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Acetylcarnitine and cholinergic receptors

K W Reed, W J Murray, E B Roche

    Journal of Pharmaceutical Sciences
    |September 1, 1980
    PubMed
    Summary

    Acetylcarnitine has slight cholinergic properties. Molecular modeling suggests its shape partially explains its low activity, with the S-isomer showing higher potential activity than the R-isomer.

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    Area of Science:

    • Biochemistry
    • Molecular Biology
    • Pharmacology

    Background:

    • Acetylcarnitine is a naturally occurring compound found in vertebrate muscle.
    • It structurally resembles acetylcholine and exhibits minor cholinergic properties.
    • Understanding its conformational properties is key to explaining its biological activity.

    Purpose of the Study:

    • To perform conformational analysis of acetylcarnitine using computational methods.
    • To compare the preferred conformations of acetylcarnitine with established models of cholinergic receptor binding.
    • To elucidate the structural basis for acetylcarnitine's observed cholinergic activity.

    Main Methods:

    • Extended Hückel Theory (EHT) for conformational analysis.
    • Complete Neglect of Differential Overlap (CNDO/2) molecular orbital calculations.
    • Comparison of computed conformations against Kier and Chothia-Pauling receptor models.

    Main Results:

    • Preferred conformations of acetylcarnitine did not align with the Kier model.
    • Low energy barriers allow for conformational flexibility.
    • The Chothia-Pauling model indicated potential activity for the S-isomer exclusively.

    Conclusions:

    • Computational analysis partially explains the limited cholinergic activity of acetylcarnitine.
    • The stereochemistry of acetylcarnitine influences its interaction with cholinergic receptors.
    • (S)-acetylcarnitine demonstrates greater potential for receptor interaction compared to the R-isomer.

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