Fluorescent probe compound and its preparation method and application

A fluorescent probe and compound technology, applied in the field of biological analysis, can solve the problems of cumbersome ligand operations and low accuracy, and achieve the effects of clear binding sites, convenient and fast detection, and good stability

Active Publication Date: 2022-08-09
HUNAN AGRICULTURAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] The purpose of the present invention is to provide a fluorescent probe compound and its preparation method and application, which can effectively detect The ability of the sample to be tested to bind to ERRα, with high accuracy and simple operation, can be used for high-throughput rapid screening

Method used

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  • Fluorescent probe compound and its preparation method and application
  • Fluorescent probe compound and its preparation method and application
  • Fluorescent probe compound and its preparation method and application

Examples

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preparation example Construction

[0063] A second aspect of the present invention provides a method for preparing a fluorescent probe compound represented by formula (I), comprising the following steps:

[0064] In the presence of the reaction solvent I and the catalyst I, the compound represented by the formula (II) and the organic fluorescent molecule having the reactivity with the amino group are reacted I,

[0065]

[0066] According to the present invention, the compound represented by the formula (II) can provide a ligand with specific interaction with the ERRα protein, and different organic fluorescent molecules with reactivity with amino groups can be selected according to the application requirements to interact with the compound represented by the formula (II). The compounds shown form the corresponding fluorescent probe compounds.

[0067] Preferably, the organic fluorescent molecules having reactivity with amino groups are selected from:

[0068] one of the.

[0069] In the present inventi...

preparation example 1

[0104] (1) Dissolve 1 g of 4-fluoro-3-(trifluoromethyl)benzonitrile and 0.8 g of 4-hydroxy-3-methoxybenzaldehyde in 10 mL of dimethylformamide (DMF), and then add 2.2 g's K 2 CO 3 , heated to 65°C overnight to obtain reaction solution I, which was diluted with 1 mL of ice water, and then extracted three times with 10 mL of ethyl acetate. The liquid is acetic acid / n-hexane, and the volume ratio is 1:10) to obtain the compound shown in the formula (III) of 1.4g pale yellow;

[0105] (2) 1.3 g of the compound represented by the formula (III), 515 mg of 2,4-thiazolidinedione and 3.3 g of sodium acetate (NaOAc) were added to 20 mL of acetonitrile (ACN), and the temperature was 100°C The reaction was carried out for 24 h to obtain reaction solution II, and the organic phase of reaction solution II was spin-dried, and then purified by silica gel column chromatography (the eluent was acetic acid / n-hexane, and the volume ratio was 1:2) to obtain 857 mg of yellow solid, which was the ...

preparation example 2

[0109] (1) 0.8 g of 4-fluoro-3-(trifluoromethyl)benzonitrile and 0.7 g of 4-hydroxy-3-methoxybenzaldehyde were dissolved in 10 mL of dimethylformamide, and then 1.8 g of Na 2 CO 3 , heated to 60°C overnight to obtain reaction solution I, which was diluted with 1 mL of ice water, and then extracted three times with 10 mL of ethyl acetate. The liquid is acetic acid / n-hexane, and the volume ratio is 1:10) to obtain the compound shown in the pale yellow formula (III);

[0110] (2) 1 g of the compound represented by the formula (III), 0.4 g of 2,4-thiazolidinedione and 2.4 g of potassium acetate were added to 20 mL of acetonitrile, and reacted for 30 h at a temperature of 80 °C to obtain a reaction solution II, the organic phase of the reaction solution II is spin-dried, and then purified by silica gel column chromatography (the eluent is acetic acid / n-hexane, the volume ratio is 1:2) to obtain a yellow solid, which is the compound shown in formula (IV) ;

[0111] (3) Dissolve ...

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Abstract

The invention relates to the field of biological analysis, and discloses a fluorescent probe compound and a preparation method and application thereof. A class of fluorescent probe compounds, having the structure shown in formula (I), wherein R is an organic fluorescent molecular group having reactivity with amino groups; the present invention also provides the preparation of the fluorescent probe compounds shown in formula (I) The method includes the following steps: in the presence of a reaction solvent I and a catalyst I, the compound represented by the formula (II) and an organic fluorescent molecule having reactivity with an amino group are reacted I; the fluorescent probe compound provided by the present invention can be It can effectively detect the binding ability of the sample to be tested and ERRα, with high accuracy and simple operation, and can be used for high-throughput rapid screening;

Description

technical field [0001] The present invention relates to the field of biological analysis, in particular, to a fluorescent probe compound and a preparation method and application thereof. Background technique [0002] Estrogen Related Receptorα (ERRα) is a member of the nuclear receptor family, and its endogenous ligands have not yet been resolved. The nuclear receptor ER has a high similarity and is named estrogen-related receptor. Although natural estrogen cannot directly bind to ERRα, ERRα can compete with the classical estrogen receptor ER to bind estrogen response elements and co-activators during signal transduction, thereby affecting estrogen-related physiological functions. Studies have shown that ERRα plays an important role in the estrogen signaling pathway of breast cancer cells, and its expression is correlated with poor prognosis of breast cancer patients. Therefore, ERRα is regarded as a potential biomarker and drug therapy target for breast cancer. The expres...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D471/14C07D417/12C07F5/02C09K11/06G01N21/64G01N33/68
CPCC07D471/14C07D417/12C07F5/022C09K11/06G01N21/6428G01N33/68C09K2211/1007C09K2211/1014C09K2211/1037C09K2211/1088C09K2211/1055G01N2021/6432
Inventor 曹林英杨远罗琳何森李鑫张佳大
Owner HUNAN AGRICULTURAL UNIV
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