Hydrogen peroxide (H2O2) is responsible for numerous damages when overproduced, and its detection is crucial for a better understanding of H2O2-mediated signaling in physiological and pathological processes. For this purpose, various “off–on” small fluorescent probes relying on a boronate trigger have been prepared, and this design has also been involved in the development of H2O2-activated prodrugs or theranostic tools. However, this design suffers from slow kinetics, preventing activation by H2O2 with a short response time. Therefore, faster H2O2-reactive groups are awaited. To address this issue, we have successfully developed and characterized a prototypic borinic-based fluorescent probe containing a coumarin scaffold. We determined its in vitro kinetic constants toward H2O2-promoted oxidation. We measured 1.9 × 104m−1⋅s−1 as a second-order rate constant, which is 10,000-fold faster than its well-established boronic counterpart (1.8 m−1⋅s−1). This improved reactivity was also effective in a cellular context, rendering borinic acids an advantageous trigger for H2O2-mediated release of effectors such as fluorescent moieties.
Detection of hydrogen peroxide (H<sub>2</sub>O<sub>2</sub>), which is responsible for numerous damages when overproduced, is crucial for a better understanding of H<sub>2</sub>O<sub>2</sub>-mediated signalling in physiological and pathological processes. For this purpose, various“<i>off-on</i>” small fluorescent probes relying on a boronate trigger have been developed. However, they suffer from low kinetics and do not allow forH<sub>2</sub>O<sub>2</sub>-detection<sub></sub>with a short response time. Therefore, more reactive sensors are still awaited. To address this issue, we have successfully developed the first generation of borinic-based fluorescent probes containing a coumarin-scaffold. We determined the <i>in vitro</i>kinetic constants of the probe toward H<sub>2</sub>O<sub>2</sub>-promotedoxidation. We measured 1.9x10<sup>4</sup>m<sup>-1</sup>.s<sup>-1</sup>as a second order rate constant, which is 10 000 faster than its boronic counterpart (1.8 m<sup>-1</sup>.s<sup>-1</sup>). This remarkable reactivity was also effective in a cellular context, rendering the borinic trigger an advantageous new tool for H<sub>2</sub>O<sub>2</sub>detection.
Detection of hydrogen peroxide (H<sub>2</sub>O<sub>2</sub>), which is responsible for numerous damages when overproduced, is crucial for a better understanding of H<sub>2</sub>O<sub>2</sub>-mediated signalling in physiological and pathological processes. For this purpose, various“<i>off-on</i>” small fluorescent probes relying on a boronate trigger have been developed. However, they suffer from low kinetics and do not allow forH<sub>2</sub>O<sub>2</sub>-detection<sub></sub>with a short response time. Therefore, more reactive sensors are still awaited. To address this issue, we have successfully developed the first generation of borinic-based fluorescent probes containing a coumarin-scaffold. We determined the <i>in vitro</i>kinetic constants of the probe toward H<sub>2</sub>O<sub>2</sub>-promotedoxidation. We measured 1.9x10<sup>4</sup>m<sup>-1</sup>.s<sup>-1</sup>as a second order rate constant, which is 10 000 faster than its boronic counterpart (1.8 m<sup>-1</sup>.s<sup>-1</sup>). This remarkable reactivity was also effective in a cellular context, rendering the borinic trigger an advantageous new tool for H<sub>2</sub>O<sub>2</sub>detection.
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