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

Xiaolong Sun, Qingling Xu, Gyoungmi Kim, Stephen E. Flower, John P. Lowe, Juyoung Yoon*, John S. Fossey, Xuhong Qian, Steven D. Bull, Tony D. James

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

168 Citations (Scopus)

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
DOIs
Publication statusPublished - 1 Jan 2014

ASJC Scopus subject areas

  • General Chemistry

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