Structure-activity relationships for Poly(phenylene)vinylene derivatives as antibacterial agents

Autores
Tolosa, Juan; Serrano de las Heras, Gemma; Carrión, Blanca; Segura, Tomás; Páez, Paulina Laura; de Lera-Garrido, Fernando J.; Rodríguez-López, Julián; García-Martínez, Joaquín C.
Año de publicación
2018
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
A series of poly(phenylene)vinylene (PPV) derivatives with different geometries and peripheral functional groups have been synthesized by Horner-Wadsworth-Emmons reaction. Compounds bearing carboxylic acid or quaternary ammonium functional groups prepared by this metal-free protocol were weakly active against both Gram-negative and Gram-positive bacteria, which is in contrast to previously reported results. The activity of polyanionic derivatives was higher for Gram-negative bacteria and showed bacteriostatic behavior, whereas polycationic derivatives were clearly more active against Gram-positive bacteria and behaved as bactericidal agents. The spatial disposition of the active groups seems to play a key role, with the highest activity observed for a C3v geometry. The presence of quaternary ammonium functional groups also facilitated the internalization of the molecules into the bacteria. Levels of cytotoxicity similar to that of the solvent were obtained for most compounds against COS-1 and VERO cells.
Fil: Tolosa, Juan. Universidad de Castilla-La Mancha; España
Fil: Serrano de las Heras, Gemma. Complejo Hospitalario Universitario de Albacete; España
Fil: Carrión, Blanca. Complejo Hospitalario Universitario de Albacete; España
Fil: Segura, Tomás. Complejo Hospitalario Universitario de Albacete; España
Fil: Páez, Paulina Laura. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Unidad de Investigación y Desarrollo en Tecnología Farmacéutica. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Unidad de Investigación y Desarrollo en Tecnología Farmacéutica; Argentina
Fil: de Lera-Garrido, Fernando J.. Universidad de Castilla-La Mancha; España
Fil: Rodríguez-López, Julián. Universidad de Castilla-La Mancha; España
Fil: García-Martínez, Joaquín C.. Universidad de Castilla-La Mancha; España
Materia
ANTIBACTERIAL
BIOLOGICALLY ACTIVE COMPOUNDS
INTERNALIZATION
POLY(PHENYLENE)VINYLENES
STRUCTURE-ACTIVITY RELATIONSHIPS
Nivel de accesibilidad
acceso abierto
Condiciones de uso
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
Repositorio
CONICET Digital (CONICET)
Institución
Consejo Nacional de Investigaciones Científicas y Técnicas
OAI Identificador
oai:ri.conicet.gov.ar:11336/88107
Acceder
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oai_identifier_str oai:ri.conicet.gov.ar:11336/88107
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Structure-activity relationships for Poly(phenylene)vinylene derivatives as antibacterial agentsTolosa, JuanSerrano de las Heras, GemmaCarrión, BlancaSegura, TomásPáez, Paulina Laurade Lera-Garrido, Fernando J.Rodríguez-López, JuliánGarcía-Martínez, Joaquín C.ANTIBACTERIALBIOLOGICALLY ACTIVE COMPOUNDSINTERNALIZATIONPOLY(PHENYLENE)VINYLENESSTRUCTURE-ACTIVITY RELATIONSHIPShttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1A series of poly(phenylene)vinylene (PPV) derivatives with different geometries and peripheral functional groups have been synthesized by Horner-Wadsworth-Emmons reaction. Compounds bearing carboxylic acid or quaternary ammonium functional groups prepared by this metal-free protocol were weakly active against both Gram-negative and Gram-positive bacteria, which is in contrast to previously reported results. The activity of polyanionic derivatives was higher for Gram-negative bacteria and showed bacteriostatic behavior, whereas polycationic derivatives were clearly more active against Gram-positive bacteria and behaved as bactericidal agents. The spatial disposition of the active groups seems to play a key role, with the highest activity observed for a C3v geometry. The presence of quaternary ammonium functional groups also facilitated the internalization of the molecules into the bacteria. Levels of cytotoxicity similar to that of the solvent were obtained for most compounds against COS-1 and VERO cells.Fil: Tolosa, Juan. Universidad de Castilla-La Mancha; EspañaFil: Serrano de las Heras, Gemma. Complejo Hospitalario Universitario de Albacete; EspañaFil: Carrión, Blanca. Complejo Hospitalario Universitario de Albacete; EspañaFil: Segura, Tomás. Complejo Hospitalario Universitario de Albacete; EspañaFil: Páez, Paulina Laura. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Unidad de Investigación y Desarrollo en Tecnología Farmacéutica. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Unidad de Investigación y Desarrollo en Tecnología Farmacéutica; ArgentinaFil: de Lera-Garrido, Fernando J.. Universidad de Castilla-La Mancha; EspañaFil: Rodríguez-López, Julián. Universidad de Castilla-La Mancha; EspañaFil: García-Martínez, Joaquín C.. Universidad de Castilla-La Mancha; EspañaWiley2018-07-03info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/88107Tolosa, Juan; Serrano de las Heras, Gemma; Carrión, Blanca; Segura, Tomás; Páez, Paulina Laura; et al.; Structure-activity relationships for Poly(phenylene)vinylene derivatives as antibacterial agents; Wiley; Chemistry Select; 3; 25; 3-7-2018; 7327-73327327-7332CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/url/https://onlinelibrary.wiley.com/doi/full/10.1002/slct.201801287info:eu-repo/semantics/altIdentifier/doi/10.1002/slct.201801287info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-10-22T11:08:41Zoai:ri.conicet.gov.ar:11336/88107instacron:CONICETInstitucionalhttp://ri.conicet.gov.ar/Organismo científico-tecnológicoNo correspondehttp://ri.conicet.gov.ar/oai/requestdasensio@conicet.gov.ar; lcarlino@conicet.gov.arArgentinaNo correspondeNo correspondeNo correspondeopendoar:34982025-10-22 11:08:41.362CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Structure-activity relationships for Poly(phenylene)vinylene derivatives as antibacterial agents
title Structure-activity relationships for Poly(phenylene)vinylene derivatives as antibacterial agents
spellingShingle Structure-activity relationships for Poly(phenylene)vinylene derivatives as antibacterial agents
Tolosa, Juan
ANTIBACTERIAL
BIOLOGICALLY ACTIVE COMPOUNDS
INTERNALIZATION
POLY(PHENYLENE)VINYLENES
STRUCTURE-ACTIVITY RELATIONSHIPS
title_short Structure-activity relationships for Poly(phenylene)vinylene derivatives as antibacterial agents
title_full Structure-activity relationships for Poly(phenylene)vinylene derivatives as antibacterial agents
title_fullStr Structure-activity relationships for Poly(phenylene)vinylene derivatives as antibacterial agents
title_full_unstemmed Structure-activity relationships for Poly(phenylene)vinylene derivatives as antibacterial agents
title_sort Structure-activity relationships for Poly(phenylene)vinylene derivatives as antibacterial agents
dc.creator.none.fl_str_mv Tolosa, Juan
Serrano de las Heras, Gemma
Carrión, Blanca
Segura, Tomás
Páez, Paulina Laura
de Lera-Garrido, Fernando J.
Rodríguez-López, Julián
García-Martínez, Joaquín C.
author Tolosa, Juan
author_facet Tolosa, Juan
Serrano de las Heras, Gemma
Carrión, Blanca
Segura, Tomás
Páez, Paulina Laura
de Lera-Garrido, Fernando J.
Rodríguez-López, Julián
García-Martínez, Joaquín C.
author_role author
author2 Serrano de las Heras, Gemma
Carrión, Blanca
Segura, Tomás
Páez, Paulina Laura
de Lera-Garrido, Fernando J.
Rodríguez-López, Julián
García-Martínez, Joaquín C.
author2_role author
author
author
author
author
author
author
dc.subject.none.fl_str_mv ANTIBACTERIAL
BIOLOGICALLY ACTIVE COMPOUNDS
INTERNALIZATION
POLY(PHENYLENE)VINYLENES
STRUCTURE-ACTIVITY RELATIONSHIPS
topic ANTIBACTERIAL
BIOLOGICALLY ACTIVE COMPOUNDS
INTERNALIZATION
POLY(PHENYLENE)VINYLENES
STRUCTURE-ACTIVITY RELATIONSHIPS
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv A series of poly(phenylene)vinylene (PPV) derivatives with different geometries and peripheral functional groups have been synthesized by Horner-Wadsworth-Emmons reaction. Compounds bearing carboxylic acid or quaternary ammonium functional groups prepared by this metal-free protocol were weakly active against both Gram-negative and Gram-positive bacteria, which is in contrast to previously reported results. The activity of polyanionic derivatives was higher for Gram-negative bacteria and showed bacteriostatic behavior, whereas polycationic derivatives were clearly more active against Gram-positive bacteria and behaved as bactericidal agents. The spatial disposition of the active groups seems to play a key role, with the highest activity observed for a C3v geometry. The presence of quaternary ammonium functional groups also facilitated the internalization of the molecules into the bacteria. Levels of cytotoxicity similar to that of the solvent were obtained for most compounds against COS-1 and VERO cells.
Fil: Tolosa, Juan. Universidad de Castilla-La Mancha; España
Fil: Serrano de las Heras, Gemma. Complejo Hospitalario Universitario de Albacete; España
Fil: Carrión, Blanca. Complejo Hospitalario Universitario de Albacete; España
Fil: Segura, Tomás. Complejo Hospitalario Universitario de Albacete; España
Fil: Páez, Paulina Laura. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Unidad de Investigación y Desarrollo en Tecnología Farmacéutica. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Unidad de Investigación y Desarrollo en Tecnología Farmacéutica; Argentina
Fil: de Lera-Garrido, Fernando J.. Universidad de Castilla-La Mancha; España
Fil: Rodríguez-López, Julián. Universidad de Castilla-La Mancha; España
Fil: García-Martínez, Joaquín C.. Universidad de Castilla-La Mancha; España
description A series of poly(phenylene)vinylene (PPV) derivatives with different geometries and peripheral functional groups have been synthesized by Horner-Wadsworth-Emmons reaction. Compounds bearing carboxylic acid or quaternary ammonium functional groups prepared by this metal-free protocol were weakly active against both Gram-negative and Gram-positive bacteria, which is in contrast to previously reported results. The activity of polyanionic derivatives was higher for Gram-negative bacteria and showed bacteriostatic behavior, whereas polycationic derivatives were clearly more active against Gram-positive bacteria and behaved as bactericidal agents. The spatial disposition of the active groups seems to play a key role, with the highest activity observed for a C3v geometry. The presence of quaternary ammonium functional groups also facilitated the internalization of the molecules into the bacteria. Levels of cytotoxicity similar to that of the solvent were obtained for most compounds against COS-1 and VERO cells.
publishDate 2018
dc.date.none.fl_str_mv 2018-07-03
dc.type.none.fl_str_mv info:eu-repo/semantics/article
info:eu-repo/semantics/publishedVersion
http://purl.org/coar/resource_type/c_6501
info:ar-repo/semantics/articulo
format article
status_str publishedVersion
dc.identifier.none.fl_str_mv http://hdl.handle.net/11336/88107
Tolosa, Juan; Serrano de las Heras, Gemma; Carrión, Blanca; Segura, Tomás; Páez, Paulina Laura; et al.; Structure-activity relationships for Poly(phenylene)vinylene derivatives as antibacterial agents; Wiley; Chemistry Select; 3; 25; 3-7-2018; 7327-7332
7327-7332
CONICET Digital
CONICET
url http://hdl.handle.net/11336/88107
identifier_str_mv Tolosa, Juan; Serrano de las Heras, Gemma; Carrión, Blanca; Segura, Tomás; Páez, Paulina Laura; et al.; Structure-activity relationships for Poly(phenylene)vinylene derivatives as antibacterial agents; Wiley; Chemistry Select; 3; 25; 3-7-2018; 7327-7332
7327-7332
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/url/https://onlinelibrary.wiley.com/doi/full/10.1002/slct.201801287
info:eu-repo/semantics/altIdentifier/doi/10.1002/slct.201801287
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
eu_rights_str_mv openAccess
rights_invalid_str_mv https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
dc.format.none.fl_str_mv application/pdf
application/pdf
dc.publisher.none.fl_str_mv Wiley
publisher.none.fl_str_mv Wiley
dc.source.none.fl_str_mv reponame:CONICET Digital (CONICET)
instname:Consejo Nacional de Investigaciones Científicas y Técnicas
reponame_str CONICET Digital (CONICET)
collection CONICET Digital (CONICET)
instname_str Consejo Nacional de Investigaciones Científicas y Técnicas
repository.name.fl_str_mv CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicas
repository.mail.fl_str_mv dasensio@conicet.gov.ar; lcarlino@conicet.gov.ar
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score 12.982451

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