Replacement of a chlorine with a methylsulfonyl group in the metabolism of propachlor (2-chloro-N-isopropylacetanilide)

Bakke, J. E.; Feil, V. J.; Price, C. E.

doi:10.1002/bms.1200030506

Cited by 33 publications

(3 citation statements)

References 4 publications

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“…PCB, DDE, PCT, polychlorinated dibenzo-p-dioxin (PCDD) and related metabolites are considered to belong to the latter. Bakke et al (7) pointed out that the process of cleavage of the C-S bond of metabolites was thought to be catalyzed by C-S lyase of intestinal microorganism and intestinal tissues. In the case of alfoqualone, serial methylsulfonyl metabolite in urine decreased significantly on antibiotic treatment or bile duct ligation.…”

Section: Excretion Routes Of Xenobiotic Compoundsmentioning

confidence: 99%

“…The serial methylsulfonyl pathway for xenobiotic metabolism has been studied in numerous laboratories for numerous compounds such as the drugs cafffeine (1), bromazepam (2), bromovalerylurea (3), acetoaminophen (4), alfoqualone (5), and 3-hydroxyxanthine (6); pesticides and fungicides, including propachlor (7), napthalene (8), (9) and PCNB (10); and pollutants such as DDE (11), PCBs (11)(12)(13), HCB (14) and monochlorodibenzo-p-dioxin (15). During the time that xenobiotic thioether derivatives were discovered, precursors including glutathione, cysteinylglycine, cysteine and N-acetylcysteine (mercapturic acid) conjugates (2,4,5,7,14) have been reported. Furthermore, it is believed that serial methylsulfonyl metabolites might be discovered by more detailed analysis.…”

Section: Introductionmentioning

confidence: 99%

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Mechanism of Biosynthesis of Methylsulfones from PCBs and Related Compounds

Mio¹,

Sumino²

1985

Environmental Health Perspectives

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, methylthio-, methylsulfinyl-and methysulfonyl 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 CD3-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.

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Section: Excretion Routes Of Xenobiotic Compoundsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Mechanism of Biosynthesis of Methylsulfones from PCBs and Related Compounds

Mio¹,

Sumino²

1985

Environmental Health Perspectives

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“…Methylsulfonylation, the process leading to the formation of mercapto-(-SH), methylthio-(-SCH3), methylsulfinyl-(-SOCH3) and methylsulfonyl-(SO2CH3) metabolites of xenobiotics, is one of the many novel biological pathways of metabolism discovered during the past several years. The serial methylsulfonyl pathway for xenobiotic metabolism has been studied in numerous laboratories for numerous compounds such as the drugs cafffeine (1), bromazepam (2), bromovalerylurea (3), acetoaminophen (4), alfoqualone (5), and 3-hydroxy- xanthine (6); pesticides and fungicides, including propachlor (7), napthalene (8), AF-2 (9) and PCNB (10); and pollutants such as DDE (11), PCBs (11)(12)(13), HCB (14) and monochlorodibenzo-p-dioxin (15). During the time that xenobiotic thioether derivatives were discovered, precursors including glutathione, cysteinylglycine, cysteine and N-acetylcysteine (mercapturic acid) conjugates (2,4,5,7,14) have been reported.…”

Section: Introductionmentioning

confidence: 99%

Mechanism of biosynthesis of methylsulfones from PCBs and related compounds.

Mio¹,

Sumino²

1985

Environ Health Perspect

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Mercapto-, methylthio-, methylsulfinyl- and methysulfonyl 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 CD3-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.

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Environmental applications of mass spectrometry

Alford

1978

Biol. Mass Spectrom.

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The 1976 publications reporting organic and spark source mass spectrometric studies on environmental samples were compiled. Emphasis was placed on pollutants identified rather than methods and techniques used, and reports that did not incorporate data obtained by a technique's application were not included. The 349 reports cited vary from those reporting hundreds of identified pollutants to those describing the analysis of only one sample containing one or a few pollutants. The following sample types were not considered to be environment samples: forensic samples, synthetic or 'standards' samples, and samples analyzed for drug residues.

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Replacement of a chlorine with a methylsulfonyl group in the metabolism of propachlor (2-chloro-N-isopropylacetanilide)

Cited by 33 publications

References 4 publications

Mechanism of Biosynthesis of Methylsulfones from PCBs and Related Compounds

Mechanism of Biosynthesis of Methylsulfones from PCBs and Related Compounds

Mechanism of biosynthesis of methylsulfones from PCBs and related compounds.

Environmental applications of mass spectrometry

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