Chemical Communications 2014-10-21

¹⁹F magnetic resonance probes for live-cell detection of peroxynitrite using an oxidative decarbonylation reaction.

Kevin J Bruemmer, Sara Merrikhihaghi, Christina T Lollar, Siti Nur Sarah Morris, Johannes H Bauer, Alexander R Lippert

Index: Chem. Commun. (Camb.) 50(82) , 12311-4, (2014)

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Abstract

We report a newly discovered oxidative decarbonylation reaction of isatins that is selectively mediated by peroxynitrite (ONOO(-)) to provide anthranilic acid derivatives. We have harnessed this rapid and selective transformation to develop two reaction-based probes, 5-fluoroisatin and 6-fluoroisatin, for the low-background readout of ONOO(-) using (19)F magnetic resonance spectroscopy. 5-fluoroisatin was used to non-invasively detect ONOO(-) formation in living lung epithelial cells stimulated with interferon-γ (IFN-γ).