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ID: ALA4706750

Journal: ACS Med Chem Lett

Title: Design and Catalyzed Activation of Mycophenolic Acid Prodrugs.

Authors: Plunk MA,Quintana JM,Darden CM,Lawrence MC,Naziruddin B,Kane RR

Abstract: Mycophenolic acid (MPA) and its morpholino ester prodrug mycophenolate mofetil (MMF) are widely used in solid organ transplantation. These drugs prevent rejection due to their potent inhibition of inosine-5'-monophosphate dehydrogenase (IMPDH), an enzyme vital for lymphocyte proliferation. As a strategy to provide localized immunosuppression in cell transplantation, four mycophenolic acid prodrugs designed to release MPA by two distinct mechanisms were synthesized and characterized. A nitrobenzyl ether prodrug was effectively converted to MPA upon exposure to bacterial nitroreductase, while a propargyl ether was converted to the active drug by immobilized Pd nanoparticles. In vitro, both prodrugs were inactive against IMPDH and exhibited reduced toxicity relative to the active drug, suggesting their potential for providing localized immunosuppression.

CiteXplore: 34055230

DOI: 10.1021/acsmedchemlett.1c00079