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Research ArticleArticle

In Vitro Metabolism of Fenthion and Fenthion Sulfoxide by Liver Preparations of Sea Bream, Goldfish, and Rats

Shigeyuki Kitamura, Tomoharu Suzuki, Tomoko Kadota, Mayumi Yoshida, Koji Ohashi and Shigeru Ohta
Drug Metabolism and Disposition February 2003, 31 (2) 179-186; DOI: https://doi.org/10.1124/dmd.31.2.179
Shigeyuki Kitamura
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Tomoharu Suzuki
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Tomoko Kadota
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Mayumi Yoshida
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Koji Ohashi
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Shigeru Ohta
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Abstract

The in vitro metabolism of fenthion and its sulfoxide (fenthion sulfoxide) in sea bream (Pagrus major) and goldfish (Carassius auratus) was investigated and compared with that in rats. Fenthion was oxidized to fenthion sulfoxide and the oxon derivative, but not to its sulfone, in the presence of NADPH by liver microsomes of sea bream, goldfish, and rats. These liver microsomal activities of the fish were lower than those of rats but were of the same order of magnitude. The NADPH-linked oxon- and sulfoxide-forming activities of liver microsomes of the fish and rats were inhibited by SKF 525-A, metyrapone, α-naphthoflavone, and carbon monoxide. The oxidizing activity to fenthion sulfoxide was also inhibited by α-naphthylthiourea. Several cytochrome P450 isoforms and flavin-containing monooxygenase 1 exhibited these oxidase activities. Fenthion sulfoxide was reduced to fenthion with liver cytosol of the fish and rats upon addition of 2-hydroxypyrimidine,N1-methylnicotinamide, or butyraldehyde, each of which is an electron donor of aldehyde oxidase, under anaerobic conditions. The activity was inhibited by menadione, β-estradiol, and chlorpromazine, which are inhibitors of aldehyde oxidase. The activities in the fish livers were similar to those of rat liver. Aldehyde oxidase purified from the livers of sea bream and rats exhibited the reducing activity. Thus, fenthion and fenthion sulfoxide are interconvertible in fish and rats through the activities of cytochrome P450, flavin-containing monooxygenase, and aldehyde oxidase.

Footnotes

  • This work was supported by Grant-in-Aid for Scientific Research on Priority Area (13027256) from the Japanese Ministry of Education, Science, Sports and Culture, and Grant-in-Aid for Scientific Research (C13672343) from Japan Society for the Promotion of Science.

  • Abbreviations used are::
    fenthion
    O,O-dimethyl-O-(4-methylmercapto)-3-methylphenylthiophosphate
    P450
    cytochrome P450
    FMO
    flavin-containing monooxygenase
    EDTA
    EDTA disodium salt
    DMAC
    p-dimethylaminocinnamaldehyde
    EROD
    ethoxyresorufin-O-dealkylase
    MROD
    methoxyresorufin-O-dealkylase
    PROD
    pentoxyresorufin-O-dealkylase
    HPLC
    high-performance liquid chromatography
    TLC
    thin-layer chromatography
    GC-MS
    gas chromatography-mass spectrometry
    SKF 525-A
    β-diethylaminoethyldiphenylpropylacetate
    • Received July 23, 2002.
    • Accepted November 4, 2002.
  • The American Society for Pharmacology and Experimental Therapeutics
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Drug Metabolism and Disposition: 31 (2)
Drug Metabolism and Disposition
Vol. 31, Issue 2
1 Feb 2003
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Research ArticleArticle

In Vitro Metabolism of Fenthion and Fenthion Sulfoxide by Liver Preparations of Sea Bream, Goldfish, and Rats

Shigeyuki Kitamura, Tomoharu Suzuki, Tomoko Kadota, Mayumi Yoshida, Koji Ohashi and Shigeru Ohta
Drug Metabolism and Disposition February 1, 2003, 31 (2) 179-186; DOI: https://doi.org/10.1124/dmd.31.2.179

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Research ArticleArticle

In Vitro Metabolism of Fenthion and Fenthion Sulfoxide by Liver Preparations of Sea Bream, Goldfish, and Rats

Shigeyuki Kitamura, Tomoharu Suzuki, Tomoko Kadota, Mayumi Yoshida, Koji Ohashi and Shigeru Ohta
Drug Metabolism and Disposition February 1, 2003, 31 (2) 179-186; DOI: https://doi.org/10.1124/dmd.31.2.179
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