A dual-emission fluorescent probe for discriminating cysteine from homocysteine and glutathione in living cells and zebrafish models |
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| Institution: | 1. College of Chemistry & Chemical Engineering, Central South University, Changsha, Hunan Province, 410083, China;2. College of Chemistry and Molecular Engineering, Zhengzhou University, Zhengzhou, Henan Province, 450001, China;1. Tianjin Key Laboratory for Photoelectric Materials and Devices, and Key Laboratory of Display Materials & Photoelectric Devices, Ministry of Education, School of Materials Science & Engineering, Tianjin University of Technology, Tianjin 300384, China;2. School of Materials Science and Engineering, Harbin Institute of Technology, Harbin 150001, China;1. Department of Chemistry, Taiyuan Normal University, Jinzhong 030619, China;2. Shanxi Analytical Science Academy, Taiyuan 030006, China;1. Key Laboratory of Nonferrous Metal Chemistry and Resources Utilization of Gansu Province and State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou, 730000, China;2. Department of Anatomy and Histology, Lanzhou University School of Basic Medical Sciences, Lanzhou, China |
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| Abstract: | Cellular biothiols function crucially and differently in physiological and pathological processes. However, it is still challenging to detect and discriminate thiols within a single one molecule, especially for cysteine (Cys) and homocysteine (Hcy). In this study, a simple two-emission turn-on fluorescent biothiol probe (ICN-NBD) was rationally designed and synthesized through a facile ether bond linking 7-nitro-1,2,3-benzoxadiazole (NBD) and phenanthroimidazole containing a cyano tail. The probe in the presence of Cys elicited two fluorescence responses at 470 nm and 550 nm under excitation at 365 nm and 480 nm, respectively, because of the concomitant generation of both the fluorophore and NBD-N-Cys. In contrast, addition of Hcy and glutathione (GSH) could result in only a blue fluorescence enhancement at 470 nm. which was reasonably attributed to rearrangement from NBD-S-Hcy/GSH to NBD-N-Hcy/GSH as a result of geometrical constraints or solvent effects. Therefore, the fluorescent probe with the NBD scaffold could detect biothiols and simultaneously discriminate Cys from Hcy/GSH in both blue and green channels. The probe has been successfully applied for visualizing biothiols in living cells and zebrafish. |
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| Keywords: | Dual-emission fluorescent probe Discrimination of biothiols NBD Living cell Zebrafish models |
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