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Xenobiotic cholesteryl ester formation

R Fears, K H Baggaley, P Walker

    Xenobiotica; the Fate of Foreign Compounds in Biological Systems
    |July 1, 1982
    PubMed
    Summary
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    A novel compound, 1-(4-carboxyphenoxy)-10-(4-chlorophenoxy) decane (CCD), forms a cholesterol conjugate metabolite in rat livers. This metabolite enhances hepatic lysosomal cholesteryl ester hydrolase, potentially contributing to CCD's hypocholesterolemic effects.

    Area of Science:

    • Pharmacology
    • Biochemistry
    • Medicinal Chemistry

    Background:

    • The novel hypolipidaemic compound 1-(4-carboxyphenoxy)-10-(4-chlorophenoxy) decane (CCD) has been developed.
    • Understanding the metabolic fate and mechanism of action of hypolipidaemic agents is crucial for drug development.

    Purpose of the Study:

    • To identify and characterize the metabolite formed from CCD administration in rats.
    • To elucidate the mechanism by which CCD exerts its hypocholesterolemic activity.

    Main Methods:

    • Oral administration of CCD (250 mg/kg) to rats for seven days.
    • Analysis of liver metabolites using nuclear magnetic resonance (n.m.r.) spectroscopy and mass spectrometry.
    • In vitro assays to assess the effect of the metabolite on hepatic lysosomal cholesteryl ester hydrolase activity.

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    Main Results:

    • A lipophilic, cholesterol-containing metabolite accumulated in rat livers.
    • The metabolite was identified as the cholesterol conjugate of CCD, confirmed by synthesized reference material.
    • The xenobiotic cholesteryl ester was not further metabolized and not transported by lipoproteins.
    • In vitro, the xenobiotic cholesteryl ester enhanced hepatic lysosomal cholesteryl ester hydrolase activity.

    Conclusions:

    • CCD is metabolized in vivo to its cholesterol conjugate.
    • The enhanced activity of hepatic lysosomal cholesteryl ester hydrolase by the xenobiotic cholesteryl ester may explain the hypocholesterolemic effect of CCD.