Société Française de Biochimie et Biologie Moléculaire


University of Rouen, COBRA Lab. UMR 6014
Evaluation of borinic acids as new, fast hydrogen peroxide–responsive triggers.”
Proceedings of the National Academy of Sciences 2021, 118, e2107503118; DOI: 10.1073/pnas.2107503118


Blaise GATIN-FRAUDET, 29 years old, obtained his PhD degree in 2020 in Organic Chemistry under the supervision of Drs. Dominique URBAN (ICMMO) and Boris VAUZEILLES (ICSN) at the Paris-Saclay University. During his thesis, he evaluated new probes for the cellular imaging of hydrogen peroxide, based on a new type of molecular triggers: borinic acids. This work was the subject of the selected article. In 2021, he joined the group of Prof. Pierre-Yves Renard (COBRA, University of Normandy) and he is interested in the development of a warning system for organophosphorus nerve agents combining enzymes and fluorogenic probes.


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Résumé de l'article

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−1s−1 as a second-order rate constant, which is 10,000-fold faster than its well-established boronic counterpart (1.8 M−1s−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.