Antimicrobial photodynamic polymeric films bearing biscarbazol triphenylamine end-capped dendrimeric Zn(II) porphyrin
A novel biscarbazol triphenylamine end-capped dendrimeric zinc(II) porphyrin (DP 5) was synthesized by click chemistry. This compound is a cruciform dendrimer that bears a nucleus of zinc(II) tetrapyrrolic macrocycle substituted at the meso positions by four identical substituents. These are formed...
| Autores: | , , , , , , , , |
|---|---|
| Tipo de recurso: | artículo |
| Estado: | Versión publicada |
| Fecha de publicación: | 2019 |
| País: | Argentina |
| Institución: | Consejo Nacional de Investigaciones Científicas y Técnicas |
| Repositorio: | CONICET Digital (CONICET) |
| Idioma: | inglés |
| OAI Identifier: | oai:ri.conicet.gov.ar:11336/119707 |
| Acceso en línea: | http://hdl.handle.net/11336/119707 |
| Access Level: | acceso abierto |
| Palabra clave: | ANTIBACTERIAL SURFACE CARBAZOLE CLICK CHEMISTRY PHOTODYNAMIC INACTIVATION POLYMERIC FILMS PORPHYRIN https://purl.org/becyt/ford/1.4 https://purl.org/becyt/ford/1 |
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oai:ri.conicet.gov.ar:11336/119707 |
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AR |
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Argentina |
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| dc.title.none.fl_str_mv |
Antimicrobial photodynamic polymeric films bearing biscarbazol triphenylamine end-capped dendrimeric Zn(II) porphyrin |
| title |
Antimicrobial photodynamic polymeric films bearing biscarbazol triphenylamine end-capped dendrimeric Zn(II) porphyrin |
| spellingShingle |
Antimicrobial photodynamic polymeric films bearing biscarbazol triphenylamine end-capped dendrimeric Zn(II) porphyrin Heredia, Daniel Alejandro ANTIBACTERIAL SURFACE CARBAZOLE CLICK CHEMISTRY PHOTODYNAMIC INACTIVATION POLYMERIC FILMS PORPHYRIN https://purl.org/becyt/ford/1.4 https://purl.org/becyt/ford/1 |
| title_short |
Antimicrobial photodynamic polymeric films bearing biscarbazol triphenylamine end-capped dendrimeric Zn(II) porphyrin |
| title_full |
Antimicrobial photodynamic polymeric films bearing biscarbazol triphenylamine end-capped dendrimeric Zn(II) porphyrin |
| title_fullStr |
Antimicrobial photodynamic polymeric films bearing biscarbazol triphenylamine end-capped dendrimeric Zn(II) porphyrin |
| title_full_unstemmed |
Antimicrobial photodynamic polymeric films bearing biscarbazol triphenylamine end-capped dendrimeric Zn(II) porphyrin |
| title_sort |
Antimicrobial photodynamic polymeric films bearing biscarbazol triphenylamine end-capped dendrimeric Zn(II) porphyrin |
| dc.creator.none.fl_str_mv |
Heredia, Daniel Alejandro Martinez, Sol Romina Durantini, Andres Matías Pérez, María Eugenia Mangione, Maria Ines Durantini, Javier Esteban Gervaldo, Miguel Andres Otero, Luis Alberto Durantini, Edgardo Néstor |
| author |
Heredia, Daniel Alejandro |
| author_facet |
Heredia, Daniel Alejandro Martinez, Sol Romina Durantini, Andres Matías Pérez, María Eugenia Mangione, Maria Ines Durantini, Javier Esteban Gervaldo, Miguel Andres Otero, Luis Alberto Durantini, Edgardo Néstor |
| author_role |
author |
| author2 |
Martinez, Sol Romina Durantini, Andres Matías Pérez, María Eugenia Mangione, Maria Ines Durantini, Javier Esteban Gervaldo, Miguel Andres Otero, Luis Alberto Durantini, Edgardo Néstor |
| author2_role |
author author author author author author author author |
| dc.subject.none.fl_str_mv |
ANTIBACTERIAL SURFACE CARBAZOLE CLICK CHEMISTRY PHOTODYNAMIC INACTIVATION POLYMERIC FILMS PORPHYRIN https://purl.org/becyt/ford/1.4 https://purl.org/becyt/ford/1 |
| topic |
ANTIBACTERIAL SURFACE CARBAZOLE CLICK CHEMISTRY PHOTODYNAMIC INACTIVATION POLYMERIC FILMS PORPHYRIN https://purl.org/becyt/ford/1.4 https://purl.org/becyt/ford/1 |
| description |
A novel biscarbazol triphenylamine end-capped dendrimeric zinc(II) porphyrin (DP 5) was synthesized by click chemistry. This compound is a cruciform dendrimer that bears a nucleus of zinc(II) tetrapyrrolic macrocycle substituted at the meso positions by four identical substituents. These are formed by a tetrafluorophenyl group that possesses a triazole unit in the para position. This nitrogenous heterocyclic is connected to a 4,4′-di(N-carbazolyl)triphenylamine group by means of a phenylenevinylene bridge, which allows the conjugation between the nucleus and this external electropolymerizable carbazoyl group. In this structure, dendrimeric arms act as light-harvesting antennas, increasing the absorption of blue light, and as electroactive moieties. The electrochemical oxidation of the carbazole groups contained in the terminal arms of the DP 5 was used to obtain novel, stable, and reproducible fully π-conjugated photoactive polymeric films (FDP 5). First, the spectroscopic characteristics and photodynamic properties of DP 5 were compared with its constitutional components derived of porphyrin P 6 and carbazole D 7 moieties in solution. The fluorescence emissions of the dendrimeric units in DP 5 were more strongly quenched by the tetrapyrrolic macrocycle, indicating photoinduced energy transfer. In addition, FDP 5 film showed the Soret and Q absorption bands and red fluorescence emission of the corresponding zinc(II) porphyrin. Also, FDP 5 film was highly stable to photobleaching, and it was able to produce singlet molecular oxygen in both N,N-dimethylformamide (DMF) and water. Therefore, the porphyrin units embedded in the polymeric matrix of FDP 5 film mainly retain the photochemical properties. Photodynamic inactivation mediated by FDP 5 film was investigated in Staphylococcus aureus and Escherichia coli. When a cell suspension was deposited on the surface, complete eradication of S. aureus and a 99% reduction in E. coli survival were found after 15 and 30 min of irradiation, respectively. Also, FDP 5 film was highly effective to eliminate individual bacteria attached to the surface. In addition, photodynamic inactivation (PDI) sensitized by FDP 5 film produced >99.99% bacterial killing in biofilms formed on the surface after 60 min irradiation. The results indicate that FDP 5 film represents an interesting and versatile photodynamic active material to eradicate bacteria as planktonic cells, individual attached microbes, or biofilms. |
| publishDate |
2019 |
| dc.date.none.fl_str_mv |
2019-07-16 |
| 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/11336/119707 Heredia, Daniel Alejandro; Martinez, Sol Romina; Durantini, Andres Matías; Pérez, María Eugenia; Mangione, Maria Ines; et al.; Antimicrobial photodynamic polymeric films bearing biscarbazol triphenylamine end-capped dendrimeric Zn(II) porphyrin; American Chemical Society; ACS Applied Materials & Interfaces; 11; 31; 16-7-2019; 27574-27587 1944-8252 1944-8244 CONICET Digital CONICET |
| url |
http://hdl.handle.net/11336/119707 |
| identifier_str_mv |
Heredia, Daniel Alejandro; Martinez, Sol Romina; Durantini, Andres Matías; Pérez, María Eugenia; Mangione, Maria Ines; et al.; Antimicrobial photodynamic polymeric films bearing biscarbazol triphenylamine end-capped dendrimeric Zn(II) porphyrin; American Chemical Society; ACS Applied Materials & Interfaces; 11; 31; 16-7-2019; 27574-27587 1944-8252 1944-8244 CONICET Digital CONICET |
| dc.language.none.fl_str_mv |
eng |
| language |
eng |
| dc.relation.none.fl_str_mv |
info:eu-repo/semantics/altIdentifier/url/http://pubs.acs.org/doi/10.1021/acsami.9b09119 info:eu-repo/semantics/altIdentifier/doi/ 10.1021/acsami.9b09119 |
| 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 |
American Chemical Society |
| publisher.none.fl_str_mv |
American Chemical Society |
| 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 |
| _version_ |
1799195513752387584 |
| spelling |
Antimicrobial photodynamic polymeric films bearing biscarbazol triphenylamine end-capped dendrimeric Zn(II) porphyrinHeredia, Daniel AlejandroMartinez, Sol RominaDurantini, Andres MatíasPérez, María EugeniaMangione, Maria InesDurantini, Javier EstebanGervaldo, Miguel AndresOtero, Luis AlbertoDurantini, Edgardo NéstorANTIBACTERIAL SURFACECARBAZOLECLICK CHEMISTRYPHOTODYNAMIC INACTIVATIONPOLYMERIC FILMSPORPHYRINhttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1A novel biscarbazol triphenylamine end-capped dendrimeric zinc(II) porphyrin (DP 5) was synthesized by click chemistry. This compound is a cruciform dendrimer that bears a nucleus of zinc(II) tetrapyrrolic macrocycle substituted at the meso positions by four identical substituents. These are formed by a tetrafluorophenyl group that possesses a triazole unit in the para position. This nitrogenous heterocyclic is connected to a 4,4′-di(N-carbazolyl)triphenylamine group by means of a phenylenevinylene bridge, which allows the conjugation between the nucleus and this external electropolymerizable carbazoyl group. In this structure, dendrimeric arms act as light-harvesting antennas, increasing the absorption of blue light, and as electroactive moieties. The electrochemical oxidation of the carbazole groups contained in the terminal arms of the DP 5 was used to obtain novel, stable, and reproducible fully π-conjugated photoactive polymeric films (FDP 5). First, the spectroscopic characteristics and photodynamic properties of DP 5 were compared with its constitutional components derived of porphyrin P 6 and carbazole D 7 moieties in solution. The fluorescence emissions of the dendrimeric units in DP 5 were more strongly quenched by the tetrapyrrolic macrocycle, indicating photoinduced energy transfer. In addition, FDP 5 film showed the Soret and Q absorption bands and red fluorescence emission of the corresponding zinc(II) porphyrin. Also, FDP 5 film was highly stable to photobleaching, and it was able to produce singlet molecular oxygen in both N,N-dimethylformamide (DMF) and water. Therefore, the porphyrin units embedded in the polymeric matrix of FDP 5 film mainly retain the photochemical properties. Photodynamic inactivation mediated by FDP 5 film was investigated in Staphylococcus aureus and Escherichia coli. When a cell suspension was deposited on the surface, complete eradication of S. aureus and a 99% reduction in E. coli survival were found after 15 and 30 min of irradiation, respectively. Also, FDP 5 film was highly effective to eliminate individual bacteria attached to the surface. In addition, photodynamic inactivation (PDI) sensitized by FDP 5 film produced >99.99% bacterial killing in biofilms formed on the surface after 60 min irradiation. The results indicate that FDP 5 film represents an interesting and versatile photodynamic active material to eradicate bacteria as planktonic cells, individual attached microbes, or biofilms.Fil: Heredia, Daniel Alejandro. Universidad Nacional de Río Cuarto. Instituto para el Desarrollo Agroindustrial y de la Salud. - Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto para el Desarrollo Agroindustrial y de la Salud; ArgentinaFil: Martinez, Sol Romina. Universidad Nacional de Río Cuarto. Instituto para el Desarrollo Agroindustrial y de la Salud. - Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto para el Desarrollo Agroindustrial y de la Salud; ArgentinaFil: Durantini, Andres Matías. Universidad Nacional de Río Cuarto. Instituto para el Desarrollo Agroindustrial y de la Salud. - Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto para el Desarrollo Agroindustrial y de la Salud; ArgentinaFil: Pérez, María Eugenia. Universidad Nacional de Río Cuarto. Instituto para el Desarrollo Agroindustrial y de la Salud. - Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto para el Desarrollo Agroindustrial y de la Salud; ArgentinaFil: Mangione, Maria Ines. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario. Instituto de Química Rosario. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario; ArgentinaFil: Durantini, Javier Esteban. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas Fisicoquímicas y Naturales. Instituto de Investigaciones en Tecnologías Energéticas y Materiales Avanzados. - Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto de Investigaciones en Tecnologías Energéticas y Materiales Avanzados; ArgentinaFil: Gervaldo, Miguel Andres. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas Fisicoquímicas y Naturales. Instituto de Investigaciones en Tecnologías Energéticas y Materiales Avanzados. - Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto de Investigaciones en Tecnologías Energéticas y Materiales Avanzados; ArgentinaFil: Otero, Luis Alberto. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas Fisicoquímicas y Naturales. Instituto de Investigaciones en Tecnologías Energéticas y Materiales Avanzados. - Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto de Investigaciones en Tecnologías Energéticas y Materiales Avanzados; ArgentinaFil: Durantini, Edgardo Néstor. Universidad Nacional de Río Cuarto. Instituto para el Desarrollo Agroindustrial y de la Salud. - Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto para el Desarrollo Agroindustrial y de la Salud; ArgentinaAmerican Chemical Society2019-07-16info: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/11336/119707Heredia, Daniel Alejandro; Martinez, Sol Romina; Durantini, Andres Matías; Pérez, María Eugenia; Mangione, Maria Ines; et al.; Antimicrobial photodynamic polymeric films bearing biscarbazol triphenylamine end-capped dendrimeric Zn(II) porphyrin; American Chemical Society; ACS Applied Materials & Interfaces; 11; 31; 16-7-2019; 27574-275871944-82521944-8244CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/url/http://pubs.acs.org/doi/10.1021/acsami.9b09119info:eu-repo/semantics/altIdentifier/doi/ 10.1021/acsami.9b09119info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2024-05-08T13:54:51Zoai:ri.conicet.gov.ar:11336/119707instacron: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 13:54:52.233CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse |
| score |
15,811543 |