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Cavity type chelating agent and preparation method thereof

A chelating agent, crypt-shaped technology, applied in the field of homogeneous fluorescence immunoassay, can solve the problems of reducing the signal/noise ratio, reducing the analytical sensitivity, difficult to provide measurement signals, etc., to improve the sensitivity, reduce non-specific reactions, long fluorescence lifetime Effect

Inactive Publication Date: 2018-11-23
CHANGCHUN INST OF APPLIED CHEMISTRY - CHINESE ACAD OF SCI
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  • Claims
  • Application Information

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Problems solved by technology

However, the Raman scattering produced by the liquid phase and the 300-600nm background fluorescence produced by the macromolecules overlap with the measured fluorescence wavelength, and its fluorescence lifetime is 1-50ns, which reduces the signal / noise ratio and reduces the sensitivity of the analysis.
Another limiting factor in the sensitivity of homogeneous immunoassays is that the measurement signal depends on the addition of an initiator or quencher to generate a measurement signal or to clear the measurement signal, which is difficult to provide a strong enough measurement signal

Method used

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  • Cavity type chelating agent and preparation method thereof
  • Cavity type chelating agent and preparation method thereof
  • Cavity type chelating agent and preparation method thereof

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preparation example Construction

[0042] The present invention also provides the preparation method of cryptate, this method comprises:

[0043] Step 1: Solvent, N,N',N,N'-[bis(2,2'-bipyridine-6,6'-dimethyl)]diamine, Li 2 CO 3 Add it into the reaction flask, reflux for 0.5-1.5h, then dropwise add the solution of 6,6'-dibromodimethyl-2,2'-bipyridyl-4-carboxylate methyl ester, and continue the reaction for 30-50h, Cooled to room temperature, the reaction solution was suction filtered, rotary evaporated, and separated by column chromatography to obtain the first intermediate;

[0044] The solvent is preferably acetonitrile, and the N,N',N,N'-[bis(2,2'-bipyridine-6,6'-dimethyl)]diamine and 6,6'- The molar ratio of methyl dibromodimethyl-2,2'-bipyridine-4-carboxylate is preferably 1:(1-2.5); more preferably 1:(1.5-2). The dripping time is preferably 1-2.5h; the specific reaction is as follows:

[0045]

[0046] Step 2: Add the solvent and the first intermediate obtained in Step 1 to the reaction flask, and t...

Embodiment 1

[0054] Embodiment 1 Preparation of chelating agent formula I

[0055] The compound N,N',N,N'-[bis(2,2'-bipyridine-6,6'-dimethyl)]diamine 0.338mmol and Li 2 CO 3 (3.387mmol) was dissolved in 267mL of acetonitrile, heated to reflux for 1h, slowly added dropwise 6,6'-dibromodimethyl-2,2'-bipyridine-4-carboxylic acid methyl ester (0.339mmol) within 1.0h 67mL of acetonitrile solution, reflux reaction for 30h, cooled to room temperature, the reaction solution was suction filtered, and rotary evaporated to obtain a crude product, which was separated by column chromatography to obtain the first intermediate C4 with a yield of 51.5%;

[0056] The first intermediate compound C4 (7.91 × 10 -5 mol), methanol 30mL, EuCl 3 (2.32×10 -4 mol) methanol solution was added to the reaction flask, stirred and refluxed for 23h, cooled to room temperature, and blown dry with nitrogen to obtain 47 mg of white precipitate, the second intermediate C5, which was dried for later use without purificati...

Embodiment 2

[0060] Embodiment 2 Preparation of chelating agent formula I

[0061] The compound N,N',N,N'-[bis(2,2'-bipyridine-6,6'-dimethyl)]diamine (0.338mmol) and Li 2 CO 3 (3.387mmol) acetonitrile solution, after heating up to reflux for 1h, slowly dropwise add 6,6'-dibromodimethyl-2,2'-bipyridine-4-carboxylic acid methyl ester (0.507mmol) in 1.0h Acetonitrile solution was reacted for 35 hours, cooled to room temperature, the reaction solution was suction filtered, and rotary evaporated to obtain a crude product, which was separated by column chromatography to obtain the first intermediate C4 with a yield of 53.9%.

[0062] The first intermediate compound C4 (7.91 × 10 -5 mol) with absolute methanol 30mL, EuCl 3 (1.58×10 -4 mol) methanol solution was added to the reaction flask, stirred and heated to reflux, continued to react for 23 h, cooled to room temperature, and blown dry the liquid in the cup with nitrogen to obtain 47 mg of the second intermediate C5 as a white precipitate....

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Abstract

The invention provides a cavity type chelating agent and a preparation method thereof, and belongs to the technical field of homogeneous fluorescence immunoassay. A structural formula of the chelatingagent is shown in a formula 1. The structure is characterized in that a single linkage group is introduced to the site 4 of pyridine to mark the protein; the non-specific reaction in the marking process is favorably reduced. The chelating agent has the advantages that the heat stability and dynamics chelating stability are realized, the proper exciting wavelength and transmission wavelength are realized, the chelating agent and the rare earth ions can reach the triple stages of energy transfer, the covalence-binding functional groups can be formed between the chelating agent and the biological molecules, and the fluorescence lifetime is longer. The invention also provides the preparation method of the cavity type chelating agent. The cavity type chelating agent is characterized in that the wavelength range of exciting spectrum is 258 to 356nm, and the maximum exciting wavelength is 331nm; the fluorescence spectrum peaks of europium ion feature are 595nm, 612nm and 615nm, and the fluorescence lifetime is longer than 800s.

Description

technical field [0001] The invention belongs to the technical field of homogeneous fluorescence immunoassay, and in particular relates to a cryptate chelating agent and a preparation method thereof. Background technique [0002] Homogeneous immunoassay is an analytical method that can be directly measured in liquid phase without repeated washing to separate bound and free markers. This method is simple, fast, and easy to realize automatic operation, so it has long been one of the main goals pursued by immunoassay methodology research. [0003] Boguslaski et al. used fluorescent dyes instead of enzyme-labeled homogeneous immunoassays. However, the Raman scattering produced by the liquid phase and the 300-600nm background fluorescence produced by the macromolecules overlap with the measured fluorescence wavelength, and its fluorescence lifetime is 1-50ns, which reduces the signal / noise ratio and reduces the sensitivity of the analysis. . Another limiting factor in the sensi...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D471/22C09K11/06G01N21/64
CPCC07D471/22C09K11/06C09K2211/182G01N21/6428G01N2021/6432
Inventor 潘利华常宇王杰陈华鑫曹雪崔恩超
Owner CHANGCHUN INST OF APPLIED CHEMISTRY - CHINESE ACAD OF SCI
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