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Quinoline acylhydrazone derivative-based fluorescence probe, and preparation method and application thereof

A quinoline acyl hydrazone, fluorescent probe technology, applied in fluorescence/phosphorescence, chemical instruments and methods, luminescent materials, etc., can solve problems such as metabolic disorders, disruption of zinc ion metabolic balance, many diseases, etc. Wide application value, strong selective effect

Inactive Publication Date: 2017-04-19
HENAN POLYTECHNIC UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, if the metabolic balance of zinc ions in the body is destroyed, it may cause metabolic disorders and many diseases. In addition, due to the large amount of mining and extensive use of zinc ions, zinc has also become an important metal pollutant.

Method used

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  • Quinoline acylhydrazone derivative-based fluorescence probe, and preparation method and application thereof
  • Quinoline acylhydrazone derivative-based fluorescence probe, and preparation method and application thereof
  • Quinoline acylhydrazone derivative-based fluorescence probe, and preparation method and application thereof

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Experimental program
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Effect test

Embodiment 1

[0026] A fluorescent probe based on quinoline acylhydrazone derivatives, characterized in that the quinoline acylhydrazone derivatives have the following structural formula:

[0027]

[0028] The preparation method of the fluorescent probe based on quinoline acylhydrazone derivatives comprises the following steps: dissolving 0.001-0.01mol of quinoline-8-carbaldehyde in 0.01-0.05L of absolute ethanol, and then adding 0.001-0.01 mol of acetylhydrazide, stirred at normal temperature and pressure for 4-6 hours, a large amount of solids were precipitated, filtered under reduced pressure, and the filter residue was washed with alcohol solution to obtain the fluorescent probe of the quinoline acylhydrazone derivative.

Embodiment 2

[0030] Synthesis of Quinolinylhydrazone Derivatives

[0031]

[0032] Dissolve 1.57 g of quinoline-8-carbaldehyde in 50 mL of absolute ethanol, then add 0.94 g of acetylhydrazide, stir and react at room temperature and pressure for 5 hours, a large amount of solid precipitates, filter under reduced pressure, wash the filter residue with absolute ethanol to obtain a white solid It is the target product, and the yield of the target product is 90.6%.

[0033] Quinoline acylhydrazone derivative nuclear magnetic resonance analysis results are as follows:

[0034] 1 H NMR (400 MHz, DMSO- d 6 ),δ(ppm): 10.19 (s, 1H, NH), 9.87 (s, 1H, NH),8.08-8.10 (d, 1H, Aryl-H), 7.93-7.95 (d, 1H, Aryl-H) , 7.74-7.76 (m, 1H, Aryl-H), 7.74-7.76 (m, 1H, Aryl-H), 7.58-7.65 (m, 2H, Aryl-H), 7.33-7.37 (m, 1H,Aryl- H), 7.02-7.09 (m, 2H, Aryl-H), 6.20-6.27 (m, 2H, Aryl-H), 6.03 (s, 1H, Aryl-H), 5.97 (s, 1H, Aryl-H) , 5.11 (s, 1H, NH), 4.60 (s, 1H, NH), 3.70 (s,3H, CH 3 ), 3.29 (s, 6H, 2CH 3 ), 2...

Embodiment 3

[0037] The structure of complexes formed by quinoline acylhydrazone derivatives with divalent zinc ions

[0038] Dissolve 0.0213 g of quinoline acylhydrazone derivatives in 5 mL of absolute ethanol, then add 0.0110 g of zinc acetate dihydrate, stir and react at room temperature and pressure for 0.5 h, let stand at room temperature, and slowly evaporate the solvent to obtain the quinoline acylhydrazone zinc complex single crystal. For specific crystal structures, see image 3 . It shows that the quinoline acylhydrazone derivatives of the present invention can form stable complexes with zinc ions.

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Abstract

The invention discloses a quinoline acylhydrazone derivative-based fluorescence probe. A preparation method of the fluorescence probe comprises the following steps: 1, dissolving quinoline-8-carboxaldehyde in anhydrous ethanol, and adding acethydrazide; 2, stirring a mixture obtained in step 1 at normal temperature under normal pressure, and carrying out a reaction for 4-6 h to precipitate a white solid; 3, carrying out reduced pressure filtration on the solid obtained in step 2, and taking filter residues; and 4, washing the filter residues obtained in step 3 by using an alcohol solution to obtain the quinoline acylhydrazone derivative-based fluorescence probe. The quinoline acylhydrazone derivative-based fluorescence probe has the advantages of simple synthesis and easily available raw materials, has a high selective fluorescence identification effect on divalent zinc ions to make a fluorescence-free solution containing the divalent zinc ions have yellow fluorescence, can realize naked eye discrimination detection, and especially can be applied as a fluorescence probe to the detection of the zinc ions in cells.

Description

technical field [0001] The invention belongs to the field of organic synthesis, and specifically relates to quinoline acylhydrazone derivatives and their preparation methods and applications. Background technique [0002] Zinc is one of the essential trace elements for the human body, and plays an extremely important role in important physiological processes such as human growth and development, reproductive inheritance, immunity, and endocrine. However, if the metabolic balance of zinc ions in the body is destroyed, it may cause metabolic disorders and many diseases. In addition, due to the large amount of mining and extensive use of zinc ions, zinc has also become an important metal pollutant. In view of its importance to life and the environment, scientists have been working on the detection of zinc ions in biological and environmental systems using selective fluorescent and fluorescent sensing probes. [0003] In recent years, molecular probe technology has become an im...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D215/12C09K11/06G01N21/64
CPCC07D215/12C09K11/06C09K2211/1029G01N21/6428G01N21/6486
Inventor 吴伟娜王元陈兴颖陈泽华李慧军徐周庆吴浩
Owner HENAN POLYTECHNIC UNIV
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