Fluorine-substituted tetracationic ABAB-phthalocyanines for efficient photodynamic inactivation of Gram-positive and Gram-negative bacteria

Herein, we report the synthesis and characterization of new amphiphilic phthalocyanines (Pcs), the study of their singlet oxygen generation capabilities, and biological assays to determine their potential as photosensitizers for photodynamic inactivation of bacteria. In particular, Pcs with an ABAB...

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Detalles Bibliográficos
Autores: Revuelta-Maza, Miguel, González-Jiménez, Patricia, Hally, Cormac, Agut, Montserrat, Nonell, Santi, Torre Ponce, Gema de la, Torres Cebada, Tomás
Tipo de recurso: artículo
Fecha de publicación:2019
País:España
Institución:Universidad Autónoma de Madrid
Repositorio:Biblos-e Archivo. Repositorio Institucional de la UAM
Idioma:inglés
OAI Identifier:oai:repositorio.uam.es:10486/699465
Acceso en línea:http://hdl.handle.net/10486/699465
https://dx.doi.org/10.1016/j.ejmech.2019.111957
Access Level:acceso abierto
Palabra clave:Amphiphile
Bacteria
Cationic
Photodynamic inactivation
Phthalocyanine
Química
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spelling Fluorine-substituted tetracationic ABAB-phthalocyanines for efficient photodynamic inactivation of Gram-positive and Gram-negative bacteriaRevuelta-Maza, MiguelGonzález-Jiménez, PatriciaHally, CormacAgut, MontserratNonell, SantiTorre Ponce, Gema de laTorres Cebada, TomásAmphiphileBacteriaCationicPhotodynamic inactivationPhthalocyanineQuímicaHerein, we report the synthesis and characterization of new amphiphilic phthalocyanines (Pcs), the study of their singlet oxygen generation capabilities, and biological assays to determine their potential as photosensitizers for photodynamic inactivation of bacteria. In particular, Pcs with an ABAB geometry (where A and B refer to differently substituted isoindole constituents) have been synthesized. These molecules are endowed with bulky bis(trifluoromethylphenyl) groups in two facing isoindoles, which hinder aggregation and favour singlet oxygen generation, and pyridinium or alkylammonium moieties in the other two isoindoles. In particular, two water-soluble Pc derivatives (PS-1 and PS-2) have proved to be efficient in the photoinactivation of S. aureus and E. coli, selected as models of Gram-positive and Gram-negative bacteriaThis work has been supported by MINECO, Spain (CTQ2017-85393-P and CTQ2016-78454-C2-1-R)ElsevierDepartamento de Química OrgánicaFacultad de Ciencias20192019-12-10research articlehttp://purl.org/coar/resource_type/c_2df8fbb1AMhttp://purl.org/coar/version/c_ab4af688f83e57aainfo:eu-repo/semantics/articleapplication/pdfhttp://hdl.handle.net/10486/699465https://dx.doi.org/10.1016/j.ejmech.2019.111957reponame:Biblos-e Archivo. Repositorio Institucional de la UAMinstname:Universidad Autónoma de MadridInglésengopen accesshttp://purl.org/coar/access_right/c_abf2info:eu-repo/semantics/openAccessoai:repositorio.uam.es:10486/6994652026-06-23T12:46:27Z
dc.title.none.fl_str_mv Fluorine-substituted tetracationic ABAB-phthalocyanines for efficient photodynamic inactivation of Gram-positive and Gram-negative bacteria
title Fluorine-substituted tetracationic ABAB-phthalocyanines for efficient photodynamic inactivation of Gram-positive and Gram-negative bacteria
spellingShingle Fluorine-substituted tetracationic ABAB-phthalocyanines for efficient photodynamic inactivation of Gram-positive and Gram-negative bacteria
Revuelta-Maza, Miguel
Amphiphile
Bacteria
Cationic
Photodynamic inactivation
Phthalocyanine
Química
title_short Fluorine-substituted tetracationic ABAB-phthalocyanines for efficient photodynamic inactivation of Gram-positive and Gram-negative bacteria
title_full Fluorine-substituted tetracationic ABAB-phthalocyanines for efficient photodynamic inactivation of Gram-positive and Gram-negative bacteria
title_fullStr Fluorine-substituted tetracationic ABAB-phthalocyanines for efficient photodynamic inactivation of Gram-positive and Gram-negative bacteria
title_full_unstemmed Fluorine-substituted tetracationic ABAB-phthalocyanines for efficient photodynamic inactivation of Gram-positive and Gram-negative bacteria
title_sort Fluorine-substituted tetracationic ABAB-phthalocyanines for efficient photodynamic inactivation of Gram-positive and Gram-negative bacteria
dc.creator.none.fl_str_mv Revuelta-Maza, Miguel
González-Jiménez, Patricia
Hally, Cormac
Agut, Montserrat
Nonell, Santi
Torre Ponce, Gema de la
Torres Cebada, Tomás
author Revuelta-Maza, Miguel
author_facet Revuelta-Maza, Miguel
González-Jiménez, Patricia
Hally, Cormac
Agut, Montserrat
Nonell, Santi
Torre Ponce, Gema de la
Torres Cebada, Tomás
author_role author
author2 González-Jiménez, Patricia
Hally, Cormac
Agut, Montserrat
Nonell, Santi
Torre Ponce, Gema de la
Torres Cebada, Tomás
author2_role author
author
author
author
author
author
dc.contributor.none.fl_str_mv Departamento de Química Orgánica
Facultad de Ciencias
dc.subject.none.fl_str_mv Amphiphile
Bacteria
Cationic
Photodynamic inactivation
Phthalocyanine
Química
topic Amphiphile
Bacteria
Cationic
Photodynamic inactivation
Phthalocyanine
Química
description Herein, we report the synthesis and characterization of new amphiphilic phthalocyanines (Pcs), the study of their singlet oxygen generation capabilities, and biological assays to determine their potential as photosensitizers for photodynamic inactivation of bacteria. In particular, Pcs with an ABAB geometry (where A and B refer to differently substituted isoindole constituents) have been synthesized. These molecules are endowed with bulky bis(trifluoromethylphenyl) groups in two facing isoindoles, which hinder aggregation and favour singlet oxygen generation, and pyridinium or alkylammonium moieties in the other two isoindoles. In particular, two water-soluble Pc derivatives (PS-1 and PS-2) have proved to be efficient in the photoinactivation of S. aureus and E. coli, selected as models of Gram-positive and Gram-negative bacteria
publishDate 2019
dc.date.none.fl_str_mv 2019
2019-12-10
dc.type.none.fl_str_mv research article
http://purl.org/coar/resource_type/c_2df8fbb1
AM
http://purl.org/coar/version/c_ab4af688f83e57aa
dc.type.openaire.fl_str_mv info:eu-repo/semantics/article
format article
dc.identifier.none.fl_str_mv http://hdl.handle.net/10486/699465
https://dx.doi.org/10.1016/j.ejmech.2019.111957
url http://hdl.handle.net/10486/699465
https://dx.doi.org/10.1016/j.ejmech.2019.111957
dc.language.none.fl_str_mv Inglés
eng
language_invalid_str_mv Inglés
language eng
dc.rights.none.fl_str_mv open access
http://purl.org/coar/access_right/c_abf2
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
eu_rights_str_mv openAccess
dc.format.none.fl_str_mv application/pdf
dc.publisher.none.fl_str_mv Elsevier
publisher.none.fl_str_mv Elsevier
dc.source.none.fl_str_mv reponame:Biblos-e Archivo. Repositorio Institucional de la UAM
instname:Universidad Autónoma de Madrid
instname_str Universidad Autónoma de Madrid
reponame_str Biblos-e Archivo. Repositorio Institucional de la UAM
collection Biblos-e Archivo. Repositorio Institucional de la UAM
repository.name.fl_str_mv
repository.mail.fl_str_mv
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