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α-Helix-Mimicking Sulfono-γ-AApeptide Inhibitors for p53–MDM2/MDMX Protein–Protein Interactions

Peng Sang, Yan Shi, Junhao Lu, Lihong Chen, Leixiang Yang, Wade M. Borcherds, Sami Abdulkadir, Qi Li, Gary W. Daughdrill, Jiandong Chen, Jianfeng Cai

2020Journal of Medicinal Chemistry67 citationsDOIOpen Access PDF

Abstract

values of 26 nM and 0.891 μM toward MDM2, respectively, is among the most potent unnatural peptidomimetic inhibitors disrupting the p53-MDM2/MDMX interaction. Using fluorescence polarization assays, circular dichroism, nuclear magnetic resonance spectroscopy, and computational simulations, we demonstrate that sulfono-γ-AApeptides adopt helical structures resembling p53 and competitively inhibit the p53-MDM2 interaction by binding to the hydrophobic cleft of MDM2. Intriguingly, the stapled sulfono-γ-AApeptides showed promising cellular activity by enhancing p53 transcriptional activity and inducing expression of MDM2 and p21. Moreover, sulfono-γ-AApeptides exhibited remarkable resistance to proteolysis, augmenting their biological potential. Our results suggest that sulfono-γ-AApeptides are a new class of unnatural helical foldamers that disrupt PPIs.

Topics & Concepts

MDMXPeptidomimeticChemistryCircular dichroismProtein–protein interactionMdm2ProteolysisBiophysicsHelix (gastropod)BiochemistryStereochemistryPeptideEnzymeGeneBiologyEcologySnailChemical Synthesis and AnalysisClick Chemistry and ApplicationsRNA and protein synthesis mechanisms