A fluorescent sensor for fast detection of peroxynitrite by removing of C=N in a benzothiazole derivative

Youming Shen; Xiangyang Zhang; Youyu Zhang; Haitao Li; Lingcong Dai; Xinju Peng; Zhen Peng; Yingting Xie

doi:10.1016/j.aca.2018.01.046

A fluorescent sensor for fast detection of peroxynitrite by removing of C=N in a benzothiazole derivative

Anal Chim Acta. 2018 Jul 19:1014:71-76. doi: 10.1016/j.aca.2018.01.046. Epub 2018 Feb 3.

Authors

Youming Shen¹, Xiangyang Zhang², Youyu Zhang³, Haitao Li⁴, Lingcong Dai¹, Xinju Peng¹, Zhen Peng¹, Yingting Xie¹

Affiliations

¹ Hunan Province Cooperative Innovation Center for the Construction & Development of Dongting Lake Ecological Economic Zone, Collaborative Innovation Center for Efficient and Health Production of Fisheries in Hunan Province, College of Chemistry and Materials Engineering, Hunan University of Arts and Science, Changde, 415000, PR China.
² Hunan Province Cooperative Innovation Center for the Construction & Development of Dongting Lake Ecological Economic Zone, Collaborative Innovation Center for Efficient and Health Production of Fisheries in Hunan Province, College of Chemistry and Materials Engineering, Hunan University of Arts and Science, Changde, 415000, PR China. Electronic address: zhangxiangy06@163.com.
³ Key Laboratory of Chemical Biology and Traditional Chinese Medicine Research (Ministry of Education), College of Chemistry and Chemical Engineering, Hunan Normal University, Changsha 410081, PR China. Electronic address: zhangyy@hunnu.edu.cn.
⁴ Key Laboratory of Chemical Biology and Traditional Chinese Medicine Research (Ministry of Education), College of Chemistry and Chemical Engineering, Hunan Normal University, Changsha 410081, PR China.

PMID: 29523254
DOI: 10.1016/j.aca.2018.01.046

Abstract

A simple structured reaction-based probe for peroxynitrite (ONOO^-) was developed by using benzothiazole hydrazone base of the excited-state intramolecular proton transfer (ESIPT) dye. It was constructed from 2-hydrazinylpyridine and 3-(benzo[d]thiazol-2-yl)-2-hydroxy-5-methylbenzaldehyde which possesses itself weak fluorescence and displayed prominent fluorescence response towards ONOO^- by oxidizes the C=N bond to an aldehyde in aqueous solution. The probe exhibited excellent selectivity and high sensivity towards ONOO^- with a low dectection limit of 5.8 × 10^-8 M in physiological condition. Moreover, the probe could realize fast recognition to ONOO^- in as short as 60 s. In addition, the probe was also successfully used for living cell imaging.

Keywords: Benzothiazole derivative; Cell imaging; Fast-detection; Fluorescent chemosensor; ONOO(−) sensor.

MeSH terms

Benzothiazoles / chemistry*
Fluorescent Dyes / chemical synthesis
Fluorescent Dyes / chemistry*
HeLa Cells
Humans
Hydrogen-Ion Concentration
Peroxynitrous Acid / analysis*
Solvents / chemistry
Spectrometry, Fluorescence
Tumor Cells, Cultured

Substances

Benzothiazoles
Fluorescent Dyes
Solvents
Peroxynitrous Acid
benzothiazole