Many inflammatory processes are associated with an increase in the production of reactive
oxygen species (ROS). Chemical probes that specifically detect ROS are potentially useful tools for
the early diagnosis of inflammatory diseases as well as cancer. Herein we have developed a library of
coumarin hybrids by condensation of various heterocyclic quaternary salts to a 7-hydroxycoumarin
scaffold. From our library we identified one benzothiazole-coumarin hybrid as a red-fluorescent
compound with emission maxima around 620 nm and a strong fluorogenic response. Furthermore, we
proved that this scaffold is suitable for the preparation of activatable probes, such as by modification with a boronate
group for selective sensing of hydrogen peroxide (H2O2). In vitro assays confirmed the reactivity and subsequent emission
of our probe upon incubation with H2O2 with good selectivity over different ROS and reactive nitrogen species (RNS) as
well as minimal toxicity in cells. Finally cell imaging experiments were performed in murine macrophages and validated
the utility of the activatable probe for the detection of H2O2 in living cells.
Keywords: Fluorescence, coumarin, reactive oxygen species, imaging, macrophages, inflammation.
Rights & PermissionsPrintExport