Synthesis and photodynamic properties of 5,10,15,20-tetrakis[3-(N-ethyl-N-methylcarbazoyl)]chlorin and its analogous porphyrin in solution and in human red blood cells

Autores
Ferreyra, Darío David; Spesia, Mariana Belen; Milanesio, María Elisa; Durantini, Edgardo Néstor
Año de publicación
2014
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
The spectroscopic and the photodynamic properties of 5,10,15,20-tetrakis[3-(N-ethyl-N-methylcarbazoyl)]chlorin (TEMCC) and its analogous porphyrin (TEMCP) were investigated in N,N-dimethylformamide (DMF) and in human red blood (HRB) cells. A more intense absorption band at 650 nm was obtained for TEMCC in comparison with TEMCP. Both photosensitizers showed red fluorescence emission with quantum yields of 0.13 and 0.23 for TEMCP and TEMCC, respectively. The photodynamic activity of TEMCC was higher that TEMCP in DMF, with a quantum yield of singlet molecular oxygen of 0.49. Moreover, in presence of NADH these photosensitizers produced superoxide anion radical. In vitro experiments showed that TEMCC was a highly effective agent to hemolyze the HRB cells. A decrease in the HRB cells osmotic stability was observed after photodynamic treatment with TEMCC. Studies of photodynamic action mechanism showed that the photohemolysis of HRB cells was protected in the presence of azide ion. Also, a reduction on the cell photodamage was found using mannitol. In contrast, the photohemolytic effect considerably increased in D2O. Therefore, the photodynamic activity of TEMCC in HRB cells was mediated by a contribution of type I and type II photooxidative mechanisms.
Fil: Ferreyra, Darío David. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas Fisicoquímicas y Naturales. Departamento de Química; Argentina
Fil: Spesia, Mariana Belen. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas Fisicoquímicas y Naturales. Departamento de Química; Argentina
Fil: Milanesio, María Elisa. Consejo Nacional de Investigaciones Científicas y Técnicas; 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; Argentina. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas Fisicoquímicas y Naturales. Departamento de Química; Argentina
Materia
Chlorin
Carbazole
Photodynamic Activity
Erythrocytes
Photohemolysis
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:11336/33605
Acceder
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oai_identifier_str oai:ri.conicet.gov.ar:11336/33605
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Synthesis and photodynamic properties of 5,10,15,20-tetrakis[3-(N-ethyl-N-methylcarbazoyl)]chlorin and its analogous porphyrin in solution and in human red blood cellsFerreyra, Darío DavidSpesia, Mariana BelenMilanesio, María ElisaDurantini, Edgardo NéstorChlorinCarbazolePhotodynamic ActivityErythrocytesPhotohemolysishttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1The spectroscopic and the photodynamic properties of 5,10,15,20-tetrakis[3-(N-ethyl-N-methylcarbazoyl)]chlorin (TEMCC) and its analogous porphyrin (TEMCP) were investigated in N,N-dimethylformamide (DMF) and in human red blood (HRB) cells. A more intense absorption band at 650 nm was obtained for TEMCC in comparison with TEMCP. Both photosensitizers showed red fluorescence emission with quantum yields of 0.13 and 0.23 for TEMCP and TEMCC, respectively. The photodynamic activity of TEMCC was higher that TEMCP in DMF, with a quantum yield of singlet molecular oxygen of 0.49. Moreover, in presence of NADH these photosensitizers produced superoxide anion radical. In vitro experiments showed that TEMCC was a highly effective agent to hemolyze the HRB cells. A decrease in the HRB cells osmotic stability was observed after photodynamic treatment with TEMCC. Studies of photodynamic action mechanism showed that the photohemolysis of HRB cells was protected in the presence of azide ion. Also, a reduction on the cell photodamage was found using mannitol. In contrast, the photohemolytic effect considerably increased in D2O. Therefore, the photodynamic activity of TEMCC in HRB cells was mediated by a contribution of type I and type II photooxidative mechanisms.Fil: Ferreyra, Darío David. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas Fisicoquímicas y Naturales. Departamento de Química; ArgentinaFil: Spesia, Mariana Belen. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas Fisicoquímicas y Naturales. Departamento de Química; ArgentinaFil: Milanesio, María Elisa. Consejo Nacional de Investigaciones Científicas y Técnicas; 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; Argentina. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas Fisicoquímicas y Naturales. Departamento de Química; ArgentinaElsevier Science Sa2014-02info: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/pdfhttp://hdl.handle.net/11336/33605Ferreyra, Darío David; Milanesio, María Elisa; Durantini, Edgardo Néstor; Spesia, Mariana Belen; Synthesis and photodynamic properties of 5,10,15,20-tetrakis[3-(N-ethyl-N-methylcarbazoyl)]chlorin and its analogous porphyrin in solution and in human red blood cells; Elsevier Science Sa; Journal of Photochemistry and Photobiology A: Chemistry; 282; 2-2014; 16-241010-6030CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/doi/10.1016/j.jphotochem.2014.02.004info:eu-repo/semantics/altIdentifier/url/http://www.sciencedirect.com/science/article/pii/S1010603014000458info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-29T10:19:01Zoai:ri.conicet.gov.ar:11336/33605instacron: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 10:19:01.626CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Synthesis and photodynamic properties of 5,10,15,20-tetrakis[3-(N-ethyl-N-methylcarbazoyl)]chlorin and its analogous porphyrin in solution and in human red blood cells
title Synthesis and photodynamic properties of 5,10,15,20-tetrakis[3-(N-ethyl-N-methylcarbazoyl)]chlorin and its analogous porphyrin in solution and in human red blood cells
spellingShingle Synthesis and photodynamic properties of 5,10,15,20-tetrakis[3-(N-ethyl-N-methylcarbazoyl)]chlorin and its analogous porphyrin in solution and in human red blood cells
Ferreyra, Darío David
Chlorin
Carbazole
Photodynamic Activity
Erythrocytes
Photohemolysis
title_short Synthesis and photodynamic properties of 5,10,15,20-tetrakis[3-(N-ethyl-N-methylcarbazoyl)]chlorin and its analogous porphyrin in solution and in human red blood cells
title_full Synthesis and photodynamic properties of 5,10,15,20-tetrakis[3-(N-ethyl-N-methylcarbazoyl)]chlorin and its analogous porphyrin in solution and in human red blood cells
title_fullStr Synthesis and photodynamic properties of 5,10,15,20-tetrakis[3-(N-ethyl-N-methylcarbazoyl)]chlorin and its analogous porphyrin in solution and in human red blood cells
title_full_unstemmed Synthesis and photodynamic properties of 5,10,15,20-tetrakis[3-(N-ethyl-N-methylcarbazoyl)]chlorin and its analogous porphyrin in solution and in human red blood cells
title_sort Synthesis and photodynamic properties of 5,10,15,20-tetrakis[3-(N-ethyl-N-methylcarbazoyl)]chlorin and its analogous porphyrin in solution and in human red blood cells
dc.creator.none.fl_str_mv Ferreyra, Darío David
Spesia, Mariana Belen
Milanesio, María Elisa
Durantini, Edgardo Néstor
author Ferreyra, Darío David
author_facet Ferreyra, Darío David
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 Chlorin
Carbazole
Photodynamic Activity
Erythrocytes
Photohemolysis
topic Chlorin
Carbazole
Photodynamic Activity
Erythrocytes
Photohemolysis
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 and the photodynamic properties of 5,10,15,20-tetrakis[3-(N-ethyl-N-methylcarbazoyl)]chlorin (TEMCC) and its analogous porphyrin (TEMCP) were investigated in N,N-dimethylformamide (DMF) and in human red blood (HRB) cells. A more intense absorption band at 650 nm was obtained for TEMCC in comparison with TEMCP. Both photosensitizers showed red fluorescence emission with quantum yields of 0.13 and 0.23 for TEMCP and TEMCC, respectively. The photodynamic activity of TEMCC was higher that TEMCP in DMF, with a quantum yield of singlet molecular oxygen of 0.49. Moreover, in presence of NADH these photosensitizers produced superoxide anion radical. In vitro experiments showed that TEMCC was a highly effective agent to hemolyze the HRB cells. A decrease in the HRB cells osmotic stability was observed after photodynamic treatment with TEMCC. Studies of photodynamic action mechanism showed that the photohemolysis of HRB cells was protected in the presence of azide ion. Also, a reduction on the cell photodamage was found using mannitol. In contrast, the photohemolytic effect considerably increased in D2O. Therefore, the photodynamic activity of TEMCC in HRB cells was mediated by a contribution of type I and type II photooxidative mechanisms.
Fil: Ferreyra, Darío David. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas Fisicoquímicas y Naturales. Departamento de Química; Argentina
Fil: Spesia, Mariana Belen. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas Fisicoquímicas y Naturales. Departamento de Química; Argentina
Fil: Milanesio, María Elisa. Consejo Nacional de Investigaciones Científicas y Técnicas; 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; Argentina. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas Fisicoquímicas y Naturales. Departamento de Química; Argentina
description The spectroscopic and the photodynamic properties of 5,10,15,20-tetrakis[3-(N-ethyl-N-methylcarbazoyl)]chlorin (TEMCC) and its analogous porphyrin (TEMCP) were investigated in N,N-dimethylformamide (DMF) and in human red blood (HRB) cells. A more intense absorption band at 650 nm was obtained for TEMCC in comparison with TEMCP. Both photosensitizers showed red fluorescence emission with quantum yields of 0.13 and 0.23 for TEMCP and TEMCC, respectively. The photodynamic activity of TEMCC was higher that TEMCP in DMF, with a quantum yield of singlet molecular oxygen of 0.49. Moreover, in presence of NADH these photosensitizers produced superoxide anion radical. In vitro experiments showed that TEMCC was a highly effective agent to hemolyze the HRB cells. A decrease in the HRB cells osmotic stability was observed after photodynamic treatment with TEMCC. Studies of photodynamic action mechanism showed that the photohemolysis of HRB cells was protected in the presence of azide ion. Also, a reduction on the cell photodamage was found using mannitol. In contrast, the photohemolytic effect considerably increased in D2O. Therefore, the photodynamic activity of TEMCC in HRB cells was mediated by a contribution of type I and type II photooxidative mechanisms.
publishDate 2014
dc.date.none.fl_str_mv 2014-02
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/11336/33605
Ferreyra, Darío David; Milanesio, María Elisa; Durantini, Edgardo Néstor; Spesia, Mariana Belen; Synthesis and photodynamic properties of 5,10,15,20-tetrakis[3-(N-ethyl-N-methylcarbazoyl)]chlorin and its analogous porphyrin in solution and in human red blood cells; Elsevier Science Sa; Journal of Photochemistry and Photobiology A: Chemistry; 282; 2-2014; 16-24
1010-6030
CONICET Digital
CONICET
url http://hdl.handle.net/11336/33605
identifier_str_mv Ferreyra, Darío David; Milanesio, María Elisa; Durantini, Edgardo Néstor; Spesia, Mariana Belen; Synthesis and photodynamic properties of 5,10,15,20-tetrakis[3-(N-ethyl-N-methylcarbazoyl)]chlorin and its analogous porphyrin in solution and in human red blood cells; Elsevier Science Sa; Journal of Photochemistry and Photobiology A: Chemistry; 282; 2-2014; 16-24
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.2014.02.004
info:eu-repo/semantics/altIdentifier/url/http://www.sciencedirect.com/science/article/pii/S1010603014000458
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
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dc.publisher.none.fl_str_mv Elsevier Science Sa
publisher.none.fl_str_mv Elsevier Science Sa
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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