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A kind of hydrogen peroxide fluorescent probe and its preparation method and application

A fluorescent probe and reaction technology, applied in chemical instruments and methods, fluorescence/phosphorescence, material analysis through optical means, etc., can solve the problems of insufficient selectivity and interference of hydrogen peroxide, and achieve good application prospects, high Effect of selectivity and light property stabilization

Active Publication Date: 2022-05-06
YUNNAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the existing boronate-based probes have the disadvantage of being interfered by other active oxygen molecules (such as peroxynitroso, etc.), and the selectivity to hydrogen peroxide is not high enough.

Method used

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  • A kind of hydrogen peroxide fluorescent probe and its preparation method and application
  • A kind of hydrogen peroxide fluorescent probe and its preparation method and application
  • A kind of hydrogen peroxide fluorescent probe and its preparation method and application

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preparation example Construction

[0039] The present invention provides a method for preparing the fluorescent probe described in the above technical solution, comprising the following steps:

[0040] Mixing the first compound of the structure shown in formula II, hydrogenation salt and anhydrous organic solvent to carry out the first substitution reaction; mixing the reaction solution obtained by the first substitution reaction with the second compound of the structure shown in formula III The second substitution reaction obtains the fluorescent probe of the structure shown in formula I;

[0041]

[0042] In the present invention, unless otherwise specified, all raw material components are commercially available products well known to those skilled in the art.

[0043]In the present invention, the first compound of the structure shown in the formula II is preferably prepared by the following method: under a protective atmosphere, 2,4-dihydroxybenzaldehyde, 2-cyclohexen-1-one and mixed The solvents are mix...

Embodiment 1

[0064] Under nitrogen protection, dissolve 4mmol 2,4-dihydroxybenzaldehyde and 4mmol 2-cyclohexen-1-one in 12mL tetrahydrofuran aqueous solution (water: tetrahydrofuran volume ratio = 1:1), at room temperature under stirring conditions After 3 days of substitution reaction, 12 mL of dilute hydrochloric acid with a concentration of 1 mol / L was added to quench the reaction, and the resulting reaction solution was extracted 3 times with ethyl acetate, and the volume of ethyl acetate added each time was 50 mL, and the organic phases were combined and dried over anhydrous sodium sulfate , filtered, the resulting filtrate was distilled under reduced pressure and then separated and purified by gel chromatography column to obtain the first compound (19% yield) of the structure shown in formula II, wherein the eluent used for the separation and purification of the gel chromatography column was A volume ratio of 6:1 petroleum ether-ethyl acetate mixed solvent;

[0065]Put 4mmol of 4-(hy...

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Abstract

The invention provides a fluorescent probe and its preparation method and application, belonging to the field of hydrogen peroxide detection. The fluorescent probe provided by the invention has the structure shown in formula I. The molecule of the fluorescent probe provided by the present invention contains a phenylboronic ester structure capable of interacting with hydrogen peroxide, has anti-interference properties to other active oxygen, active nitrogen, active sulfur and other substances, and has high selectivity to hydrogen peroxide ; The phenylboronic acid ester in the fluorescent probe reacts with hydrogen peroxide and is disconnected and oxidized to a hydroxyl group. The fluorescence intensity of the fluorescent probe is about 30 times higher than that before reacting with hydrogen peroxide, and the color and fluorescence change sensitivity High, thereby realizing the highly selective, highly sensitive identification and detection of hydrogen peroxide in water or cells; moreover, the fluorescent probe molecules provided by the invention have good permeability and low toxicity, and can realize intracellular peroxide Fluorescent detection of hydrogen oxide; detection of hydrogen peroxide in water or cells has a good application prospect.

Description

technical field [0001] The invention relates to the technical field of hydrogen peroxide detection, in particular to a fluorescent probe and its preparation method and application. Background technique [0002] Hydrogen peroxide (H 2 o 2 ) is an important reactive oxygen species (ROS), which is mainly produced in the mitochondrial aerobic respiration electron transport chain. Involved in many pathological and physiological processes including wound healing, immunity and stem cell proliferation. Excessive accumulation of hydrogen peroxide in cells will cause metabolic disorders in organisms, leading to a series of diseases such as inflammation, aging, cancer, diabetes and neurodegenerative diseases. At the same time, hydrogen peroxide is closely related to cell apoptosis and cell proliferation. Therefore, hydrogen peroxide detection and analysis technology is of great significance for the research of related diseases. [0003] The detection of hydrogen peroxide mainly in...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F5/02C09K11/06G01N21/64A61K49/00A61P35/00
CPCC07F5/025C09K11/06G01N21/643G01N21/6428A61K49/0021A61P35/00C09K2211/1088C09K2211/1007C09K2211/1096
Inventor 周莹杨索房街芹贾明轩王光科
Owner YUNNAN UNIV