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Open AccessCommunication

Thiocoumarin Caged Nucleotides: Synthetic Access and Their Photophysical Properties

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Institute of Organic Chemistry, University of Freiburg, Albertstr. 21, 79104 Freiburg, Germany
2
Cluster of Excellence livMatS @ FIT—Freiburg Center for Interactive Materials and Bioinspired Technologies, University of Freiburg, Georges-Köhler-Allee 105, 79110 Freiburg, Germany
3
Institute of Physical Chemistry, University of Freiburg, Albertstr. 21, 79104 Freiburg, Germany
*
Author to whom correspondence should be addressed.
Academic Editor: Marie Migaud
Molecules 2020, 25(22), 5325; https://doi.org/10.3390/molecules25225325
Received: 29 October 2020 / Revised: 7 November 2020 / Accepted: 13 November 2020 / Published: 15 November 2020
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. View Full-Text
Keywords: thio-DEACM; photocage; nucleotides; photochemistry thio-DEACM; photocage; nucleotides; photochemistry
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MDPI and ACS Style

Ma, J.; Ripp, A.; Wassy, D.; Dürr, T.; Qiu, D.; Häner, M.; Haas, T.; Popp, C.; Bezold, D.; Richert, S.; Esser, B.; Jessen, H.J. Thiocoumarin Caged Nucleotides: Synthetic Access and Their Photophysical Properties. Molecules 2020, 25, 5325. https://doi.org/10.3390/molecules25225325

AMA Style

Ma J, Ripp A, Wassy D, Dürr T, Qiu D, Häner M, Haas T, Popp C, Bezold D, Richert S, Esser B, Jessen HJ. Thiocoumarin Caged Nucleotides: Synthetic Access and Their Photophysical Properties. Molecules. 2020; 25(22):5325. https://doi.org/10.3390/molecules25225325

Chicago/Turabian Style

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. 2020. "Thiocoumarin Caged Nucleotides: Synthetic Access and Their Photophysical Properties" Molecules 25, no. 22: 5325. https://doi.org/10.3390/molecules25225325

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