Issue 5, 2022

Diazaborines oxidize slowly with H2O2 but rapidly with peroxynitrite in aqueous buffer

Abstract

Reactive oxygen species (ROS) such as hydrogen peroxide (H2O2) and peroxynitrite (ONOO) oxidize arylboronic acids to their corresponding phenols. When used in molecular imaging probes and in ROS-responsive molecules, however, simple arylboronic acids struggle to discriminate between H2O2 and ONOO because of their fast rate of reaction with both ROS. Here, we show that diazaborines (DABs) react slowly with H2O2 but rapidly with peroxynitrite in an aqueous buffer. In addition to their slow reaction with H2O2, the immediate product of DAB oxidation with H2O2 and ONOO can yield a kinetically trapped C[double bond, length as m-dash]N Z-isomer that slowly equilibrates with its E-isomer. Taken together, our work shows that diazaborines exhibit enhanced kinetic discrimination between H2O2 and ONOO compared to arylboronic acids, opening up new opportunities for diazaborine-based tools in chemical biology.

Graphical abstract: Diazaborines oxidize slowly with H2O2 but rapidly with peroxynitrite in aqueous buffer

Supplementary files

Article information

Article type
Communication
Submitted
24 Ago 2021
Accepted
07 Jan 2022
First published
07 Jan 2022

Org. Biomol. Chem., 2022,20, 995-999

Diazaborines oxidize slowly with H2O2 but rapidly with peroxynitrite in aqueous buffer

J. G. Haggett, G. S. Han, A. R. Moser, J. V. A. Golzwarden, S. Vyas and D. W. Domaille, Org. Biomol. Chem., 2022, 20, 995 DOI: 10.1039/D1OB01668G

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