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Research ArticleArticle

Metabolism of Dipropyl Disulfide by Rat Liver Phase I and Phase II Enzymes and by Isolated Perfused Rat Liver

Caroline Teyssier and Marie-Hélène Siess
Drug Metabolism and Disposition June 2000, 28 (6) 648-654;
Caroline Teyssier
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Marie-Hélène Siess
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Abstract

The metabolism of dipropyl disulfide (DPDS), anAllium sulfur compound, was investigated in rat liver cell subfractions and in an isolated perfused rat liver. DPDS is oxidized to dipropyl thiosulfinate (DPDSO) by rat microsomes. The contribution of cytochrome P450 enzymes (CYPs) or flavin-containing monooxygenases (FMO) to the formation of DPDSO from its precursor was investigated. In rat microsomes, the reaction followed Michaelis-Menten kinetics with aKm = 0.52 ± 0.1 mM and aVmax = 5.91 ± 0.5 nmol/min/mg of protein, respectively (mean ± S.E., n = 4). Both FMOs and CYPs were involved in DPDS oxidation, although the contribution of CYPs was predominant. Liver microsomes from phenobarbital-treated rats showed a 3.2-fold increase in the rate of formation of DPDSO. Among many CYP isoform-specific inhibitors, only CYP2B1/2 inhibitors decreased the formation of DPDSO and the best correlation between the rate of DPDS oxidation with specific monooxygenase activities was found with a marker of CYP2B1/2 activity. The action of phase II enzymes on DPDS metabolism was studied by incubating DPDS or DPDSO with liver cytosols or microsomes. Two metabolites were formed from DPDS: propylglutathione sulfide conjugate and propylmercaptan, whereas with DPDSO, only the glutathione conjugate was observed. No conjugate compound was detected in the presence of UDP-glucuronyl transferases. When isolated rat liver was perfused with DPDS, different metabolites were obtained in the output and in the liver tissues: propylmercaptan appeared in the output, whereas methylpropyl sulfide, methylpropyl sulfone, and propylglutathione sulfide were detected in the liver tissue.

Footnotes

  • Send reprint requests to: Caroline Teyssier, Unitéde Toxicologie Nutritionnelle, Institut National de la Recherche Agronomique, 17 rue Sully, 21034 Dijon Cedex, France. E-mail:teyssier{at}dijon.inra.fr

  • This work was supported by the Conseil Régional de Bourgogne.

  • Abbreviations used are::
    DADS
    diallyl disulfide
    AM
    allyl mercaptan
    GC-MS
    gas chromatography-mass spectrometry
    CYP
    cytochrome P450
    DADSO
    allicin
    DPDS
    dipropyl disulfide
    DPDSO
    dipropyl thiosulfinate
    ECOD
    7-ethoxycoumarin deethylase
    EROD
    ethoxyresorufin O-deethylase
    FMO
    flavin-containing monooxygenase
    FTIR
    Fourier transform infrared
    GSH
    reduced glutathione
    GST
    glutathioneS-transferase
    MMO
    methimazole oxidase
    MPS
    methylpropyl sulfide
    MPSO2
    methylpropyl sulfone
    PGS
    propylglutathione sulfide
    PM
    propyl mercaptan
    PNPH
    p-nitrophenol hydroxylase
    PROD
    pentoxyresorufin depentylase
    UDGPA
    uridine diphosphate glucuronic acid
    UGT
    UDP-glucuronyl transferase
    • Received October 28, 1999.
    • Accepted February 22, 2000.
  • The American Society for Pharmacology and Experimental Therapeutics
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Drug Metabolism and Disposition: 28 (6)
Drug Metabolism and Disposition
Vol. 28, Issue 6
1 Jun 2000
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Research ArticleArticle

Metabolism of Dipropyl Disulfide by Rat Liver Phase I and Phase II Enzymes and by Isolated Perfused Rat Liver

Caroline Teyssier and Marie-Hélène Siess
Drug Metabolism and Disposition June 1, 2000, 28 (6) 648-654;

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Research ArticleArticle

Metabolism of Dipropyl Disulfide by Rat Liver Phase I and Phase II Enzymes and by Isolated Perfused Rat Liver

Caroline Teyssier and Marie-Hélène Siess
Drug Metabolism and Disposition June 1, 2000, 28 (6) 648-654;
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