Fluorescent probe having hydrogen peroxide detection function and preparation method and application thereof

A fluorescent probe and reaction technology, applied in chemical instruments and methods, organic chemistry, fluorescence/phosphorescence, etc., can solve the problems of complex synthesis route, enzymatic decomposition, low content, etc., and achieve simple preparation route, low synthesis cost, processing handy effect

Active Publication Date: 2019-07-05
XIANGTAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In addition, the presence of H in living organisms 2 o 2 The phenomenon that the content is low and is easily decomposed by enzymes in the living body
Currently reported H 2 o 2 Fluorescent probes generally have problems such as narrow detection range and complex synthesis routes.

Method used

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  • Fluorescent probe having hydrogen peroxide detection function and preparation method and application thereof
  • Fluorescent probe having hydrogen peroxide detection function and preparation method and application thereof
  • Fluorescent probe having hydrogen peroxide detection function and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] One capable of detecting H 2 o 2 The preparation method of fluorescent probe comprises the following steps:

[0028] (1) Preparation of 2,5-bis(4-pyridyl)thiazolo[5,4-d]thiazole: Dithiooxamide (1mmol) and 4 -Pyridinecarbaldehyde (3mmol) was dissolved in 10mL of anhydrous N,N'-dimethylformamide, heated to reflux at 150°C, reacted for 8h, filtered, then rinsed with deionized water, and dried in vacuo to obtain 2,5-bis (4-pyridyl)thiazolo[5,4-d]thiazole.

[0029] (2) Preparation of fluorescent probe N,N'-bis(4-methylenemethylphenylboronic acid) 2,5-bis(4-pyridinium salt)thiazolo[5,4-d]thiazole dibromide: 2 , 5-bis(4-pyridyl)thiazolo[5,4-d]thiazole (0.1mmol) and 4-bromomethylphenylboronic acid pinacol ester (7mmol) were dissolved in 10mL of acetonitrile and heated to 90°C for reaction 6h, filtered, rinsed with n-hexane, and dried under vacuum to obtain the small molecule fluorescent probe N,N'-bis(4-methylenemethylphenylboronic acid) 2,5-bis(4-pyridinium salt)thiazolo[5...

Embodiment 2

[0031] Prepare 11 parts of fluorescent probe solution with distilled water, the solution concentration is 2.5μM, the volume is 3mL, and then, the H 2 o 2 0 μM (a), 15 μM (b), 20 μM (c), 100 μM (d) in 30 μL of HO 2 o 2 Solution is added in every part of probe solution, after stirring at room temperature for 30S, measure the fluorescence intensity of every part of solution, 395nm is used as excitation wavelength, then obtain the fluorescence emission spectrum change pattern of every part of solution ( image 3 ). The test results show that with the H 2 o 2 As the concentration increases, the fluorescence intensity of the fluorescent probe decreases. and H 2 o 2 When the concentration is greater than 20 μM, the fluorescence intensity decreases significantly.

Embodiment 3

[0033] Prepare 1 part of the fluorescent probe solution with distilled water, the solution concentration is 2.5 μM, the volume is 3 mL, and then add 100 μM (d) 30 μL of H 2 o 2 solution into the probe solution, after stirring at room temperature, measure the fluorescence intensity of the solution along with the reaction time, 395nm is used as the excitation wavelength, then obtain the fluorescence emission spectrum change spectrum of the solution ( Figure 4 ). The test results show that with the increase of the reaction time, the fluorescence intensity of the fluorescent probe decreases, and when the reaction time is 3 minutes, the fluorescence intensity decreases obviously.

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Abstract

The invention discloses a fluorescent probe having a hydrogen peroxide (H2O2) detection function and a preparation method and application thereof. The fluorescent probe is a novel fluorescent probe prepared by using 4-pyridine formaldehyde, dithiooxamide and 4-bromomethyl phenylborate pinacol ester as raw materials. Further studies show that the probe can achieve rapid and sensitive detection of H2O2. Compared with existing fluorescence detection technologies, the fluorescent probe obtained by means of the method has the advantages that the selectivity to H2O2 is high, there are no organic solvent residues, the response is sensitive, a synthesis route is simple, and a detection method is simple. The preparation method is applicable to practical production application and has a great application prospect in the technical fields of analytical chemistry, medicine, life science, environmental engineering and the like.

Description

technical field [0001] The invention belongs to the technical field of small molecule fluorescent probe materials, in particular to a detectable hydrogen peroxide (H 2 o 2 ) water-soluble small molecule fluorescent probe and its preparation method and application. Background technique [0002] h 2 o 2 It is a common reactive oxygen species in organisms and plays an important role in cell activities. h 2 o 2 It is the precursor of other active oxygen and also the by-product of other active oxygen. When the H in the organism 2 o 2 When excessive, oxidative stress may occur, resulting in certain diseases, such as cancer, diabetes, cardiovascular disease, neurodegeneration, Alzheimer's disease, etc. Therefore, in chemical science, environmental science, life science, clinical diagnosis and other fields to H 2 o 2 detection is of great significance. Currently, H 2 o 2 Conventional methods for detection include spectrophotometry, titration, chromatography, electroche...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F5/04C09K11/06G01N21/64
CPCC07F5/04C09K11/06C09K2211/1007C09K2211/1029C09K2211/1037C09K2211/1096G01N21/6428G01N21/6486
Inventor 熊迪许珍珠吴志民胡琼喻超刘跃进罗佳钰
Owner XIANGTAN UNIV
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