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

Research output: Contribution to journalArticle

131 Citations (Scopus)
57 Downloads (Pure)

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

Fingerprint

Peroxynitrous Acid
Fluorescent Dyes
Cells
Imaging techniques
Water
Fluorescence
Fructose
Boronic Acids
Monosaccharides
Nitrogen
Oxygen
Oxidation
Sensors
Experiments

Cite this

A water-soluble boronate-based fluorescent probe for the selective detection of peroxynitrite and imaging in living cells. / Sun, Xiaolong; Xu, Q.; Kim, G.; Flower, S.E.; Lowe, J; Yoon, J.; Fossey, J.S.; Qian, X.; Bull, S.D.; James, T.D.

In: Chemical Science, Vol. 5, No. 9, 01.09.2014, p. 3368-3373.

Research output: Contribution to journalArticle

@article{be786dbae0a84f1289608cd12e99f790,
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 Q. Xu and G. Kim and S.E. Flower and J Lowe and J. Yoon and J.S. Fossey and X. Qian and S.D. Bull and T.D. James",
year = "2014",
month = "9",
day = "1",
doi = "10.1039/c4sc01417k",
language = "English",
volume = "5",
pages = "3368--3373",
journal = "Chemical Science",
issn = "2041-6520",
publisher = "Royal Society of Chemistry",
number = "9",

}

TY - JOUR

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

AU - Sun, Xiaolong

AU - Xu, Q.

AU - Kim, G.

AU - Flower, S.E.

AU - Lowe, J

AU - Yoon, J.

AU - Fossey, J.S.

AU - Qian, X.

AU - Bull, S.D.

AU - James, T.D.

PY - 2014/9/1

Y1 - 2014/9/1

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.

U2 - 10.1039/c4sc01417k

DO - 10.1039/c4sc01417k

M3 - Article

VL - 5

SP - 3368

EP - 3373

JO - Chemical Science

JF - Chemical Science

SN - 2041-6520

IS - 9

ER -