Chalcogen-based ratiometric reversible BODIPY redox sensors for the determination of enantioselective methionine sulfoxide reductase activity.

ABSTRACT

Many serious diseases are associated with degenerative changes caused by oxidative stress triggered by elevated concentrations of reactive oxygen species (ROS) in cells. Therefore, the development of suitable probes for monitoring such processes is of great importance. Here, we introduce a series of sulfur- and selenium-substituted BODIPY derivatives as reversible redox sensors for ROS and enzymatic redox processes. Significant differences in emission maxima and fluorescence quantum yields between the reduced and oxidized forms make them excellent ratiometric turn-on/off probes. Installation of polar sulfonate groups improved their aqueous solubility while retaining their sensing properties, which allowed the probes to monitor the enzymatic activity of enantioselective methionine sulfoxide reductase.