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6-dansylamide-indole fluorescent probe and its preparation method and application

A technology of dansylamide and fluorescent probes, applied in the direction of fluorescence/phosphorescence, chemical instruments and methods, luminescent materials, etc., can solve the problems of differentiation, difficulty, difficult culture medium, etc., and achieve accurate detection results, low cost, and easy operation simple effect

Active Publication Date: 2020-06-19
SHANDONG ZHUSHITANG MEDICAL TREATMENT INSTR CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, this method has great limitations, which are mainly reflected in the fact that cells are usually in a transparent color under visible light, and it is difficult to distinguish them from the surrounding connective tissue or tissue culture fluid.
This is especially difficult for live cell assays

Method used

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  • 6-dansylamide-indole fluorescent probe and its preparation method and application
  • 6-dansylamide-indole fluorescent probe and its preparation method and application
  • 6-dansylamide-indole fluorescent probe and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034] In this embodiment, the name and structural formula of the 6-dansylamide-indole fluorescent probe are as follows:

[0035]

[0036] The preparation method of above 6-dansylamide-N-methyl-indole is as follows:

[0037] Weigh dansyl chloride (1327 mg, 4.92 mmol) dissolved in 3 ml of pyridine, weigh 6-amino-indole (500 mg, 3.78 mmol) dissolved in 4 ml of pyridine, slowly drop into the dansyl chloride solution, Stirred under ice bath for 2 hours to room temperature, protected by argon, reacted overnight. 100 ml of double distilled water was added to the reaction to terminate the reaction, and the reaction mixture was precipitated. The precipitated solid was dissolved with 100 ml of ethyl acetate, washed twice with 60 ml of sodium bicarbonate, twice with 20 ml of saturated sodium chloride, and twice with 50 ml of water. Sodium sulfate was added to remove water, and 1954 mg of intermediate was obtained through column chromatography;

[0038]Intermediate 1 (60 mg, 0.164 ...

Embodiment 2

[0042] In this embodiment, the name and structural formula of the 6-dansylamide-indole fluorescent probe are as follows:

[0043]

[0044] The above 6-dansylamide- N -Ethyl-indole is prepared as follows:

[0045] Weigh dansyl chloride (1327 mg, 4.92 mmol) dissolved in 3 ml of pyridine, weigh 6-amino-indole (500 mg, 3.78 mmol) dissolved in 4 ml of pyridine, slowly drop into the dansyl chloride solution, Stirred under ice bath for 2 hours to room temperature, protected by argon, reacted overnight. 100 ml of double distilled water was added to the reaction to terminate the reaction, and the reaction mixture was precipitated. The precipitated solid was dissolved with 100 ml of ethyl acetate, washed twice with 60 ml of sodium bicarbonate, twice with 20 ml of saturated sodium chloride, and twice with 50 ml of water. Sodium sulfate was added to remove water, and 1954 mg of intermediate was obtained through column chromatography;

[0046] Intermediate 1 (60 mg, 0.164 mmol) and ...

Embodiment 3

[0050] In this embodiment, the name and structural formula of the 6-dansylamide-indole fluorescent probe are as follows:

[0051]

[0052] The above 6-dansylamide- N -Propyl-indole is prepared as follows:

[0053] Weigh dansyl chloride (1327 mg, 4.92 mmol) dissolved in 3 ml of pyridine, weigh 6-amino-indole (500 mg, 3.78 mmol) dissolved in 4 ml of pyridine, slowly drop into the dansyl chloride solution, Stirred under ice bath for 2 hours to room temperature, protected by argon, reacted overnight. 100 ml of double distilled water was added to the reaction to terminate the reaction, and the reaction mixture was precipitated. The precipitated solid was dissolved with 100 ml of ethyl acetate, washed twice with 60 ml of sodium bicarbonate, twice with 20 ml of saturated sodium chloride, and twice with 50 ml of water. Sodium sulfate was added to remove water, and 1954 mg of intermediate was obtained through column chromatography;

[0054] Intermediate 1 (60 mg, 0.164 mmol) and...

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Abstract

The invention discloses a 6-dansyl amide-indole fluorescence probe shown as a general formula (I) as well as a preparation method and application thereof. The structure of the compounds is formed by connecting a hydrocarbonyl on the basis of 6-dansyl amide-indole parent nucleus. Due to the presence of dansyl amide, the compounds have fluorescence characteristics; due to the presence of hydrocarbonchains, the compounds can rapidly permeate into living tumor cells, and fluorescence images with distinct characteristics subjected to cytoplasm staining and cell nucleus non-staining are formed. However, for dead tumor cells, the compounds have fluorescence staining characteristics completely different from those of the living cells. Therefore, the compounds can be applied to detection of activities of tumor cells in biomedicine related industries. The structural formula is as shown in the specification (I).

Description

technical field [0001] The invention belongs to the technical field of chemical analysis and detection, and specifically relates to a 6-dansylamide-indole fluorescent probe and its preparation method and application. Background technique [0002] Living cells are isolated from the outside world through a complete cell membrane due to their own survival requirements, thereby forming a stable physiological environment within the cell, including: pH value, nutrient composition, and various material composition ratios. When cells die, although cell death can occur in different ways, such as apoptosis, necrosis, and autophagy, and each form of death has a special signaling pathway to initiate and regulate, the process of cell death is accompanied by intracellular The environment changes, and all undergo a morphological change. In general, morphological changes during cell death mainly include changes in cell shape, compaction of the cell matrix, shrinkage of the nucleus, and rup...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D209/08C09K11/06G01N21/64C09B57/00
CPCC07D209/08C09B57/00C09K11/06C09K2211/1011C09K2211/1029G01N21/6428G01N2021/6439
Inventor 朱坤福刘亚平祝蕾
Owner SHANDONG ZHUSHITANG MEDICAL TREATMENT INSTR CO LTD