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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...
Autores principales: | , , , , , , , , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
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Nature Publishing Group UK
2023
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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. |
format | Online Article Text |
id | pubmed-10520035 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2023 |
publisher | Nature Publishing Group UK |
record_format | MEDLINE/PubMed |
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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