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Fluorescence probe for detecting hypochlorite ion as well as preparation method and application thereof

A fluorescent probe and hypochlorite technology, applied in the direction of fluorescence/phosphorescence, chemical instruments and methods, luminescent materials, etc., can solve the problems of detection affected by other ions, fluorescence color changes, long reaction time, etc., and achieve fluorescence intensity enhancement , high selectivity and sensitivity, high sensitivity effect

Active Publication Date: 2019-10-22
NANJING FORESTRY UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the reported ClO - Ionic fluorescent probes still have many deficiencies, such as: only the fluorescent color changes, the sensitivity is not high, the detection is affected by other ions, and the reaction time is long, etc.

Method used

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  • Fluorescence probe for detecting hypochlorite ion as well as preparation method and application thereof
  • Fluorescence probe for detecting hypochlorite ion as well as preparation method and application thereof
  • Fluorescence probe for detecting hypochlorite ion as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] The preparation method of 3-3-(4 "-formyl-1 ', 1 "-biphenyl-4'-formaldehyde oxime) nopinone-based fluoroboron complex, the reaction formula is as follows:

[0031]

[0032] Specific steps are as follows:

[0033] 1. Preparation of 3-(4″-formyl-1′, 1″-biphenyl-4′-formaldoxime)nopinone:

[0034] Add 0.04mol 3-(4″-formyl-1′,1″-biphenyl-4′-carbonyl)nopineone, 0.06mol hydroxylamine and 30mL ethyl acetate in sequence to a condenser equipped with a stirrer, thermometer and reflux In a three-necked flask, the reaction was carried out under reflux for 6 h, and the reaction progress was tracked by thin-layer chromatography. Add 50 mL of ethyl acetate to the reaction solution, wash with distilled water, dry the organic phase over anhydrous sodium sulfate, filter, and concentrate to recover the solvent to obtain 3-(4″-formyl-1′,1″-biphenyl-4′- formaldehyde oxime) nopinone crude product. The crude product of 3-(4″-formyl-1′, 1″-biphenyl-4′-formaldehyde oxime) nopinone was subj...

Embodiment 2

[0038] Solid 3-(4″-formyl-1′, 1″-biphenyl-4′-formaldehyde oxime) nopinone-based fluoroboron complex and HSO 3 - , HS - , F - , Cl - , AcO - , NO 3 - , HSO 4 - , H 2 PO 4 - , ClO 4 - , SO 4 2- , CO 3 2- , ClO - , H 2 o 2 , ROO·, HO·, NO·, etc. 16 different anions and reactive oxygen species were dissolved in PBS buffer solution (10mM, pH=7.2, 6 / 4(v / v)), and the concentration was prepared to be 1.0×10 -6 M probe solution and a concentration of 1.0 x 10 -5 Solutions of 16 different anions of M. Under the condition of excitation wavelength of 350nm, the fluorescence intensity changes in the presence of different anions were measured, such as figure 1 shown. The results showed that in ClO - In the presence of ions, the maximum emission wavelength of the solution blue shifts from 550nm to 485nm. The fluorescent color of the solution changed from yellow to green under the ultraviolet light, indicating that the compound was sensitive to ClO - ions have better...

Embodiment 3

[0040] Dissolve 3-(4″-formyl-1′, 1″-biphenyl-4′-formaldoxime) nopinone-based fluoroboron complex in PBS buffer (pH=7.2, 10 mM, 6 / 4( v / v)), prepared to a concentration of 1.0×10 -6 M solution, the same ClO - Soluble in PBS buffer solution to make concentrations of 0, 1, 2, 4, 6, 8, 10, 20, 40, 60, 80, 100, 200×10 -7 M's solution. Different concentrations of ClO were measured - The UV absorption spectrum of ion-pair 3-(4″-formyl-1′, 1″-biphenyl-4′-formaldehyde oxime) nopinone-based fluoroboron complex, such as figure 2 shown. The results show that the ultraviolet absorption intensity of the compound around 280nm is obviously weakened, and the ultraviolet absorption intensity around 360nm is obviously enhanced. Illustrate that 3-(4″-formyl-1′, 1″-biphenyl-4′-formaldoxime) nopinone-based fluoroboron complex can be used as a color ratio probe for ClO - to test.

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Abstract

The invention discloses a fluorescence probe for detecting hypochlorite ion as well as a preparation method and application thereof. According to the preparation method, 3-(4''-formyl-1', 1''-biphenyl-4'-carbonyl) nopinone is used as a raw material and is subjected to a condensation reaction with hydroxylamine to obtain 3-(4''-formyl-1', 1''-biphenyl-4'-formaldoxime) nopinone; 3-(4''-formyl-1', 1''-biphenyl-4'-formaldoxime) nopinone reacts with boron trifluoride diethyl etherate to obtain 3-(4''-formyl-1', 1''-biphenyl-4'-formaldoxime) nopinone-based fluoroborate complex. The 3-(4''-formyl-1',1''-biphenyl-4'-formaldoxime) nopinone-based fluoroborate complex prepared in the invention can perform specificity reaction with the ClO-ion, the fluorescence color is changed as green from yellow under the 365nm ultraviolet light, and the fluorescence color is changed as yellow from colorless under the natural light; the fluorescence probe has specificity and high sensitivity for the ClO-ion, and has a good application prospect in the aspect of detecting hypochlorite ions.

Description

technical field [0001] The invention belongs to the technical field of fine organic synthesis, and relates to a fluorescent probe for detecting hypochlorite ions with strong specificity and high sensitivity, a preparation method and application thereof. Background technique [0002] Hypochlorous acid (HClO) is an important weakly acidic reactive oxygen species in living systems and plays a very important role in various physiological processes. In leukocytes including monocytes, neutrophils and macrophages, under the catalysis of myeloperoxidase (MPO), hydrogen peroxide oxidizes chloride ions to generate endogenous hypochlorous acid. However, excessive hypochlorous acid can lead to tissue damage and various diseases such as neuronal degeneration and necrosis, cardiovascular disease, rheumatoid arthritis, asthma and atherosclerosis. Hypochlorous acid is biologically important, and real-time monitoring of the dynamic distribution of hypochlorous acid in cells is of great sign...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F5/02C09K11/06G01N21/64G01N21/78G01N21/33
CPCC07F5/022C09K11/06C09K2211/1007C09K2211/1096G01N21/33G01N21/6428G01N21/78G01N2021/6417
Inventor 杨益琴姜倩王石发王忠龙谷文徐徐徐海军李明新杨海燕
Owner NANJING FORESTRY UNIV
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