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Aromatic planar Schiff-base copper complex and preparation method and application thereof

A Schiff base copper and complex technology, applied in copper organic compounds, pharmaceutical formulations, organic chemical methods, etc., can solve problems such as sequence-specific DNA breakage, achieve strong bonding, low preparation cost, and simple synthesis process Effect

Inactive Publication Date: 2019-09-13
SHANXI AGRI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The oxidative breakage of DNA by metal complexes can be divided into breakages targeting sugar rings and breakages targeting bases according to the breakage site. Although the oxidation of breakages targeting bases cannot directly cause DNA strand breaks, it does Under the action of alkali, heat, enzymes, etc., site-specific and even sequence-specific DNA fragmentation will eventually occur

Method used

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  • Aromatic planar Schiff-base copper complex and preparation method and application thereof
  • Aromatic planar Schiff-base copper complex and preparation method and application thereof
  • Aromatic planar Schiff-base copper complex and preparation method and application thereof

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Experimental program
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Effect test

Embodiment 1

[0027] Preparation of aromatic planar Schiff base copper complexes [CuL(H 2 O)] (ClO 4 ) • H 2 o

[0028] (1) Accurately weigh 1.0 g, 8-aminoquinoline (7 mmol) in a 100 mL round bottom beaker, add 50 mL of anhydrous methanol to dissolve it, and then add 0.5 mL of salicylaldehyde (7 mmol) Mix it evenly, reflux and condense in an oil bath at 70°C for 3 h, and then remove the solvent in the reaction system. The precipitate was separated by column chromatography, rinsed with a mixed solution of ethyl acetate and petroleum ether, and finally a colorless crystal was obtained as ligand L. Yield: 60%, Mp: 202.5℃-203.8℃, FT-IR(KBr, ν / ㎝ -1 ): 3433, 1610, 1498, 1460, 1264, 1100, 945, 755.

[0029] (2) Dissolve 0.4 mmol of ligand L in 20 mL of ethanol, slowly add 10 mL of Cu(ClO 4 ) 2 · H 2 O (0.4 mmol, 148 mg) aqueous solution, stirred at room temperature for 1 h, filtered, and the filtrate was left at room temperature to evaporate the solvent for a week, green blocky crystals su...

Embodiment 2

[0034] Electron Absorption Spectrometric Titration of Aromatic Planar Schiff Base Copper Complexes:

[0035] Weigh 0.2925 g NaCl and 0.06057 g Tris in a 50 mL small beaker, add ultrapure water to dissolve, adjust the pH to 7.2, and make 100 mL buffer solution. Calf thymus DNA (CT-DNA) was taken in a 10 mL sample tube, dissolved in buffer and prepared as a DNA stock solution with a certain concentration. Weigh 2.231 mg of the complex into a 10 mL sample tube, add 2 mL of DMF and 3 mL of water to dissolve, and make a solution with a total volume of 5 mL.

[0036] Add 2 mL of ultrapure water into the reference cell and the sample cell at room temperature, then take a certain volume of the above solution in the sample cell, and take the same volume of water in the reference cell for spectral scanning to determine the added aroma. After the concentration of the planar Schiff base copper complex, the DNA stock solution is added to the sample pool in turn, and water is also added to...

Embodiment 3

[0038] Fluorescence Quenching Test of Copper Complexes of Aromatic Planar Schiff Bases and EB-DNA

[0039] When the complex interacts with DNA, its fluorescence spectrum will change. Because the aromatic planar Schiff base copper complexes and DNA itself do not produce fluorescence, ethidium bromide (EB) needs to be introduced. Ethidium bromide is a planar conjugated molecule and has no fluorescence itself, but when it interacts with DNA, EB is inserted into the base pair of DNA, resulting in strong fluorescence. When the aromatic planar Schiff base copper complex is added, the complex binds to DNA, and the fluorescent part is quenched. The degree of binding of the complex to DNA was determined indirectly by studying the change of the fluorescence intensity of the complex quenching the EB-DNA conjugate. Specific steps are as follows:

[0040] (1) Weigh 0.2925 g of NaCl and 0.06057 g of Tris in a 50 mL small beaker, add ultrapure water to dissolve, adjust the pH to 7.2, dilu...

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Abstract

The invention discloses an aromatic planar Schiff-base copper complex. The chemical formula of the aromatic planar Schiff-base copper complex is [CuL(H2O)](ClO4)-H2O, wherein L is 8-aminoquinoline salicylidene Schiff-base, and ClO4 is perchlorate. The preparation method of the aromatic planar Schiff-base copper complex comprises synthesis of a ligand L and synthesis of an aromatic planar Schiff-base copper complex. The synthetic process is simple and has good selectivity and stability. There is intercalation of intermediate bonding between the aromatic planar Schiff-base copper complex and CT-DNA. Under the close physiological condition of existence of a redox inducer, it shows an obvious cutting effect on Pbr322 DNA; and ultraviolet light has a certain promotion effect on the cutting effect. The Pbr322 DNA can be fractured through an auto-oxidation approach, and a hydroxyl radical active matter is generated in the cutting process.

Description

technical field [0001] The invention belongs to the technical field of synthetic chemistry, and in particular relates to an aromatic planar Schiff base copper complex and its preparation method and application. Background technique [0002] With the in-depth study of the pharmacological effects of metal complexes, the research on the interaction and mechanism between transition metal complexes and macromolecular DNA has become one of the hotspots in the fields of biochemistry and medicinal chemistry. Metal complexes are a series of important biologically active compounds because they can interact well with DNA. They have cationic properties, broad spectrum of ligands, three-dimensional structure, kinetics and pharmacological characteristics, have different coordination numbers and geometric configurations, and are easy to achieve different redox states; have different thermodynamic and kinetic properties, Metal ions and ligands also have their own inherent characteristics. ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F1/08A61K31/555A61K41/00A61P35/00
CPCA61K31/555A61K41/0057A61P35/00C07B2200/13C07F1/08
Inventor 高春艳乔佩佩张鹏飞杨皇泽雷云博张永坡岳爱琴赵晋忠杜维俊
Owner SHANXI AGRI UNIV
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