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Rational design of an iminocoumarin-based fluorescence probe for peroxynitrite with high signal-to-noise ratio |
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| Authors: | Zejian Huang Lei Shi Huihong Liu Zu-Kun Zhou Hua Xiang Shengzhao Gong Guojiang Mao Guang Shao Sheng Yang |
| Institution: | 1. School of Light Chemical Technology, Guangdong Engineering Technical Research Center for Green Household Chemicals, Guangdong Industry Polytechnic, Guangzhou, Guangdong, P. R. China
Contribution: Data curation, Formal analysis, Supervision;2. School of Light Chemical Technology, Guangdong Engineering Technical Research Center for Green Household Chemicals, Guangdong Industry Polytechnic, Guangzhou, Guangdong, P. R. China;3. Laboratory of Chemical Biology and Traditional Chinese Medicine Research (Ministry of Education), College of Chemistry and Chemical Engineering, Hunan Normal University, Changsha, P. R. China Contribution: Methodology, Resources;4. School of Chemistry, Sun Yat-sen University, Guangzhou, Guangdong, P. R. China Contribution: Data curation, Resources;5. School of Light Chemical Technology, Guangdong Engineering Technical Research Center for Green Household Chemicals, Guangdong Industry Polytechnic, Guangzhou, Guangdong, P. R. China Contribution: Data curation, Resources;6. School of Light Chemical Technology, Guangdong Engineering Technical Research Center for Green Household Chemicals, Guangdong Industry Polytechnic, Guangzhou, Guangdong, P. R. China Contribution: ?Investigation, Resources;7. Henan Key Laboratory of Organic Functional Molecule and Drug Innovation, Collaborative Innovation Center of Henan Province for Green Manufacturing of Fine Chemicals, Key Laboratory of Green Chemical Media and Reactions, Ministry of Education, School of Chemistry and Chemical Engineering, Henan Normal University, Xinxiang, P. R. China;8. School of Chemistry, Sun Yat-sen University, Guangzhou, Guangdong, P. R. China;9. Laboratory of Chemical Biology and Traditional Chinese Medicine Research (Ministry of Education), College of Chemistry and Chemical Engineering, Hunan Normal University, Changsha, P. R. China |
| Abstract: | As a high reactive oxygen species (ROS) and a reactive nitrogen species (RNS), peroxynitrite anion (ONOO?) is widely present in organisms and plays influential roles in physiological and pathological processes. It is of great significance to develop effective fluorescent probes for imaging peroxynitrite variation in living systems. Herein we present a novel fluorescent probe TQC0 for monitoring ONOO? based on the iminocoumarin platform, and this probe was synthesized by the knoevenagel condensation between a dihydropyridine-salicylaldehyde derivative and 2-benzothiazole-acetonitrile, and subsequently masked with the boronate moiety. The obtained probe TQC0 exhibited a high signal-to-noise ratio (206-fold) and a quick ‘turn-on’ response (about 10 min) with great selectivity and sensitivity. Furthermore, the probe TQC0 was successfully applied for imaging ONOO? in living cells with low cytotoxicity. |
| Keywords: | fluorescent probe peroxynitrite iminocourmarin bioimaging |