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dc.contributor.author
Belzile, Mei-Ni
dc.contributor.author
Godin, Robert
dc.contributor.author
Durantini, Andres Matías
dc.contributor.author
Cosa, Gonzalo
dc.date.available
2018-09-26T18:27:09Z
dc.date.issued
2016-12
dc.identifier.citation
Belzile, Mei-Ni; Godin, Robert; Durantini, Andres Matías; Cosa, Gonzalo; Monitoring chemical and biological electron transfer reactions with a fluorogenic vitamin K analogue probe; American Chemical Society; Journal of the American Chemical Society; 138; 50; 12-2016; 16388-16397
dc.identifier.issn
0002-7863
dc.identifier.uri
http://hdl.handle.net/11336/60942
dc.description.abstract
We report herein the design, synthesis, and characterization of a two-segment fluorogenic analogue of Vitamin K, B-VKQ, prepared by coupling Vitamin K3, also known as menadione (a quinone redox center), to a boron-dipyrromethene (BODIPY) fluorophore (a lipophilic reporter segment). Oxidation-reduction reactions, spectroelectrochemical studies, and enzymatic assays conducted in the presence of DT-diaphorase illustrate that the new probe shows reversible redox behavior on par with that of Vitamin K, provides a high-sensitivity fluorescence signal, and is compatible with biological conditions, opening the door to monitor remotely (i.e., via imaging) redox processes in real time. In its oxidized form, B-VKQ is non-emissive, while upon reduction to the hydroquinone form, B-VKQH2, BODIPY fluorescence is restored, with emission quantum yield values of ca. 0.54 in toluene. Density functional theory studies validate a photoinduced electron transfer intramolecular switching mechanism, active in the non-emissive quinone form and deactivated upon reduction to the emissive dihydroquinone form. Our results highlight the potential of B-VKQ as a fluorogenic probe to study electron transfer and transport in model systems and biological structures with optimal sensitivity and desirable chemical specificity. Use of such a probe may enable a better understanding of the role that Vitamin K plays in biological redox reactions ubiquitous in key cellular processes, and help elucidate the mechanism and pathological significance of these reactions in biological systems.
dc.format
application/pdf
dc.language.iso
eng
dc.publisher
American Chemical Society
dc.rights
info:eu-repo/semantics/restrictedAccess
dc.rights.uri
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
dc.subject
Electron Transfer
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Vitamin K
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Otras Ciencias Químicas
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Ciencias Químicas
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CIENCIAS NATURALES Y EXACTAS
dc.title
Monitoring chemical and biological electron transfer reactions with a fluorogenic vitamin K analogue probe
dc.type
info:eu-repo/semantics/article
dc.type
info:ar-repo/semantics/artículo
dc.type
info:eu-repo/semantics/publishedVersion
dc.date.updated
2018-09-19T16:38:48Z
dc.identifier.eissn
1520-5126
dc.journal.volume
138
dc.journal.number
50
dc.journal.pagination
16388-16397
dc.journal.pais
Estados Unidos
dc.description.fil
Fil: Belzile, Mei-Ni. Mcgill University; Canadá
dc.description.fil
Fil: Godin, Robert. Mcgill University; Canadá
dc.description.fil
Fil: Durantini, Andres Matías. Mcgill University; Canadá. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas Fisicoquímicas y Naturales. Departamento de Química; Argentina
dc.description.fil
Fil: Cosa, Gonzalo. Mcgill University; Canadá
dc.journal.title
Journal of the American Chemical Society
dc.relation.alternativeid
info:eu-repo/semantics/altIdentifier/doi/http://dx.doi.org/10.1021/jacs.6b09735
dc.relation.alternativeid
info:eu-repo/semantics/altIdentifier/url/https://pubs.acs.org/doi/10.1021/jacs.6b09735


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