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Fluorescent probe for mitochondria-targeted viscosity determination and preparation method and application thereof

A technology of fluorescent probes and mitochondria, 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

Inactive Publication Date: 2019-07-23
UNIV OF JINAN
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, there are not many fluorescent probes that can perform fluorescence imaging of mitochondrial viscosity.

Method used

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  • Fluorescent probe for mitochondria-targeted viscosity determination and preparation method and application thereof
  • Fluorescent probe for mitochondria-targeted viscosity determination and preparation method and application thereof
  • Fluorescent probe for mitochondria-targeted viscosity determination and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

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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Abstract

The invention synthesizes a mitochondrion-targeted viscosity fluorescent probe which takes carbazole as a fluorophore and a positive nitrogen ion as a mitochondrion positioning group by virtue of molecular design. The invention also provides a simple preparation method of the fluorescent probe and application of the fluorescent probe in sensing detection on viscosities of a solution and a cell organelle micro-environment. The reagent can serve as an indicator for viscosity change in an aqueous solution and biological cells and can carry out real-time qualitative and quantitative colorimetry detection. The fluorescent probe is a simple, rapid and sensitive viscosity specific detection reagent and has a broad application prospect in the field of biological molecular detection.

Description

technical field [0001] The invention relates to a fluorescent probe for detecting viscosity in mitochondria and its preparation and detection of solution and cell viscosity by using methods such as spectral testing and cell imaging, and belongs to the field of organic small molecule fluorescent probes. Background technique [0002] Viscosity is the main factor to measure the fluidity and diffusibility of a thick fluid, and it is also the main reference index of the fluid diffusion rate. The viscosity of the microenvironment plays a very important role in pathological research, because different regions in the cell have different viscosities, and changes in viscosity often affect the progress of various metabolisms in the cell microenvironment. When cells are in a pathological state, intracellular viscosity changes. When the intracellular viscosity value changes abnormally, it will affect the activity of membrane-bound proteins, inhibit insulin synthesis, etc., leading to re...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D209/86C09K11/06G01N21/64
CPCC07D209/86C09K11/06C09K2211/1007C09K2211/1029G01N21/6486
Inventor 林伟英任明光周凯邓贝贝
Owner UNIV OF JINAN
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