Mitochondrion-targeted viscosity determination fluorescent probe as well as preparation method and application thereof
A fluorescent probe and mitochondrial technology, applied in the direction of fluorescence/phosphorescence, chemical instruments and methods, luminescent materials, etc., can solve the problem of not many fluorescent probes, achieve good targeting, high sensitivity, and broad application prospects Effect
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Embodiment 1
[0037] Example 1 Synthesis of fluorescent probe CIV1.
[0038] The synthetic route of fluorescent probe CIV1 is as follows:
[0039]
[0040] The synthesis steps of fluorescent probe CIV1 are as follows:
[0041] (1) Dissolve 2,3,3,-trimethylindole (2.0g, 12.6mmol, 1.0eq) and bromoethane (2.1g, 18.9mmol, 1.5eq) in 2mL of acetonitrile, heat to reflux at 85°C Reaction 15h. The reaction solution was spin-dried, filtered under reduced pressure, and washed with ether to obtain compound 1.
[0042] (2) Carbazole (1.0g, 6mmol, 6.0eq), 4-bromobenzaldehyde (2.2g, 12mmol, 12.0eq), copper powder (64mg, 1mmol, 1.0eq), K 2 CO 3 (1.24g, 9mmol, 9.0eq) was dissolved in 10mL of nitrobenzene, under nitrogen protection, and heated at reflux at 180°C for 24h. Use a TCL plate to detect the reaction. After the reaction is complete, cool to room temperature and separate with a silica gel column. The silica gel particle size is 200-300 mesh, and the eluent ratio is ethyl acetate / petroleum eth...
Embodiment 2
[0044] Example 2 Synthesis of fluorescent probe CIV2.
[0045] The synthetic route of fluorescent probe CIV2 is as follows:
[0046]
[0047] The synthesis steps of fluorescent probe CIV2 are as follows:
[0048] (1) The synthesis of compound 1 is the same as in Example 1.
[0049] (2) carbazole (1.0g, 6mmol, 1.0eq) and ZnCl 2 (2.45g, 18mmol, 3.0eq) was dissolved in 20mL of nitromethane, under nitrogen protection, after stirring for several minutes at room temperature, chlorobutane (1.7g, 18mmol, 3.0eq) was injected into the above reaction system with a syringe, and Reaction 5h. The reaction was detected on a TCL plate. After the reaction was complete, it was quenched with water, extracted twice with dichloromethane, washed with saturated saline for 2-3 times, and dried over anhydrous sodium sulfate. The solvent was spin-dried under reduced pressure to obtain a crude product, which was separated with a silica gel column. The silica gel particle size was 200-300 mesh, and ...
Embodiment 3
[0054] Example 3 Visual detection of viscosity by fluorescent probes CIV1 and CIV2.
[0055] 40 μL of each fluorescent probe CIV1 stock solution obtained in Example 1 was taken out and added to two 5 mL sample tubes, one was added with 3 mL of ethanol, and the other was added with 3 mL of 90% glycerol solution. The same operation was performed for the fluorescent probe CIV2. It was observed that the solution had a significant color change: the solution color of CIV1 changed from colorless to light orange ( Figure 5 A), with the viscous fluorescent probe visible to the naked eye under ultraviolet light emitting red fluorescence ( Image 6 A); The solution color of CIV2 changed from almost colorless to red ( Figure 5 B), accompanied by the viscous fluorescent probe visible to the naked eye under ultraviolet light emitting red fluorescence ( Image 6 B). It shows that CIV1 and CIV2 are fluorescent probes with chromogenic sensing function, which can be used to qualitatively ...
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