Published July 11, 2023 | Version v1
Journal article Open

Rigidized 3-aminocoumarins as fluorescent pH probes for strongly acidic environments

  • 1. Department of Organic Chemistry, Faculty of Natural Sciences, Comenius University, 842 15 Bratislava, Slovakia
  • 2. Department of Chemistry, Faculty of Natural Sciences, Matej Bel University, 974 01 Banská Bystrica, Slovakia
  • 3. Laboratory for Advanced Materials, Faculty of Natural Sciences, Comenius University, 842 15 Bratislava, Slovakia
  • 4. Department of Genetics, Faculty of Natural Sciences, Comenius University, 842 15 Bratislava, Slovakia

Description

Coumarins remain one of the most important group of fluorescent bio-probes, thanks to their high quantum yields, excellent photostability, efficient cell permeation and low (cyto)toxicity. Herein, we introduce new 3-aminocoumarin turn-on pH probes for strongly acidic conditions, capable of significantly improved 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.

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Additional details

Funding

European Commission
LAMatCU - Establishing Laboratory of Advanced Materials at the Comenius University 810701