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Three fluorescence complexes formed on basis of Eu (III) and chlorosulfonation four-tooth Beta-diketone ligands and application thereof

A technology for chlorosulfonylation of tetradentate and ligands, which is applied in the field of fluorescent complexes, can solve the problems of limited probe types, expensive probe reagents, and restrictions on the development and application of time-resolved fluorescence biochemical analysis techniques, achieving cost Effects of low, high stability, and long fluorescence lifetime

Inactive Publication Date: 2012-03-28
DALIAN UNIV OF TECH
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  • Abstract
  • Description
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Problems solved by technology

[0005] It should be pointed out that although BHHCT-Eu 3+ Several tetradentate β-diketone-europium(III) fluorescent complex biomarker probes have been developed, but the types of rare earth fluorescent complex biomarker probes are still very limited, commercial probes Needle reagents are expensive, which largely restricts the development and application of time-resolved fluorescence biochemical analysis techniques

Method used

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  • Three fluorescence complexes formed on basis of Eu (III) and chlorosulfonation four-tooth Beta-diketone ligands and application thereof
  • Three fluorescence complexes formed on basis of Eu (III) and chlorosulfonation four-tooth Beta-diketone ligands and application thereof
  • Three fluorescence complexes formed on basis of Eu (III) and chlorosulfonation four-tooth Beta-diketone ligands and application thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0028] Example 1: Synthesis of three chlorosulfonylated tetradentate β-diketone ligands BHHBCB, BPPBCB and BTBBCB

[0029] The synthetic routes of three chlorosulfonylated tetradentate β-diketone ligands are as follows: figure 1 As shown, the synthetic processes of the three ligands are similar, only in the 1,2-bis(fluoroalkyl-β-diketonyl-p-benzyl)benzene synthesis step, the type of ethyl fluoroalkylcarboxylate used The specific experimental process is as follows.

[0030] (1) Synthesis of 1,2-bis(4'-acetylbenzyl)benzene.

[0031] Add 2.64g (10mmol) of 1,2-di(bromomethyl)benzene, 5.91g (36mmol) of 4-acetylphenylboronic acid, and 6.90g (50mmol) of potassium carbonate into a round-bottomed flask containing 60mL of acetone and 20mL of water, Stir under cooling in an ice-water bath until most of it dissolves, then add 70.90 mg (0.4 mmol) of palladium chloride, heat to 50° C. under argon protection, and stir for 12 hours. After the reaction, the solvent was evaporated under redu...

Embodiment 2

[0036] Example 2: Preparation of Europium(III) complexes of three chlorosulfonylated tetradentate β-diketone ligands to label bovine serum albumin

[0037] The chlorosulfonyl groups contained in the three ligands can react with amino-containing biomolecules to form sulfonamide covalent bonds and be labeled on biomolecules. In order to investigate the use of three chlorosulfonylated tetradentate β-diketone ligands for The labeling conditions of actual biomolecules and the fluorescent properties of the complexes formed by the three ligands and europium (III) after the biomolecules are labeled. In this example, bovine serum albumin (BSA for short) was used as a model biomolecule to prepare BHHBCB, The BSA solution labeled with the trivalent europium complex of BPPBCB and BTBBCB, the specific experimental method is as follows.

[0038] After dissolving 10.0 mg of BSA in 2.0 mL of 0.05 mol / L sodium carbonate buffer solution with a pH value of 9.3, slowly add 9.0×10 -3 A solution o...

Embodiment 3

[0040] Example 3: Measurement of Fluorescence Spectra and Fluorescent Properties of Three Europium (III) Complexes Labeled BSA

[0041] Dilute the three kinds of europium (III) complex-labeled BSA solutions to an appropriate concentration with 0.05mol / L boric acid buffer solution with a pH value of 9.1, and then measure the steady-state fluorescence excitation and emission spectra and fluorescence quantum yields (φ ) and fluorescence lifetime (τ), the results are shown in Table 1.

[0042] Table 1. Fluorescence properties of BSA solutions labeled with three europium(III) complexes

[0043]

[0044] figure 2 , image 3 and Figure 4 BHHBCB-Eu are given respectively 3+ 、BPPBCB-Eu 3+ and BTBBCB-Eu 3+ The time-resolved fluorescence excitation and emission spectra of the labeled BSA solution diluted with 0.05mol / L Tris-HCl buffer solution with a pH value of 7.8. The measurement conditions are: delay time, 0.2ms; counting window time, 0.4ms; cycle time, 20ms; Excitation s...

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Abstract

The invention relates to three luorescence complexes formed on the basis of Eu (III) and chlorosulfonation four-tooth Beta-diketone ligands, as well as the application thereof. The three luorescence complexes are formed through Eu3+ and three chlorosulfonation four-tooth Beta-diketone ligands, namely 1, 2-bi (1', 1', 1', 2', 2', 3', 3' -seven fluorine-4', 6- hexanedione-6'-group- para- phenmethyl)-4- chlorine sulfonyl benzene, 1, 2-bi(1', 1', 1', 2', 2'- pentafluoride-3', 5'- pentanedione-5'-group- para- phenmethyl)-4- chlorine sulfonyl benzene and 1, 2-bi(1', 1', 1'- trifluoride-2', 4'- butanedione-4'-group- para- phenmethyl)-4- chlorine sulfonyl benzene. The three chlorosulfonation four-tooth Beta-diketone ligands are that three probes are covalently attached with moleculars such as protein containing amino group, amino acid, peptide, nucleic acid and the like and used as fluorescence labelings for the moleculars, and used for biological determinations such as time-resolved fluoroimmunoassay and the like.

Description

technical field [0001] The present invention relates to three kinds of fluorescent complexes formed based on europium (III) and chlorosulfonylated tetradentate β-diketone ligands and their application, specifically three kinds of trivalent europium that can be used for biomolecular labeling Preparation of fluorescent complexes of ions with chlorosulfonylated tetradentate β-diketones and their application in time-resolved fluorescence biochemical detection. Background technique [0002] Rare earth ions (including Eu 3+ , Tb 3+ 、Sm 3+ 、Dy 3+ ) fluorescent complexes have very special fluorescent properties, such as ultra-long fluorescence lifetime, Stokes shift above 200 nm and sharp fluorescence emission spectrum, so they are widely used as fluorescent labeling probes for biomolecules in time-resolved fluorescence biochemistry Analyze technical fields. As a highly sensitive biochemical analysis technique, time-resolved fluorescence biochemical analysis methods such as tim...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C309/86C07C303/08C09K11/06G01N21/64G01N33/533
Inventor 袁景利张琳叶志强王桂兰
Owner DALIAN UNIV OF TECH
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