pH‐Responsive Aminobenzocoumarins as Fluorescent Probes for Biological Acidity

Author:

Schniererová Karin1ORCID,Janeková Hana2ORCID,Joniak Jakub1ORCID,Putala Martin1ORCID,Štacko Peter2ORCID,Stankovičová Henrieta1ORCID

Affiliation:

1. Department of Organic Chemistry Faculty of Natural Sciences Comenius University in Bratislava Ilkovičova 6 842 15 Bratislava Slovakia

2. Department of Chemistry University of Zurich Wintherthurerstrasse 190 8057 Zurich Switzerland

Abstract

AbstractRegulation of pH plays an essential role in orchestrating the delicate cellular machinery responsible for life as we know it. Its abnormal values are indicative of aberrant cellular behavior and associated with pathologies including cancer progression or solid tumors. Here, we report a series of bent and linear aminobenzocoumarins decorated with different substituents. We investigate their photophysical properties and demonstrate that the probes display strong pH‐responsive fluorescence “turn on” behavior in highly acidic environments, with enhancement up to 300‐fold. In combination with their low cytotoxicity, this behavior enabled their application in bioimaging of acidic lysosomes in live human cells. We believe that these molecules serve as attractive lead structures for future rational design of novel biocompatible fluorescent pH probes.

Funder

Agentúra na Podporu Výskumu a Vývoja

Schweizerischer Nationalfonds zur Förderung der Wissenschaftlichen Forschung

Publisher

Wiley

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