Journal
ORGANIC & BIOMOLECULAR CHEMISTRY
Volume 20, Issue 5, Pages 995-999Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/d1ob01668g
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Funding
- Colorado School of Mines
- Colorado Office of Economic Development and International Trade
- Children's Hospital Colorado
- Mines Undergraduate Research Fellowship
- National Institute of Health [S10-RR026641]
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Diazaborines exhibit enhanced kinetic discrimination between H2O2 and ONOO- compared to arylboronic acids, opening up new opportunities for diazaborine-based tools in chemical biology.
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=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.
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