Thiocoumarin Caged Nucleotides: Synthetic Access and Their Photophysical Properties

Photocages have been successfully applied in cellular signaling studies for the controlled release of metabolites with high spatio-temporal resolution. Commonly, coumarin photocages are activated by UV light and the quantum yields of uncaging are relatively low, which can limit their applications in...

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Detalles Bibliográficos
Autores principales: Ma, Jiahui, Ripp, Alexander, Wassy, Daniel, Dürr, Tobias, Qiu, Danye, Häner, Markus, Haas, Thomas, Popp, Christoph, Bezold, Dominik, Richert, Sabine, Esser, Birgit, Jessen, Henning J.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2020
Materias:
Communication
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7696096/
https://www.ncbi.nlm.nih.gov/pubmed/33203096
http://dx.doi.org/10.3390/molecules25225325
Descripción
Sumario:Photocages have been successfully applied in cellular signaling studies for the controlled release of metabolites with high spatio-temporal resolution. Commonly, coumarin photocages are activated by UV light and the quantum yields of uncaging are relatively low, which can limit their applications in vivo. Here, syntheses, the determination of the photophysical properties, and quantum chemical calculations of 7-diethylamino-4-hydroxymethyl-thiocoumarin (thio-DEACM) and caged adenine nucleotides are reported and compared to the widely used 7-diethylamino-4-hydroxymethyl-coumarin (DEACM) caging group. In this comparison, thio-DEACM stands out as a phosphate cage with improved photophysical properties, such as red-shifted absorption and significantly faster photolysis kinetics.

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