A cyanine-based near-infrared fluorescent probe for highly sensitive and selective detection of hypochlorous acid and bioimaging

Huihui Li; Lingmei Guan; Xiaojie Zhang; Huan Yu; Dejian Huang; Mingtai Sun; Suhua Wang

doi:10.1016/j.talanta.2016.09.008

A cyanine-based near-infrared fluorescent probe for highly sensitive and selective detection of hypochlorous acid and bioimaging

Talanta. 2016 Dec 1:161:592-598. doi: 10.1016/j.talanta.2016.09.008. Epub 2016 Sep 5.

Authors

Huihui Li¹, Lingmei Guan², Xiaojie Zhang², Huan Yu³, Dejian Huang⁴, Mingtai Sun⁵, Suhua Wang⁶

Affiliations

¹ Institute of Intelligent Machines, Chinese Academy of Sciences, Hefei, Anhui, 230031 China; Department of Chemistry, University of Science and Technology of China, Hefei, Anhui, 230026 China.
² State Key Laboratory for Structural Chemistry of Unstable and Stable Species, Center for Molecular Sciences, Institute of Chemistry, Chinese Academy of Sciences, Beijing, 100190 China.
³ Institute of Intelligent Machines, Chinese Academy of Sciences, Hefei, Anhui, 230031 China.
⁴ Food Science and Technology Programme, Department of Chemistry, National University of Singapore, 3 Science Drive 3, Singapore, 117543 Singapore.
⁵ Institute of Intelligent Machines, Chinese Academy of Sciences, Hefei, Anhui, 230031 China. Electronic address: mtsun@iim.ac.cn.
⁶ Institute of Intelligent Machines, Chinese Academy of Sciences, Hefei, Anhui, 230031 China; Department of Chemistry, University of Science and Technology of China, Hefei, Anhui, 230026 China. Electronic address: shwang@iim.ac.cn.

PMID: 27769452
DOI: 10.1016/j.talanta.2016.09.008

Abstract

Hypochlorous acid (HOCl) is a kind of reactive oxygen species which plays an important role in biological process. HOCl detection is of great importance in disease prevention and treatment. Herein, a cyanine-based near-infrared (NIR) fluorescent probe for HOCl has been designed and synthesized. This probe can react with HOCl in a dose-response manner along with the fluorescence of the probe quenched, the reaction through an electrophilic addition to the double bond and subsequent oxidation reaction. Experiments indicate that the probe can be acted as a selective and sensitive indicator for HOCl and the limit of detection for HOCl is estimated to be 22nM. What's more, this probe shows a low toxicity to cells and can be applied to visualize HOCl molecules in living cells. Therefore, the proposed method may make a significant contribution to HOCl detection.

Keywords: Cell imaging; Fluorescent; Hypochlorous acid; Near-infrared.

MeSH terms

Cell Membrane Permeability
Cell Survival / drug effects
Fluorescence
Fluorescent Dyes / chemistry*
Fluorescent Dyes / pharmacology
Humans
Hydrogen-Ion Concentration
Hypochlorous Acid / analysis*
Hypochlorous Acid / chemistry
MCF-7 Cells
Microscopy, Confocal
Spectrometry, Mass, Electrospray Ionization

Substances

Fluorescent Dyes
Hypochlorous Acid