Structure-activity relationship study of cationic carbosilane dendritic systems as antibacterial agents

This work focuses on the antibacterial activity against Gram-positive Staphylococcus aureus and Gramnegative Escherichia coli and the hemolytic properties of two types of ammonium cationic carbosilane systems: dendrimers and dendrons. The effects of: i) the generation, ii) the type of peripheral gro...

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Autores: Fuentes Paniagua, María Elena, Sánchez-Nieves Fernández, Javier|||0000-0003-0410-2285, Hernández Ros, José Manuel, Fernández Ezequiel, Alba, Soliveri de Carranza, Juan|||0000-0001-8200-0132, Copa Patiño, José Luis|||0000-0002-2162-3907, Gómez Ramírez, Rafael|||0000-0001-6448-2414, Mata de la Mata, Francisco Javier de la|||0000-0003-0418-3935
Tipo de recurso: artículo
Fecha de publicación:2016
País:España
Institución:Universidad de Alcalá (UAH)
Repositorio:e_Buah Biblioteca Digital Universidad de Alcalá
Idioma:inglés
OAI Identifier:oai:ebuah.uah.es:10017/34040
Acceso en línea:http://hdl.handle.net/10017/34040
https://dx.doi.org/10.1039/C5RA25901K
Access Level:acceso abierto
Palabra clave:Dendritic
Cationic
Antibacterial
Resistance assay
Biofilm
Chemistry
Química
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spelling Structure-activity relationship study of cationic carbosilane dendritic systems as antibacterial agentsFuentes Paniagua, María ElenaSánchez-Nieves Fernández, Javier|||0000-0003-0410-2285Hernández Ros, José ManuelFernández Ezequiel, AlbaSoliveri de Carranza, Juan|||0000-0001-8200-0132Copa Patiño, José Luis|||0000-0002-2162-3907Gómez Ramírez, Rafael|||0000-0001-6448-2414Mata de la Mata, Francisco Javier de la|||0000-0003-0418-3935DendriticCationicAntibacterialResistance assayBiofilmChemistryQuímicaThis work focuses on the antibacterial activity against Gram-positive Staphylococcus aureus and Gramnegative Escherichia coli and the hemolytic properties of two types of ammonium cationic carbosilane systems: dendrimers and dendrons. The effects of: i) the generation, ii) the type of peripheral groups near the cationic charges (a SiMe2 moiety or a S atom depending on the synthetic procedure, hydrosilylation or thiol-ene addition, respectively), iii) the core of dendrimers (polyphenoxo vs. Si atom) and iv) the focal point of dendrons (-N3, -NH2, -OH) have been assessed. The structure-activity relationship analysis indicates the importance of an adequate balance between the hydrophilic and lipophilic fragments of these molecules to reach the best antibacterial activity. Regarding hemolysis, lowest toxicity values were registered for dendritic systems with a sulfur atom close to the surface and, in the particular case of dendrons, for those with a hydroxyl focal point. One dendrimer and one dendron, both bearing a sulfur atom close to the surface, scored best in the activity-toxicity relationship analysis and were chosen for resistance assays. No changes in the inhibitory and bactericidal capacity in the case of the dendron and only a slight increase of these values for the dendrimer were observed after 15 subculture cycles. Furthermore, these two compounds stayed active towards different strains of resistant bacteria and avoid formation of biofilm at concentrations over the minimum inhibitory concentration (MIC).Ministerio de Economía y Empresa20162016-01-01journal articlehttp://purl.org/coar/resource_type/c_6501NAhttp://purl.org/coar/version/c_be7fb7dd8ff6fe43info:eu-repo/semantics/articleapplication/pdfhttp://hdl.handle.net/10017/34040https://dx.doi.org/10.1039/C5RA25901Kreponame:e_Buah Biblioteca Digital Universidad de Alcaláinstname:Universidad de Alcalá (UAH)InglésengMinisterio de Economía y Competitividad http://dx.doi.org/10.13039/501100003329 Not available CTQ2011-23245 DISEÑO DE NANOSISTEMAS DENDRÍTICOS BIFUNCIONALES DE NATURALEZA CARBOSILANO PARA SU APLICACIÓN EN BIOMEDICINAopen accesshttp://purl.org/coar/access_right/c_abf2Attribution-NonCommercial-NoDerivatives 4.0 Internationalhttp://creativecommons.org/licenses/by-nc-nd/4.0/info:eu-repo/semantics/openAccessoai:ebuah.uah.es:10017/340402026-06-18T11:13:07Z
dc.title.none.fl_str_mv Structure-activity relationship study of cationic carbosilane dendritic systems as antibacterial agents
title Structure-activity relationship study of cationic carbosilane dendritic systems as antibacterial agents
spellingShingle Structure-activity relationship study of cationic carbosilane dendritic systems as antibacterial agents
Fuentes Paniagua, María Elena
Dendritic
Cationic
Antibacterial
Resistance assay
Biofilm
Chemistry
Química
title_short Structure-activity relationship study of cationic carbosilane dendritic systems as antibacterial agents
title_full Structure-activity relationship study of cationic carbosilane dendritic systems as antibacterial agents
title_fullStr Structure-activity relationship study of cationic carbosilane dendritic systems as antibacterial agents
title_full_unstemmed Structure-activity relationship study of cationic carbosilane dendritic systems as antibacterial agents
title_sort Structure-activity relationship study of cationic carbosilane dendritic systems as antibacterial agents
dc.creator.none.fl_str_mv Fuentes Paniagua, María Elena
Sánchez-Nieves Fernández, Javier|||0000-0003-0410-2285
Hernández Ros, José Manuel
Fernández Ezequiel, Alba
Soliveri de Carranza, Juan|||0000-0001-8200-0132
Copa Patiño, José Luis|||0000-0002-2162-3907
Gómez Ramírez, Rafael|||0000-0001-6448-2414
Mata de la Mata, Francisco Javier de la|||0000-0003-0418-3935
author Fuentes Paniagua, María Elena
author_facet Fuentes Paniagua, María Elena
Sánchez-Nieves Fernández, Javier|||0000-0003-0410-2285
Hernández Ros, José Manuel
Fernández Ezequiel, Alba
Soliveri de Carranza, Juan|||0000-0001-8200-0132
Copa Patiño, José Luis|||0000-0002-2162-3907
Gómez Ramírez, Rafael|||0000-0001-6448-2414
Mata de la Mata, Francisco Javier de la|||0000-0003-0418-3935
author_role author
author2 Sánchez-Nieves Fernández, Javier|||0000-0003-0410-2285
Hernández Ros, José Manuel
Fernández Ezequiel, Alba
Soliveri de Carranza, Juan|||0000-0001-8200-0132
Copa Patiño, José Luis|||0000-0002-2162-3907
Gómez Ramírez, Rafael|||0000-0001-6448-2414
Mata de la Mata, Francisco Javier de la|||0000-0003-0418-3935
author2_role author
author
author
author
author
author
author
dc.subject.none.fl_str_mv Dendritic
Cationic
Antibacterial
Resistance assay
Biofilm
Chemistry
Química
topic Dendritic
Cationic
Antibacterial
Resistance assay
Biofilm
Chemistry
Química
description This work focuses on the antibacterial activity against Gram-positive Staphylococcus aureus and Gramnegative Escherichia coli and the hemolytic properties of two types of ammonium cationic carbosilane systems: dendrimers and dendrons. The effects of: i) the generation, ii) the type of peripheral groups near the cationic charges (a SiMe2 moiety or a S atom depending on the synthetic procedure, hydrosilylation or thiol-ene addition, respectively), iii) the core of dendrimers (polyphenoxo vs. Si atom) and iv) the focal point of dendrons (-N3, -NH2, -OH) have been assessed. The structure-activity relationship analysis indicates the importance of an adequate balance between the hydrophilic and lipophilic fragments of these molecules to reach the best antibacterial activity. Regarding hemolysis, lowest toxicity values were registered for dendritic systems with a sulfur atom close to the surface and, in the particular case of dendrons, for those with a hydroxyl focal point. One dendrimer and one dendron, both bearing a sulfur atom close to the surface, scored best in the activity-toxicity relationship analysis and were chosen for resistance assays. No changes in the inhibitory and bactericidal capacity in the case of the dendron and only a slight increase of these values for the dendrimer were observed after 15 subculture cycles. Furthermore, these two compounds stayed active towards different strains of resistant bacteria and avoid formation of biofilm at concentrations over the minimum inhibitory concentration (MIC).
publishDate 2016
dc.date.none.fl_str_mv 2016
2016-01-01
dc.type.none.fl_str_mv journal article
http://purl.org/coar/resource_type/c_6501
NA
http://purl.org/coar/version/c_be7fb7dd8ff6fe43
dc.type.openaire.fl_str_mv info:eu-repo/semantics/article
format article
dc.identifier.none.fl_str_mv http://hdl.handle.net/10017/34040
https://dx.doi.org/10.1039/C5RA25901K
url http://hdl.handle.net/10017/34040
https://dx.doi.org/10.1039/C5RA25901K
dc.language.none.fl_str_mv Inglés
eng
language_invalid_str_mv Inglés
language eng
dc.relation.none.fl_str_mv Ministerio de Economía y Competitividad http://dx.doi.org/10.13039/501100003329 Not available CTQ2011-23245 DISEÑO DE NANOSISTEMAS DENDRÍTICOS BIFUNCIONALES DE NATURALEZA CARBOSILANO PARA SU APLICACIÓN EN BIOMEDICINA
dc.rights.none.fl_str_mv open access
http://purl.org/coar/access_right/c_abf2
Attribution-NonCommercial-NoDerivatives 4.0 International
http://creativecommons.org/licenses/by-nc-nd/4.0/
dc.rights.openaire.fl_str_mv info:eu-repo/semantics/openAccess
rights_invalid_str_mv open access
http://purl.org/coar/access_right/c_abf2
Attribution-NonCommercial-NoDerivatives 4.0 International
http://creativecommons.org/licenses/by-nc-nd/4.0/
eu_rights_str_mv openAccess
dc.format.none.fl_str_mv application/pdf
dc.source.none.fl_str_mv reponame:e_Buah Biblioteca Digital Universidad de Alcalá
instname:Universidad de Alcalá (UAH)
instname_str Universidad de Alcalá (UAH)
reponame_str e_Buah Biblioteca Digital Universidad de Alcalá
collection e_Buah Biblioteca Digital Universidad de Alcalá
repository.name.fl_str_mv
repository.mail.fl_str_mv
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