Synthesis, properties and photodynamic inactivation of Escherichia coli by novel cationic fullerene C60 derivatives

Autores
Spesia, Mariana Belen; Milanesio, María Elisa; Durantini, Edgardo Néstor
Año de publicación
2008
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
A novel N,N-dimethyl-2-(40-N,N,N-trimethylaminophenyl)fulleropyrrolidinium iodide (DTC602+) has been synthesized by 1,3-dipolar cycloaddition using 4-(N,N-dimethylamino) benzaldehyde, N-methylglycine and fullerene C60. This approach produced an N-methyl-2-(40-N,N-dimethylaminophenyl) fulleropyrrolidine with 38% yield. Exhaustive methylation of this fullerene derivative with methyl iodide yielded 95% of dicationic DTC602+. The spectroscopic and photodynamic properties of the DTC602+were compared with a non-charged N-methyl-2-(40-acetamidophenyl)fulleropyrrolidine (MAC60) and a monocationic N,N-dimethyl-2-(40-acetamidophenyl)fulleropyrrolidinium iodide (DTC602+). The dicationic DTC602+is essentially aggregated in solution of different solvents and it is partially dissolved as monomer in benzene/benzyl-n-hexadecyldimethyl ammonium chloride (BHDC) 0.1 M/water (W0 = 10) reverse micelles. The singlet molecular oxygen, O2 (1Dg), production was evaluated using 1,3-diphenylisobenzofuran. The photodynamic effect was strongly dependent on the medium, diminishes when the sensitizer is aggregated and increases in an appropriately surrounded microenvironment. The photodynamic inactivation produced by these fullerene derivatives was investigated in vitro on a typical Gram-negative bacterium, Escherichia coli. Photosensitized inactivation of E. coli cellular suspensions by DTC602+ exhibits aw3.5 log decrease of cell survival (99.97% of cellular inactivation), when the cultures are treated with 1 mM of sensitizer and irradiated for 30 min. This photosensitized inactivation remains high even after one washing step. Also, the photodynamic activity was confirmed by growth delay of E. coli cultures. The growth was arrested when E. coli was exposed to 2 mM of cationic fullerene and irradiated, whereas a negligible effect was found for the non-charged MAC60. These studies indicate that dicationic DTC602+ is an interesting agent with potential applications in photodynamic inactivation of bacteria.
Fil: Spesia, Mariana Belen. 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: 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
Fullerene
Synthesis
Photodynamic inactivation
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:11336/242174
Acceder
id CONICETDig_21ac00c3172a08172056b0036002f46c
oai_identifier_str oai:ri.conicet.gov.ar:11336/242174
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Synthesis, properties and photodynamic inactivation of Escherichia coli by novel cationic fullerene C60 derivativesSpesia, Mariana BelenMilanesio, María ElisaDurantini, Edgardo NéstorFullereneSynthesisPhotodynamic inactivationhttps://purl.org/becyt/ford/1.6https://purl.org/becyt/ford/1A novel N,N-dimethyl-2-(40-N,N,N-trimethylaminophenyl)fulleropyrrolidinium iodide (DTC602+) has been synthesized by 1,3-dipolar cycloaddition using 4-(N,N-dimethylamino) benzaldehyde, N-methylglycine and fullerene C60. This approach produced an N-methyl-2-(40-N,N-dimethylaminophenyl) fulleropyrrolidine with 38% yield. Exhaustive methylation of this fullerene derivative with methyl iodide yielded 95% of dicationic DTC602+. The spectroscopic and photodynamic properties of the DTC602+were compared with a non-charged N-methyl-2-(40-acetamidophenyl)fulleropyrrolidine (MAC60) and a monocationic N,N-dimethyl-2-(40-acetamidophenyl)fulleropyrrolidinium iodide (DTC602+). The dicationic DTC602+is essentially aggregated in solution of different solvents and it is partially dissolved as monomer in benzene/benzyl-n-hexadecyldimethyl ammonium chloride (BHDC) 0.1 M/water (W0 = 10) reverse micelles. The singlet molecular oxygen, O2 (1Dg), production was evaluated using 1,3-diphenylisobenzofuran. The photodynamic effect was strongly dependent on the medium, diminishes when the sensitizer is aggregated and increases in an appropriately surrounded microenvironment. The photodynamic inactivation produced by these fullerene derivatives was investigated in vitro on a typical Gram-negative bacterium, Escherichia coli. Photosensitized inactivation of E. coli cellular suspensions by DTC602+ exhibits aw3.5 log decrease of cell survival (99.97% of cellular inactivation), when the cultures are treated with 1 mM of sensitizer and irradiated for 30 min. This photosensitized inactivation remains high even after one washing step. Also, the photodynamic activity was confirmed by growth delay of E. coli cultures. The growth was arrested when E. coli was exposed to 2 mM of cationic fullerene and irradiated, whereas a negligible effect was found for the non-charged MAC60. These studies indicate that dicationic DTC602+ is an interesting agent with potential applications in photodynamic inactivation of bacteria.Fil: Spesia, Mariana Belen. 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: 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 France-Editions Scientifiques Medicales Elsevier2008-04info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/242174Spesia, Mariana Belen; Milanesio, María Elisa; Durantini, Edgardo Néstor; Synthesis, properties and photodynamic inactivation of Escherichia coli by novel cationic fullerene C60 derivatives; Elsevier France-Editions Scientifiques Medicales Elsevier; European Journal of Medical Chemistry; 43; 4; 4-2008; 853-8610223-5234CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/url/https://www.sciencedirect.com/science/article/pii/S0223523407002644info:eu-repo/semantics/altIdentifier/doi/10.1016/j.ejmech.2007.06.014info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-03T09:47:58Zoai:ri.conicet.gov.ar:11336/242174instacron: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 09:47:58.505CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Synthesis, properties and photodynamic inactivation of Escherichia coli by novel cationic fullerene C60 derivatives
title Synthesis, properties and photodynamic inactivation of Escherichia coli by novel cationic fullerene C60 derivatives
spellingShingle Synthesis, properties and photodynamic inactivation of Escherichia coli by novel cationic fullerene C60 derivatives
Spesia, Mariana Belen
Fullerene
Synthesis
Photodynamic inactivation
title_short Synthesis, properties and photodynamic inactivation of Escherichia coli by novel cationic fullerene C60 derivatives
title_full Synthesis, properties and photodynamic inactivation of Escherichia coli by novel cationic fullerene C60 derivatives
title_fullStr Synthesis, properties and photodynamic inactivation of Escherichia coli by novel cationic fullerene C60 derivatives
title_full_unstemmed Synthesis, properties and photodynamic inactivation of Escherichia coli by novel cationic fullerene C60 derivatives
title_sort Synthesis, properties and photodynamic inactivation of Escherichia coli by novel cationic fullerene C60 derivatives
dc.creator.none.fl_str_mv Spesia, Mariana Belen
Milanesio, María Elisa
Durantini, Edgardo Néstor
author Spesia, Mariana Belen
author_facet Spesia, Mariana Belen
Milanesio, María Elisa
Durantini, Edgardo Néstor
author_role author
author2 Milanesio, María Elisa
Durantini, Edgardo Néstor
author2_role author
author
dc.subject.none.fl_str_mv Fullerene
Synthesis
Photodynamic inactivation
topic Fullerene
Synthesis
Photodynamic inactivation
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.6
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv A novel N,N-dimethyl-2-(40-N,N,N-trimethylaminophenyl)fulleropyrrolidinium iodide (DTC602+) has been synthesized by 1,3-dipolar cycloaddition using 4-(N,N-dimethylamino) benzaldehyde, N-methylglycine and fullerene C60. This approach produced an N-methyl-2-(40-N,N-dimethylaminophenyl) fulleropyrrolidine with 38% yield. Exhaustive methylation of this fullerene derivative with methyl iodide yielded 95% of dicationic DTC602+. The spectroscopic and photodynamic properties of the DTC602+were compared with a non-charged N-methyl-2-(40-acetamidophenyl)fulleropyrrolidine (MAC60) and a monocationic N,N-dimethyl-2-(40-acetamidophenyl)fulleropyrrolidinium iodide (DTC602+). The dicationic DTC602+is essentially aggregated in solution of different solvents and it is partially dissolved as monomer in benzene/benzyl-n-hexadecyldimethyl ammonium chloride (BHDC) 0.1 M/water (W0 = 10) reverse micelles. The singlet molecular oxygen, O2 (1Dg), production was evaluated using 1,3-diphenylisobenzofuran. The photodynamic effect was strongly dependent on the medium, diminishes when the sensitizer is aggregated and increases in an appropriately surrounded microenvironment. The photodynamic inactivation produced by these fullerene derivatives was investigated in vitro on a typical Gram-negative bacterium, Escherichia coli. Photosensitized inactivation of E. coli cellular suspensions by DTC602+ exhibits aw3.5 log decrease of cell survival (99.97% of cellular inactivation), when the cultures are treated with 1 mM of sensitizer and irradiated for 30 min. This photosensitized inactivation remains high even after one washing step. Also, the photodynamic activity was confirmed by growth delay of E. coli cultures. The growth was arrested when E. coli was exposed to 2 mM of cationic fullerene and irradiated, whereas a negligible effect was found for the non-charged MAC60. These studies indicate that dicationic DTC602+ is an interesting agent with potential applications in photodynamic inactivation of bacteria.
Fil: Spesia, Mariana Belen. 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: 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 A novel N,N-dimethyl-2-(40-N,N,N-trimethylaminophenyl)fulleropyrrolidinium iodide (DTC602+) has been synthesized by 1,3-dipolar cycloaddition using 4-(N,N-dimethylamino) benzaldehyde, N-methylglycine and fullerene C60. This approach produced an N-methyl-2-(40-N,N-dimethylaminophenyl) fulleropyrrolidine with 38% yield. Exhaustive methylation of this fullerene derivative with methyl iodide yielded 95% of dicationic DTC602+. The spectroscopic and photodynamic properties of the DTC602+were compared with a non-charged N-methyl-2-(40-acetamidophenyl)fulleropyrrolidine (MAC60) and a monocationic N,N-dimethyl-2-(40-acetamidophenyl)fulleropyrrolidinium iodide (DTC602+). The dicationic DTC602+is essentially aggregated in solution of different solvents and it is partially dissolved as monomer in benzene/benzyl-n-hexadecyldimethyl ammonium chloride (BHDC) 0.1 M/water (W0 = 10) reverse micelles. The singlet molecular oxygen, O2 (1Dg), production was evaluated using 1,3-diphenylisobenzofuran. The photodynamic effect was strongly dependent on the medium, diminishes when the sensitizer is aggregated and increases in an appropriately surrounded microenvironment. The photodynamic inactivation produced by these fullerene derivatives was investigated in vitro on a typical Gram-negative bacterium, Escherichia coli. Photosensitized inactivation of E. coli cellular suspensions by DTC602+ exhibits aw3.5 log decrease of cell survival (99.97% of cellular inactivation), when the cultures are treated with 1 mM of sensitizer and irradiated for 30 min. This photosensitized inactivation remains high even after one washing step. Also, the photodynamic activity was confirmed by growth delay of E. coli cultures. The growth was arrested when E. coli was exposed to 2 mM of cationic fullerene and irradiated, whereas a negligible effect was found for the non-charged MAC60. These studies indicate that dicationic DTC602+ is an interesting agent with potential applications in photodynamic inactivation of bacteria.
publishDate 2008
dc.date.none.fl_str_mv 2008-04
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/11336/242174
Spesia, Mariana Belen; Milanesio, María Elisa; Durantini, Edgardo Néstor; Synthesis, properties and photodynamic inactivation of Escherichia coli by novel cationic fullerene C60 derivatives; Elsevier France-Editions Scientifiques Medicales Elsevier; European Journal of Medical Chemistry; 43; 4; 4-2008; 853-861
0223-5234
CONICET Digital
CONICET
url http://hdl.handle.net/11336/242174
identifier_str_mv Spesia, Mariana Belen; Milanesio, María Elisa; Durantini, Edgardo Néstor; Synthesis, properties and photodynamic inactivation of Escherichia coli by novel cationic fullerene C60 derivatives; Elsevier France-Editions Scientifiques Medicales Elsevier; European Journal of Medical Chemistry; 43; 4; 4-2008; 853-861
0223-5234
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/url/https://www.sciencedirect.com/science/article/pii/S0223523407002644
info:eu-repo/semantics/altIdentifier/doi/10.1016/j.ejmech.2007.06.014
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
dc.publisher.none.fl_str_mv Elsevier France-Editions Scientifiques Medicales Elsevier
publisher.none.fl_str_mv Elsevier France-Editions Scientifiques Medicales Elsevier
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 13.13397

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