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Related Experiment Videos

Short-circuiting the visual cycle with retinotoxic aromatic amines.

P S Bernstein, J R Lichtman, R R Rando

    Proceedings of the National Academy of Sciences of the United States of America
    |March 1, 1986
    PubMed
    Summary

    Certain aromatic amines, including metabolites of drugs like phenacetin, are retinotoxic, inhibiting retinoid accumulation. These compounds likely work by catalyzing the isomerization of 11-cis-retinal to its all-trans form.

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    Area of Science:

    • Biochemistry
    • Pharmacology
    • Ophthalmology

    Background:

    • 1,5-di-(p-aminophenoxy)pentane is a retinotoxic drug that inhibits 11-cis-retinoid accumulation.
    • This drug depletes preformed retinoid stores in the eye.

    Purpose of the Study:

    • To determine if the retinotoxic effects of 1,5-di-(p-aminophenoxy)pentane are specific.
    • To investigate the mechanism by which aromatic amines cause retinotoxicity.
    • To assess the potential retinotoxicity of clinically used drugs metabolized into aromatic amines.

    Main Methods:

    • Investigated the effects of various primary aromatic amines with hydrophobic tails on retinoids.
    • Examined the metabolic products of drugs like phenacetin for retinotoxic amines.
    • Studied the isomerization of 11-cis-retinal catalyzed by aromatic amines in liposomes and n-heptane.

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    Main Results:

    • The retinotoxic effects are not specific to 1,5-di-(p-aminophenoxy)pentane but are shared by similar aromatic amines.
    • Clinically used drugs, such as phenacetin, can be metabolized into retinotoxic amines.
    • Aromatic amines catalyze the isomerization of 11-cis-retinal to all-trans-retinal, with significantly increased rates in liposomes.

    Conclusions:

    • Hydrophobic aromatic amines are generally retinotoxic and warrant reassessment of drugs containing these structures.
    • The proposed mechanism involves amine-catalyzed isomerization of 11-cis-retinal, explaining the lack of structural specificity.
    • The observed in vitro rates of amine-catalyzed isomerization are sufficient to explain in vivo effects.