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Thiocoumarin Caged Nucleotides: Synthetic Access and Their Photophysical Properties.

ABSTRACT: 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.

SUBMITTER: Ma J

PROVIDER: S-EPMC7696096 | biostudies-literature | 2020 Nov

REPOSITORIES: biostudies-literature

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Thiocoumarin Caged Nucleotides: Synthetic Access and Their Photophysical Properties.

Ma Jiahui J Ripp Alexander A Wassy Daniel D Dürr Tobias T Qiu Danye D Häner Markus M Haas Thomas T Popp Christoph C Bezold Dominik D Richert Sabine S Esser Birgit B Jessen Henning J HJ

Molecules (Basel, Switzerland) 20201115 22

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 a ...[more]

PMID: 33203096

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