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Pseudoirreversible Inhibition of Prostate-Specific Membrane Antigen by Phosphoramidate Peptidomimetics

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    Pseudoirreversible Inhibition of Prostate-Specific Membrane Antigen by Phosphoramidate Peptidomimetics†
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    Department of Chemistry, Washington State University, Pullman, Washington 99164-4630
    †This work was supported in part the National Institutes of Health, MBRS SCORE Program-NIGMS (S06-GM052588), the National Cancer Institute (1R21CA122126-01), and the U.S. Department of Defense (W81XWH-06-1-0039).
    * To whom correspondence should be addressed. Telephone: (509) 335-7613. Fax: (509) 335-8867. E-mail: [email protected]
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    Biochemistry

    Cite this: Biochemistry 2008, 47, 48, 12658–12660
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    https://doi.org/10.1021/bi801883v
    Published November 4, 2008
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    The mode of inhibition for phosphoramidate peptidomimetic inhibitors of prostate-specific membrane antigen was determined by inhibition reversibility experiments. The results revealed that these inhibitors can be classified into three types: pseudoirreversible (compounds 1−3), moderately reversible (compounds 4−9), and rapidly reversible inhibitors (compounds 10 and 11). Representative compounds from each class were further evaluated for their ability to induce cellular internalization of PSMA. Results from these experiments revealed that the pseudoirreversible inhibitor 1 induced the greatest PSMA internalization. The discovery of pseudoirreversible PSMA inhibitors is expected to provide a new avenue of investigation and therapeutic applications for prostate cancer and neurological disorders.

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    Cite this: Biochemistry 2008, 47, 48, 12658–12660
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    https://doi.org/10.1021/bi801883v
    Published November 4, 2008
    Copyright © 2008 American Chemical Society
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