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Fluorescent probe compound, and preparation method and application thereof

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: 2021-12-14
HUNAN AGRICULTURAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

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 preparation method and application thereof
  • Fluorescent probe compound, and preparation method and application thereof
  • Fluorescent probe compound, and preparation method and application thereof

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preparation example Construction

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

[0064] Under the condition that reaction solvent I and catalyst I exist, the compound shown in formula (II) is reacted I with the organic fluorescent molecule that has reactivity with amino group,

[0065]

[0066] According to the present invention, the compound represented by the formula (II) can provide a ligand that specifically interacts with the ERRα protein, and different organic fluorescent molecules with reactivity with the amino group can be selected according to application requirements, so as to be compatible with the formula (II) The compounds shown form the corresponding fluorescent probe compounds.

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

[0068] One of.

[0069] In the present invention, the reaction solvent I is N,N-dimethylfo...

preparation example 1

[0104] (1) Dissolve 1g of 4-fluoro-3-(trifluoromethyl)benzonitrile and 0.8g of 4-hydroxyl-3-methoxybenzaldehyde in 10mL of dimethylformamide (DMF), then add 2.2 K of g 2 CO 3 , heated to 65°C overnight to obtain the reaction solution I, the reaction solution I was diluted with 1mL of ice water, then extracted three times with 10mL of ethyl acetate, after the three extracts were combined, concentrated by drying, and passed through silica gel column chromatography (elution Liquid is acetic acid / normal hexane, volume ratio is 1:10) obtains the compound shown in the formula (III) of 1.4g pale yellow;

[0105] (2) 1.3g of the compound represented by formula (III), 515mg of 2,4-thiazolidinedione and 3.3g of sodium acetate (NaOAc) were added to 20mL of acetonitrile (ACN), at a temperature of 100°C After reacting for 24 hours to obtain reaction solution II, the organic phase of reaction solution II was spin-dried, and then purified by silica gel column chromatography (eluent was ace...

preparation example 2

[0109] (1) Dissolve 0.8g of 4-fluoro-3-(trifluoromethyl)benzonitrile and 0.7g of 4-hydroxyl-3-methoxybenzaldehyde in 10mL of dimethylformamide, then add 1.8g of Na 2 CO 3 , heated to 60°C overnight to obtain the reaction solution I, the reaction solution I was diluted with 1mL of ice water, then extracted three times with 10mL of ethyl acetate, after the three extracts were combined, dried and concentrated, passed through silica gel column chromatography (eluted Liquid is acetic acid / normal hexane, volume ratio is 1:10) obtains the compound shown in the pale yellow formula (III);

[0110] (2) Add 1g of the compound represented by formula (III), 0.4g of 2,4-thiazolidinedione and 2.4g of potassium acetate into 20mL of acetonitrile, and react for 30h 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 ...

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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. The fluorescent probe compound has a structure as shown in a formula (I), and R in the formula (I) is an organic fluorescent molecular group with reaction activity with amino. The invention also provides the preparation method of the fluorescent probe compound as shown in the formula (I). The preparation method comprises the following step: in the presence of a reaction solvent I and a catalyst I, carrying out reaction I on a compound as shown in the formula (II) and an organic fluorescent molecule with amino reaction activity. The fluorescent probe compound provided by the invention can effectively detect the binding capacity of a to-be-detected sample and ERRalpha, is high in accuracy and simple to operate, and can be used for high-flux rapid screening.

Description

technical field [0001] The invention relates to the field of biological analysis, in particular to a fluorescent probe compound and its preparation method and application. Background technique [0002] Estrogen Related Receptor α (Estrogen Related Receptor α, ERRα), a member of the nuclear receptor family, its endogenous ligand has not yet been resolved, is listed as an orphan nuclear receptor, because its DNA sequence is similar to the classic estrogen The nuclear receptor ER has a high similarity, so it is named estrogen-related receptor. Although natural estrogen cannot directly bind to ERRα, ERRα can compete with the classic estrogen receptor ER for binding to estrogen response elements and coactivators 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 the poor prognosis of breast cance...

Claims

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Application Information

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Patent Type & Authority Applications(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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