Synthesis, spectroscopic properties and photodynamic activity of porphyrin–fullerene C60 dyads with application in the photodynamic inactivation of Staphylococcus aureus

Autores
Ballatore, María Belén; Spesia, Mariana Belen; Milanesio, María Elisa; Durantini, Edgardo Néstor
Año de publicación
2014
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
A covalently linked porphyrin–fullerene C60 dyad 5 was synthesized by 1,3-dipolar cycloaddition using 5-(4-formylphenyl)-10,15,20-tris[3-(N-ethylcarbazoyl)]porphyrin, N-methylglycine and fullerene C60. Methylation of 5 was used to obtain a cationic dyad 6. Spectroscopic properties were compared in toluene, N,N-dimethylformamide (DMF) and toluene/sodium bis(2-ethylhexyl)sulfosuccinate (AOT)/water reverse micelles. Absorption spectra of the dyads were essentially a superposition of the spectra of the porphyrin and fullerene reference compounds, indicating a very weak interaction between the chromophores in the ground state. The fluorescence emission of the porphyrin moiety in the dyads was strongly quenched by the attached fullerene C60 unit. The singlet molecular oxygen, O2(1Δg), productions (ΦΔ) were strongly dependent on the solvent polarity. Similar ΦΔ values were obtained for 5,10,15,20-tetrakis[3-(N-ethylcarbazoyl)]porphyrin (TCP) in both solvents. Also, dyad 5 showed a high O2(1Δg) generation in toluene. However, O2(1Δg) production mediated by 5 considerably diminished in the more polar solvent DMF. Also, a high photodynamic activity involving O2(1Δg) was found for both dyads in a simple biomimetic system formed by AOT reverse micelles. The photoinactivation ability of these dyads was investigated in Staphylococcus aureus cell suspensions. Photosensitized inactivation of S. aureus by dyad 6 exhibits a 4.5 log decrease of cell survival (99.997% cell inactivation), when the cultures are treated with 5 μM photosensitizer and irradiated with visible light (350–800 nm) for 30 min. Under these conditions, a lower photocytotoxic effect was found for 5 (3.2 log decrease). Furthermore, photoinactivation induced by 6 was higher than those obtained with the separate moieties of the dyad. Therefore, molecular structures formed by porphyrin–fullerene C60 dyads represent interesting photosensitizers to inactivate S. aureus.
Fil: Ballatore, María Belén. 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: Spesia, Mariana Belen. 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
Dyad
Photodynamic Properties
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:11336/34751
Acceder
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oai_identifier_str oai:ri.conicet.gov.ar:11336/34751
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Synthesis, spectroscopic properties and photodynamic activity of porphyrin–fullerene C60 dyads with application in the photodynamic inactivation of Staphylococcus aureusBallatore, María BelénSpesia, Mariana BelenMilanesio, María ElisaDurantini, Edgardo NéstorDyadPhotodynamic Propertieshttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1A covalently linked porphyrin–fullerene C60 dyad 5 was synthesized by 1,3-dipolar cycloaddition using 5-(4-formylphenyl)-10,15,20-tris[3-(N-ethylcarbazoyl)]porphyrin, N-methylglycine and fullerene C60. Methylation of 5 was used to obtain a cationic dyad 6. Spectroscopic properties were compared in toluene, N,N-dimethylformamide (DMF) and toluene/sodium bis(2-ethylhexyl)sulfosuccinate (AOT)/water reverse micelles. Absorption spectra of the dyads were essentially a superposition of the spectra of the porphyrin and fullerene reference compounds, indicating a very weak interaction between the chromophores in the ground state. The fluorescence emission of the porphyrin moiety in the dyads was strongly quenched by the attached fullerene C60 unit. The singlet molecular oxygen, O2(1Δg), productions (ΦΔ) were strongly dependent on the solvent polarity. Similar ΦΔ values were obtained for 5,10,15,20-tetrakis[3-(N-ethylcarbazoyl)]porphyrin (TCP) in both solvents. Also, dyad 5 showed a high O2(1Δg) generation in toluene. However, O2(1Δg) production mediated by 5 considerably diminished in the more polar solvent DMF. Also, a high photodynamic activity involving O2(1Δg) was found for both dyads in a simple biomimetic system formed by AOT reverse micelles. The photoinactivation ability of these dyads was investigated in Staphylococcus aureus cell suspensions. Photosensitized inactivation of S. aureus by dyad 6 exhibits a 4.5 log decrease of cell survival (99.997% cell inactivation), when the cultures are treated with 5 μM photosensitizer and irradiated with visible light (350–800 nm) for 30 min. Under these conditions, a lower photocytotoxic effect was found for 5 (3.2 log decrease). Furthermore, photoinactivation induced by 6 was higher than those obtained with the separate moieties of the dyad. Therefore, molecular structures formed by porphyrin–fullerene C60 dyads represent interesting photosensitizers to inactivate S. aureus.Fil: Ballatore, María Belén. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas Fisicoquímicas y Naturales. Departamento de Química; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; ArgentinaFil: Spesia, Mariana Belen. 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 Masson2014-07info: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/pdfapplication/pdfapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/34751Ballatore, María Belén; Spesia, Mariana Belen; Milanesio, María Elisa; Durantini, Edgardo Néstor; Synthesis, spectroscopic properties and photodynamic activity of porphyrin–fullerene C60 dyads with application in the photodynamic inactivation of Staphylococcus aureus; Elsevier Masson; European Journal of Medical Chemistry; 83; 7-2014; 685-6940223-5234CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/doi/10.1016/j.ejmech.2014.06.077info:eu-repo/semantics/altIdentifier/url/https://www.sciencedirect.com/science/article/pii/S0223523414006060info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-nd/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-03T09:51:33Zoai:ri.conicet.gov.ar:11336/34751instacron: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:34982025-09-03 09:51:33.37CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Synthesis, spectroscopic properties and photodynamic activity of porphyrin–fullerene C60 dyads with application in the photodynamic inactivation of Staphylococcus aureus
title Synthesis, spectroscopic properties and photodynamic activity of porphyrin–fullerene C60 dyads with application in the photodynamic inactivation of Staphylococcus aureus
spellingShingle Synthesis, spectroscopic properties and photodynamic activity of porphyrin–fullerene C60 dyads with application in the photodynamic inactivation of Staphylococcus aureus
Ballatore, María Belén
Dyad
Photodynamic Properties
title_short Synthesis, spectroscopic properties and photodynamic activity of porphyrin–fullerene C60 dyads with application in the photodynamic inactivation of Staphylococcus aureus
title_full Synthesis, spectroscopic properties and photodynamic activity of porphyrin–fullerene C60 dyads with application in the photodynamic inactivation of Staphylococcus aureus
title_fullStr Synthesis, spectroscopic properties and photodynamic activity of porphyrin–fullerene C60 dyads with application in the photodynamic inactivation of Staphylococcus aureus
title_full_unstemmed Synthesis, spectroscopic properties and photodynamic activity of porphyrin–fullerene C60 dyads with application in the photodynamic inactivation of Staphylococcus aureus
title_sort Synthesis, spectroscopic properties and photodynamic activity of porphyrin–fullerene C60 dyads with application in the photodynamic inactivation of Staphylococcus aureus
dc.creator.none.fl_str_mv Ballatore, María Belén
Spesia, Mariana Belen
Milanesio, María Elisa
Durantini, Edgardo Néstor
author Ballatore, María Belén
author_facet Ballatore, María Belén
Spesia, Mariana Belen
Milanesio, María Elisa
Durantini, Edgardo Néstor
author_role author
author2 Spesia, Mariana Belen
Milanesio, María Elisa
Durantini, Edgardo Néstor
author2_role author
author
author
dc.subject.none.fl_str_mv Dyad
Photodynamic Properties
topic Dyad
Photodynamic Properties
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 covalently linked porphyrin–fullerene C60 dyad 5 was synthesized by 1,3-dipolar cycloaddition using 5-(4-formylphenyl)-10,15,20-tris[3-(N-ethylcarbazoyl)]porphyrin, N-methylglycine and fullerene C60. Methylation of 5 was used to obtain a cationic dyad 6. Spectroscopic properties were compared in toluene, N,N-dimethylformamide (DMF) and toluene/sodium bis(2-ethylhexyl)sulfosuccinate (AOT)/water reverse micelles. Absorption spectra of the dyads were essentially a superposition of the spectra of the porphyrin and fullerene reference compounds, indicating a very weak interaction between the chromophores in the ground state. The fluorescence emission of the porphyrin moiety in the dyads was strongly quenched by the attached fullerene C60 unit. The singlet molecular oxygen, O2(1Δg), productions (ΦΔ) were strongly dependent on the solvent polarity. Similar ΦΔ values were obtained for 5,10,15,20-tetrakis[3-(N-ethylcarbazoyl)]porphyrin (TCP) in both solvents. Also, dyad 5 showed a high O2(1Δg) generation in toluene. However, O2(1Δg) production mediated by 5 considerably diminished in the more polar solvent DMF. Also, a high photodynamic activity involving O2(1Δg) was found for both dyads in a simple biomimetic system formed by AOT reverse micelles. The photoinactivation ability of these dyads was investigated in Staphylococcus aureus cell suspensions. Photosensitized inactivation of S. aureus by dyad 6 exhibits a 4.5 log decrease of cell survival (99.997% cell inactivation), when the cultures are treated with 5 μM photosensitizer and irradiated with visible light (350–800 nm) for 30 min. Under these conditions, a lower photocytotoxic effect was found for 5 (3.2 log decrease). Furthermore, photoinactivation induced by 6 was higher than those obtained with the separate moieties of the dyad. Therefore, molecular structures formed by porphyrin–fullerene C60 dyads represent interesting photosensitizers to inactivate S. aureus.
Fil: Ballatore, María Belén. 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: Spesia, Mariana Belen. 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 A covalently linked porphyrin–fullerene C60 dyad 5 was synthesized by 1,3-dipolar cycloaddition using 5-(4-formylphenyl)-10,15,20-tris[3-(N-ethylcarbazoyl)]porphyrin, N-methylglycine and fullerene C60. Methylation of 5 was used to obtain a cationic dyad 6. Spectroscopic properties were compared in toluene, N,N-dimethylformamide (DMF) and toluene/sodium bis(2-ethylhexyl)sulfosuccinate (AOT)/water reverse micelles. Absorption spectra of the dyads were essentially a superposition of the spectra of the porphyrin and fullerene reference compounds, indicating a very weak interaction between the chromophores in the ground state. The fluorescence emission of the porphyrin moiety in the dyads was strongly quenched by the attached fullerene C60 unit. The singlet molecular oxygen, O2(1Δg), productions (ΦΔ) were strongly dependent on the solvent polarity. Similar ΦΔ values were obtained for 5,10,15,20-tetrakis[3-(N-ethylcarbazoyl)]porphyrin (TCP) in both solvents. Also, dyad 5 showed a high O2(1Δg) generation in toluene. However, O2(1Δg) production mediated by 5 considerably diminished in the more polar solvent DMF. Also, a high photodynamic activity involving O2(1Δg) was found for both dyads in a simple biomimetic system formed by AOT reverse micelles. The photoinactivation ability of these dyads was investigated in Staphylococcus aureus cell suspensions. Photosensitized inactivation of S. aureus by dyad 6 exhibits a 4.5 log decrease of cell survival (99.997% cell inactivation), when the cultures are treated with 5 μM photosensitizer and irradiated with visible light (350–800 nm) for 30 min. Under these conditions, a lower photocytotoxic effect was found for 5 (3.2 log decrease). Furthermore, photoinactivation induced by 6 was higher than those obtained with the separate moieties of the dyad. Therefore, molecular structures formed by porphyrin–fullerene C60 dyads represent interesting photosensitizers to inactivate S. aureus.
publishDate 2014
dc.date.none.fl_str_mv 2014-07
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/11336/34751
Ballatore, María Belén; Spesia, Mariana Belen; Milanesio, María Elisa; Durantini, Edgardo Néstor; Synthesis, spectroscopic properties and photodynamic activity of porphyrin–fullerene C60 dyads with application in the photodynamic inactivation of Staphylococcus aureus; Elsevier Masson; European Journal of Medical Chemistry; 83; 7-2014; 685-694
0223-5234
CONICET Digital
CONICET
url http://hdl.handle.net/11336/34751
identifier_str_mv Ballatore, María Belén; Spesia, Mariana Belen; Milanesio, María Elisa; Durantini, Edgardo Néstor; Synthesis, spectroscopic properties and photodynamic activity of porphyrin–fullerene C60 dyads with application in the photodynamic inactivation of Staphylococcus aureus; Elsevier Masson; European Journal of Medical Chemistry; 83; 7-2014; 685-694
0223-5234
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.ejmech.2014.06.077
info:eu-repo/semantics/altIdentifier/url/https://www.sciencedirect.com/science/article/pii/S0223523414006060
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
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dc.publisher.none.fl_str_mv Elsevier Masson
publisher.none.fl_str_mv Elsevier Masson
dc.source.none.fl_str_mv reponame: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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