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Tetraphenylethylene indole derivative, preparation method therefor and application of tetraphenylethylene indole derivative in cell imaging and thiol compound analysis

A technology of indole derivatives and tetraphenylethylene, which is applied in the field of bioluminescent probes, can solve the problems that restrict the application of fluorescence emission of organic light-emitting molecules, and achieve the effects of sensitive potential indication results and low biological toxicity

Inactive Publication Date: 2017-12-01
BEIJING UNIV OF CHEM TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

This restricts the practical application of organic light-emitting molecules

Method used

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  • Tetraphenylethylene indole derivative, preparation method therefor and application of tetraphenylethylene indole derivative in cell imaging and thiol compound analysis
  • Tetraphenylethylene indole derivative, preparation method therefor and application of tetraphenylethylene indole derivative in cell imaging and thiol compound analysis
  • Tetraphenylethylene indole derivative, preparation method therefor and application of tetraphenylethylene indole derivative in cell imaging and thiol compound analysis

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Experimental program
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Effect test

Embodiment 1

[0033] The synthesis of tetraphenylethylene derivatives, concrete steps are as follows:

[0034] The first step: weigh 4,4-dimethoxydiphenyl ketone (7.3g, 0.03M), 4,4-dibromodiphenyl ketone (10.2g, 0.03M) and zinc powder (15.7g, 0.24M) was placed in a 500mL two-necked flask, and 200mL of anhydrous tetrahydrofuran was quickly added as a reaction solvent. The reaction bottle is well connected with the condensing device, and the whole reaction system is in a sealed state. Air was removed from the system at -78°C. Slowly inject 0.12 mol of titanium tetrachloride (13.16 mL) at low temperature (0°C). After returning to room temperature, the reaction system was transferred to an oil bath, heated to 80°C and stirred for 9 hours. After the reaction is completed, add an appropriate amount of saturated potassium carbonate solution to terminate the reaction, filter, extract the crude product with water and dichloromethane, spin the dichloromethane part to obtain the crude product, and ...

Embodiment 2

[0042] Cytotoxicity experiments, the steps are as follows:

[0043] 1) Add 100 μL / well (approximately 1×10 4 ), set at 37°C 5% CO 2 Cultured in a cell culture incubator for 24 hours.

[0044] 2) Add 1-500 μg / L tetraphenylethylene derivatives.

[0045] 3) Place the 96-well plate at 37°C in 5% CO 2 The cells were cultured in an incubator for 24 hours.

[0046] 4) Add 50 μL of 1×MTT to each well and incubate at 37° C. for 4 hours to reduce MTT to formazan.

[0047] 5) Aspirate the supernatant, add 150 μL DMSO to each well to make formazan, and shake well with a plate shaker.

[0048] 6) A microplate reader detects the optical density of each well at a wavelength of 490nm.

Embodiment 3

[0050] Cell imaging experiments, the steps are as follows:

[0051] 1) Human cervical cancer cells were cultured for 24 hours in a 35mm surface dish with a cover glass.

[0052] 2), configuration 10 -3 μmol / L tetraphenylethylene derivatives were co-cultured with the cultured cells for 30min.

[0053] 3) Carry out confocal imaging under 488nm excitation light.

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Abstract

The invention provides a tetraphenylethylene indole derivative molecule, a preparation method therefor and an application of the tetraphenylethylene indole derivative molecule in the fields of cell imaging and detection of thiols in cells. According to the application, two indole salt structures are introduced to a tetraphenyl ethylene molecule, and the molecule is applied to the cell imaging and thiol compound analysis as a fluorescence molecule probe by using fluorescence emission characteristics of the molecule. Due to the introduction of the two indole salt structures, the interaction between the molecule probe and the surface of a mitochondrion in a cell can be enhanced, then, the selective imaging of the mitochondrion and the detection of a membrane potential of the mitochondrion are achieved, and a more-sensitive potential indicating result is obtained. The induced luminescence integrated fluorescence molecule provided by the invention has the advantages of low cell toxicity and good luminescence stability, can be applied to the analysis of thiol compounds, the mitochondrion imaging of the cells and the detection of membrane potential changes of mitochondria and shows a potential application value in the field of biomedicines.

Description

technical field [0001] The invention relates to the technical field of biological fluorescent probes, more specifically, to a tetraphenylethylene indole derivative molecule and a preparation method thereof, as well as applications in the fields of cell imaging and detection of thiols in cells. Background technique [0002] Traditional organic fluorescent small molecules usually become solid with the increase of the concentration of fluorescent molecules in the solution, resulting in a decrease in the fluorescence of the system or being directly quenched, which are typical aggregation-induced quenching molecules. This restricts the practical application of organic light-emitting molecules for fluorescence emission. In order to overcome the disadvantages of this kind of luminescent molecules, in 2001 Professor Tang Benzhong’s research group discovered the phenomenon of aggregation-induced emission (AIE) of organic molecules, that is, the fluorescence of these molecules is weak...

Claims

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Application Information

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IPC IPC(8): C07D209/12C07C41/30C07C43/225C07C45/00C07C47/575C09K11/06G01N21/64
Inventor 王卓苏姗
Owner BEIJING UNIV OF CHEM TECH
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