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Distinguishable multi-substance detection based on three-channel NIR fluorescent probe in physiology and pathology of living cells and zebrafish

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Chinese Chemical Letters 2021年第12期32卷 3870-3875页

作者： Sha Li Fangjun Huo Yongkang Yue Kaiqing Ma Ying Wen Caixia Yin Institute of Molecular Science Key Laboratory of Chemical Biology and Molecular Engineering of Ministry of EducationShanxi UniversityTaiyuan 030006China Research Institute of Applied Chemistry Shanxi UniversityTaiyuan 030006China

Mitochondria is the main organelle for the production of reactive sulfur species(RSS), such as homocysteine(Hcy), cysteine(Cys), glutathione(GSH) and sulfur dioxide(SO_(2)). These compounds participate in a large number of physiological processes and play an extremely important role in maintaining the balance of life systems. Abnormal concentration and metabolism are closely related to many diseases. Due to their similarities in chemical properties, it is challenging to develop a single fluorescent probe to distinguish them simultaneously. Here, we synthesized the probe PI-CO–NBD with three fluorophores, NBD-Cl and benzopyranate as the reaction sites of GSH/Cys/Hcy and SO_(2), respectively. Three biothiols all could cleavage ether bond to release benzopyrylium and coumarin moiety, which emitted red and blue fluorescence,but Cys/Hcy also could do intramolecular rearrangement after nucleophilic substitution, resulting in yellow fluorescence. Thus the probe can distinguish Cys/Hcy and GSH. Subsequently, only SO_(2)could quench red fluorescence by adding C=C of benzopyrylium. The probe also could localize well in mitochondria by oxonium ion for all kinds of cells. The probe not only could detect above sulfur-containing active substances of intracellular and extracellular but also monitor the level of them under oxidative stress and apoptosis process in living cells and zebrafish.

关键词： Mitochondrial-targeted discrimination detection Distinguishable Multi-substance Three channels

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