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Artículo

Monitoring chemical and biological electron transfer reactions with a fluorogenic vitamin K analogue probe

Belzile, Mei-Ni; Godin, Robert; Durantini, Andres MatíasIcon ; Cosa, Gonzalo
Fecha de publicación: 12/2016
Editorial: American Chemical Society
Revista: Journal of the American Chemical Society
ISSN: 0002-7863
e-ISSN: 1520-5126
Idioma: Inglés
Tipo de recurso: Artículo publicado
Clasificación temática:
Otras Ciencias Químicas

Resumen

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.
Palabras clave: Electron Transfer , Vitamin K
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info:eu-repo/semantics/openAccess Excepto donde se diga explícitamente, este item se publica bajo la siguiente descripción: Creative Commons Attribution-NonCommercial-ShareAlike 2.5 Unported (CC BY-NC-SA 2.5)
Identificadores
URI: http://hdl.handle.net/11336/60942
DOI: http://dx.doi.org/10.1021/jacs.6b09735
URL: https://pubs.acs.org/doi/10.1021/jacs.6b09735
Colecciones
Articulos(CCT - CORDOBA)
Articulos de CTRO.CIENTIFICO TECNOL.CONICET - CORDOBA
Citación
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
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