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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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
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author 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.
author_facet 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.
author_sort Ma, Jiahui
collection PubMed
description 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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spelling pubmed-76960962020-11-29 Thiocoumarin Caged Nucleotides: Synthetic Access and Their Photophysical Properties 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. Molecules Communication 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. MDPI 2020-11-15 /pmc/articles/PMC7696096/ /pubmed/33203096 http://dx.doi.org/10.3390/molecules25225325 Text en © 2020 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (http://creativecommons.org/licenses/by/4.0/).
spellingShingle Communication
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.
Thiocoumarin Caged Nucleotides: Synthetic Access and Their Photophysical Properties
title Thiocoumarin Caged Nucleotides: Synthetic Access and Their Photophysical Properties
title_full Thiocoumarin Caged Nucleotides: Synthetic Access and Their Photophysical Properties
title_fullStr Thiocoumarin Caged Nucleotides: Synthetic Access and Their Photophysical Properties
title_full_unstemmed Thiocoumarin Caged Nucleotides: Synthetic Access and Their Photophysical Properties
title_short Thiocoumarin Caged Nucleotides: Synthetic Access and Their Photophysical Properties
title_sort thiocoumarin caged nucleotides: synthetic access and their photophysical properties
topic Communication
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7696096/
https://www.ncbi.nlm.nih.gov/pubmed/33203096
http://dx.doi.org/10.3390/molecules25225325
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