A near-infrared fluorescent probe for H2S based on tandem reaction to construct iminocoumarin-benzothiazole and its application in food, water, living cells

Keli Zhong; Yuqing He; Longlong Deng; Xiaomei Yan; Xuepeng Li; Yiwei Tang; Shuhua Hou; Lijun Tang

doi:10.1016/j.aca.2020.06.050

A near-infrared fluorescent probe for H₂S based on tandem reaction to construct iminocoumarin-benzothiazole and its application in food, water, living cells

Anal Chim Acta. 2020 Aug 29:1127:49-56. doi: 10.1016/j.aca.2020.06.050. Epub 2020 Jul 8.

Authors

Keli Zhong¹, Yuqing He¹, Longlong Deng¹, Xiaomei Yan², Xuepeng Li³, Yiwei Tang⁴, Shuhua Hou¹, Lijun Tang⁵

Affiliations

¹ College of Chemistry and Chemical Engineering, College of Food Science and Technology, Bohai University, Food Safety Key Lab of Liaoning Province, National & Local Joint Engineering Research Center of Storage, Processing and Safety Control Technology for Fresh Agricultural and Aquatic Products, Bohai University, Jinzhou, 121013, China.
² College of Laboratory Medicine, Dalian Medical University, Dalian, 116044, China.
³ College of Chemistry and Chemical Engineering, College of Food Science and Technology, Bohai University, Food Safety Key Lab of Liaoning Province, National & Local Joint Engineering Research Center of Storage, Processing and Safety Control Technology for Fresh Agricultural and Aquatic Products, Bohai University, Jinzhou, 121013, China. Electronic address: lixuepeng@bhu.edu.cn.
⁴ College of Food Science and Technology, Agricultural University of Hebei, Baoding, 071001, China.
⁵ College of Chemistry and Chemical Engineering, College of Food Science and Technology, Bohai University, Food Safety Key Lab of Liaoning Province, National & Local Joint Engineering Research Center of Storage, Processing and Safety Control Technology for Fresh Agricultural and Aquatic Products, Bohai University, Jinzhou, 121013, China. Electronic address: ljtang@bhu.edu.cn.

PMID: 32800137
DOI: 10.1016/j.aca.2020.06.050

Abstract

With the merits of non-destructive, high penetration ability and minimizing autofluorescence, near-infrared (NIR) fluorescent probes have attracted much attention. In this paper, a NIR emission fluorescent turn-on probe THQ-L for H₂S was synthesized by the knoevenagel condensation between tetrahydroquinoxaline-6- formaldehyde derivative and 2-benzothiazoleacetonitrile. THQ-L can recognize H₂S through tandem reaction triggered by HS^- to construct 1,4-diethylpiperazine-modified iminocoumarin-benzothiazole, which produces a strong red fluorescent signal. THQ-L displayed an excellent selectivity toward H₂S, a large stokes shift (126 nm), a high signal-to-noise ratio (200-fold), the detection limits of 38.3 nM in PBS (10 mM, pH 7.4, 30% THF). The application study indicates that THQ-L can sensitively detect H₂S in red wine, natural waters, living cells and can be prepared for a test paper strip for the qualitative detection of H₂S.

Keywords: Bioimaging; Fluorescent probe; Food sample; Hydrogen sulfide; Near-infrared.

MeSH terms

Benzothiazoles
Fluorescent Dyes*
HeLa Cells
Humans
Hydrogen Sulfide*
Water

Substances

Benzothiazoles
Fluorescent Dyes
Water
Hydrogen Sulfide