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

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-fluoroisati...

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Bibliographic Details
Published in:Chemical communications (Cambridge, England) England), 2014-10, Vol.50 (82), p.12311-12314
Main Authors: Bruemmer, Kevin J, Merrikhihaghi, Sara, Lollar, Christina T, Morris, Siti Nur Sarah, Bauer, Johannes H, Lippert, Alexander R
Format: Article
Language:English
Subjects:
Cell Line, Tumor
Epithelial Cells - metabolism
Fluorescent Dyes - chemistry
Fluorescent Dyes - pharmacology
Humans
Interferon-gamma - pharmacology
Isatin - chemistry
Isatin - pharmacology
Lung - cytology
Magnetic Resonance Spectroscopy
Oxidation-Reduction
Peroxynitrous Acid - chemistry
Peroxynitrous Acid - metabolism
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Summary: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).
ISSN:1364-548X
DOI:10.1039/c4cc04292a