Synthesis, spectroscopic properties and photodynamic activity of a fulleropyrrolidine bearing a basic amino group and its dicationic analog against Staphylococcus aureus

Autores
Agazzi, Maximiliano Luis; Spesia, Mariana Belen; Gsponer, Natalia Soledad; Milanesio, María Elisa; Durantini, Edgardo Néstor
Año de publicación
2015
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
N-Methyl-2-[4-(3-N,N-dimethylaminopropoxy)phenyl]fulleropyrrolidine (MPC60) was synthesized by 1,3-dipolar cycloaddition reaction of 4-(3-N,N-dimethylaminopropoxy)benzaldehyde, N-methylglycine and fullerene C60 in 43% yield. The amine groups of MPC60 were methylated with dimethyl sulfate to obtain a dicationic fullerene DPC602+ in 96 % yield. Absorption spectra of these fullerenes in N,N-dimethylformamide (DMF) and toluene/sodium bis(2-ethylhexyl) sulfosuccinate (AOT)/water reverse micelles showed strong absorptions in the UV region, with a peak at 430 nm and broader range of absorption up to 710 nm. Fluorescence quantum yields of about 10-4 were calculated for these compounds in DMF. A higher singlet molecular oxygen, O2(1Δg), generation was found for MPC60 than DPC602+ in DMF. The photodynamic activity of these photosensitizers remained high in a simple biomimetic AOT system. Also, the formation of superoxide anion radical induced by MPC60 and DPC602+ was detected in presence of NADH. Decomposition of l-tryptophan in DMF mediated by both fullerenes indicated a possible contribution of type I photoprocess. Photosensitized inactivation of Staphylococcus aureus was investigated using different conditions. Cell suspensions of 108 cells/mL incubated with 0.5 μM fullerene and irradiated for 30 min exhibited a 4.4 and 5.0 log decrease of cell survival by MPC60 and DPC602+, respectively. Therefore, these fullerene derivatives can be used as effective photosensitizers for the photodynamic inactivation of S. aureus cells.
Fil: Agazzi, Maximiliano Luis. 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: 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. Centro Científico Tecnológico Conicet - Córdoba; Argentina
Fil: Gsponer, Natalia Soledad. 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: 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. Centro Científico Tecnológico Conicet - Córdoba; 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. Centro Científico Tecnológico Conicet - Córdoba; Argentina
Materia
BACTERIA
FULLERENE
PHOTODYNAMIC INACTIVATION
PHOTOSENSITIZER
STAPHYLOCOCCUS AUREUS
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:11336/180102
Acceder
id CONICETDig_214bd71cb742414a65b39bb61fbedc55
oai_identifier_str oai:ri.conicet.gov.ar:11336/180102
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Synthesis, spectroscopic properties and photodynamic activity of a fulleropyrrolidine bearing a basic amino group and its dicationic analog against Staphylococcus aureusAgazzi, Maximiliano LuisSpesia, Mariana BelenGsponer, Natalia SoledadMilanesio, María ElisaDurantini, Edgardo NéstorBACTERIAFULLERENEPHOTODYNAMIC INACTIVATIONPHOTOSENSITIZERSTAPHYLOCOCCUS AUREUShttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1N-Methyl-2-[4-(3-N,N-dimethylaminopropoxy)phenyl]fulleropyrrolidine (MPC60) was synthesized by 1,3-dipolar cycloaddition reaction of 4-(3-N,N-dimethylaminopropoxy)benzaldehyde, N-methylglycine and fullerene C60 in 43% yield. The amine groups of MPC60 were methylated with dimethyl sulfate to obtain a dicationic fullerene DPC602+ in 96 % yield. Absorption spectra of these fullerenes in N,N-dimethylformamide (DMF) and toluene/sodium bis(2-ethylhexyl) sulfosuccinate (AOT)/water reverse micelles showed strong absorptions in the UV region, with a peak at 430 nm and broader range of absorption up to 710 nm. Fluorescence quantum yields of about 10-4 were calculated for these compounds in DMF. A higher singlet molecular oxygen, O2(1Δg), generation was found for MPC60 than DPC602+ in DMF. The photodynamic activity of these photosensitizers remained high in a simple biomimetic AOT system. Also, the formation of superoxide anion radical induced by MPC60 and DPC602+ was detected in presence of NADH. Decomposition of l-tryptophan in DMF mediated by both fullerenes indicated a possible contribution of type I photoprocess. Photosensitized inactivation of Staphylococcus aureus was investigated using different conditions. Cell suspensions of 108 cells/mL incubated with 0.5 μM fullerene and irradiated for 30 min exhibited a 4.4 and 5.0 log decrease of cell survival by MPC60 and DPC602+, respectively. Therefore, these fullerene derivatives can be used as effective photosensitizers for the photodynamic inactivation of S. aureus cells.Fil: Agazzi, Maximiliano Luis. 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: 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. Centro Científico Tecnológico Conicet - Córdoba; ArgentinaFil: Gsponer, Natalia Soledad. 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: 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. Centro Científico Tecnológico Conicet - Córdoba; 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. Centro Científico Tecnológico Conicet - Córdoba; ArgentinaElsevier Science SA2015-05info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfapplication/pdfapplication/pdfapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/180102Agazzi, Maximiliano Luis; Spesia, Mariana Belen; Gsponer, Natalia Soledad; Milanesio, María Elisa; Durantini, Edgardo Néstor; Synthesis, spectroscopic properties and photodynamic activity of a fulleropyrrolidine bearing a basic amino group and its dicationic analog against Staphylococcus aureus; Elsevier Science SA; Journal of Photochemistry and Photobiology A: Chemistry; 310; 5-2015; 171-1791010-6030CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/doi/10.1016/j.jphotochem.2015.05.022info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-03T09:45:45Zoai:ri.conicet.gov.ar:11336/180102instacron: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 09:45:46.119CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Synthesis, spectroscopic properties and photodynamic activity of a fulleropyrrolidine bearing a basic amino group and its dicationic analog against Staphylococcus aureus
title Synthesis, spectroscopic properties and photodynamic activity of a fulleropyrrolidine bearing a basic amino group and its dicationic analog against Staphylococcus aureus
spellingShingle Synthesis, spectroscopic properties and photodynamic activity of a fulleropyrrolidine bearing a basic amino group and its dicationic analog against Staphylococcus aureus
Agazzi, Maximiliano Luis
BACTERIA
FULLERENE
PHOTODYNAMIC INACTIVATION
PHOTOSENSITIZER
STAPHYLOCOCCUS AUREUS
title_short Synthesis, spectroscopic properties and photodynamic activity of a fulleropyrrolidine bearing a basic amino group and its dicationic analog against Staphylococcus aureus
title_full Synthesis, spectroscopic properties and photodynamic activity of a fulleropyrrolidine bearing a basic amino group and its dicationic analog against Staphylococcus aureus
title_fullStr Synthesis, spectroscopic properties and photodynamic activity of a fulleropyrrolidine bearing a basic amino group and its dicationic analog against Staphylococcus aureus
title_full_unstemmed Synthesis, spectroscopic properties and photodynamic activity of a fulleropyrrolidine bearing a basic amino group and its dicationic analog against Staphylococcus aureus
title_sort Synthesis, spectroscopic properties and photodynamic activity of a fulleropyrrolidine bearing a basic amino group and its dicationic analog against Staphylococcus aureus
dc.creator.none.fl_str_mv Agazzi, Maximiliano Luis
Spesia, Mariana Belen
Gsponer, Natalia Soledad
Milanesio, María Elisa
Durantini, Edgardo Néstor
author Agazzi, Maximiliano Luis
author_facet Agazzi, Maximiliano Luis
Spesia, Mariana Belen
Gsponer, Natalia Soledad
Milanesio, María Elisa
Durantini, Edgardo Néstor
author_role author
author2 Spesia, Mariana Belen
Gsponer, Natalia Soledad
Milanesio, María Elisa
Durantini, Edgardo Néstor
author2_role author
author
author
author
dc.subject.none.fl_str_mv BACTERIA
FULLERENE
PHOTODYNAMIC INACTIVATION
PHOTOSENSITIZER
STAPHYLOCOCCUS AUREUS
topic BACTERIA
FULLERENE
PHOTODYNAMIC INACTIVATION
PHOTOSENSITIZER
STAPHYLOCOCCUS AUREUS
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv N-Methyl-2-[4-(3-N,N-dimethylaminopropoxy)phenyl]fulleropyrrolidine (MPC60) was synthesized by 1,3-dipolar cycloaddition reaction of 4-(3-N,N-dimethylaminopropoxy)benzaldehyde, N-methylglycine and fullerene C60 in 43% yield. The amine groups of MPC60 were methylated with dimethyl sulfate to obtain a dicationic fullerene DPC602+ in 96 % yield. Absorption spectra of these fullerenes in N,N-dimethylformamide (DMF) and toluene/sodium bis(2-ethylhexyl) sulfosuccinate (AOT)/water reverse micelles showed strong absorptions in the UV region, with a peak at 430 nm and broader range of absorption up to 710 nm. Fluorescence quantum yields of about 10-4 were calculated for these compounds in DMF. A higher singlet molecular oxygen, O2(1Δg), generation was found for MPC60 than DPC602+ in DMF. The photodynamic activity of these photosensitizers remained high in a simple biomimetic AOT system. Also, the formation of superoxide anion radical induced by MPC60 and DPC602+ was detected in presence of NADH. Decomposition of l-tryptophan in DMF mediated by both fullerenes indicated a possible contribution of type I photoprocess. Photosensitized inactivation of Staphylococcus aureus was investigated using different conditions. Cell suspensions of 108 cells/mL incubated with 0.5 μM fullerene and irradiated for 30 min exhibited a 4.4 and 5.0 log decrease of cell survival by MPC60 and DPC602+, respectively. Therefore, these fullerene derivatives can be used as effective photosensitizers for the photodynamic inactivation of S. aureus cells.
Fil: Agazzi, Maximiliano Luis. 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: 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. Centro Científico Tecnológico Conicet - Córdoba; Argentina
Fil: Gsponer, Natalia Soledad. 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: 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. Centro Científico Tecnológico Conicet - Córdoba; 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. Centro Científico Tecnológico Conicet - Córdoba; Argentina
description N-Methyl-2-[4-(3-N,N-dimethylaminopropoxy)phenyl]fulleropyrrolidine (MPC60) was synthesized by 1,3-dipolar cycloaddition reaction of 4-(3-N,N-dimethylaminopropoxy)benzaldehyde, N-methylglycine and fullerene C60 in 43% yield. The amine groups of MPC60 were methylated with dimethyl sulfate to obtain a dicationic fullerene DPC602+ in 96 % yield. Absorption spectra of these fullerenes in N,N-dimethylformamide (DMF) and toluene/sodium bis(2-ethylhexyl) sulfosuccinate (AOT)/water reverse micelles showed strong absorptions in the UV region, with a peak at 430 nm and broader range of absorption up to 710 nm. Fluorescence quantum yields of about 10-4 were calculated for these compounds in DMF. A higher singlet molecular oxygen, O2(1Δg), generation was found for MPC60 than DPC602+ in DMF. The photodynamic activity of these photosensitizers remained high in a simple biomimetic AOT system. Also, the formation of superoxide anion radical induced by MPC60 and DPC602+ was detected in presence of NADH. Decomposition of l-tryptophan in DMF mediated by both fullerenes indicated a possible contribution of type I photoprocess. Photosensitized inactivation of Staphylococcus aureus was investigated using different conditions. Cell suspensions of 108 cells/mL incubated with 0.5 μM fullerene and irradiated for 30 min exhibited a 4.4 and 5.0 log decrease of cell survival by MPC60 and DPC602+, respectively. Therefore, these fullerene derivatives can be used as effective photosensitizers for the photodynamic inactivation of S. aureus cells.
publishDate 2015
dc.date.none.fl_str_mv 2015-05
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/11336/180102
Agazzi, Maximiliano Luis; Spesia, Mariana Belen; Gsponer, Natalia Soledad; Milanesio, María Elisa; Durantini, Edgardo Néstor; Synthesis, spectroscopic properties and photodynamic activity of a fulleropyrrolidine bearing a basic amino group and its dicationic analog against Staphylococcus aureus; Elsevier Science SA; Journal of Photochemistry and Photobiology A: Chemistry; 310; 5-2015; 171-179
1010-6030
CONICET Digital
CONICET
url http://hdl.handle.net/11336/180102
identifier_str_mv Agazzi, Maximiliano Luis; Spesia, Mariana Belen; Gsponer, Natalia Soledad; Milanesio, María Elisa; Durantini, Edgardo Néstor; Synthesis, spectroscopic properties and photodynamic activity of a fulleropyrrolidine bearing a basic amino group and its dicationic analog against Staphylococcus aureus; Elsevier Science SA; Journal of Photochemistry and Photobiology A: Chemistry; 310; 5-2015; 171-179
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.2015.05.022
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
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
_version_ 1842268751881306112
score 13.13397

Publicaciones similares