A water-soluble boronate-based fluorescent probe for the selective detection of peroxynitrite and imaging in living cells

Xiaolong Sun, Q. Xu, G. Kim, S.E. Flower, J Lowe, J. Yoon, J.S. Fossey, X. Qian, S.D. Bull, T.D. James

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Abstract

A water-soluble boronate-based fluorescent probe was evaluated for the detection of peroxynitrite (ONOO) in the presence of a monosaccharide. The enhanced fluorescence of the probe when bound with d-fructose was switched off in the presence of peroxynitrite. In contrast, other reactive oxygen/nitrogen species (ROS/RNS) led to only slight fluorescence decreases due to protection by an internal N-B interaction. The interaction of the probe with d-fructose not only strengthens the fluorescence signal, but also protects the boronic acid from oxidation by other ROS/RNS. Therefore, under conditions generating various ROS/RNS, the boronate-based saccharide complex preferentially reacts with peroxynitrite. The probe was used in cell imaging experiments for the detection of endogenous and exogenous peroxynitrite. The sensor displays good "on-off" responses towards peroxynitrite, both in RAW 264.7 cells and HeLa cells.
Original languageEnglish
Pages (from-to)3368-3373
Number of pages6
JournalChemical Science
Volume5
Issue number9
Early online date23 May 2014
DOIs
Publication statusPublished - 1 Sep 2014

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