the trans, trans-muconaldehyde. The role of hydroxyl radicals in the formation of muconaldehyde was investigated by using dimethyl sulfoxide, mannitol, and ethanol as .OH scavengers. These scavengers, at concentrations of 10 and 100 mM, were found to cause a dose-dependent decrease in the formation of muconaldehyde.
- Research Organization:
- UMDNJ-Rutgers Medical School/Rutgers Univ., Piscataway
- OSTI ID:
- 5002717
- Journal Information:
- J. Free Radi. Biol. Medic.; (United States), Vol. 5-6
- Country of Publication:
- United States
- Language:
- English
Similar Records
Chromatographic and spectrophotometric characterization of adducts formed during the reaction of trans,trans-muconaldehyde with sup 14 C-deoxyguanosine 5 prime -phosphate
Metabolism and toxicity of trans,trans-Muconaldehyde, an open-ring microsomal metabolite of benzene
Related Subjects
59 BASIC BIOLOGICAL SCIENCES
BENZENE
METABOLITES
ALDEHYDES
ASCORBIC ACID
CARBON 14 COMPOUNDS
DMSO
HYDROGEN PEROXIDE
HYDROXIDES
IN VITRO
IRON
METABOLISM
SPECTROPHOTOMETRY
TOXICITY
TRACER TECHNIQUES
AROMATICS
ELEMENTS
HYDROCARBONS
HYDROGEN COMPOUNDS
ISOTOPE APPLICATIONS
LABELLED COMPOUNDS
METALS
ORGANIC COMPOUNDS
ORGANIC SULFUR COMPOUNDS
OXYGEN COMPOUNDS
PEROXIDES
SULFOXIDES
TRANSITION ELEMENTS
VITAMINS
560301* - Chemicals Metabolism & Toxicology- Cells- (-1987)
550201 - Biochemistry- Tracer Techniques