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Fluorescent probe as well as preparation method and application thereof

A fluorescent probe and reaction technology, applied in fluorescence/phosphorescence, chemical instruments and methods, luminescent materials, etc., can solve the problems of insufficient selectivity and interference of hydrogen peroxide, and achieve good application prospects, high selectivity, high Effect of Sensitivity Recognition and Detection

Active Publication Date: 2021-07-16
YUNNAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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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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  • Fluorescent probe as well as preparation method and application thereof
  • Fluorescent probe as well as preparation method and application thereof
  • Fluorescent probe as well as preparation method and application thereof

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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 as well as a preparation method and application thereof, and belongs to the technical field of hydrogen peroxide detection. The fluorescent probe provided by the invention has a structure as shown in a formula I. Molecules of the fluorescent probe provided by the invention contain a phenylboronic acid ester structure capable of acting with hydrogen peroxide, so that the fluorescent probe has interference resistance to other substances such as active oxygen, active nitrogen and active sulfur, and has high selectivity to hydrogen peroxide; the phenylboronic acid ester in the fluorescent probe is disconnected after reacting with hydrogen peroxide and is oxidized into hydroxyl, wherein the fluorescence intensity of the fluorescent probe is improved by about 30 times compared with that before reacting with hydrogen peroxide, and the color and fluorescence change sensitivity is high, so that high-selectivity and high-sensitivity recognition and detection of hydrogen peroxide in water or cells are realized; moreover, the fluorescence probe molecule provided by the invention has good cell penetrating permeability and low toxicity, and can realize fluorescence detection of hydrogen peroxide in cells; in conclusion, the fluorescence probe has a good application prospect in detection of hydrogen peroxide in water or cells.

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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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
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