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
- Location
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Deutsche Nationalbibliothek Frankfurt am Main
- Extent
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Online-Ressource
- Language
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Englisch
- Notes
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Molecules. - 25, 22 (2020) , 5325, ISSN: 1420-3049
- Event
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Veröffentlichung
- (where)
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Freiburg
- (who)
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Universität
- (when)
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2020
- Creator
- DOI
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10.3390/molecules25225325
- URN
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urn:nbn:de:bsz:25-freidok-1701221
- Rights
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Der Zugriff auf das Objekt ist unbeschränkt möglich.
- Last update
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25.03.2025, 1:49 PM CET
Data provider
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Deutsche Nationalbibliothek. If you have any questions about the object, please contact the data provider.
Associated
- Ma, Jiahui
- Ripp, Alexander
- Wassy, Daniel
- Dürr-Mayer, Tobias
- Qiu, Danye
- Häner, Markus
- Haas, Thomas Michael
- Popp, Christoph
- Bezold, Dominik
- Richert, Sabine
- Esser, Birgit
- Jessen, Henning Jacob
- Universität
Time of origin
- 2020
Other Objects (12)
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Untersuchungen zur intrazellulären Freisetzung von Nucleosidphosphaten
Investigations on the synthesis and degradation of polyphosphate in vitro and its correlation to magic spot nucleotides
Photocages, photocaged nucleotides and subcellular delivery
Four phosphates at one blow: access to pentaphosphorylated magic spot nucleotides and their analysis by capillary electrophoresis
The 8th young faculty meeting – an active crowd attuned to modern challenges
Novel shades of inositol pyrophosphates – in vitro and in cellulo evaluation of inositol pyrophosphate probes
Synthesis of bisdiphosphoinositol polyphosphate prometabolites
Design of sensors for highly phosphorylated natural compounds
Rapid synthesis of nucleoside triphosphates and analogues
Synthesis of novel photocaged thiamine triphosphate prometabolites and investigations towards an efficient bidirectional synthesis of asymmetric dinucleoside polyphosphates
Development of novel p-amidites and their application in the synthesis of the most densely phosphorylated compounds
Cyclotriphosphate: a brief history, recent developments, and perspectives in synthesis
Untersuchungen zur intrazellulären Freisetzung von Nucleosidphosphaten
Investigations on the synthesis and degradation of polyphosphate in vitro and its correlation to magic spot nucleotides
Photocages, photocaged nucleotides and subcellular delivery
Four phosphates at one blow: access to pentaphosphorylated magic spot nucleotides and their analysis by capillary electrophoresis
The 8th young faculty meeting – an active crowd attuned to modern challenges
Novel shades of inositol pyrophosphates – in vitro and in cellulo evaluation of inositol pyrophosphate probes
Synthesis of bisdiphosphoinositol polyphosphate prometabolites
Design of sensors for highly phosphorylated natural compounds
Rapid synthesis of nucleoside triphosphates and analogues
Synthesis of novel photocaged thiamine triphosphate prometabolites and investigations towards an efficient bidirectional synthesis of asymmetric dinucleoside polyphosphates
Development of novel p-amidites and their application in the synthesis of the most densely phosphorylated compounds