Red-Fluorescent Activatable Probes for the Detection of Hydrogen Peroxide in Living Cells

Title:Red-Fluorescent Activatable Probes for the Detection of Hydrogen Peroxide in Living Cells

Volume: 19 Issue: 5

Author(s): Claudia Garcia-Guzman, Antonio Fernandez, Nicolaos Avlonitis, Mark Bradley and Marc Vendrell

Affiliation:

Keywords: Fluorescence, coumarin, reactive oxygen species, imaging, macrophages, inflammation.

Abstract: 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.

Cite this article as:

Garcia-Guzman Claudia, Fernandez Antonio, Avlonitis Nicolaos, Bradley Mark and Vendrell Marc, Red-Fluorescent Activatable Probes for the Detection of Hydrogen Peroxide in Living Cells, Combinatorial Chemistry & High Throughput Screening 2016; 19 (5) . https://dx.doi.org/10.2174/1386207319666160408151313