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Evaluation of borinic acids as new, fast hydrogen peroxide-responsive triggers [Chemistry]
Proceedings of the National Academy of Sciences of the United States of America  (IF11.205),  Pub Date : 2021-12-14, DOI: 10.1073/pnas.2107503118
Blaise Gatin-Fraudet, Roxane Ottenwelter, Thomas Le Saux, Stéphanie Norsikian, Mathilde Pucher, Thomas Lombès, Aurélie Baron, Philippe Durand, Gilles Doisneau, Yann Bourdreux, Bogdan I. Iorga, Marie Erard, Ludovic Jullien, Dominique Guianvarc’h, Dominique Urban, Boris Vauzeilles

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 × 104 m−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.