A simple and an easy-to-synthesize turn-on fluorescent probe for rapid detection of Zn2+ and its application in bioimaging

• Published in: Tetrahedron letters 2020-11, Vol.61 (46), p.152507, Article 152507
• Main Authors: Jiao, Shu-Yan, Kong, Lu-Ming, Liu, Guo-Qun, Jia, Xu, Tian, Jia, Liu, Ya-Ge, Zhang, Liu-Xue, Zhang, Wang-Xi, Li, Ying-Hua, Huang, Zeng
• Format: Article
• Language: English
• Subjects: Cell imaging; DFT calculations; Fluorescent probe; Reversibility; Zn2
• ISSN: 0040-4039; 1873-3581
• DOI: 10.1016/j.tetlet.2020.152507

[Display omitted] •A novel fluorescent probe 1 for rapid detection of Zn2+ was developed.•The structure and the synthetic route of probe 1 were simple.•Probe 1 can discriminate Zn2+ from Cd2+ and other cations.•Probe 1 can be used for determination of Zn2+ ion in living cells. A simple novel and an easy-to-synthesize fluorescent probe 1 for detection of Zn2+ based on 1-(4-amino-2-hydroxyphenyl)ethan-1-one was developed. Probe 1 exhibited an effectively selective and sensitive recognition towards Zn2+ over Cd2+ and other cations. The Job's plot and HRMS experiments reveal the formation of 1:1 binding stoichiometry between probe 1 and Zn2+. The association constant (K) of probe 1 with Zn2+ was calculated to be 7.998 × 104 M−1. The detection limit of probe 1 towards Zn2+ was calculated at very low concentration up to 46 nM. The perfect reversibility of probe 1 for sensing Zn2+ was also demonstrated. Detection mechanism of Zn2+ ion by probe 1 was suggested through the analytical tools like UV–vis, FESEM, TEM, 1H NMR titration and the DFT calculations experiments. More importantly, the fluorescence imaging in C6 cells suggested that simple sensor had great potential in the application of biological imaging.