Rigidized 3-aminocoumarins as fluorescent probes for strongly acidic environments and rapid yeast vacuolar lumen staining: mechanism and application

Coumarins remain one of the most important groups of fluorescent bio-probes, thanks to their high quantum yields, moderate photostability, efficient cell permeation and low (cyto)toxicity. Herein, we introduce new 3-aminocoumarins as turn-on pH probes under strongly acidic conditions and for indicat...

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Bibliographic Details
Published in:Physical chemistry chemical physics : PCCP 2023-08, Vol.25 (3), p.2212-2217
Main Authors: Joniak, Jakub, Stankovi ová, Henrieta, Budzák, Šimon, Sýkora, Milan, Gaplovská-Kyselá, Katarína, Filo, Juraj, Cigá, Marek
Format: Article
Language:English
Subjects:
Emission analysis
Fluorescent indicators
Staining
Toxicity
Yeast
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Summary:Coumarins remain one of the most important groups of fluorescent bio-probes, thanks to their high quantum yields, moderate photostability, efficient cell permeation and low (cyto)toxicity. Herein, we introduce new 3-aminocoumarins as turn-on pH probes under strongly acidic conditions and for indicators capable of significantly improving yeast vacuolar lumen staining compared to the commercial CMAC derivatives. We present the details of the on-off switching mechanism revealed by the TD-DFT and ab initio calculations complemented by a Franck-Condon analysis of the probes' emission profiles. Rigidized 3-aminocoumarins represent interesting yellowish-green-fluorescent turn-on pH probes under strongly acidic conditions and indicators capable of significantly improving yeast vacuolar lumen staining compared to the commercial CMAC derivates.
ISSN:1463-9076
1463-9084
DOI:10.1039/d3cp01090b