A near-infrared fluorescent probe based on SNAr reaction for H2S/GSH detection in living cells and zebrafish. (April 2019)

• Record Type: Journal Article
• Authors: Zhang, Han; Xia, Xiang; Zhao, Hong; Zhang, Guo-Ning; Jiang, Dao-Yong; Xue, Xing-Ying; Zhang, Jiao
• Is Part Of: Dyes and pigments. Volume 163(2019)
• Page Start: 183
• Page End: 189
• Publication Date: 2019-04
• Subjects: Dicyanoisophorone -- Near-infrared emission -- SNAr -- Fluorescent probe; Dyes and dyeing -- Periodicals; Pigments -- Periodicals; 667.2
• DOI: 10.1016/j.dyepig.2018.11.050
• Languages: English
• ISSNs: 0143-7208

Abstract

Abstract: Hydrogen sulfide (H2 S) and biothiols such as cysteine (Cys), homocysteine (Hcy) and glutathione (GSH), play critical roles in physiological and pathological processes. However, due to the challenge in sensing H2 S and biothiols simultaneously, it is of great importance to solve this problem in biological processes. Herein, a near-infrared fluorescent probe (HZ-NBD) based on SN Ar reactions was exploited to achieve the sensitive and selective detection of H2 S and glutathione (GSH) simultaneously in the same conditions. The design strategy was employing dicyanoisophorone based fluorescent dye as the fluorophore, the NBD moiety as a response unit and a quencher of fluorophore. The probe exhibited a low limit of detection to H2 S (13.2 nM) and GSH (112 nM) as well as a favourable large stokes shift (112 nm). The reaction mechanism was investigated via mass spectra. What's more, owing to the advantages of low cytotoxicity, fast response and strong anti-interference ability, the probe HZ-NBD was successfully applied to bioimage H2 S and GSH in HepG2 cells and zebrafish. Highlights: Near infrared emission at 672 nm. Distinguish H2 S and GSH simultaneously over Hcy and Cys. Fluorescence imaging in zebrafish/cells in vivo and vitro. High sensitivity (13.2 nM for H2 S, 112.0 nM for GSH) and selectivity.