Sensitive detection and imaging of endogenous peroxynitrite using a benzo[d]thiazole derived cyanine probe

Tianxin Hou; Kui Zhang; Xiaoxuan Kang; Xueling Guo; Libo Du; Xinfeng Chen; Long Yu; Ji Yue; Hongwei Ge; Yang Liu; Abdullah M Asiri; Khalid A Alamry; Huan Yu; Suhua Wang

doi:10.1016/j.talanta.2018.12.083

Sensitive detection and imaging of endogenous peroxynitrite using a benzo[d]thiazole derived cyanine probe

Talanta. 2019 May 1:196:345-351. doi: 10.1016/j.talanta.2018.12.083. Epub 2018 Dec 26.

Authors

Tianxin Hou¹, Kui Zhang², Xiaoxuan Kang³, Xueling Guo³, Libo Du³, Xinfeng Chen¹, Long Yu¹, Ji Yue¹, Hongwei Ge¹, Yang Liu³, Abdullah M Asiri⁴, Khalid A Alamry⁴, Huan Yu⁵, Suhua Wang⁶

Affiliations

¹ MOE Key Laboratory of Resources and Environmental System Optimization, College of Environmental Science and Engineering, North China Electric Power University, Beijing 102206, China.
² School of Chemistry and Chemical Engineering, Anhui University of Technology, MaAnshan, Anhui 243032, China.
³ 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.
⁴ Chemistry Department, Faculty of Science, King Abdulaziz University, Jeddah, Saudi Arabia.
⁵ School of Pharmacy, Anhui Medical University, Hefei 230032, China. Electronic address: hyu@iim.ac.cn.
⁶ MOE Key Laboratory of Resources and Environmental System Optimization, College of Environmental Science and Engineering, North China Electric Power University, Beijing 102206, China; Chemistry Department, Faculty of Science, King Abdulaziz University, Jeddah, Saudi Arabia. Electronic address: wangsuhua@ncepu.edu.cn.

PMID: 30683374
DOI: 10.1016/j.talanta.2018.12.083

Abstract

Peroxynitrite is a short-lived endogenous reactive species and plays important roles in many physiological and pathological processes. In this work, we synthesized a near-infrared probe based on the structure of benzothiazole derived cyanine for determination of peroxynitrite (ONOO^-). The designed probe specifically reacted with ONOO^- through oxidative cleavage of conjugated C˭C double bonds and generating the non-fluorescent product. Meanwhile, the characteristic absorption of the probe at 630 nm greatly decreased after reaction with ONOO^-, accompanied by drastic color change from bright blue to green yellow, which exhibited a distinct visual feature. It was demonstrated that the probe could be used to measure ONOO^- in a dose-response manner and had a detection limit lower as 26 nM. Furthermore, the probe Cy-SN was applied for the imaging of endogenous ONOO^- in living cells by confocal microscopy, which showed good cell permeability and low cytotoxicity. Successful application of probe for exogenous colorimetric detection and endogenous fluorescence imaging of ONOO^- is suggesting its great potential applications in biological analysis.

Keywords: Fluorescent probe·Peroxynitrite·Benzothiazole derived cyanine·Colorimetric·Endogenous fluorescence imaging.