Evaluation of borinic acids as new, fast hydrogen peroxide–responsive triggers

Abstract

Significance Hydrogen peroxide plays an important role in the fine balance between physiological and pathological processes. To detect this diffusible small molecule, we expanded the scope of organic triggers in developing borinic acids as an alternative and more sensitive trigger than the most conventional boronate-based sensors. We discovered that borinic acid is 10,000-fold more reactive than its boronic counterpart toward H 2 O 2 -mediated oxidation. An accurate determination of oxidation kinetic constants and computational experiments corroborate this higher reactivity. This improvement also proved effective for in-cell detection of exogenously as well as endogenously produced H 2 O 2 . We believe borinic acids represent a new and efficient tool allowing for the development of new devices for a better understanding of H 2 O 2 -mediated signaling processes.