Proton-Dependent switching of a novel amino chlorin derivative as a fluorescent probe and photosensitizer for acidic media

Autores
Heredia, Daniel Alejandro; Durantini, Andrés M.; Sarotti, Ariel Marcelo; Gsponer, Natalia Soledad; Ferreyra, Darío David; Bertolotti, Sonia Graciela; Milanesio, María Elisa; Durantini, Edgardo Néstor
Año de publicación
2018
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
A novel chlorin derivative (TPCF20-NMe2) was synthesized as a syn adduct of a pyrrolidinefused chlorin carrying an C-linked N,N-dimethylaminophenyl residue. The absorption spectrum of TPCF20-NMe2 was basically identical to that of TPCF20 in N,N-dimethylformamide, indicating a very weak interaction between the chlorin macrocycle and the amine group in the ground state. However, the fluorescence emission of the chlorin moiety in TPCF20-NMe2 was effectively quenched by the attached amine unit. In addition, TPCF20-NMe2 was not able to produce tripletexcited state or photosensitize singlet molecular oxygen. Spectroscopic and redox properties indicated that in this chlorin intramolecular photoinduced electron transfer can take place from the N,N-dimethylaminophenyl group to the chlorin macrocycle. Thus, the addition of an acid medium was used to protonate the amino group leading to a considerable increase in the fluorescenceemission, triplet excited state formation and singlet molecular oxygen production. Photodynamic inactivation of Escherichia coli sensitized by TPCF20-NMe2 was negligible at neutral pH. However, this chlorin becomes highly effective in inactivating E. coli cells under acidic conditions. Therefore,these results indicate that TPCF20-NMe2 is an interesting molecular structure in which protonation of amino group can be used as an off/on molecular switch activating red fluorescence emission and photodynamic activity capable of eradicating bacteria
Fil: Heredia, Daniel Alejandro. 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, Andrés M.. 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: Sarotti, Ariel Marcelo. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas.; Argentina
Fil: Gsponer, Natalia Soledad. 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: Ferreyra, Darío David. 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: Bertolotti, Sonia Graciela. Comisión Nacional de Investigación Científica y Tecnológica; Chile. Universidad de Buenos Aires. Facultad de Cs.exactas y Naturales. Departamento de Química Inorganica, Anal.y Qca.física. Area de Fotoquímica; Argentina
Fil: Milanesio, María Elisa. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas Fisicoquímicas y Naturales. Departamento de Química; Argentina. Comisión Nacional de Investigación Científica y Tecnológica; Chile
Fil: Durantini, Edgardo Néstor. Comisión Nacional de Investigación Científica y Tecnológica; Chile. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas Fisicoquímicas y Naturales. Departamento de Química; Argentina
Materia
CHLORIN
PHOTOINDUCED ELECTRON TRANSFER
PHOTOSENSITIZERS
PHOTODYNAMIC INACTIVATION
PROTON-DEPENDENT SWITCHING
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:11336/102134
Acceder
id CONICETDig_a874df60daee8ebe24af283ae280ab27
oai_identifier_str oai:ri.conicet.gov.ar:11336/102134
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Proton-Dependent switching of a novel amino chlorin derivative as a fluorescent probe and photosensitizer for acidic mediaHeredia, Daniel AlejandroDurantini, Andrés M.Sarotti, Ariel MarceloGsponer, Natalia SoledadFerreyra, Darío DavidBertolotti, Sonia GracielaMilanesio, María ElisaDurantini, Edgardo NéstorCHLORINPHOTOINDUCED ELECTRON TRANSFERPHOTOSENSITIZERSPHOTODYNAMIC INACTIVATIONPROTON-DEPENDENT SWITCHINGhttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1A novel chlorin derivative (TPCF20-NMe2) was synthesized as a syn adduct of a pyrrolidinefused chlorin carrying an C-linked N,N-dimethylaminophenyl residue. The absorption spectrum of TPCF20-NMe2 was basically identical to that of TPCF20 in N,N-dimethylformamide, indicating a very weak interaction between the chlorin macrocycle and the amine group in the ground state. However, the fluorescence emission of the chlorin moiety in TPCF20-NMe2 was effectively quenched by the attached amine unit. In addition, TPCF20-NMe2 was not able to produce tripletexcited state or photosensitize singlet molecular oxygen. Spectroscopic and redox properties indicated that in this chlorin intramolecular photoinduced electron transfer can take place from the N,N-dimethylaminophenyl group to the chlorin macrocycle. Thus, the addition of an acid medium was used to protonate the amino group leading to a considerable increase in the fluorescenceemission, triplet excited state formation and singlet molecular oxygen production. Photodynamic inactivation of Escherichia coli sensitized by TPCF20-NMe2 was negligible at neutral pH. However, this chlorin becomes highly effective in inactivating E. coli cells under acidic conditions. Therefore,these results indicate that TPCF20-NMe2 is an interesting molecular structure in which protonation of amino group can be used as an off/on molecular switch activating red fluorescence emission and photodynamic activity capable of eradicating bacteriaFil: Heredia, Daniel Alejandro. 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, Andrés M.. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas Fisicoquímicas y Naturales. Departamento de Química; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; ArgentinaFil: Sarotti, Ariel Marcelo. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas.; ArgentinaFil: Gsponer, Natalia Soledad. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas Fisicoquímicas y Naturales. Departamento de Química; ArgentinaFil: Ferreyra, Darío David. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas Fisicoquímicas y Naturales. Departamento de Química; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; ArgentinaFil: Bertolotti, Sonia Graciela. Comisión Nacional de Investigación Científica y Tecnológica; Chile. Universidad de Buenos Aires. Facultad de Cs.exactas y Naturales. Departamento de Química Inorganica, Anal.y Qca.física. Area de Fotoquímica; ArgentinaFil: Milanesio, María Elisa. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas Fisicoquímicas y Naturales. Departamento de Química; Argentina. Comisión Nacional de Investigación Científica y Tecnológica; ChileFil: Durantini, Edgardo Néstor. Comisión Nacional de Investigación Científica y Tecnológica; Chile. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas Fisicoquímicas y Naturales. Departamento de Química; ArgentinaWiley VCH Verlag2018-04info: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/11336/102134Heredia, Daniel Alejandro; Durantini, Andrés M.; Sarotti, Ariel Marcelo; Gsponer, Natalia Soledad; Ferreyra, Darío David; et al.; Proton-Dependent switching of a novel amino chlorin derivative as a fluorescent probe and photosensitizer for acidic media; Wiley VCH Verlag; Chemistry- A European Journal; 24; 22; 4-2018; 5950-59610947-6539CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/doi/info:eu-repo/semantics/altIdentifier/doi/10.1002/chem.201800060info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-11-05T09:36:49Zoai:ri.conicet.gov.ar:11336/102134instacron: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:34982025-11-05 09:36:49.78CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Proton-Dependent switching of a novel amino chlorin derivative as a fluorescent probe and photosensitizer for acidic media
title Proton-Dependent switching of a novel amino chlorin derivative as a fluorescent probe and photosensitizer for acidic media
spellingShingle Proton-Dependent switching of a novel amino chlorin derivative as a fluorescent probe and photosensitizer for acidic media
Heredia, Daniel Alejandro
CHLORIN
PHOTOINDUCED ELECTRON TRANSFER
PHOTOSENSITIZERS
PHOTODYNAMIC INACTIVATION
PROTON-DEPENDENT SWITCHING
title_short Proton-Dependent switching of a novel amino chlorin derivative as a fluorescent probe and photosensitizer for acidic media
title_full Proton-Dependent switching of a novel amino chlorin derivative as a fluorescent probe and photosensitizer for acidic media
title_fullStr Proton-Dependent switching of a novel amino chlorin derivative as a fluorescent probe and photosensitizer for acidic media
title_full_unstemmed Proton-Dependent switching of a novel amino chlorin derivative as a fluorescent probe and photosensitizer for acidic media
title_sort Proton-Dependent switching of a novel amino chlorin derivative as a fluorescent probe and photosensitizer for acidic media
dc.creator.none.fl_str_mv Heredia, Daniel Alejandro
Durantini, Andrés M.
Sarotti, Ariel Marcelo
Gsponer, Natalia Soledad
Ferreyra, Darío David
Bertolotti, Sonia Graciela
Milanesio, María Elisa
Durantini, Edgardo Néstor
author Heredia, Daniel Alejandro
author_facet Heredia, Daniel Alejandro
Durantini, Andrés M.
Sarotti, Ariel Marcelo
Gsponer, Natalia Soledad
Ferreyra, Darío David
Bertolotti, Sonia Graciela
Milanesio, María Elisa
Durantini, Edgardo Néstor
author_role author
author2 Durantini, Andrés M.
Sarotti, Ariel Marcelo
Gsponer, Natalia Soledad
Ferreyra, Darío David
Bertolotti, Sonia Graciela
Milanesio, María Elisa
Durantini, Edgardo Néstor
author2_role author
author
author
author
author
author
author
dc.subject.none.fl_str_mv CHLORIN
PHOTOINDUCED ELECTRON TRANSFER
PHOTOSENSITIZERS
PHOTODYNAMIC INACTIVATION
PROTON-DEPENDENT SWITCHING
topic CHLORIN
PHOTOINDUCED ELECTRON TRANSFER
PHOTOSENSITIZERS
PHOTODYNAMIC INACTIVATION
PROTON-DEPENDENT SWITCHING
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 novel chlorin derivative (TPCF20-NMe2) was synthesized as a syn adduct of a pyrrolidinefused chlorin carrying an C-linked N,N-dimethylaminophenyl residue. The absorption spectrum of TPCF20-NMe2 was basically identical to that of TPCF20 in N,N-dimethylformamide, indicating a very weak interaction between the chlorin macrocycle and the amine group in the ground state. However, the fluorescence emission of the chlorin moiety in TPCF20-NMe2 was effectively quenched by the attached amine unit. In addition, TPCF20-NMe2 was not able to produce tripletexcited state or photosensitize singlet molecular oxygen. Spectroscopic and redox properties indicated that in this chlorin intramolecular photoinduced electron transfer can take place from the N,N-dimethylaminophenyl group to the chlorin macrocycle. Thus, the addition of an acid medium was used to protonate the amino group leading to a considerable increase in the fluorescenceemission, triplet excited state formation and singlet molecular oxygen production. Photodynamic inactivation of Escherichia coli sensitized by TPCF20-NMe2 was negligible at neutral pH. However, this chlorin becomes highly effective in inactivating E. coli cells under acidic conditions. Therefore,these results indicate that TPCF20-NMe2 is an interesting molecular structure in which protonation of amino group can be used as an off/on molecular switch activating red fluorescence emission and photodynamic activity capable of eradicating bacteria
Fil: Heredia, Daniel Alejandro. 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, Andrés M.. 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: Sarotti, Ariel Marcelo. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas.; Argentina
Fil: Gsponer, Natalia Soledad. 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: Ferreyra, Darío David. 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: Bertolotti, Sonia Graciela. Comisión Nacional de Investigación Científica y Tecnológica; Chile. Universidad de Buenos Aires. Facultad de Cs.exactas y Naturales. Departamento de Química Inorganica, Anal.y Qca.física. Area de Fotoquímica; Argentina
Fil: Milanesio, María Elisa. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas Fisicoquímicas y Naturales. Departamento de Química; Argentina. Comisión Nacional de Investigación Científica y Tecnológica; Chile
Fil: Durantini, Edgardo Néstor. Comisión Nacional de Investigación Científica y Tecnológica; Chile. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas Fisicoquímicas y Naturales. Departamento de Química; Argentina
description A novel chlorin derivative (TPCF20-NMe2) was synthesized as a syn adduct of a pyrrolidinefused chlorin carrying an C-linked N,N-dimethylaminophenyl residue. The absorption spectrum of TPCF20-NMe2 was basically identical to that of TPCF20 in N,N-dimethylformamide, indicating a very weak interaction between the chlorin macrocycle and the amine group in the ground state. However, the fluorescence emission of the chlorin moiety in TPCF20-NMe2 was effectively quenched by the attached amine unit. In addition, TPCF20-NMe2 was not able to produce tripletexcited state or photosensitize singlet molecular oxygen. Spectroscopic and redox properties indicated that in this chlorin intramolecular photoinduced electron transfer can take place from the N,N-dimethylaminophenyl group to the chlorin macrocycle. Thus, the addition of an acid medium was used to protonate the amino group leading to a considerable increase in the fluorescenceemission, triplet excited state formation and singlet molecular oxygen production. Photodynamic inactivation of Escherichia coli sensitized by TPCF20-NMe2 was negligible at neutral pH. However, this chlorin becomes highly effective in inactivating E. coli cells under acidic conditions. Therefore,these results indicate that TPCF20-NMe2 is an interesting molecular structure in which protonation of amino group can be used as an off/on molecular switch activating red fluorescence emission and photodynamic activity capable of eradicating bacteria
publishDate 2018
dc.date.none.fl_str_mv 2018-04
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/11336/102134
Heredia, Daniel Alejandro; Durantini, Andrés M.; Sarotti, Ariel Marcelo; Gsponer, Natalia Soledad; Ferreyra, Darío David; et al.; Proton-Dependent switching of a novel amino chlorin derivative as a fluorescent probe and photosensitizer for acidic media; Wiley VCH Verlag; Chemistry- A European Journal; 24; 22; 4-2018; 5950-5961
0947-6539
CONICET Digital
CONICET
url http://hdl.handle.net/11336/102134
identifier_str_mv Heredia, Daniel Alejandro; Durantini, Andrés M.; Sarotti, Ariel Marcelo; Gsponer, Natalia Soledad; Ferreyra, Darío David; et al.; Proton-Dependent switching of a novel amino chlorin derivative as a fluorescent probe and photosensitizer for acidic media; Wiley VCH Verlag; Chemistry- A European Journal; 24; 22; 4-2018; 5950-5961
0947-6539
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/doi/
info:eu-repo/semantics/altIdentifier/doi/10.1002/chem.201800060
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
application/pdf
application/pdf
application/pdf
application/pdf
dc.publisher.none.fl_str_mv Wiley VCH Verlag
publisher.none.fl_str_mv Wiley VCH Verlag
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 13.084122

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