Porphyrins containing basic aliphatic amino groups as potential broad-spectrum antimicrobial agents

Autores
Scanone, Ana Coral; Gsponer, Natalia Soledad; Alvarez, María Gabriela; Durantini, Edgardo Néstor
Año de publicación
2018
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
New porphyrin derivatives bearing basic aliphatic amino groups were synthesized from the condensation of meso-4-[(3-N,N-dimethylaminopropoxy)phenyl]dipyrromethane, pentafluorobenzaldehyde and 4-(3-N,N-dimethylaminopropoxy)benzaldehyde. The reaction was catalyzed by trifluoroacetic acid in acetonitrile. This approach was used to obtain porphyrins with different patterns of substitution, of which three of them were isolated: 5,15-di(4-pentafluorophenyl)-10,20-di[4-(3-N,N-dimethylaminopropoxy)phenyl]porphyrin (F10APP), 5-(4-pentafluorophenyl)-10,15,20-tris[4-(3-N,N-dimethylaminopropoxy)phenyl]porphyrin (F5APP) and 5,10,15,20-tetrakis[4-(3-N,N-dimethylaminopropoxy)phenyl]porphyrin (TAPP). The UV–vis spectroscopic characterizations and the photodynamic effect of these compounds were compared in N,N-dimethylformamide. These porphyrins showed red fluorescence emission with quantum yields of 0.09-0.15. Moreover, they sensitized the production of singlet molecular oxygen, reaching quantum yields values of 0.33-0.53. Photodynamic inactivation was studied in two bacteria, Staphylococcus aureus and Escherichia coli, and a yeast Candida albicans. High amount of cell-bound porphyrin was obtained at short times (<2 min) of incubation. After 15 min irradiation, a 7 log reduction of S. aureus was found for cells treated with 1 μM F5APP. Similar photokilling was obtained in E. coli, but using 7.5 μM F5APP and 30 min irradiation. Under these conditions, a decrease of 5 log was observed in C. albicans cells. An increase in cell survival was observed by addition of sodium azide, whereas a slight protective effect was found in the presence of D-mannitol. Moreover, the photoinactivation mediated by these porphyrins was higher in D2O than in water. Thus, these porphyrins induced the photodynamic activity mainly through the intermediacy of O2(1Δg). In particular, F5APP was a highly effective photosensitizer with application as a broad-spectrum antimicrobial. This porphyrin contains three basic aliphatic amino groups that may be protonated at physiological pH. In addition, it is substituted by a lipophilic pentafluorophenyl group, which confers an amphiphilic character to the tetrapyrrolic macrocycle. This effect can increase the interaction with the cell envelopment, improving the photocytotoxic activity against the microorganisms.
Fil: Scanone, Ana Coral. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas Fisicoquímicas y Naturales. Departamento de Química; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba; Argentina
Fil: Gsponer, Natalia Soledad. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba; Argentina. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas Fisicoquímicas y Naturales. Departamento de Química; Argentina
Fil: Alvarez, María Gabriela. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas Fisicoquímicas y Naturales. Departamento de Química; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba; Argentina
Fil: Durantini, Edgardo Néstor. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba; Argentina. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas Fisicoquímicas y Naturales. Departamento de Química; Argentina
Materia
ANTIMICROBIAL PHOTODYNAMIC THERAPY
MICROORGANISMS
PHOTODYNAMIC ACTIVITY
PHOTOINACTIVATION
PHOTOSENSITIZER
PORPHYRIN
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:11336/100531

id CONICETDig_d9093f3f58d0973247e0db4d0531df9e
oai_identifier_str oai:ri.conicet.gov.ar:11336/100531
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Porphyrins containing basic aliphatic amino groups as potential broad-spectrum antimicrobial agentsScanone, Ana CoralGsponer, Natalia SoledadAlvarez, María GabrielaDurantini, Edgardo NéstorANTIMICROBIAL PHOTODYNAMIC THERAPYMICROORGANISMSPHOTODYNAMIC ACTIVITYPHOTOINACTIVATIONPHOTOSENSITIZERPORPHYRINhttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1New porphyrin derivatives bearing basic aliphatic amino groups were synthesized from the condensation of meso-4-[(3-N,N-dimethylaminopropoxy)phenyl]dipyrromethane, pentafluorobenzaldehyde and 4-(3-N,N-dimethylaminopropoxy)benzaldehyde. The reaction was catalyzed by trifluoroacetic acid in acetonitrile. This approach was used to obtain porphyrins with different patterns of substitution, of which three of them were isolated: 5,15-di(4-pentafluorophenyl)-10,20-di[4-(3-N,N-dimethylaminopropoxy)phenyl]porphyrin (F10APP), 5-(4-pentafluorophenyl)-10,15,20-tris[4-(3-N,N-dimethylaminopropoxy)phenyl]porphyrin (F5APP) and 5,10,15,20-tetrakis[4-(3-N,N-dimethylaminopropoxy)phenyl]porphyrin (TAPP). The UV–vis spectroscopic characterizations and the photodynamic effect of these compounds were compared in N,N-dimethylformamide. These porphyrins showed red fluorescence emission with quantum yields of 0.09-0.15. Moreover, they sensitized the production of singlet molecular oxygen, reaching quantum yields values of 0.33-0.53. Photodynamic inactivation was studied in two bacteria, Staphylococcus aureus and Escherichia coli, and a yeast Candida albicans. High amount of cell-bound porphyrin was obtained at short times (<2 min) of incubation. After 15 min irradiation, a 7 log reduction of S. aureus was found for cells treated with 1 μM F5APP. Similar photokilling was obtained in E. coli, but using 7.5 μM F5APP and 30 min irradiation. Under these conditions, a decrease of 5 log was observed in C. albicans cells. An increase in cell survival was observed by addition of sodium azide, whereas a slight protective effect was found in the presence of D-mannitol. Moreover, the photoinactivation mediated by these porphyrins was higher in D2O than in water. Thus, these porphyrins induced the photodynamic activity mainly through the intermediacy of O2(1Δg). In particular, F5APP was a highly effective photosensitizer with application as a broad-spectrum antimicrobial. This porphyrin contains three basic aliphatic amino groups that may be protonated at physiological pH. In addition, it is substituted by a lipophilic pentafluorophenyl group, which confers an amphiphilic character to the tetrapyrrolic macrocycle. This effect can increase the interaction with the cell envelopment, improving the photocytotoxic activity against the microorganisms.Fil: Scanone, Ana Coral. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas Fisicoquímicas y Naturales. Departamento de Química; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba; ArgentinaFil: Gsponer, Natalia Soledad. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba; Argentina. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas Fisicoquímicas y Naturales. Departamento de Química; ArgentinaFil: Alvarez, María Gabriela. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas Fisicoquímicas y Naturales. Departamento de Química; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba; ArgentinaFil: Durantini, Edgardo Néstor. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba; Argentina. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas Fisicoquímicas y Naturales. Departamento de Química; ArgentinaElsevier Science2018-12info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/100531Scanone, Ana Coral; Gsponer, Natalia Soledad; Alvarez, María Gabriela; Durantini, Edgardo Néstor; Porphyrins containing basic aliphatic amino groups as potential broad-spectrum antimicrobial agents; Elsevier Science; Photodiagnosis Photodynamic Therapy; 24; 12-2018; 220-2271572-1000CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/doi/10.1016/j.pdpdt.2018.09.017info:eu-repo/semantics/altIdentifier/url/https://www.sciencedirect.com/science/article/abs/pii/S1572100018302734info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-29T09:43:37Zoai:ri.conicet.gov.ar:11336/100531instacron: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 09:43:38.059CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Porphyrins containing basic aliphatic amino groups as potential broad-spectrum antimicrobial agents
title Porphyrins containing basic aliphatic amino groups as potential broad-spectrum antimicrobial agents
spellingShingle Porphyrins containing basic aliphatic amino groups as potential broad-spectrum antimicrobial agents
Scanone, Ana Coral
ANTIMICROBIAL PHOTODYNAMIC THERAPY
MICROORGANISMS
PHOTODYNAMIC ACTIVITY
PHOTOINACTIVATION
PHOTOSENSITIZER
PORPHYRIN
title_short Porphyrins containing basic aliphatic amino groups as potential broad-spectrum antimicrobial agents
title_full Porphyrins containing basic aliphatic amino groups as potential broad-spectrum antimicrobial agents
title_fullStr Porphyrins containing basic aliphatic amino groups as potential broad-spectrum antimicrobial agents
title_full_unstemmed Porphyrins containing basic aliphatic amino groups as potential broad-spectrum antimicrobial agents
title_sort Porphyrins containing basic aliphatic amino groups as potential broad-spectrum antimicrobial agents
dc.creator.none.fl_str_mv Scanone, Ana Coral
Gsponer, Natalia Soledad
Alvarez, María Gabriela
Durantini, Edgardo Néstor
author Scanone, Ana Coral
author_facet Scanone, Ana Coral
Gsponer, Natalia Soledad
Alvarez, María Gabriela
Durantini, Edgardo Néstor
author_role author
author2 Gsponer, Natalia Soledad
Alvarez, María Gabriela
Durantini, Edgardo Néstor
author2_role author
author
author
dc.subject.none.fl_str_mv ANTIMICROBIAL PHOTODYNAMIC THERAPY
MICROORGANISMS
PHOTODYNAMIC ACTIVITY
PHOTOINACTIVATION
PHOTOSENSITIZER
PORPHYRIN
topic ANTIMICROBIAL PHOTODYNAMIC THERAPY
MICROORGANISMS
PHOTODYNAMIC ACTIVITY
PHOTOINACTIVATION
PHOTOSENSITIZER
PORPHYRIN
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv New porphyrin derivatives bearing basic aliphatic amino groups were synthesized from the condensation of meso-4-[(3-N,N-dimethylaminopropoxy)phenyl]dipyrromethane, pentafluorobenzaldehyde and 4-(3-N,N-dimethylaminopropoxy)benzaldehyde. The reaction was catalyzed by trifluoroacetic acid in acetonitrile. This approach was used to obtain porphyrins with different patterns of substitution, of which three of them were isolated: 5,15-di(4-pentafluorophenyl)-10,20-di[4-(3-N,N-dimethylaminopropoxy)phenyl]porphyrin (F10APP), 5-(4-pentafluorophenyl)-10,15,20-tris[4-(3-N,N-dimethylaminopropoxy)phenyl]porphyrin (F5APP) and 5,10,15,20-tetrakis[4-(3-N,N-dimethylaminopropoxy)phenyl]porphyrin (TAPP). The UV–vis spectroscopic characterizations and the photodynamic effect of these compounds were compared in N,N-dimethylformamide. These porphyrins showed red fluorescence emission with quantum yields of 0.09-0.15. Moreover, they sensitized the production of singlet molecular oxygen, reaching quantum yields values of 0.33-0.53. Photodynamic inactivation was studied in two bacteria, Staphylococcus aureus and Escherichia coli, and a yeast Candida albicans. High amount of cell-bound porphyrin was obtained at short times (<2 min) of incubation. After 15 min irradiation, a 7 log reduction of S. aureus was found for cells treated with 1 μM F5APP. Similar photokilling was obtained in E. coli, but using 7.5 μM F5APP and 30 min irradiation. Under these conditions, a decrease of 5 log was observed in C. albicans cells. An increase in cell survival was observed by addition of sodium azide, whereas a slight protective effect was found in the presence of D-mannitol. Moreover, the photoinactivation mediated by these porphyrins was higher in D2O than in water. Thus, these porphyrins induced the photodynamic activity mainly through the intermediacy of O2(1Δg). In particular, F5APP was a highly effective photosensitizer with application as a broad-spectrum antimicrobial. This porphyrin contains three basic aliphatic amino groups that may be protonated at physiological pH. In addition, it is substituted by a lipophilic pentafluorophenyl group, which confers an amphiphilic character to the tetrapyrrolic macrocycle. This effect can increase the interaction with the cell envelopment, improving the photocytotoxic activity against the microorganisms.
Fil: Scanone, Ana Coral. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas Fisicoquímicas y Naturales. Departamento de Química; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba; Argentina
Fil: Gsponer, Natalia Soledad. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba; Argentina. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas Fisicoquímicas y Naturales. Departamento de Química; Argentina
Fil: Alvarez, María Gabriela. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas Fisicoquímicas y Naturales. Departamento de Química; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba; Argentina
Fil: Durantini, Edgardo Néstor. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba; Argentina. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas Fisicoquímicas y Naturales. Departamento de Química; Argentina
description New porphyrin derivatives bearing basic aliphatic amino groups were synthesized from the condensation of meso-4-[(3-N,N-dimethylaminopropoxy)phenyl]dipyrromethane, pentafluorobenzaldehyde and 4-(3-N,N-dimethylaminopropoxy)benzaldehyde. The reaction was catalyzed by trifluoroacetic acid in acetonitrile. This approach was used to obtain porphyrins with different patterns of substitution, of which three of them were isolated: 5,15-di(4-pentafluorophenyl)-10,20-di[4-(3-N,N-dimethylaminopropoxy)phenyl]porphyrin (F10APP), 5-(4-pentafluorophenyl)-10,15,20-tris[4-(3-N,N-dimethylaminopropoxy)phenyl]porphyrin (F5APP) and 5,10,15,20-tetrakis[4-(3-N,N-dimethylaminopropoxy)phenyl]porphyrin (TAPP). The UV–vis spectroscopic characterizations and the photodynamic effect of these compounds were compared in N,N-dimethylformamide. These porphyrins showed red fluorescence emission with quantum yields of 0.09-0.15. Moreover, they sensitized the production of singlet molecular oxygen, reaching quantum yields values of 0.33-0.53. Photodynamic inactivation was studied in two bacteria, Staphylococcus aureus and Escherichia coli, and a yeast Candida albicans. High amount of cell-bound porphyrin was obtained at short times (<2 min) of incubation. After 15 min irradiation, a 7 log reduction of S. aureus was found for cells treated with 1 μM F5APP. Similar photokilling was obtained in E. coli, but using 7.5 μM F5APP and 30 min irradiation. Under these conditions, a decrease of 5 log was observed in C. albicans cells. An increase in cell survival was observed by addition of sodium azide, whereas a slight protective effect was found in the presence of D-mannitol. Moreover, the photoinactivation mediated by these porphyrins was higher in D2O than in water. Thus, these porphyrins induced the photodynamic activity mainly through the intermediacy of O2(1Δg). In particular, F5APP was a highly effective photosensitizer with application as a broad-spectrum antimicrobial. This porphyrin contains three basic aliphatic amino groups that may be protonated at physiological pH. In addition, it is substituted by a lipophilic pentafluorophenyl group, which confers an amphiphilic character to the tetrapyrrolic macrocycle. This effect can increase the interaction with the cell envelopment, improving the photocytotoxic activity against the microorganisms.
publishDate 2018
dc.date.none.fl_str_mv 2018-12
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/11336/100531
Scanone, Ana Coral; Gsponer, Natalia Soledad; Alvarez, María Gabriela; Durantini, Edgardo Néstor; Porphyrins containing basic aliphatic amino groups as potential broad-spectrum antimicrobial agents; Elsevier Science; Photodiagnosis Photodynamic Therapy; 24; 12-2018; 220-227
1572-1000
CONICET Digital
CONICET
url http://hdl.handle.net/11336/100531
identifier_str_mv Scanone, Ana Coral; Gsponer, Natalia Soledad; Alvarez, María Gabriela; Durantini, Edgardo Néstor; Porphyrins containing basic aliphatic amino groups as potential broad-spectrum antimicrobial agents; Elsevier Science; Photodiagnosis Photodynamic Therapy; 24; 12-2018; 220-227
1572-1000
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.pdpdt.2018.09.017
info:eu-repo/semantics/altIdentifier/url/https://www.sciencedirect.com/science/article/abs/pii/S1572100018302734
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
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)
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
_version_ 1844613373529948160
score 13.070432