N‑[(Thiophen-3-yl)methyl]benzamides as fusion inhibitors of influenza virus targeting H1 and H5 hemagglutinin

Novel antiviral drugs are needed to prepare for infections from influenza A virus (IAV). Here, a series of N-[(thiophen-3-yl)methyl]benzamides, which target the hemagglutinin (HA)-mediated fusion process, is reported. The most active compound, VF-57a, displays a 50% effective concentration (EC50) of...

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Detalles Bibliográficos
Autores: Francesconi, Valeria, Rimaux, Silke, Valdivia, Aitor, Martín López, Juan, Escriche Molina, Celia, Mestdagh, Cato, Van Berwaer, Ria, Schurmans, Lieselotte, Verleye, Kaat, Noppen, Samuel, Lozano, Oscar, Stevaert, Annelies, Luque Garriga, F. Xavier, Niesens, Lieve, Vázquez Cruz, Santiago
Tipo de recurso: artículo
Estado:Versión publicada
Fecha de publicación:2025
País:España
Institución:Universidad de Barcelona
Repositorio:Dipòsit Digital de la UB
OAI Identifier:oai:diposit.ub.edu:2445/227287
Acceso en línea:https://hdl.handle.net/2445/227287
Access Level:acceso abierto
Palabra clave:Inhibidors enzimàtics
Influenzavirus
Lligands
Enzyme inhibitors
Influenza viruses
Ligands
Descripción
Sumario:Novel antiviral drugs are needed to prepare for infections from influenza A virus (IAV). Here, a series of N-[(thiophen-3-yl)methyl]benzamides, which target the hemagglutinin (HA)-mediated fusion process, is reported. The most active compound, VF-57a, displays a 50% effective concentration (EC50) of∼0.8 <em>μ</em>M and an antiviral selectivity index >130 in Madin−Darby canine kidney (MDCK) cells infected with A/H1N1 virus. VF-57a proved to be a strong inhibitor of A/H1N1 and A/H5N1 pseudovirus entry (EC50 values of 0.3 and 0.8 <em>μ</em>M, respectively). Cell−cell fusion assays in HA-expressing cells, surface plasmon resonance-based assessment of HA protein refolding, and resistance studies suggested that VF-57a prevents the conformational change of HA at acidic pH. Molecular modeling highlighted the role of the dimethylthiophene moiety and the amide-based tether in anchoring to the binding cavity of HA. Our findings support the further development of this class of IAV fusion inhibitors against A/H1N1 and A/H5N1 viruses.