Synthesis and properties of 5,10,15,20-tetrakis[4-(3-N,N-dimethylaminopropoxy)phenyl] chlorin as potential broad-spectrum antimicrobial photosensitizers

A novel 5,10,15,20-tetrakis[4-(3-N,N-dimethylaminopropoxy)phenyl]chlorin (TAPC) was synthesized by reduction of the corresponding porphyrin TAPP with p-toluenesulfonhydrazide, followed by selective oxidation with o-chloranil. Spectroscopic properties and the photodynamic activity of these photosensi...

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Autores: Ferreyra, Darío David, Reynoso, Eugenia, Cordero Gabrielli, Paula Verónica, Spesia, Mariana Belen, Alvarez, María Gabriela, Milanesio, María Elisa, Durantini, Edgardo Néstor
Tipo de recurso: artículo
Estado:Versión publicada
Fecha de publicación:2016
País:Argentina
Institución:Consejo Nacional de Investigaciones Científicas y Técnicas
Repositorio:CONICET Digital (CONICET)
Idioma:inglés
OAI Identifier:oai:ri.conicet.gov.ar:11336/61694
Acceso en línea:http://hdl.handle.net/11336/61694
Access Level:acceso abierto
Palabra clave:Chlorin
Microorganisms
Photodynamic Activity
Photoinactivation
Porphyrin
https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
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network_acronym_str AR
network_name_str Argentina
repository_id_str
dc.title.none.fl_str_mv Synthesis and properties of 5,10,15,20-tetrakis[4-(3-N,N-dimethylaminopropoxy)phenyl] chlorin as potential broad-spectrum antimicrobial photosensitizers
title Synthesis and properties of 5,10,15,20-tetrakis[4-(3-N,N-dimethylaminopropoxy)phenyl] chlorin as potential broad-spectrum antimicrobial photosensitizers
spellingShingle Synthesis and properties of 5,10,15,20-tetrakis[4-(3-N,N-dimethylaminopropoxy)phenyl] chlorin as potential broad-spectrum antimicrobial photosensitizers
Ferreyra, Darío David
Chlorin
Microorganisms
Photodynamic Activity
Photoinactivation
Porphyrin
https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
title_short Synthesis and properties of 5,10,15,20-tetrakis[4-(3-N,N-dimethylaminopropoxy)phenyl] chlorin as potential broad-spectrum antimicrobial photosensitizers
title_full Synthesis and properties of 5,10,15,20-tetrakis[4-(3-N,N-dimethylaminopropoxy)phenyl] chlorin as potential broad-spectrum antimicrobial photosensitizers
title_fullStr Synthesis and properties of 5,10,15,20-tetrakis[4-(3-N,N-dimethylaminopropoxy)phenyl] chlorin as potential broad-spectrum antimicrobial photosensitizers
title_full_unstemmed Synthesis and properties of 5,10,15,20-tetrakis[4-(3-N,N-dimethylaminopropoxy)phenyl] chlorin as potential broad-spectrum antimicrobial photosensitizers
title_sort Synthesis and properties of 5,10,15,20-tetrakis[4-(3-N,N-dimethylaminopropoxy)phenyl] chlorin as potential broad-spectrum antimicrobial photosensitizers
dc.creator.none.fl_str_mv Ferreyra, Darío David
Reynoso, Eugenia
Cordero Gabrielli, Paula Verónica
Spesia, Mariana Belen
Alvarez, María Gabriela
Milanesio, María Elisa
Durantini, Edgardo Néstor
author Ferreyra, Darío David
author_facet Ferreyra, Darío David
Reynoso, Eugenia
Cordero Gabrielli, Paula Verónica
Spesia, Mariana Belen
Alvarez, María Gabriela
Milanesio, María Elisa
Durantini, Edgardo Néstor
author_role author
author2 Reynoso, Eugenia
Cordero Gabrielli, Paula Verónica
Spesia, Mariana Belen
Alvarez, María Gabriela
Milanesio, María Elisa
Durantini, Edgardo Néstor
author2_role author
author
author
author
author
author
dc.subject.none.fl_str_mv Chlorin
Microorganisms
Photodynamic Activity
Photoinactivation
Porphyrin
https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
topic Chlorin
Microorganisms
Photodynamic Activity
Photoinactivation
Porphyrin
https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
description A novel 5,10,15,20-tetrakis[4-(3-N,N-dimethylaminopropoxy)phenyl]chlorin (TAPC) was synthesized by reduction of the corresponding porphyrin TAPP with p-toluenesulfonhydrazide, followed by selective oxidation with o-chloranil. Spectroscopic properties and the photodynamic activity of these photosensitizers were compared in N,N-dimethylformamide. An increase in the absorption band at 650 nm was found for the chlorin derivative with respect to TAPP. These photosensitizers emit red fluorescence with quantum yields of 0.15. Both compounds were able to photosensitize singlet molecular oxygen with quantum yields of about 0.5. Also, the formation of superoxide anion radical was detected in the presence of TAPC or TAPP and NADH. Photodynamic inactivation was investigated on a Gram-positive bacterium Staphylococcus aureus, a Gram-negative bacterium Escherichia coli and a fungal yeast Candida albicans cells. In vitro experiments showed that TAPC or TAPP were rapidly bound to microbial cells at short incubation periods. These photosensitizers, without intrinsic positive charges, contain four basic amino groups. These substituents can be protonated at physiological pH, increasing the interaction with the cell envelopment. Photosensitized inactivation improved with an increase of both photosensitizer concentrations and irradiation times. After 15 min irradiation, a 7 log reduction of S. aureus was found for treated with 1 μM photosensitizer. Similar result was obtained with E. coli after using 5 μM photosensitizer and 30 min irradiation. Also, the last conditions produced a decrease of 5 log in C. albicans cells. Therefore, TAPC was highly effective as a broad-spectrum antimicrobial photosensitizer.
publishDate 2016
dc.date.none.fl_str_mv 2016-05
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/11336/61694
Ferreyra, Darío David; Reynoso, Eugenia; Cordero Gabrielli, Paula Verónica; Spesia, Mariana Belen; Alvarez, María Gabriela; et al.; Synthesis and properties of 5,10,15,20-tetrakis[4-(3-N,N-dimethylaminopropoxy)phenyl] chlorin as potential broad-spectrum antimicrobial photosensitizers; Elsevier Science Sa; Journal of Photochemistry and Photobiology B: Biology; 158; 5-2016; 243-251
1011-1344
CONICET Digital
CONICET
url http://hdl.handle.net/11336/61694
identifier_str_mv Ferreyra, Darío David; Reynoso, Eugenia; Cordero Gabrielli, Paula Verónica; Spesia, Mariana Belen; Alvarez, María Gabriela; et al.; Synthesis and properties of 5,10,15,20-tetrakis[4-(3-N,N-dimethylaminopropoxy)phenyl] chlorin as potential broad-spectrum antimicrobial photosensitizers; Elsevier Science Sa; Journal of Photochemistry and Photobiology B: Biology; 158; 5-2016; 243-251
1011-1344
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.jphotobiol.2016.02.021
info:eu-repo/semantics/altIdentifier/url/https://www.sciencedirect.com/science/article/pii/S1011134415301998
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
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
instname_str Consejo Nacional de Investigaciones Científicas y Técnicas
reponame_str CONICET Digital (CONICET)
collection CONICET Digital (CONICET)
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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spelling Synthesis and properties of 5,10,15,20-tetrakis[4-(3-N,N-dimethylaminopropoxy)phenyl] chlorin as potential broad-spectrum antimicrobial photosensitizersFerreyra, Darío DavidReynoso, EugeniaCordero Gabrielli, Paula VerónicaSpesia, Mariana BelenAlvarez, María GabrielaMilanesio, María ElisaDurantini, Edgardo NéstorChlorinMicroorganismsPhotodynamic ActivityPhotoinactivationPorphyrinhttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1A novel 5,10,15,20-tetrakis[4-(3-N,N-dimethylaminopropoxy)phenyl]chlorin (TAPC) was synthesized by reduction of the corresponding porphyrin TAPP with p-toluenesulfonhydrazide, followed by selective oxidation with o-chloranil. Spectroscopic properties and the photodynamic activity of these photosensitizers were compared in N,N-dimethylformamide. An increase in the absorption band at 650 nm was found for the chlorin derivative with respect to TAPP. These photosensitizers emit red fluorescence with quantum yields of 0.15. Both compounds were able to photosensitize singlet molecular oxygen with quantum yields of about 0.5. Also, the formation of superoxide anion radical was detected in the presence of TAPC or TAPP and NADH. Photodynamic inactivation was investigated on a Gram-positive bacterium Staphylococcus aureus, a Gram-negative bacterium Escherichia coli and a fungal yeast Candida albicans cells. In vitro experiments showed that TAPC or TAPP were rapidly bound to microbial cells at short incubation periods. These photosensitizers, without intrinsic positive charges, contain four basic amino groups. These substituents can be protonated at physiological pH, increasing the interaction with the cell envelopment. Photosensitized inactivation improved with an increase of both photosensitizer concentrations and irradiation times. After 15 min irradiation, a 7 log reduction of S. aureus was found for treated with 1 μM photosensitizer. Similar result was obtained with E. coli after using 5 μM photosensitizer and 30 min irradiation. Also, the last conditions produced a decrease of 5 log in C. albicans cells. Therefore, TAPC was highly effective as a broad-spectrum antimicrobial photosensitizer.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: Reynoso, Eugenia. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas Fisicoquímicas y Naturales. Departamento de Química; ArgentinaFil: Cordero Gabrielli, Paula Verónica. 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: Alvarez, María Gabriela. 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 Sa2016-05info: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/11336/61694Ferreyra, Darío David; Reynoso, Eugenia; Cordero Gabrielli, Paula Verónica; Spesia, Mariana Belen; Alvarez, María Gabriela; et al.; Synthesis and properties of 5,10,15,20-tetrakis[4-(3-N,N-dimethylaminopropoxy)phenyl] chlorin as potential broad-spectrum antimicrobial photosensitizers; Elsevier Science Sa; Journal of Photochemistry and Photobiology B: Biology; 158; 5-2016; 243-2511011-1344CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/doi/10.1016/j.jphotobiol.2016.02.021info:eu-repo/semantics/altIdentifier/url/https://www.sciencedirect.com/science/article/pii/S1011134415301998info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2024-05-08T13:38:50Zoai:ri.conicet.gov.ar:11336/61694instacron: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:34982024-05-08 13:38:51.151CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
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