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Water-soluble fluorescent dye for cell fluorescent developing

A technology of compound and general formula, which is applied in the field of synthesis of water-soluble fluorescent dye compounds, can solve the problems of unlabeled cells, fluorescence quenching, limitation, etc., and achieve the effects of excellent luminescence performance, short synthesis route, and strong practical value

Inactive Publication Date: 2017-09-08
NORTHWEST UNIV(CN)
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

A variety of organic dyes have been widely used in cell fluorescence color development, but when cells continue to aggregate, traditional organic dyes will undergo fluorescence quenching, and many fluorescent dyes have poor water solubility, so they cannot label cells. To a large extent, it limits the application of fluorescence chromogenic imaging in cells, which poses great difficulties to the study of cells

Method used

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  • Water-soluble fluorescent dye for cell fluorescent developing
  • Water-soluble fluorescent dye for cell fluorescent developing
  • Water-soluble fluorescent dye for cell fluorescent developing

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] Embodiment 1: (R in general formula 1 does not exist)

[0034]

[0035] (1) in N 2 7.18g of zinc powder was added to 80mL of dry THF, and stirred at 0°C for 10mins. In an ice bath, use a syringe to dispense 6 mL of TiCl 4 Slowly added dropwise to the reaction, heated to reflux for 2h. Then, 5 g of benzophenone (compound 1) was dissolved in 20 mL of THF, slowly added dropwise using a constant pressure dropping funnel, and heated to reflux for 12 h. After the reaction, use 10% K 2 CO 3 The solution was quenched and extracted with ethyl acetate, the organic phase was washed with water, the organic phase was collected and washed with anhydrous Mg 2 SO 4 dry. Finally, the solvent of the organic phase was removed using a rotary evaporator, and the obtained product was washed with ethanol to finally obtain 3.8 g of white solid tetraphenylethylene.

[0036] (2) Dissolve tetraphenylethylene (compound 2) obtained in (1) in CH 2 Cl 2 , and slowly add 3mL of Br 2 , s...

Embodiment 2

[0041] Embodiment 2: (R in general formula 1 is a double bond for the parent nucleus)

[0042]

[0043] (1) in N2 Next, compound 3, 42 mg of palladium acetate, 200 g of K 2 CO 3 and 44mg of tricyclohexylphosphine were added to the reaction tube, then 10mL of DMF and 130g of 4-vinylpyridine were added, heated to reflux for 48h, and then cooled to room temperature. The solvent was removed by rotary evaporator with CHCl 3 The product was extracted and washed with water, the organic phase was collected and washed with anhydrous Mg 2 SO 4 dry. Finally, the organic phase was purified by silica gel column chromatography, the eluent was CHCl3:MeOH=30:1, and the yellow product 6 was finally obtained.

[0044] (2) Compound 6 with 29mg BrCH 2 CH 2 COOH was dissolved in 1mL DMF and heated to reflux for 24h. Then, cool to room temperature, add excess acetone, collect the precipitate, wash the precipitate with acetone and petroleum ether, and dry in vacuum to obtain the final co...

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Abstract

The invention discloses a compound shown as a general structural formula (I). The compound is obtained by using tetraphenylethylene as a mother nucleus, using simple coupling reactions of Suzuki, Heck and the like and a substitution reaction of Sn2 as well as introducing a water-soluble group for designing and synthesizing. The compounds have the advantages of excellent luminescent properties, water solubility, short synthetic route, simple and convenient method and high practical value. (The formula is shown in the description).

Description

[0001] Technical field [0001] The present invention relates to the synthesis of a series of water-soluble fluorescent dye compounds that can be applied to cell fluorescence color development and its cell color development function. Background technique [0002] Traditional biological detection methods include radioactive isotope labeling, microscope observation and electrochemistry, but isotope labeling has the risk of radiation and with the arrival of half-life, the detection signal will be greatly reduced; microscope observation is not effective due to the limitation of magnification Observing the specific process of biological activities and electrochemical monitoring are easy to destroy biological samples. These shortcomings have led to great limitations in the practical application of traditional biological detection methods. However, compared with traditional detection methods, fluorescence analysis technology has become the most important biological detection method beca...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D213/20C07D213/127C09K11/06C09B57/00G01N21/64
CPCC07D213/127C07D213/20C09B57/00C09K11/06C09K2211/1007C09K2211/1029G01N21/6486
Inventor 曹利平李亚雯董运红
Owner NORTHWEST UNIV(CN)
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