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dc.contributor.author
Ferreyra, Darío David  
dc.contributor.author
Reynoso, Eugenia  
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Cordero Gabrielli, Paula Verónica  
dc.contributor.author
Spesia, Mariana Belen  
dc.contributor.author
Alvarez, María Gabriela  
dc.contributor.author
Milanesio, María Elisa  
dc.contributor.author
Durantini, Edgardo Néstor  
dc.date.available
2018-10-04T18:31:03Z  
dc.date.issued
2016-05  
dc.identifier.citation
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  
dc.identifier.issn
1011-1344  
dc.identifier.uri
http://hdl.handle.net/11336/61694  
dc.description.abstract
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.  
dc.format
application/pdf  
dc.language.iso
eng  
dc.publisher
Elsevier Science Sa  
dc.rights
info:eu-repo/semantics/openAccess  
dc.rights.uri
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/  
dc.subject
Chlorin  
dc.subject
Microorganisms  
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Photodynamic Activity  
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Photoinactivation  
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Porphyrin  
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Otras Ciencias Químicas  
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Ciencias Químicas  
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CIENCIAS NATURALES Y EXACTAS  
dc.title
Synthesis and properties of 5,10,15,20-tetrakis[4-(3-N,N-dimethylaminopropoxy)phenyl] chlorin as potential broad-spectrum antimicrobial photosensitizers  
dc.type
info:eu-repo/semantics/article  
dc.type
info:ar-repo/semantics/artículo  
dc.type
info:eu-repo/semantics/publishedVersion  
dc.date.updated
2018-09-24T14:12:09Z  
dc.journal.volume
158  
dc.journal.pagination
243-251  
dc.journal.pais
Países Bajos  
dc.journal.ciudad
Amsterdam  
dc.description.fil
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; Argentina  
dc.description.fil
Fil: 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; Argentina  
dc.description.fil
Fil: 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; Argentina  
dc.description.fil
Fil: 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; Argentina  
dc.description.fil
Fil: 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; Argentina  
dc.description.fil
Fil: 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; Argentina  
dc.description.fil
Fil: 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; Argentina  
dc.journal.title
Journal of Photochemistry and Photobiology B: Biology  
dc.relation.alternativeid
info:eu-repo/semantics/altIdentifier/doi/https://dx.doi.org/10.1016/j.jphotobiol.2016.02.021  
dc.relation.alternativeid
info:eu-repo/semantics/altIdentifier/url/https://www.sciencedirect.com/science/article/pii/S1011134415301998