ArticleMolecules (Basel, Switzerland)2020
Naphthoquinones as Covalent Reversible Inhibitors of Cysteine Proteases-Studies on Inhibition Mechanism and Kinetics.
Article in Molecules (Basel, Switzerland), 2020. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 16 papers.
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16 citing papers in PubMed, 34 citations in OpenAlex.
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- Structural Modifications of Covalent Cathepsin S Inhibitors: Impact on Affinity, Selectivity, and Permeability.ACS medicinal chemistry letters · 2024Article
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- Development of Novel Peptidyl Nitriles Targeting Rhodesain and Falcipain-2 for the Treatment of Sleeping Sickness and Malaria.International journal of molecular sciences · 2024Article
- Peptidyl nitroalkene inhibitors of main protease rationalized by computational and crystallographic investigations as antivirals against SARS-CoV-2.Communications chemistry · 2024Article
- Structure-based lead optimization of peptide-based vinyl methyl ketones as SARS-CoV-2 main protease inhibitors.European journal of medicinal chemistry · 2023Article
- Development of Reduced Peptide Bond Pseudopeptide Michael Acceptors for the Treatment of Human African Trypanosomiasis.Molecules (Basel, Switzerland) · 2022Article
- Identification of novel small-molecular inhibitors of Staphylococcus aureus sortase A using hybrid virtual screening.The Journal of antibiotics · 2022Article
- Identification of Vitamin K3 and its analogues as covalent inhibitors of SARS-CoV-2 3CLInternational journal of biological macromolecules · 2021Article
- Binding of SARS-CoV Covalent Non-Covalent Inhibitors to the SARS-CoV-2 Papain-Like Protease and Ovarian Tumor Domain Deubiquitinases.Biomolecules · 2021Article
- GNPS-guided discovery of xylacremolide C and D, evaluation of their putative biosynthetic origin and bioactivity studies of xylacremolide A and B.RSC advances · 2021Article
- An insight into the interaction between α-ketoamide- based inhibitor and coronavirus main protease: A detailed in silico study.Biophysical chemistry · 2021Article
- A Small Molecule Inhibitor of Pex3-Pex19 Interaction Disrupts Glycosome Biogenesis and Causes Lethality inFrontiers in cell and developmental biology · 2021Article
- 2-Sulfonylpyrimidines as Privileged Warheads for the Development ofFrontiers in molecular biosciences · 2021Article
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13 authors at 3 institutions in 1 country.
Funding
Abstract
The facile synthesis and detailed investigation of a class of highly potent protease inhibitors based on 1,4-naphthoquinones with a dipeptidic recognition motif (HN-l-Phe-l-Leu-OR) in the 2-position and an electron-withdrawing group (EWG) in the 3-position is presented. One of the compound representatives, namely the acid with EWG = CN and with R = H proved to be a highly potent rhodesain inhibitor with nanomolar affinity. The respective benzyl ester (R = Bn) was found to be hydrolyzed by the target enzyme itself yielding the free acid. Detailed kinetic and mass spectrometry studies revealed a reversible covalent binding mode. Theoretical calculations with different density functionals (DFT) as well as wavefunction-based approaches were performed to elucidate the mode of action.
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