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Generation of potent antibacterial compounds through enzymatic and chemical modifications of the trans-δ-viniferin scaffold

Stilbene dimers are well-known for their diverse biological activities. In particular, previous studies have demonstrated the high antibacterial potential of a series of trans-δ-viniferin-related compounds against gram-positive bacteria such as Staphylococcus aureus. The trans-δ-viniferin scaffold h...

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Autores principales: Huber, Robin, Marcourt, Laurence, Héritier, Margaux, Luscher, Alexandre, Guebey, Laurie, Schnee, Sylvain, Michellod, Emilie, Guerrier, Stéphane, Wolfender, Jean-Luc, Scapozza, Leonardo, Köhler, Thilo, Gindro, Katia, Queiroz, Emerson Ferreira
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Nature Publishing Group UK 2023
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10520035/
https://www.ncbi.nlm.nih.gov/pubmed/37749179
http://dx.doi.org/10.1038/s41598-023-43000-5
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author Huber, Robin
Marcourt, Laurence
Héritier, Margaux
Luscher, Alexandre
Guebey, Laurie
Schnee, Sylvain
Michellod, Emilie
Guerrier, Stéphane
Wolfender, Jean-Luc
Scapozza, Leonardo
Köhler, Thilo
Gindro, Katia
Queiroz, Emerson Ferreira
author_facet Huber, Robin
Marcourt, Laurence
Héritier, Margaux
Luscher, Alexandre
Guebey, Laurie
Schnee, Sylvain
Michellod, Emilie
Guerrier, Stéphane
Wolfender, Jean-Luc
Scapozza, Leonardo
Köhler, Thilo
Gindro, Katia
Queiroz, Emerson Ferreira
author_sort Huber, Robin
collection PubMed
description Stilbene dimers are well-known for their diverse biological activities. In particular, previous studies have demonstrated the high antibacterial potential of a series of trans-δ-viniferin-related compounds against gram-positive bacteria such as Staphylococcus aureus. The trans-δ-viniferin scaffold has multiple chemical functions and can therefore be modified in various ways to generate derivatives. Here we report the synthesis of 40 derivatives obtained by light isomerization, O-methylation, halogenation and dimerization of other stilbene monomers. The antibacterial activities of all generated trans-δ-viniferin derivatives were evaluated against S. aureus and information on their structure–activity relationships (SAR) was obtained using a linear regression model. Our results show how several parameters, such as the O-methylation pattern and the presence of halogen atoms at specific positions, can determine the antibacterial activity. Taken together, these results can serve as a starting point for further SAR investigations.
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spelling pubmed-105200352023-09-27 Generation of potent antibacterial compounds through enzymatic and chemical modifications of the trans-δ-viniferin scaffold Huber, Robin Marcourt, Laurence Héritier, Margaux Luscher, Alexandre Guebey, Laurie Schnee, Sylvain Michellod, Emilie Guerrier, Stéphane Wolfender, Jean-Luc Scapozza, Leonardo Köhler, Thilo Gindro, Katia Queiroz, Emerson Ferreira Sci Rep Article Stilbene dimers are well-known for their diverse biological activities. In particular, previous studies have demonstrated the high antibacterial potential of a series of trans-δ-viniferin-related compounds against gram-positive bacteria such as Staphylococcus aureus. The trans-δ-viniferin scaffold has multiple chemical functions and can therefore be modified in various ways to generate derivatives. Here we report the synthesis of 40 derivatives obtained by light isomerization, O-methylation, halogenation and dimerization of other stilbene monomers. The antibacterial activities of all generated trans-δ-viniferin derivatives were evaluated against S. aureus and information on their structure–activity relationships (SAR) was obtained using a linear regression model. Our results show how several parameters, such as the O-methylation pattern and the presence of halogen atoms at specific positions, can determine the antibacterial activity. Taken together, these results can serve as a starting point for further SAR investigations. Nature Publishing Group UK 2023-09-25 /pmc/articles/PMC10520035/ /pubmed/37749179 http://dx.doi.org/10.1038/s41598-023-43000-5 Text en © The Author(s) 2023 https://creativecommons.org/licenses/by/4.0/Open Access This article is licensed under a Creative Commons Attribution 4.0 International License, which permits use, sharing, adaptation, distribution and reproduction in any medium or format, as long as you give appropriate credit to the original author(s) and the source, provide a link to the Creative Commons licence, and indicate if changes were made. The images or other third party material in this article are included in the article's Creative Commons licence, unless indicated otherwise in a credit line to the material. If material is not included in the article's Creative Commons licence and your intended use is not permitted by statutory regulation or exceeds the permitted use, you will need to obtain permission directly from the copyright holder. To view a copy of this licence, visit http://creativecommons.org/licenses/by/4.0/ (https://creativecommons.org/licenses/by/4.0/) .
spellingShingle Article
Huber, Robin
Marcourt, Laurence
Héritier, Margaux
Luscher, Alexandre
Guebey, Laurie
Schnee, Sylvain
Michellod, Emilie
Guerrier, Stéphane
Wolfender, Jean-Luc
Scapozza, Leonardo
Köhler, Thilo
Gindro, Katia
Queiroz, Emerson Ferreira
Generation of potent antibacterial compounds through enzymatic and chemical modifications of the trans-δ-viniferin scaffold
title Generation of potent antibacterial compounds through enzymatic and chemical modifications of the trans-δ-viniferin scaffold
title_full Generation of potent antibacterial compounds through enzymatic and chemical modifications of the trans-δ-viniferin scaffold
title_fullStr Generation of potent antibacterial compounds through enzymatic and chemical modifications of the trans-δ-viniferin scaffold
title_full_unstemmed Generation of potent antibacterial compounds through enzymatic and chemical modifications of the trans-δ-viniferin scaffold
title_short Generation of potent antibacterial compounds through enzymatic and chemical modifications of the trans-δ-viniferin scaffold
title_sort generation of potent antibacterial compounds through enzymatic and chemical modifications of the trans-δ-viniferin scaffold
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10520035/
https://www.ncbi.nlm.nih.gov/pubmed/37749179
http://dx.doi.org/10.1038/s41598-023-43000-5
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