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Optimization of a Piperidine CD4-Mimetic Scaffold Sensitizing HIV-1 Infected Cells to Antibody-Dependent Cellular Cytotoxicity
Journal article   Peer reviewed

Optimization of a Piperidine CD4-Mimetic Scaffold Sensitizing HIV-1 Infected Cells to Antibody-Dependent Cellular Cytotoxicity

Daniel Lee, Ling Niu, Shilei Ding, Huile Zhu, William D. Tolbert, Halima Medjahed, Guillaume Beaudoin-Bussieres, Cameron Abrams, Andres Finzi, Marzena Pazgier, …
ACS medicinal chemistry letters, v 15(11), pp 1961-1969
14 Nov 2024
PMID: 39563795
url
https://doi.org/10.1021/acsmedchemlett.4c00403View
Published, Version of Record (VoR) Open

Abstract

Chemistry, Medicinal Life Sciences & Biomedicine Pharmacology & Pharmacy Science & Technology
The ability of the HIV-1 accessory proteins Nef and Vpu to decrease CD4 protects infected cells from antibody-dependent cellular cytotoxicity (ADCC) by limiting the exposure of vulnerable epitopes to envelope glycoprotein (Env). Small-molecule CD4 mimetics (CD4mcs) based on piperidine scaffolds represent a new family of agents capable of sensitizing HIV-1-infected cells to ADCC by exposing CD4-induced (CD4i) epitopes on Env that are recognized by non-neutralizing antibodies which are abundant in plasma of people living with HIV. Here, we employed the combined methods of parallel synthesis, structure-based design, and optimization to generate a new line of piperidine-based CD4mcs, which sensitize HIV-1 infected cells to ADCC activity. The X-ray crystallographic study of the CD4mcs within the gp120 residues suggests that the positioning of the CD4mc inside the Phe43 cavity and synergistic contact of the CD4mc with the beta 20-21 loop and the alpha 1-helix lead to improved antiviral activity.

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Web of Science research areas
Chemistry, Medicinal
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