Effects of synthetic tetronamides and methylated denigrins on bacterial quorum sensing and biofilm formation

Detrimental biofilms of bacterial pathogens cause chronic infections with a high-level tolerance to antibiotics. To identify new control agents, we synthesized and tested a total of 14 tetronamides (including 5 new compounds) and 6 denigrin intermediates on the model species Escherichia coli. At a c...

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Detalles Bibliográficos
Autores: Sweta Roy, Jaime Acosta, Milandip Karak, Isabela Ramirez-velez, Kohei Torikai, Dacheng Ren, Luiz Cláudio de Almeida Barbosa
Tipo de recurso: artículo
Estado:Versión publicada
Fecha de publicación:2023
País:Brasil
Institución:Universidade Federal de Minas Gerais (UFMG)
Repositorio:Repositório Institucional da UFMG
Idioma:inglés
OAI Identifier:oai:repositorio.ufmg.br:1843/80563
Acceso en línea:https://doi.org/10.1021/acsomega.3c01729
http://hdl.handle.net/1843/80563
Access Level:acceso abierto
Palabra clave:Biofilm inhibition
Tetronamides
Denigrins
Butenolide
Patologia
Bactéria
Bactérias patogênicas
Biologia
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spelling Effects of synthetic tetronamides and methylated denigrins on bacterial quorum sensing and biofilm formationBiofilm inhibitionTetronamidesDenigrinsButenolidePatologiaBactériaBactérias patogênicasBiologiaDetrimental biofilms of bacterial pathogens cause chronic infections with a high-level tolerance to antibiotics. To identify new control agents, we synthesized and tested a total of 14 tetronamides (including 5 new compounds) and 6 denigrin intermediates on the model species Escherichia coli. At a concentration of 50 μg/mL, two tetronamides and two methylated denigrins exhibited significant inhibitory effects against biofilm formation of E. coli RP437, e.g., by 60 and 94%, respectively. Structural analysis of the tested compounds revealed that p-methoxybenzylidene and p-methoxyphenethyl moieties of denigrins are important for biofilm inhibition, while the former group is also essential to the activity against quorum sensing (QS) via AI-2. Specifically, tetramethyldenigrin B has strong inhibitory effects against both E. coli biofilm formation and AI-2-mediated QS and thus provides a promising lead structure for designing better control agents. Consistently, tetramethyldenigrin B also showed inhibitory activity against biofilm formation of uropathogenic E. coli. Together, these findings provide new insights for the rational design of novel biofilm and QS inhibitors.Universidade Federal de Minas GeraisBrasilICX - DEPARTAMENTO DE QUÍMICAUFMG2025-03-07T18:35:39Z2025-03-07T18:35:39Z2023-10-02info:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/articlepdfapplication/pdfhttps://doi.org/10.1021/acsomega.3c017292470-1343http://hdl.handle.net/1843/80563engACS Omegainfo:eu-repo/semantics/openAccessreponame:Repositório Institucional da UFMGinstname:Universidade Federal de Minas Gerais (UFMG)instacron:UFMGSweta RoyJaime AcostaMilandip KarakIsabela Ramirez-velezKohei TorikaiDacheng RenLuiz Cláudio de Almeida Barbosa2025-03-07T18:35:39Zoai:repositorio.ufmg.br:1843/80563Repositório InstitucionalPUBhttps://repositorio.ufmg.br/oairepositorio@ufmg.bropendoar:2025-03-07T18:35:39Repositório Institucional da UFMG - Universidade Federal de Minas Gerais (UFMG)false
dc.title.none.fl_str_mv Effects of synthetic tetronamides and methylated denigrins on bacterial quorum sensing and biofilm formation
title Effects of synthetic tetronamides and methylated denigrins on bacterial quorum sensing and biofilm formation
spellingShingle Effects of synthetic tetronamides and methylated denigrins on bacterial quorum sensing and biofilm formation
Sweta Roy
Biofilm inhibition
Tetronamides
Denigrins
Butenolide
Patologia
Bactéria
Bactérias patogênicas
Biologia
title_short Effects of synthetic tetronamides and methylated denigrins on bacterial quorum sensing and biofilm formation
title_full Effects of synthetic tetronamides and methylated denigrins on bacterial quorum sensing and biofilm formation
title_fullStr Effects of synthetic tetronamides and methylated denigrins on bacterial quorum sensing and biofilm formation
title_full_unstemmed Effects of synthetic tetronamides and methylated denigrins on bacterial quorum sensing and biofilm formation
title_sort Effects of synthetic tetronamides and methylated denigrins on bacterial quorum sensing and biofilm formation
dc.creator.none.fl_str_mv Sweta Roy
Jaime Acosta
Milandip Karak
Isabela Ramirez-velez
Kohei Torikai
Dacheng Ren
Luiz Cláudio de Almeida Barbosa
author Sweta Roy
author_facet Sweta Roy
Jaime Acosta
Milandip Karak
Isabela Ramirez-velez
Kohei Torikai
Dacheng Ren
Luiz Cláudio de Almeida Barbosa
author_role author
author2 Jaime Acosta
Milandip Karak
Isabela Ramirez-velez
Kohei Torikai
Dacheng Ren
Luiz Cláudio de Almeida Barbosa
author2_role author
author
author
author
author
author
dc.subject.por.fl_str_mv Biofilm inhibition
Tetronamides
Denigrins
Butenolide
Patologia
Bactéria
Bactérias patogênicas
Biologia
topic Biofilm inhibition
Tetronamides
Denigrins
Butenolide
Patologia
Bactéria
Bactérias patogênicas
Biologia
description Detrimental biofilms of bacterial pathogens cause chronic infections with a high-level tolerance to antibiotics. To identify new control agents, we synthesized and tested a total of 14 tetronamides (including 5 new compounds) and 6 denigrin intermediates on the model species Escherichia coli. At a concentration of 50 μg/mL, two tetronamides and two methylated denigrins exhibited significant inhibitory effects against biofilm formation of E. coli RP437, e.g., by 60 and 94%, respectively. Structural analysis of the tested compounds revealed that p-methoxybenzylidene and p-methoxyphenethyl moieties of denigrins are important for biofilm inhibition, while the former group is also essential to the activity against quorum sensing (QS) via AI-2. Specifically, tetramethyldenigrin B has strong inhibitory effects against both E. coli biofilm formation and AI-2-mediated QS and thus provides a promising lead structure for designing better control agents. Consistently, tetramethyldenigrin B also showed inhibitory activity against biofilm formation of uropathogenic E. coli. Together, these findings provide new insights for the rational design of novel biofilm and QS inhibitors.
publishDate 2023
dc.date.none.fl_str_mv 2023-10-02
2025-03-07T18:35:39Z
2025-03-07T18:35:39Z
dc.type.status.fl_str_mv info:eu-repo/semantics/publishedVersion
dc.type.driver.fl_str_mv info:eu-repo/semantics/article
format article
status_str publishedVersion
dc.identifier.uri.fl_str_mv https://doi.org/10.1021/acsomega.3c01729
2470-1343
http://hdl.handle.net/1843/80563
url https://doi.org/10.1021/acsomega.3c01729
http://hdl.handle.net/1843/80563
identifier_str_mv 2470-1343
dc.language.iso.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv ACS Omega
dc.rights.driver.fl_str_mv info:eu-repo/semantics/openAccess
eu_rights_str_mv openAccess
dc.format.none.fl_str_mv pdf
application/pdf
dc.publisher.none.fl_str_mv Universidade Federal de Minas Gerais
Brasil
ICX - DEPARTAMENTO DE QUÍMICA
UFMG
publisher.none.fl_str_mv Universidade Federal de Minas Gerais
Brasil
ICX - DEPARTAMENTO DE QUÍMICA
UFMG
dc.source.none.fl_str_mv reponame:Repositório Institucional da UFMG
instname:Universidade Federal de Minas Gerais (UFMG)
instacron:UFMG
instname_str Universidade Federal de Minas Gerais (UFMG)
instacron_str UFMG
institution UFMG
reponame_str Repositório Institucional da UFMG
collection Repositório Institucional da UFMG
repository.name.fl_str_mv Repositório Institucional da UFMG - Universidade Federal de Minas Gerais (UFMG)
repository.mail.fl_str_mv repositorio@ufmg.br
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score 15,300719

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