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Compound of di-butanedione, complexes of europium, combination of containing the complexes and application

A bis-butyledione and compound technology, which is applied in the field of new-type bis-butyledione compounds, can solve problems such as insufficient chelation degree of europium complexes, decreased coating capacity on the surface of nano-microspheres, and decreased luminous efficiency.

Active Publication Date: 2008-10-29
BEYOND DIAGNOSTICS (SHANGHAI) CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0022] Due to the insufficient chelation degree of the existing europium complexes, the metal europium ions will be chelated on the surface of the nano-microspheres, resulting in a decrease in the coating capacity of the nano-microspheres surface
and reduce the luminous efficiency
After placing the composition containing the metal chelate (a) and the compound (b) with double bonds having two aryl groups in the nano-scale luminescent microspheres, it was found that the coating of the luminescent microspheres Capacity drops up to 40%; luminous efficiency drops by 30%-40%
[0023] Therefore, it is necessary to develop a new metal chelate compound with strong chelating force, which can avoid the reaction of metal europium ions and the surface groups of nano-microspheres, thereby avoiding the surface coating capacity and luminous efficiency of nano-microspheres. Decline

Method used

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  • Compound of di-butanedione, complexes of europium, combination of containing the complexes and application
  • Compound of di-butanedione, complexes of europium, combination of containing the complexes and application
  • Compound of di-butanedione, complexes of europium, combination of containing the complexes and application

Examples

Experimental program
Comparison scheme
Effect test

Synthetic example 1

[0126] Synthesis of compound (A) containing unsaturated ethylenic bond: 34.4g (0.2mol) bromoaniline is dissolved in 125ml DMF, add 0.6mol bromotetradecane and 0.6mol diisopropylethylamine, the reaction solution is heated to 100°C, then reacted for 12 hours. The reaction solution was added with 300ml of dichloromethane, washed with water three times to remove DMF. The dichloromethane was removed and the product was recrystallized from ethanol. Obtain N, N-disubstituted p-bromoaniline (compound of formula I), the productive rate of reaction is 70%

[0127]

[0128] to a dropping funnel, thermometer and reflux condenser Add 100ml dry THF in the round-bottomed three-necked flask, then add 3g metal magnesium bars, add a small amount of N, N-disubstituted p-bromoaniline product (formula I compound) obtained above under reflux conditions to start the reaction, and add A small amount of iodine is added to help the reaction start. Dissolve 0.11 mol of the above-mentioned N,N-di...

Synthetic example 2

[0134] Synthesis of Compounds Containing Unsaturated Ethylenic Bonds (B)

[0135] Dissolve 34.4g (0.2mol) of bromoaniline in 125ml of DMF, add 0.6mol of bromobutane and 0.6mol of diisopropylethylamine, heat the reaction solution to 100°C, and react for 12 hours. The reaction solution was added with 300ml of dichloromethane, washed with water three times to remove DMF. The dichloromethane was removed and the product was recrystallized from ethanol. Obtain N, N-disubstituted p-bromoaniline (compound of formula 1), the productive rate of reaction is 70%

[0136]

[0137] Add 100ml of dry THF to a 500ml round-bottomed three-necked flask equipped with a dropping funnel, a thermometer and a reflux condenser, then add 3g of metal magnesium bars, and add a small amount of the above-obtained N,N-disubstituted p-bromoaniline product (compound of formula 1) to initiate the reaction. 0.11mol of the above N,N-disubstituted p-bromoaniline product (compound of formula 1) was dissolved ...

Synthetic example 3

[0143] Synthetic Ligand Compound 1

[0144]

[0145] (1) Dissolve 2.3g o-phenylbiphenyl in 20ml dry CH 2 Cl 2 solution, add 2.94g AlCl 3 , and then cooled to 0 °C. Add 2 g of CH under vigorous stirring 3 C(O)Cl (available from Aldrich / Sigma). After the addition was complete, the reaction was allowed to react at room temperature for 1-2 hours. The organic solution was washed three times with water, and then dried over anhydrous sodium sulfate. 2.6 g of product (81% yield) were obtained after removal of the solvent.

[0146]

[0147] 1 H NMR: 7.1-7.9ppm (multiplet, 12H), 2.3ppm (singlett, 6H)

[0148] (2) Dissolve 1.6g of the above product in 20ml of anhydrous ether, add 1g of CH 3 ONa (sodium methoxide) and 2g CF 3 -C(O)OEt (ethyl trifluoroacetate). The reaction was allowed to stir at room temperature for 2-3 hours. Then wash with water three times. Organic layer is dried with anhydrous sodium sulfate, obtains 1.6g product (productive rate 80%) after removing...

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PUM

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Abstract

A chemically luminous composition contains the Eu matches and enyl-bond contained compound. It can be used for immonoanalysis.

Description

technical field [0001] The present invention relates to a novel dibutyldiketone compound, a europium complex containing the compound as a ligand and a composition containing the europium complex. The invention also relates to the use of said composition in chemiluminescent immunoassays. Background technique [0002] So far, the immunoassay methods of trace bioactive substances in organisms have gone through various stages such as radioimmunoassay (RIA), fluorescence immunoassay (FIA), enzyme-linked immunoassay (EIA), and chemiluminescence immunoassay. This evolution process is mainly based on the continuous improvement of the demand for the sensitivity, accuracy, and simplicity of operation of the detection method. [0003] Just like the evolution of radioimmunoassay (RIA) analysis technology from invention to application, chemiluminescence immunoassay has become a powerful analytical method and technology to replace radioimmunoassay. In the international field, chemilumin...

Claims

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Application Information

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IPC IPC(8): C07C49/80C07F5/00C07D327/06C07D265/30C07D417/04G01N33/53C09K11/06
Inventor 何元
Owner BEYOND DIAGNOSTICS (SHANGHAI) CO LTD
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