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dc.contributor.author
Durantini, Andres Matías
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Greene, Lana E.
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Lincoln, Richard
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Martínez, Sol R.
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Cosa, Gonzalo
dc.date.available
2017-08-28T18:18:59Z
dc.date.issued
2016-01
dc.identifier.citation
Durantini, Andres Matías; Greene, Lana E.; Lincoln, Richard; Martínez, Sol R.; Cosa, Gonzalo; Reactive Oxygen Species Mediated Activation of a Dormant Singlet Oxygen Photosensitizer: From Autocatalytic Singlet Oxygen Amplification to Chemicontrolled Photodynamic Therapy; American Chemical Society; Journal of the American Chemical Society; 138; 4; 1-2016; 1215-1225
dc.identifier.issn
0002-7863
dc.identifier.uri
http://hdl.handle.net/11336/23128
dc.description.abstract
Here we show the design, preparation, and characterization of a dormant singlet oxygen (1O2) photosensitizer that is activated upon its reaction with reactive oxygen species (ROS), including 1O2 itself, in what constitutes an autocatalytic process. The compound is based on a two segment photosensitizer–trap molecule where the photosensitizer segment consists of a Br-substituted boron-dipyrromethene (BODIPY) dye. The trap segment consists of the chromanol ring of α-tocopherol, the most potent naturally occurring lipid soluble antioxidant. Time-resolved absorption, fluorescence, and 1O2 phosphorescence studies together with fluorescence and 1O2 phosphorescence emission quantum yields collected on Br2B–PMHC and related bromo and iodo-substituted BODIPY dyes show that the trap segment provides a total of three layers of intramolecular suppression of 1O2 production. Oxidation of the trap segment with ROS restores the sensitizing properties of the photosensitizer segment resulting in ∼40-fold enhancement in 1O2 production. The juxtaposed antioxidant (chromanol) and prooxidant (Br-BODIPY) antagonistic chemical activities of the two-segment compound enable the autocatalytic, and in general ROS-mediated, activation of 1O2 sensitization providing a chemical cue for the spatiotemporal control of 1O2.The usefulness of this approach to selectively photoactivate the production of singlet oxygen in ROS stressed vs regular cells was successfully tested via the photodynamic inactivation of a ROS stressed Gram negative Escherichia coli strain.
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application/pdf
dc.language.iso
eng
dc.publisher
American Chemical Society
dc.rights
info:eu-repo/semantics/openAccess
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https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
dc.subject
Photodynamic Therapy
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Autocalysis
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Reactive Oxygen Species
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Singlet Oxygen
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Otras Ciencias Químicas
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Ciencias Químicas
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CIENCIAS NATURALES Y EXACTAS
dc.title
Reactive Oxygen Species Mediated Activation of a Dormant Singlet Oxygen Photosensitizer: From Autocatalytic Singlet Oxygen Amplification to Chemicontrolled Photodynamic Therapy
dc.type
info:eu-repo/semantics/article
dc.type
info:ar-repo/semantics/artículo
dc.type
info:eu-repo/semantics/publishedVersion
dc.date.updated
2017-08-14T17:44:52Z
dc.identifier.eissn
1520-5126
dc.journal.volume
138
dc.journal.number
4
dc.journal.pagination
1215-1225
dc.journal.pais
Estados Unidos
dc.journal.ciudad
Washington
dc.description.fil
Fil: Durantini, Andres Matías. McGill University; Canadá. Unversidad Nacional de Río Cuarto. Facultad de Ciencias Exactas, Fisicoquímicas y Naturales. Departamento de Química; Argentina
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Fil: Greene, Lana E.. McGill University; Canadá
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Fil: Lincoln, Richard. McGill University; Canadá
dc.description.fil
Fil: Martínez, Sol R.. McGill University; Canadá. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto Multidisciplinario de Biología Vegetal. Universidad Nacional de Córdoba. Facultad de Ciencias Exactas Físicas y Naturales. Instituto Multidisciplinario de Biología Vegetal; Argentina
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Fil: Cosa, Gonzalo. McGill University; Canadá
dc.journal.title
Journal of the American Chemical Society
dc.relation.alternativeid
info:eu-repo/semantics/altIdentifier/url/http://pubs.acs.org/doi/abs/10.1021/jacs.5b10288
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info:eu-repo/semantics/altIdentifier/doi/http://dx.doi.org/10.1021/jacs.5b10288
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