Sequential detection of hypochlorous acid and sulfur dioxide derivatives by a red-emitting fluorescent probe and bioimaging applications in vitro and in vivo. Issue 25 (26th May 2022)

• Record Type: Journal Article
• Authors: Liu, Jianhua; Yin, Haoyuan; Shang, Zhuye; Gu, Pengli; He, Guangjie; Meng, Qingtao; Zhang, Run; Zhang, Zhiqiang
• Is Part Of: RSC advances. Volume 12:Issue 25(2022)
• Page Start: 15861
• Page End: 15869
• Publication Date: 2022-05-26
• Subjects: Chemistry -- Periodicals; 540.5
• DOI: 10.1039/d2ra01048h
• Languages: English
• ISSNs: 2046-2069

Abstract

Abstract : A red-emitting fluorescence probe (DP ) has been successfully developed for the sequential detection of hypochlorous acid (HOCl) and sulfur dioxide derivatives (SO3 2− /HSO3 − ) in vitro and in vivo . Abstract : Hypochlorous acid (HOCl) and sulfur dioxide derivatives (SO3 2− /HSO3 − ) play critical roles in complex signal transduction and oxidation pathways. Therefore, it is meaningful and valuable to detect both HOCl and SO2 derivatives in biosystems by a fluorescence imaging assay. In this work, we developed a red-emitting fluorescent probe (DP ) by the condensation of malononitrile and phenothiazine derivatives through a CC double bond. DP was designed with a donor–π–acceptor (D–π–A) structure, which enables absorption and emission in the long wavelength region. In the presence of HOCl, specific oxidation of the thioether of phenothiazine in DP to a sulfoxide derivative (DPO ) occurs, resulting in a hypochromic shift (572 nm to 482 nm) of the absorption spectra and "OFF–ON" response of the maximum emission at 608 nm. After the activation of the CC double bond by oxidation, DPO reacts specifically with SO3 2− /HSO3 − via a 1, 4-nucleophilic addition reaction leading to a decrease in the intensity of the absorption and emission spectra, which enabled the realization of sequential detection of HOCl and SO3 2− /HSO3 − by a single fluorescent probe. The detection limits of DP for HOCl and SO3 2− /HSO3 − were calculated to be 81.3 nM and 70.8 nM/65.1 nm, respectively. The results of fluorescence microscopic imaging indicated that DP shows potential for the detection of intracellular HOCl and SO3 2− /HSO3 − . Using adult zebrafish and nude mice as live animal models, DP was successfully used for the fluorescence imaging of HOCl and SO3 2− /HSO3 − in vivo .