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Pyrazine-based D-A-D type fluorescent small molecule, preparation method and applications thereof

A D-A-D, small molecule technology, applied in the field of fluorescent probes, can solve the problems of poor dye stability, easy to detach from cells, poor photostability, etc., and achieve the effects of excellent photostability, not easy to quench, and high fluorescence quantum yield.

Inactive Publication Date: 2019-12-06
XI AN JIAOTONG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, in cellular imaging, many dyes are poorly stable, tend to break out of cells and are less photostable
Dye is not selective for live versus dead cells

Method used

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  • Pyrazine-based D-A-D type fluorescent small molecule, preparation method and applications thereof
  • Pyrazine-based D-A-D type fluorescent small molecule, preparation method and applications thereof
  • Pyrazine-based D-A-D type fluorescent small molecule, preparation method and applications thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] The fluorescent small molecule 4,4'-(pyrazine-2,5-diyl)bis(N,N-bis(4-methoxyphenyl)aniline) is labeled as compound 1, and its preparation method and detection process are as follows:

[0034] (1) Weigh 242 mg of 3,6-dibromopyrazine, 4-methoxy-N-(4-methoxyphenyl)-N-(4-(4,4,5,5-tetramethyl -1,3,2-dioxaborolan-2-yl)phenyl)aniline 1.29g, Pd 2 (dba) 3 127mg, sphos88mg in 50ml reaction tube, in N 2 Add Cs under protection 2 CO 3 Solution (4mol / L) 5ml and toluene 10ml, react at 85°C for 24h. The reaction product was washed with water, extracted three times with dichloromethane, and the organic phase was collected. Purify by silica gel column chromatography to obtain 402 mg of yellow solid 4,4'-(pyrazine-2,5-diyl)bis(N,N-bis(4-methoxyphenyl)aniline) with a yield of 58%. PD 2 (dba) 3 , sphos and Cs 2 CO 3 All solutions are catalysts. The structural formula of compound 1 is as follows:

[0035]

[0036] Its NMR spectrum data: 1 HNMR (400MHz, CDCl3): δ=3.81(s, 12H)...

Embodiment 2

[0046] (1) The preparation process of the fluorescent small molecule 4,4'-(3-fluoropyrazine-2,5-diyl)bis(N,N-diphenylaniline) is as follows: the fluorescent small molecule is named compound 2;

[0047] First prepare 2,5-dibromo-3-fluoropyrazine, specifically, weigh 2.53 g of 2-amino-3,6-dibromopyrazine and NaNO 2 1.38g in a 100ml round bottom flask, slowly add HBF dropwise at 0°C 4 25ml, reacted at 20°C for 2h. The resulting reaction mixture was washed with water and extracted three times with dichloromethane, and the organic phase was collected. The resulting organic phase was purified by silica gel column chromatography to obtain 2,5-dibromo-3-fluoropyrazine. Then, 140 mg of the obtained 2,5-dibromo-3-fluoropyrazine, 523 mg of 4-(diphenylamino) phenylboronic acid pinacol ester, and 119 mg of bis(triphenylphosphine)palladium(II) dichloride were taken, Tetrabutylammonium bromide 142mg in 50ml reaction tube, in N 2 Join K under protection 2 CO 3 Solution (6mol / L) 5ml and ...

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Abstract

The invention discloses a pyrazine-based D-A-D type fluorescent small molecule, which has the following chemical structural formula defined in the specification, wherein X is simultaneously selected from hydrogen or methoxyl, and R is selected from hydrogen, fluorine and methyl ester. According to the present invention, the fluorescent small molecule is used for living cell imaging, cannot enter dead cells, has strong AIE effect, is not easily quenched under physiological conditions, and has high fluorescence quantum yield.

Description

technical field [0001] The invention belongs to the technical field of fluorescent probes, and in particular relates to a pyrazine-based D-A-D type fluorescent small molecule, a preparation method and an application. Background technique [0002] A fluorescent probe is a molecular measurement device based on spectrochemistry that selectively converts the chemical information of an analysis object into a fluorescent signal that is easily measured by an analytical instrument. It has the advantages of high sensitivity, good selectivity, and convenient use. In recent years, the field of fluorescent probes has developed rapidly due to its wide application in chemical sensing, optical materials, and biology. Especially in the detection of environmental changes in cells, fluorescent probe detection has the advantages of simple operation, high sensitivity, and resolution It has the advantages of high efficiency and can realize real-time monitoring without damage. However, in cellu...

Claims

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Application Information

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IPC IPC(8): C07D241/12C07D241/16C09K11/06G01N21/64
CPCC07D241/12C07D241/16C09K11/06C09K2211/1007C09K2211/1014C09K2211/1044G01N21/6428G01N2021/6417G01N2021/6432
Inventor 陈凯吴淑琪边晓丽王秋棠
Owner XI AN JIAOTONG UNIV
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