Spectroscopic and photodynamic properties of 5,10,15,20-tetrakis[4-(3-N,N-dimethylaminopropoxy)phenyl]porphyrin and its tetracationic derivative in different media

Autores
Mora, Sabrina Jimena; Milanesio, María Elisa; Durantini, Edgardo Néstor
Año de publicación
2013
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
The spectroscopic properties and the photodynamic activity of 5,10,15,20-tetrakis[4-(3-N,N-dimethylaminopropoxy)phenyl]porphyrin (TAPP) and its tetracationic derivative (TAPP4+) were studied in homogeneous media and in microheterogeneous systems. The results were compared with those of 5,10,15,20-tetra(4-N,N,N-trimethylammoniumphenyl)porphyrin (TMAP4+), which represents an active tetracationic photosensitizer. Absorption and fluorescence studies indicated that the tetrapyrrolic macrocycle retains its individual spectroscopic properties. Interaction with β-cyclodextrin (β-CD) was found for TAPP4+ by fluorescence emission. Also, these porphyrins interact with n-heptane/sodium bis(2-ethylhexyl)sulfosuccinate (AOT)/water reverse micelles. Photosensitization ability was evaluated using 9,10-dimethylanthracene in N,N-dimethylformamide and AOT micelles, while tetrasodium 2,2′-(anthracene-9,10-diyl)bis(methylmalonate) was used in aqueous solutions. Also, photosensitized decomposition of l-tryptophan was investigated in these media. In particular, Trp was fast photooxidized by TAPP in a biomimetic media formed by AOT reverse micelles. Therefore, this intrinsically non-charged porphyrin represents an interesting photosensitizer for the photodynamic inactivation of microorganisms.
Fil: Mora, Sabrina Jimena. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas Fisicoquímicas y Naturales. Departamento de Química; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina
Fil: Milanesio, María Elisa. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas Fisicoquímicas y Naturales. Departamento de Química; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina
Fil: Durantini, Edgardo Néstor. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas Fisicoquímicas y Naturales. Departamento de Química; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina
Materia
Porphyrin
Photodynamic Propeties
Nivel de accesibilidad
acceso abierto
Condiciones de uso
https://creativecommons.org/licenses/by-nc-nd/2.5/ar/
Repositorio
CONICET Digital (CONICET)
Institución
Consejo Nacional de Investigaciones Científicas y Técnicas
OAI Identificador
oai:ri.conicet.gov.ar:11336/23529
Acceder
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network_name_str CONICET Digital (CONICET)
spelling Spectroscopic and photodynamic properties of 5,10,15,20-tetrakis[4-(3-N,N-dimethylaminopropoxy)phenyl]porphyrin and its tetracationic derivative in different mediaMora, Sabrina JimenaMilanesio, María ElisaDurantini, Edgardo NéstorPorphyrinPhotodynamic Propetieshttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1The spectroscopic properties and the photodynamic activity of 5,10,15,20-tetrakis[4-(3-N,N-dimethylaminopropoxy)phenyl]porphyrin (TAPP) and its tetracationic derivative (TAPP4+) were studied in homogeneous media and in microheterogeneous systems. The results were compared with those of 5,10,15,20-tetra(4-N,N,N-trimethylammoniumphenyl)porphyrin (TMAP4+), which represents an active tetracationic photosensitizer. Absorption and fluorescence studies indicated that the tetrapyrrolic macrocycle retains its individual spectroscopic properties. Interaction with β-cyclodextrin (β-CD) was found for TAPP4+ by fluorescence emission. Also, these porphyrins interact with n-heptane/sodium bis(2-ethylhexyl)sulfosuccinate (AOT)/water reverse micelles. Photosensitization ability was evaluated using 9,10-dimethylanthracene in N,N-dimethylformamide and AOT micelles, while tetrasodium 2,2′-(anthracene-9,10-diyl)bis(methylmalonate) was used in aqueous solutions. Also, photosensitized decomposition of l-tryptophan was investigated in these media. In particular, Trp was fast photooxidized by TAPP in a biomimetic media formed by AOT reverse micelles. Therefore, this intrinsically non-charged porphyrin represents an interesting photosensitizer for the photodynamic inactivation of microorganisms.Fil: Mora, Sabrina Jimena. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas Fisicoquímicas y Naturales. Departamento de Química; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; ArgentinaFil: Milanesio, María Elisa. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas Fisicoquímicas y Naturales. Departamento de Química; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; ArgentinaFil: Durantini, Edgardo Néstor. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas Fisicoquímicas y Naturales. Departamento de Química; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; ArgentinaElsevier Science2013-08info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfapplication/pdfapplication/pdfapplication/pdfapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/23529Mora, Sabrina Jimena; Milanesio, María Elisa; Durantini, Edgardo Néstor; Spectroscopic and photodynamic properties of 5,10,15,20-tetrakis[4-(3-N,N-dimethylaminopropoxy)phenyl]porphyrin and its tetracationic derivative in different media; Elsevier Science; Journal of Photochemistry and Photobiology A: Chemistry; 270; 8-2013; 75-841010-6030CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/doi/10.1016/j.jphotochem.2013.07.013info:eu-repo/semantics/altIdentifier/url/http://www.sciencedirect.com/science/article/pii/S1010603013003481info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-nd/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-29T10:35:37Zoai:ri.conicet.gov.ar:11336/23529instacron: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 10:35:37.404CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Spectroscopic and photodynamic properties of 5,10,15,20-tetrakis[4-(3-N,N-dimethylaminopropoxy)phenyl]porphyrin and its tetracationic derivative in different media
title Spectroscopic and photodynamic properties of 5,10,15,20-tetrakis[4-(3-N,N-dimethylaminopropoxy)phenyl]porphyrin and its tetracationic derivative in different media
spellingShingle Spectroscopic and photodynamic properties of 5,10,15,20-tetrakis[4-(3-N,N-dimethylaminopropoxy)phenyl]porphyrin and its tetracationic derivative in different media
Mora, Sabrina Jimena
Porphyrin
Photodynamic Propeties
title_short Spectroscopic and photodynamic properties of 5,10,15,20-tetrakis[4-(3-N,N-dimethylaminopropoxy)phenyl]porphyrin and its tetracationic derivative in different media
title_full Spectroscopic and photodynamic properties of 5,10,15,20-tetrakis[4-(3-N,N-dimethylaminopropoxy)phenyl]porphyrin and its tetracationic derivative in different media
title_fullStr Spectroscopic and photodynamic properties of 5,10,15,20-tetrakis[4-(3-N,N-dimethylaminopropoxy)phenyl]porphyrin and its tetracationic derivative in different media
title_full_unstemmed Spectroscopic and photodynamic properties of 5,10,15,20-tetrakis[4-(3-N,N-dimethylaminopropoxy)phenyl]porphyrin and its tetracationic derivative in different media
title_sort Spectroscopic and photodynamic properties of 5,10,15,20-tetrakis[4-(3-N,N-dimethylaminopropoxy)phenyl]porphyrin and its tetracationic derivative in different media
dc.creator.none.fl_str_mv Mora, Sabrina Jimena
Milanesio, María Elisa
Durantini, Edgardo Néstor
author Mora, Sabrina Jimena
author_facet Mora, Sabrina Jimena
Milanesio, María Elisa
Durantini, Edgardo Néstor
author_role author
author2 Milanesio, María Elisa
Durantini, Edgardo Néstor
author2_role author
author
dc.subject.none.fl_str_mv Porphyrin
Photodynamic Propeties
topic Porphyrin
Photodynamic Propeties
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv The spectroscopic properties and the photodynamic activity of 5,10,15,20-tetrakis[4-(3-N,N-dimethylaminopropoxy)phenyl]porphyrin (TAPP) and its tetracationic derivative (TAPP4+) were studied in homogeneous media and in microheterogeneous systems. The results were compared with those of 5,10,15,20-tetra(4-N,N,N-trimethylammoniumphenyl)porphyrin (TMAP4+), which represents an active tetracationic photosensitizer. Absorption and fluorescence studies indicated that the tetrapyrrolic macrocycle retains its individual spectroscopic properties. Interaction with β-cyclodextrin (β-CD) was found for TAPP4+ by fluorescence emission. Also, these porphyrins interact with n-heptane/sodium bis(2-ethylhexyl)sulfosuccinate (AOT)/water reverse micelles. Photosensitization ability was evaluated using 9,10-dimethylanthracene in N,N-dimethylformamide and AOT micelles, while tetrasodium 2,2′-(anthracene-9,10-diyl)bis(methylmalonate) was used in aqueous solutions. Also, photosensitized decomposition of l-tryptophan was investigated in these media. In particular, Trp was fast photooxidized by TAPP in a biomimetic media formed by AOT reverse micelles. Therefore, this intrinsically non-charged porphyrin represents an interesting photosensitizer for the photodynamic inactivation of microorganisms.
Fil: Mora, Sabrina Jimena. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas Fisicoquímicas y Naturales. Departamento de Química; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina
Fil: Milanesio, María Elisa. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas Fisicoquímicas y Naturales. Departamento de Química; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina
Fil: Durantini, Edgardo Néstor. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas Fisicoquímicas y Naturales. Departamento de Química; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina
description The spectroscopic properties and the photodynamic activity of 5,10,15,20-tetrakis[4-(3-N,N-dimethylaminopropoxy)phenyl]porphyrin (TAPP) and its tetracationic derivative (TAPP4+) were studied in homogeneous media and in microheterogeneous systems. The results were compared with those of 5,10,15,20-tetra(4-N,N,N-trimethylammoniumphenyl)porphyrin (TMAP4+), which represents an active tetracationic photosensitizer. Absorption and fluorescence studies indicated that the tetrapyrrolic macrocycle retains its individual spectroscopic properties. Interaction with β-cyclodextrin (β-CD) was found for TAPP4+ by fluorescence emission. Also, these porphyrins interact with n-heptane/sodium bis(2-ethylhexyl)sulfosuccinate (AOT)/water reverse micelles. Photosensitization ability was evaluated using 9,10-dimethylanthracene in N,N-dimethylformamide and AOT micelles, while tetrasodium 2,2′-(anthracene-9,10-diyl)bis(methylmalonate) was used in aqueous solutions. Also, photosensitized decomposition of l-tryptophan was investigated in these media. In particular, Trp was fast photooxidized by TAPP in a biomimetic media formed by AOT reverse micelles. Therefore, this intrinsically non-charged porphyrin represents an interesting photosensitizer for the photodynamic inactivation of microorganisms.
publishDate 2013
dc.date.none.fl_str_mv 2013-08
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/11336/23529
Mora, Sabrina Jimena; Milanesio, María Elisa; Durantini, Edgardo Néstor; Spectroscopic and photodynamic properties of 5,10,15,20-tetrakis[4-(3-N,N-dimethylaminopropoxy)phenyl]porphyrin and its tetracationic derivative in different media; Elsevier Science; Journal of Photochemistry and Photobiology A: Chemistry; 270; 8-2013; 75-84
1010-6030
CONICET Digital
CONICET
url http://hdl.handle.net/11336/23529
identifier_str_mv Mora, Sabrina Jimena; Milanesio, María Elisa; Durantini, Edgardo Néstor; Spectroscopic and photodynamic properties of 5,10,15,20-tetrakis[4-(3-N,N-dimethylaminopropoxy)phenyl]porphyrin and its tetracationic derivative in different media; Elsevier Science; Journal of Photochemistry and Photobiology A: Chemistry; 270; 8-2013; 75-84
1010-6030
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.jphotochem.2013.07.013
info:eu-repo/semantics/altIdentifier/url/http://www.sciencedirect.com/science/article/pii/S1010603013003481
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
https://creativecommons.org/licenses/by-nc-nd/2.5/ar/
eu_rights_str_mv openAccess
rights_invalid_str_mv https://creativecommons.org/licenses/by-nc-nd/2.5/ar/
dc.format.none.fl_str_mv application/pdf
application/pdf
application/pdf
application/pdf
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dc.publisher.none.fl_str_mv Elsevier Science
publisher.none.fl_str_mv Elsevier Science
dc.source.none.fl_str_mv reponame:CONICET Digital (CONICET)
instname:Consejo Nacional de Investigaciones Científicas y Técnicas
reponame_str CONICET Digital (CONICET)
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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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