A new dicyanoisophorone-based ratiometric and colorimetric near-infrared fluorescent probe for specifically detecting hypochlorite and its bioimaging on a model of acute inflammation

• Published in: Analytica chimica acta Vol. 1094; pp. 70 - 79
• Main Authors: Lan, Jinshuai, Guo, Jing, Jiang, Xiaoyi, Chen, Yi, Hu, Zhenghao, Que, Yuanfang, Li, Hongxin, Gu, Jingyi, Ho, Rodney J.Y., Zeng, Ruifeng, Ding, Yue, Zhang, Tong
• Format: Journal Article
• Language: English
• Published: Netherlands Elsevier B.V 15.01.2020
• Subjects: Acute inflammation; Animals; Boronic Acids - chemical synthesis; Boronic Acids - chemistry; Boronic Acids - toxicity; Cell imaging; Colorimetry - methods; Fluorescent Dyes - chemical synthesis; Fluorescent Dyes - chemistry; Fluorescent Dyes - toxicity; Hep G2 Cells; Humans; Hypochlorite; Hypochlorous Acid - analysis; Hypochlorous Acid - metabolism; Inflammation - chemically induced; Inflammation - metabolism; Limit of Detection; Lipopolysaccharides; Mice; Microscopy, Confocal - methods; Microscopy, Fluorescence - methods; Nitriles - chemical synthesis; Nitriles - chemistry; Nitriles - toxicity; Ratiometric probe; RAW 264.7 Cells; Zebrafish; Zebrafish; Ratiometric probe; Cell imaging; Hypochlorite; Acute inflammation
• ISSN: 0003-2670; 1873-4324
• DOI: 10.1016/j.aca.2019.09.076

To explore how hypochlorous acid (HClO) affects human health, a highly sensitive, selective, and trace detection method for hypochlorite (ClO−) is crucial for determining its non-negligible function in both environment and living systems. Herein, a dicyanoisophorone-phenylboronic acid-based novel ratiometric near-infrared fluorescent probe (Probe 1) was designed for the rapid and specific detection of ClO− based on the intramolecular charge transfer (ICT) mechanism. Excess addition of HClO to the Probe 1 solution, 186-times ratio (I652/I582) augment were gained. And this probe provided a colorimetric and ratiometric fluorescence response to ClO− with a high selectivity, a rapid response (within 30 s), and had an extremely low detection limit (15.7 nM). In addition, owing to the good sensing properties and low cytotoxicity of Probe 1, it can be used to expediently visualize exogenous ClO− in HepG2 cells and endogenous ClO− in RAW264.7 macrophage cells. Furthermore, the probe was successfully used for the bioimaging of zebrafish with an acute inflammation. Thus, Probe 1 is a promising vehicle to identify the level of HClO in animals with associated diseases. A new ratiometric and colorimetric NIR fluorescent probe (Probe 1) for the specific detection of ClO− has been designed and synthesized on the basis of dicyanoisophorone-phenylboronic acid. And it was endowed with the following outstanding advantages: one-step synthesis, a long-wavelength emission, naked-eye assay, ratio fluorescent dual-channel detection, and feasibility in living cells and zebrafish. [Display omitted] •A new ratiometric dicyanoisophorone fluorescent Probe 1 was synthesized.•Probe 1 displays high selectivity and sensitivity to ClO− over other relevant ROS and common ions.•Probe 1 responses quickly to ClO− through distinct color change and ratiometric fluorescence variation.•Probe 1 has low cytotoxicity and is applicable for ClO− detection in living cells.•Probe 1 is successfully used for the detection of endogenous and exogenous ClO− in zebrafish.