Thiocoumarin Caged Nucleotides: Synthetic Access and Their Photophysical Properties.
nucleotides
photocage
photochemistry
thio-DEACM
Journal
Molecules (Basel, Switzerland)
ISSN: 1420-3049
Titre abrégé: Molecules
Pays: Switzerland
ID NLM: 100964009
Informations de publication
Date de publication:
15 Nov 2020
15 Nov 2020
Historique:
received:
29
10
2020
revised:
07
11
2020
accepted:
13
11
2020
entrez:
18
11
2020
pubmed:
19
11
2020
medline:
7
4
2021
Statut:
epublish
Résumé
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.
Identifiants
pubmed: 33203096
pii: molecules25225325
doi: 10.3390/molecules25225325
pmc: PMC7696096
pii:
doi:
Substances chimiques
Coumarins
0
Nucleotides
0
Adenosine Triphosphate
8L70Q75FXE
coumarin
A4VZ22K1WT
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Subventions
Organisme : Deutsche Forschungsgemeinschaft
ID : EXC-2193/1 - 390951807
Organisme : Deutsche Forschungsgemeinschaft
ID : ES 361/4-1
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