PMID: 8605289Dec 1, 1995Paper

S-methylation as a bioactivation mechanism for mono- and dithiocarbamate pesticides as aldehyde dehydrogenase inhibitors

Chemical Research in Toxicology
R E StaubJ E Casida

Abstract

S-Methylation is a new bioactivation mechanism for metam and metabolites of methyl isothiocyanate and dazomet in mice. These soil fumigants are converted to S-methyl metam [MeNHC(S)SMe] which reaches peak levels in liver, kidney, brain, and blood 10-20 min after intraperitoneal (ip) treatment. The half-life of S-methyl metam administered ip is 8-12 min in each of these tissues. S-Methyl metam-oxon [MeNHC(O)SMe] is also detected as a metabolite of each of these soil fumigants on analysis by gas chromatography/mass spectrometry with chemical ionization. The conversion of methyl isothiocyanate to S-methyl metam and its oxon probably involves conjugation with glutathione, hydrolysis to S-(N-methylthiocarbamoyl)-cysteine, cleavage by cysteine conjugate beta-lyase to release metam, and finally methylation and oxidative desulfuration. Metam and dazomet are converted to S-methyl metam by mouse liver microsomes on fortification with S-adenosylmethionine. Metam, methyl isothiocyanate, dazomet, and three metabolites (metam-oxon [MeNHC(O)SH], MeNHC(S)SMe, and MeNHC-(O)SMe) administered ip to mice at 40 mg/kg inhibit low-Km liver mitochondrial aldehyde dehydrogenase and elevate ethanol-dependent blood and brain acetaldehyde levels. Several ...Continue Reading

Citations

Jan 12, 2001·Mutation Research·F KassieS Knasmüller
Sep 27, 2008·The Journal of Biological Chemistry·Arthur P ChouJeff M Bronstein
Mar 5, 2003·Journal of Neurochemistry·Tonya C MurphyMatthew J Picklo
May 19, 2016·Journal of Agricultural and Food Chemistry·John E Casida
Oct 17, 1998·Environmental and Molecular Mutagenesis·M PelusoS Parodi
Jul 11, 2001·Journal of Neuropathology and Experimental Neurology·M J PickloT J Montine
Dec 7, 2020·Free Radical Biology & Medicine·Colin C AndersonJames R Roede
May 24, 2019·The Journal of Physical Chemistry. a·Artur MardyukovPeter R Schreiner
May 26, 2017·Journal of Agricultural and Food Chemistry·John E Casida
Sep 28, 2010·Archives of Biochemistry and Biophysics·Daniel Mansuy, Patrick M Dansette

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