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Identification of Highly Potent Human Immunodeficiency Virus Type-1 Protease Inhibitors against Lopinavir and Darunavir Resistant Viruses from Allophenylnorstatine-Based Peptidomimetics with P2 Tetrahydrofuranylglycine.

Hidaka K, Kimura T, Sankaranarayanan R, Wang J, McDaniel KF, Kempf DJ, Kameoka M, Adachi M, Kuroki R, Nguyen JT, Hayashi Y, Kiso Y
J Med Chem 61 5138-5153 (2018)
Cited: 5 times
EuropePMC logo PMID: 29852069

Abstract

The emergence of drug-resistant HIV from a widespread antiviral chemotherapy targeting HIV protease in the past decades is unavoidable and provides a challenge to develop alternative inhibitors. We synthesized a series of allophenylnorstatine-based peptidomimetics with various P3, P2, and P2́ moieties. The derivatives with P2 tetrahydrofuranylglycine (Thfg) were found to be potent against wild type HIV-1 protease and the virus, leading to a highly potent compound 21f (KNI-1657) against lopinavir/ritonavir- or darunavir-resistant strains. Co-crystal structures of 21f and the wild-type protease revealed numerous key hydrogen bonding interactions with Thfg. These results suggest that the strategy to design allophenylnorstatine-based peptidomimetics combined with Thfg residue would be promising for generating candidates to overcome multidrug resistance.

Reviews citing this publication (2)

  1. Saturated Five-Membered Thiazolidines and Their Derivatives: From Synthesis to Biological Applications. Sahiba N, Sethiya A, Soni J, Agarwal DK, Agarwal S. Top Curr Chem (Cham) 378 34 (2020)
  2. Interfacial Peptides as Affinity Modulating Agents of Protein-Protein Interactions. Ershov PV, Mezentsev YV, Ivanov AS. Biomolecules 12 106 (2022)

Articles citing this publication (3)

  1. Dimer Interface Organization is a Main Determinant of Intermonomeric Interactions and Correlates with Evolutionary Relationships of Retroviral and Retroviral-Like Ddi1 and Ddi2 Proteases. Mótyán JA, Miczi M, Tőzsér J. Int J Mol Sci 21 E1352 (2020)
  2. Drug Resistance Mechanism of M46I-Mutation-Induced Saquinavir Resistance in HIV-1 Protease Using Molecular Dynamics Simulation and Binding Energy Calculation. Rana N, Singh AK, Shuaib M, Gupta S, Habiballah MM, Alkhanani MF, Haque S, Reshi MS, Kumar S. Viruses 14 697 (2022)
  3. Protease Inhibitors Purified from the Canola Meal Extracts of Two Genetically Diverse Genotypes Exhibit Antidiabetic and Antihypertension Properties. Hussain S, Rehman AU, Luckett DJ, Naqvi SMS, Blanchard CL. Molecules 26 2078 (2021)


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