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

doi:10.1039/c4sc01417k

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

Department of Chemistry & Nanoscience

Research output: Contribution to journal › Article › peer-review

202 Scopus citations

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 language	English
Pages (from-to)	3368-3373
Number of pages	6
Journal	Chemical Science
Volume	5
Issue number	9
DOIs	https://doi.org/10.1039/c4sc01417k
State	Published - Sep 2014

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

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.",

author = "Xiaolong Sun and Qingling Xu and Gyoungmi Kim and Flower, {Stephen E.} and Lowe, {John P.} and Juyoung Yoon and Fossey, {John S.} and Xuhong Qian and Bull, {Steven D.} and James, {Tony D.}",

year = "2014",

month = sep,

doi = "10.1039/c4sc01417k",

language = "English",

volume = "5",

pages = "3368--3373",

journal = "Chemical Science",

issn = "2041-6520",

publisher = "Royal Society of Chemistry",

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T1 - A water-soluble boronate-based fluorescent probe for the selective detection of peroxynitrite and imaging in living cells

AU - Sun, Xiaolong

AU - Xu, Qingling

AU - Kim, Gyoungmi

AU - Flower, Stephen E.

AU - Lowe, John P.

AU - Yoon, Juyoung

AU - Fossey, John S.

AU - Qian, Xuhong

AU - Bull, Steven D.

AU - James, Tony D.

PY - 2014/9

Y1 - 2014/9

N2 - 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.

AB - 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.

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VL - 5

SP - 3368

EP - 3373

JO - Chemical Science

JF - Chemical Science

IS - 9

ER -

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

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