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Pyridine methylene coumarin copper ion fluorescent probe and preparation thereof

A technology of coumarin and fluorescent molecular probes, which is applied in the field of coumarin derivative copper ion fluorescent probes and its preparation, can solve the problems of abnormal biological oxidation/reduction process and neurotoxicity, and achieve simple structure, High selectivity and sensitivity, mild reaction conditions

Inactive Publication Date: 2018-12-28
HEZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

When the concentration of copper ions is lower than 1 μM, it will have harmful effects on many life processes (coenzymes of biocatalyzed reaction enzymes, biological transport processes, and biological synthesis). However, when the concentration in the organism is too high, it will be harmful to some Inhibition of essential enzymes, abnormal biological oxidation / reduction processes, neurotoxicity and other harmful effects, leading to neurodegenerative diseases such as: Alzheimer's disease, Parkinson's disease, Menkes' disease, Wilson's disease, etc.

Method used

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  • Pyridine methylene coumarin copper ion fluorescent probe and preparation thereof
  • Pyridine methylene coumarin copper ion fluorescent probe and preparation thereof
  • Pyridine methylene coumarin copper ion fluorescent probe and preparation thereof

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Experimental program
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Effect test

Embodiment 1

[0020] Embodiment 1: the synthesis of intermediate imine

[0021]

[0022] Add 1.16g of 3-amino-7-diethylaminocoumarin to 30mL of dichloromethane solution to dissolve, stir and add 618μL of pyridineformaldehyde under a magnetic stirrer, then add 2.13g of anhydrous sodium sulfate, and stir at room temperature for 24 hours . After the reaction was completed, filter, wash the solid sodium sulfate with a small amount of dichloromethane solution, and evaporate the solution to dryness under reduced pressure to obtain the crude product of the imine (the product was directly used in the next step without purification).

Embodiment 2

[0023] Embodiment 2: the synthesis of target compound I

[0024]

[0025] The crude product obtained in the previous step was dissolved in 30 mL of anhydrous methanol, and cooled in an ice bath. After the solution was completely cooled, 0.57 g of sodium borohydride was added in batches, and the reaction was continued for 2 hours in an ice bath, and the reaction was overnight at room temperature. After the reaction is over, evaporate the solution to dryness under reduced pressure, add 30 mL of distilled water and 30 mL of dichloromethane, stir and dissolve under a magnetic stirrer, pour the resulting aqueous solution directly into a separatory funnel, separate the liquids, and use 20 mL of dichloromethane for the water layer. After washing twice, the organic phases were combined, washed with saturated aqueous sodium chloride, dried over anhydrous sodium sulfate, filtered, and distilled under reduced pressure to obtain a viscous liquid. The obtained crude product was subjecte...

Embodiment 3

[0026] Embodiment 3: the mensuration of compound ultraviolet spectrum and fluorescence spectrum

[0027] Compound I was dissolved in DMSO to prepare a solution with a concentration of 2mM, and stored at 4°C; UV-Vis spectra and fluorescence spectra were in buffer solution (25mM HEPES, 0.1M NaClO 4 , pH=7.4, measured in 5% (V / V) DMSO). Add 2uL of fluorescent probe I solution into 2ml of buffer solution, mix well, and measure its ultraviolet-visible spectrum and fluorescence spectrum respectively. At the same time, the same amount of different metal ions were added to measure the change of its fluorescence properties.

[0028] The ultraviolet absorption spectrum of compound I is from as image 3 shown. Under simulated physiological environment (25mM HEPES, 0.1MNaClO 4 , pH=7.4, 5% (V / V) DMSO) before adding copper ions, the maximum absorption peak of compound I was at 226nm, and there were two absorption peaks at 265 and 389nm respectively. When copper ions are added to the s...

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Abstract

The invention relates to preparation and application of a pyridine methylene coumarin copper ion fluorescent probe. The chemical name of the fluorescent probe is 7-diethyl amino-3-(pyridine-2-methylene) aminocoumarin; the preparation of the fluorescent probe comprises the steps that (1) 3-amino-7-diethyl aminocoumarin and 2-pyridylaldehyde are dehydrated under the action of a dehydrating agent toobtain an intermediate imine compound; (2) the intermediate imine compound is reduced under the action of a reducing agent to obtain a target fluorescent molecular probe compound. The application of the fluorescent probe is to detect whether or not divalent copper ions exist by utilizing copper ions to quench the fluorescence of a molecular fluorescent probe compound. The preparation and application of the pyridine methylene coumarin copper ion fluorescent probe have the advantages that the preparation of the probe is simple, the reaction conditions are mild, the after-treatment process is relatively simple; and fluorescent probe molecules show higher selectivity and sensitivity in the detection process of the bivalent copper ions.

Description

technical field [0001] The invention belongs to the field of organic fluorescent small molecule probes, and specifically relates to a coumarin derivative copper ion fluorescent probe and a preparation method thereof. Background technique [0002] As an essential trace element in the human body, copper is a component of proteins and enzymes in the body, and plays an important role in the metabolism of the human body. Too much or too little copper ions can have a major impact on the body. When the concentration of copper ions is lower than 1 μM, it will have harmful effects on many life processes (coenzymes of biocatalyzed reaction enzymes, biological transport processes, and biological synthesis). However, when the concentration in the organism is too high, it will be harmful to some Inhibition of essential enzymes, abnormal biological oxidation / reduction processes, neurotoxicity and other harmful effects lead to degenerative diseases of the nervous system such as: Alzheimer...

Claims

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Application Information

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IPC IPC(8): C07D405/12C09K11/06G01N21/64G01N21/33
CPCC07D405/12C09K11/06C09K2211/1029C09K2211/1088G01N21/33G01N21/6428G01N2021/6432
Inventor 王素娟任爱山严小威钟星朱东建胡彩霞
Owner HEZHOU UNIV
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