Mechanism of biosynthesis of methylsulfones from PCBs and related compounds
Mercapto-, methylthio-, methylsulfinyl- and methylsulfonyl metabolites of PCBs 2,5,2',5'-tetrachlorobiphenyl, 1,3,5-trichlorobenzene and some other chlorobenzenes were identified in adipose tissues of mice, rats and guinea pigs by using GC/MS/COM systems. By means of administration of CD/sub 3/-methionine, it was confirmed that the methyl group in methylthio metabolites was derived from the methionine. Moreover, after pretreatment with either esterification of urinary metabolites in guinea pigs with 1,3,5-trichlorobenzene and 1,3-dichlorobenzene or N-acetylation after esterification, it was confirmed that cysteinylglycine, cysteine, N-acetylcysteine, cysteamine, mercaptopyruvate, mercaptolactate, mercaptacetate, thiol and disulfide conjugates were detected as a serial modified derivatives of glutathione moiety. These results are summarized as a metabolic proposed pathway of halogenated aromatic compounds. Three routes in pathway correspond to oxygenation (initial route), glutathione thioether disposition (intermediate route) and sulfoxydation (final route) in connection with both reactive intermediates of epoxide and thiol. Methylation of the thiol by S-adenosylmethionine may be important in inhibiting covalent binding of reactive intermediates with biocomponents, similar to the glutathione conjugation for the detoxification of epoxide.
- Research Organization:
- Kobe Univ. School of Medicine, Japan
- OSTI ID:
- 5321562
- Journal Information:
- Environ. Health Perspect.; (United States), Vol. 59
- Country of Publication:
- United States
- Language:
- English
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Related Subjects
CHLORINATED AROMATIC HYDROCARBONS
METABOLISM
SULFONES
BIOSYNTHESIS
ADIPOSE TISSUE
BIOLOGICAL EFFECTS
BIOLOGICAL PATHWAYS
GAS CHROMATOGRAPHY
GUINEA PIGS
MASS SPECTROSCOPY
METABOLITES
MICE
RATS
REACTION INTERMEDIATES
ANIMAL TISSUES
ANIMALS
AROMATICS
BODY
CHROMATOGRAPHY
CONNECTIVE TISSUE
HALOGENATED AROMATIC HYDROCARBONS
MAMMALS
ORGANIC CHLORINE COMPOUNDS
ORGANIC COMPOUNDS
ORGANIC HALOGEN COMPOUNDS
ORGANIC SULFUR COMPOUNDS
RODENTS
SEPARATION PROCESSES
SPECTROSCOPY
SYNTHESIS
TISSUES
VERTEBRATES
560305* - Chemicals Metabolism & Toxicology- Vertebrates- (-1987)