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

A dansulfamide, fluorescent probe technology, applied in fluorescence/phosphorescence, chemical instruments and methods, luminescent materials, etc., can solve the problems of differentiation, difficulty in culture medium, difficulty, 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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  • 4-dansylamide-indole fluorescent probe and its preparation method and application
  • 4-dansylamide-indole fluorescent probe and its preparation method and application
  • 4-dansylamide-indole fluorescent probe and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] In this embodiment, the name and structural formula of the 4-dansylamide-indole fluorescent probe are as follows:

[0034]

[0035] The preparation method of above 4-dansylamide-N-methyl-indole is as follows:

[0036] Weigh dansyl chloride (1327 mg, 4.92 mmol) dissolved in 3 ml of pyridine, weigh 4-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 1936 mg of intermediate was obtained by column chromatography.

[0037] Intermediate 1 (60 mg, 0.164 mmol...

Embodiment 2

[0041] In this embodiment, the name and structural formula of the 4-dansylamide-indole fluorescent probe are as follows:

[0042]

[0043] The above 4-dansylamide- N -Ethyl-indole is prepared as follows:

[0044] Weigh dansyl chloride (1327 mg, 4.92 mmol) dissolved in 3 ml of pyridine, weigh 4-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 1936 mg of intermediate was obtained by column chromatography.

[0045] Intermediate 1 (60 mg, 0.164 mmol) and sodiu...

Embodiment 3

[0049] In this embodiment, the name and structural formula of the 4-dansylamide-indole fluorescent probe are as follows:

[0050]

[0051] The above 4-dansylamide- N -Propyl-indole is prepared as follows:

[0052] Weigh dansyl chloride (1327 mg, 4.92 mmol) dissolved in 3 ml of pyridine, weigh 4-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 1936 mg of intermediate was obtained by column chromatography.

[0053] Intermediate 1 (60 mg, 0.164 mmol) and sodi...

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Abstract

The invention discloses 4-dansylamine-indole type fluorescent probes and a preparation method and application thereof. The 4-dansylamine-indole type fluorescent probes are represented in a general formula (I), and the structures of the fluorescent probes are formed by connecting hydrocarbonyl chains to the parent nucleus of 4-dansylamine-indole. Due to the presence of dansylamide, the compounds have fluorescent properties, and due to the presence of the hydrocarbonyl groups which substitute indole rings, the compounds can rapidly penetrate into living tumor cells and form a feature-distinctivefluorescent image with dyeing of cytoplasm and no dyeing of cell nucleus, and however, for dead tumor cells, the compounds have fluorescent dyeing characteristics different from the fluorescent dyeing characteristics for living cells completely, and therefore the probes can be applied to the detection of the activity of the tumor cells in industries related to biomedicine.

Description

technical field [0001] The invention belongs to the technical field of chemical analysis and detection, and specifically relates to a 4-dansylamide-indole fluorescent probe and its preparation method and application. Background technique [0002] Due to their own survival needs, living cells are isolated from the outside world through a complete cell membrane, 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 involves the intracellular 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 rupture of the cel...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D209/08C09K11/06G01N21/64
CPCC07D209/08C09K11/06C09K2211/1011C09K2211/1029G01N21/6486
Inventor 朱坤福薛飞朱晓肸
Owner SHANDONG ZHUSHITANG MEDICAL TREATMENT INSTR CO LTD