Phthalocyanine-sulfonamide conjugates: synthesis and photodynamic inactivation of Gram-negative and Gram-positive bacteria

Detalhes bibliográficos
Autor(a) principal: da Silva, Raquel Nunes
Data de Publicação: 2018
Outros Autores: Cunha, Ângela, Tomé, Augusto C.
Tipo de documento: Artigo
Idioma: eng
Título da fonte: Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)
Texto Completo: http://hdl.handle.net/10773/37678
Resumo: Phthalocyanines bearing four or eight sulfonamide units were synthesized and their efficiency in the photodynamic inactivation of Gram-negative (Escherichia coli) and Gram-positive (Staphylococcus aureus) bacteria was evaluated. Conjugates with simpler sulfonamide units (N,N-diethylbenzenesulfonamide, N-isopropylbenzenesulfonamide and N-(4-methoxyphenyl)benzenesulfonamide) caused stronger inactivation than those with heterocyclic groups (N-(thiazol-2-yl)benzenesulfonamide) or long alkyl chains (N-dodecylbenzenesulfonamide) in both bacteria. Furthermore, the encapsulation of the phthalocyanine-sulfonamide conjugates within polyvinylpyrrolidone micelles, used as drug delivery vehicles, in general showed to enhance the inactivation efficiency. The results show that encapsulated phthalocyanine-sulfonamide conjugates are a promising class of photosensitizers to be used in photodynamic antimicrobial therapy.
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spelling Phthalocyanine-sulfonamide conjugates: synthesis and photodynamic inactivation of Gram-negative and Gram-positive bacteriaPhthalocyanineSulfonamidePhotosensitizerPhotodynamic inactivationAntimicrobialE. coliS. aureusPhthalocyanines bearing four or eight sulfonamide units were synthesized and their efficiency in the photodynamic inactivation of Gram-negative (Escherichia coli) and Gram-positive (Staphylococcus aureus) bacteria was evaluated. Conjugates with simpler sulfonamide units (N,N-diethylbenzenesulfonamide, N-isopropylbenzenesulfonamide and N-(4-methoxyphenyl)benzenesulfonamide) caused stronger inactivation than those with heterocyclic groups (N-(thiazol-2-yl)benzenesulfonamide) or long alkyl chains (N-dodecylbenzenesulfonamide) in both bacteria. Furthermore, the encapsulation of the phthalocyanine-sulfonamide conjugates within polyvinylpyrrolidone micelles, used as drug delivery vehicles, in general showed to enhance the inactivation efficiency. The results show that encapsulated phthalocyanine-sulfonamide conjugates are a promising class of photosensitizers to be used in photodynamic antimicrobial therapy.Elsevier2023-05-11T11:23:23Z2018-06-25T00:00:00Z2018-06-25info:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/articleapplication/pdfhttp://hdl.handle.net/10773/37678eng0223-523410.1016/j.ejmech.2018.05.009da Silva, Raquel NunesCunha, ÂngelaTomé, Augusto C.info:eu-repo/semantics/openAccessreponame:Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)instname:Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informaçãoinstacron:RCAAP2024-02-22T12:13:34Zoai:ria.ua.pt:10773/37678Portal AgregadorONGhttps://www.rcaap.pt/oai/openaireopendoar:71602024-03-20T03:08:16.751458Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) - Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informaçãofalse
dc.title.none.fl_str_mv Phthalocyanine-sulfonamide conjugates: synthesis and photodynamic inactivation of Gram-negative and Gram-positive bacteria
title Phthalocyanine-sulfonamide conjugates: synthesis and photodynamic inactivation of Gram-negative and Gram-positive bacteria
spellingShingle Phthalocyanine-sulfonamide conjugates: synthesis and photodynamic inactivation of Gram-negative and Gram-positive bacteria
da Silva, Raquel Nunes
Phthalocyanine
Sulfonamide
Photosensitizer
Photodynamic inactivation
Antimicrobial
E. coli
S. aureus
title_short Phthalocyanine-sulfonamide conjugates: synthesis and photodynamic inactivation of Gram-negative and Gram-positive bacteria
title_full Phthalocyanine-sulfonamide conjugates: synthesis and photodynamic inactivation of Gram-negative and Gram-positive bacteria
title_fullStr Phthalocyanine-sulfonamide conjugates: synthesis and photodynamic inactivation of Gram-negative and Gram-positive bacteria
title_full_unstemmed Phthalocyanine-sulfonamide conjugates: synthesis and photodynamic inactivation of Gram-negative and Gram-positive bacteria
title_sort Phthalocyanine-sulfonamide conjugates: synthesis and photodynamic inactivation of Gram-negative and Gram-positive bacteria
author da Silva, Raquel Nunes
author_facet da Silva, Raquel Nunes
Cunha, Ângela
Tomé, Augusto C.
author_role author
author2 Cunha, Ângela
Tomé, Augusto C.
author2_role author
author
dc.contributor.author.fl_str_mv da Silva, Raquel Nunes
Cunha, Ângela
Tomé, Augusto C.
dc.subject.por.fl_str_mv Phthalocyanine
Sulfonamide
Photosensitizer
Photodynamic inactivation
Antimicrobial
E. coli
S. aureus
topic Phthalocyanine
Sulfonamide
Photosensitizer
Photodynamic inactivation
Antimicrobial
E. coli
S. aureus
description Phthalocyanines bearing four or eight sulfonamide units were synthesized and their efficiency in the photodynamic inactivation of Gram-negative (Escherichia coli) and Gram-positive (Staphylococcus aureus) bacteria was evaluated. Conjugates with simpler sulfonamide units (N,N-diethylbenzenesulfonamide, N-isopropylbenzenesulfonamide and N-(4-methoxyphenyl)benzenesulfonamide) caused stronger inactivation than those with heterocyclic groups (N-(thiazol-2-yl)benzenesulfonamide) or long alkyl chains (N-dodecylbenzenesulfonamide) in both bacteria. Furthermore, the encapsulation of the phthalocyanine-sulfonamide conjugates within polyvinylpyrrolidone micelles, used as drug delivery vehicles, in general showed to enhance the inactivation efficiency. The results show that encapsulated phthalocyanine-sulfonamide conjugates are a promising class of photosensitizers to be used in photodynamic antimicrobial therapy.
publishDate 2018
dc.date.none.fl_str_mv 2018-06-25T00:00:00Z
2018-06-25
2023-05-11T11:23:23Z
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 http://hdl.handle.net/10773/37678
url http://hdl.handle.net/10773/37678
dc.language.iso.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv 0223-5234
10.1016/j.ejmech.2018.05.009
dc.rights.driver.fl_str_mv info:eu-repo/semantics/openAccess
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:Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)
instname:Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informação
instacron:RCAAP
instname_str Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informação
instacron_str RCAAP
institution RCAAP
reponame_str Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)
collection Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)
repository.name.fl_str_mv Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) - Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informação
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