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  • Title: Synthesis of 3-(4-azido-5-iodosalicylamido)-4-hydroxycoumarin: photoaffinity labeling of rat liver dicoumarol-sensitive NAD(P)H: quinone reductase.
    Author: Myszka DG, Swenson RP.
    Journal: Biochem Biophys Res Commun; 1990 Oct 30; 172(2):415-22. PubMed ID: 1700703.
    Abstract:
    A photoaffinity analog of 4-hydroxycoumarin containing an arylazido derivative at the 3-position has been synthesized and characterized. This compound, 3-(4-azido-5-iodosalicylamido)-4-hydroxycoumarin, serves as a strong competitive inhibitor of the dicoumarol-sensitive NAD(P)H: quinone reductase (DT-diaphorase) from rat liver, having an apparent inhibition constant of 4.2 10(-7) M. Irradiation of the reductase with ultraviolet light in the presence 10 microM of the photoprobe resulted in the covalent labeling of 2% of the reductase molecules. The enzyme is protected from labeling to greater than 99% by the inclusion of 3 microM dicoumarol, consistent with the specific labeling of the 4-hydroxycoumarin binding site of this enzyme. Furthermore, the quinone reductase was shown to specifically labeled by the probe even when contained within crude fractions rat liver cytosol.
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