Synthesis and photodynamic properties of amphiphilic A3B- phthalocyanine derivatives bearing N-heterocycles as potential cationic phototherapeutic agents

Autores
Tempesti, Tomas Cristian; Alvarez, María Gabriela; Durantini, Edgardo Néstor
Año de publicación
2011
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
Unsymmetrically substituted A3B-phthalocyanine derivatives bearing annulated 6-membered N-heterocycles, pyridine and pyrazine rings, were synthesized by the ring expansion reaction of boron(III) subphthalocyanine chloride. A geometrically constrained subphthalocyanine unit was reacted with a range of 1,2-phthalonitrile derivatives in presence of 8-diazabicyclo[5.4.0] undec-7-ene to form the A3B-phthalocyanine. The reactions were carried out in DMSO/1-chloronaphthalene at 130-140 °C for 15 h. This synthetic strategy resulted in phthalocyanines in 37-42% yield that required only simple purification. Annulated 6-membered N-heterocycles were methylated to obtain cationic Zn(II)phthalocyanine derivatives. The spectroscopic and photodynamic properties of these photosensitizers were studied in N,N-dimethylformamide solution. Antifungal activity photoinduced by these compounds was evaluated in Candida albicans cellular suspensions. The results indicate that amphiphilic cationic phthalocyanines represent interesting agents with potential applications in photodynamic inactivation of microorganisms. © 2011 Elsevier Ltd. All rights reserved.
Fil: Tempesti, Tomas Cristian. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba; Argentina. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas Fisicoquímicas y Naturales. Departamento de Química; Argentina
Fil: Alvarez, María Gabriela. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba; Argentina. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas Fisicoquímicas y Naturales. Departamento de Química; Argentina
Fil: Durantini, Edgardo Néstor. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba; Argentina. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas Fisicoquímicas y Naturales. Departamento de Química; Argentina
Materia
Antifungal
Candida Albicans
Photodynamic Activity
Photodynamic Inactivation
Photosensitizer
Phthalocyanine
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:11336/66459
Acceder
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oai_identifier_str oai:ri.conicet.gov.ar:11336/66459
network_acronym_str CONICETDig
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network_name_str CONICET Digital (CONICET)
spelling Synthesis and photodynamic properties of amphiphilic A3B- phthalocyanine derivatives bearing N-heterocycles as potential cationic phototherapeutic agentsTempesti, Tomas CristianAlvarez, María GabrielaDurantini, Edgardo NéstorAntifungalCandida AlbicansPhotodynamic ActivityPhotodynamic InactivationPhotosensitizerPhthalocyaninehttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1Unsymmetrically substituted A3B-phthalocyanine derivatives bearing annulated 6-membered N-heterocycles, pyridine and pyrazine rings, were synthesized by the ring expansion reaction of boron(III) subphthalocyanine chloride. A geometrically constrained subphthalocyanine unit was reacted with a range of 1,2-phthalonitrile derivatives in presence of 8-diazabicyclo[5.4.0] undec-7-ene to form the A3B-phthalocyanine. The reactions were carried out in DMSO/1-chloronaphthalene at 130-140 °C for 15 h. This synthetic strategy resulted in phthalocyanines in 37-42% yield that required only simple purification. Annulated 6-membered N-heterocycles were methylated to obtain cationic Zn(II)phthalocyanine derivatives. The spectroscopic and photodynamic properties of these photosensitizers were studied in N,N-dimethylformamide solution. Antifungal activity photoinduced by these compounds was evaluated in Candida albicans cellular suspensions. The results indicate that amphiphilic cationic phthalocyanines represent interesting agents with potential applications in photodynamic inactivation of microorganisms. © 2011 Elsevier Ltd. All rights reserved.Fil: Tempesti, Tomas Cristian. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba; Argentina. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas Fisicoquímicas y Naturales. Departamento de Química; ArgentinaFil: Alvarez, María Gabriela. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba; Argentina. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas Fisicoquímicas y Naturales. Departamento de Química; ArgentinaFil: Durantini, Edgardo Néstor. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba; Argentina. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas Fisicoquímicas y Naturales. Departamento de Química; ArgentinaElsevier2011-10info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/66459Tempesti, Tomas Cristian; Alvarez, María Gabriela; Durantini, Edgardo Néstor; Synthesis and photodynamic properties of amphiphilic A3B- phthalocyanine derivatives bearing N-heterocycles as potential cationic phototherapeutic agents; Elsevier; Dyes and Pigments; 91; 1; 10-2011; 6-120143-7208CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/doi/10.1016/j.dyepig.2011.02.004info:eu-repo/semantics/altIdentifier/url/https://www.sciencedirect.com/science/article/pii/S0143720811000441info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-29T09:43:11Zoai:ri.conicet.gov.ar:11336/66459instacron: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:34982025-09-29 09:43:12.247CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Synthesis and photodynamic properties of amphiphilic A3B- phthalocyanine derivatives bearing N-heterocycles as potential cationic phototherapeutic agents
title Synthesis and photodynamic properties of amphiphilic A3B- phthalocyanine derivatives bearing N-heterocycles as potential cationic phototherapeutic agents
spellingShingle Synthesis and photodynamic properties of amphiphilic A3B- phthalocyanine derivatives bearing N-heterocycles as potential cationic phototherapeutic agents
Tempesti, Tomas Cristian
Antifungal
Candida Albicans
Photodynamic Activity
Photodynamic Inactivation
Photosensitizer
Phthalocyanine
title_short Synthesis and photodynamic properties of amphiphilic A3B- phthalocyanine derivatives bearing N-heterocycles as potential cationic phototherapeutic agents
title_full Synthesis and photodynamic properties of amphiphilic A3B- phthalocyanine derivatives bearing N-heterocycles as potential cationic phototherapeutic agents
title_fullStr Synthesis and photodynamic properties of amphiphilic A3B- phthalocyanine derivatives bearing N-heterocycles as potential cationic phototherapeutic agents
title_full_unstemmed Synthesis and photodynamic properties of amphiphilic A3B- phthalocyanine derivatives bearing N-heterocycles as potential cationic phototherapeutic agents
title_sort Synthesis and photodynamic properties of amphiphilic A3B- phthalocyanine derivatives bearing N-heterocycles as potential cationic phototherapeutic agents
dc.creator.none.fl_str_mv Tempesti, Tomas Cristian
Alvarez, María Gabriela
Durantini, Edgardo Néstor
author Tempesti, Tomas Cristian
author_facet Tempesti, Tomas Cristian
Alvarez, María Gabriela
Durantini, Edgardo Néstor
author_role author
author2 Alvarez, María Gabriela
Durantini, Edgardo Néstor
author2_role author
author
dc.subject.none.fl_str_mv Antifungal
Candida Albicans
Photodynamic Activity
Photodynamic Inactivation
Photosensitizer
Phthalocyanine
topic Antifungal
Candida Albicans
Photodynamic Activity
Photodynamic Inactivation
Photosensitizer
Phthalocyanine
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv Unsymmetrically substituted A3B-phthalocyanine derivatives bearing annulated 6-membered N-heterocycles, pyridine and pyrazine rings, were synthesized by the ring expansion reaction of boron(III) subphthalocyanine chloride. A geometrically constrained subphthalocyanine unit was reacted with a range of 1,2-phthalonitrile derivatives in presence of 8-diazabicyclo[5.4.0] undec-7-ene to form the A3B-phthalocyanine. The reactions were carried out in DMSO/1-chloronaphthalene at 130-140 °C for 15 h. This synthetic strategy resulted in phthalocyanines in 37-42% yield that required only simple purification. Annulated 6-membered N-heterocycles were methylated to obtain cationic Zn(II)phthalocyanine derivatives. The spectroscopic and photodynamic properties of these photosensitizers were studied in N,N-dimethylformamide solution. Antifungal activity photoinduced by these compounds was evaluated in Candida albicans cellular suspensions. The results indicate that amphiphilic cationic phthalocyanines represent interesting agents with potential applications in photodynamic inactivation of microorganisms. © 2011 Elsevier Ltd. All rights reserved.
Fil: Tempesti, Tomas Cristian. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba; Argentina. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas Fisicoquímicas y Naturales. Departamento de Química; Argentina
Fil: Alvarez, María Gabriela. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba; Argentina. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas Fisicoquímicas y Naturales. Departamento de Química; Argentina
Fil: Durantini, Edgardo Néstor. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba; Argentina. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas Fisicoquímicas y Naturales. Departamento de Química; Argentina
description Unsymmetrically substituted A3B-phthalocyanine derivatives bearing annulated 6-membered N-heterocycles, pyridine and pyrazine rings, were synthesized by the ring expansion reaction of boron(III) subphthalocyanine chloride. A geometrically constrained subphthalocyanine unit was reacted with a range of 1,2-phthalonitrile derivatives in presence of 8-diazabicyclo[5.4.0] undec-7-ene to form the A3B-phthalocyanine. The reactions were carried out in DMSO/1-chloronaphthalene at 130-140 °C for 15 h. This synthetic strategy resulted in phthalocyanines in 37-42% yield that required only simple purification. Annulated 6-membered N-heterocycles were methylated to obtain cationic Zn(II)phthalocyanine derivatives. The spectroscopic and photodynamic properties of these photosensitizers were studied in N,N-dimethylformamide solution. Antifungal activity photoinduced by these compounds was evaluated in Candida albicans cellular suspensions. The results indicate that amphiphilic cationic phthalocyanines represent interesting agents with potential applications in photodynamic inactivation of microorganisms. © 2011 Elsevier Ltd. All rights reserved.
publishDate 2011
dc.date.none.fl_str_mv 2011-10
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/11336/66459
Tempesti, Tomas Cristian; Alvarez, María Gabriela; Durantini, Edgardo Néstor; Synthesis and photodynamic properties of amphiphilic A3B- phthalocyanine derivatives bearing N-heterocycles as potential cationic phototherapeutic agents; Elsevier; Dyes and Pigments; 91; 1; 10-2011; 6-12
0143-7208
CONICET Digital
CONICET
url http://hdl.handle.net/11336/66459
identifier_str_mv Tempesti, Tomas Cristian; Alvarez, María Gabriela; Durantini, Edgardo Néstor; Synthesis and photodynamic properties of amphiphilic A3B- phthalocyanine derivatives bearing N-heterocycles as potential cationic phototherapeutic agents; Elsevier; Dyes and Pigments; 91; 1; 10-2011; 6-12
0143-7208
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/doi/10.1016/j.dyepig.2011.02.004
info:eu-repo/semantics/altIdentifier/url/https://www.sciencedirect.com/science/article/pii/S0143720811000441
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
application/pdf
application/pdf
dc.publisher.none.fl_str_mv Elsevier
publisher.none.fl_str_mv Elsevier
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 13.070432

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