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A kind of unsymmetrical oxamide bridged trinuclear copper complex and its preparation method and application

A technology of oxalamide bridge and copper complex, which is applied in the direction of copper organic compounds, pharmaceutical formulations, medical preparations containing active ingredients, etc., to achieve good growth inhibition, wide application range, and high selectivity

Inactive Publication Date: 2015-11-18
QINGDAO MUNICIPAL HOSPITAL
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Recently, studies by American scientists have shown that taking an appropriate amount of copper complexes to treat solid tumors can significantly inhibit tumor growth and metastasis, and improve the chance of survival. However, so far, no copper complexes have been used clinically as anticancer drugs.

Method used

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  • A kind of unsymmetrical oxamide bridged trinuclear copper complex and its preparation method and application
  • A kind of unsymmetrical oxamide bridged trinuclear copper complex and its preparation method and application
  • A kind of unsymmetrical oxamide bridged trinuclear copper complex and its preparation method and application

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] The preparation method of the asymmetric oxamide heterometallic one-dimensional coordination polymer of the present invention comprises the following steps:

[0027] 1. Preparation of unsymmetrical oxamide ligand N-(2-carboxyphenyl)-N'-[(2-aminoethyl)ethyl]oxamide

[0028] Oxamide ligand N-(2-carboxyphenyl)-N'-[(2-aminoethyl)ethyl]oxamide (H 3 The preparation method of bdeox) is as follows: Weigh 10mmol of N-(2-carboxyanilino) ethyl oxalate, dissolve it in 10mL of tetrahydrofuran / ethanol (v:v=1:1) mixed solution, and stir it at 0°C. Add dropwise to 10mL of tetrahydrofuran / ethanol (v:v=1:1) mixed solution containing 14mmol diethylenetriamine. After the addition was complete, the reaction was continued to stir in an ice bath for 6 hours, and a large amount of white solid was formed. Suction filtration, washing the filter cake with absolute ethanol and anhydrous ether several times successively, and vacuum drying at room temperature to obtain a white solid powder that is...

Embodiment 2

[0047] Example 2: Cell experiment

[0048] (1) Experimental group:

[0049] Adherent tumor cell lymphoid leukemia cells P388 and human liver cancer cells BEL7404 in the logarithmic growth phase were selected, digested with trypsin, and prepared a cell suspension of 50,000 cells / mL with RPM11640 culture medium with 10% calf serum, and inoculated in Inoculate 100 μL per well in 96 empty culture plates, at 37°C, 5% CO 2 , and cultured for 24 hours.

[0050] Add 10 μL of the obtained coordination polymer solution (dissolve the coordination polymer crystals with DMSO, dilute with physiological saline to a final concentration of 5 μg / mL), make the final volume of each well 200 μL, and make up with 1640 culture medium. 37°C, 5% CO 2 , cultured for 3 days. After culturing for 3 days, discard the supernatant, add 100 μL freshly prepared 0.5 mg / mL MTT (thiazolium blue) serum-free culture solution to each well, continue culturing at 37°C for 4 hours, carefully discard the supernatant...

Embodiment 3

[0058] Example 3: Research on the interaction with HS-DNA

[0059] UV-Vis Absorption Spectroscopy Titration

[0060] In the UV-visible spectrum test, add the same volume of Tris-HCl buffer solution and ligand solution to the reference cell and the sample cell, fix the concentration of the ligand, and scan the UV-visible spectrum in the range of 200-600nm. Add 12 μL of HS-DNA (5.16×10 -3 mol L -1 ) solution, so that the concentration ratio of DNA and ligand increases continuously until it is saturated, and the absorption value of the ligand does not change. Combining constant calculations:

[0061] [DNA] / (εa-εf)=[DNA] / (εb-εf)+1 / Kb(εb-εf)

[0062] Where εa is the molar extinction coefficient of the solution at any DNA concentration; εf is the molar extinction coefficient of the free complex; εb is the molar extinction coefficient when the complex is fully bonded to DNA; [DNA] is plotted to give a slope and intercept, the ratio of which is the binding constant Kb.

[0063] ...

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Abstract

The invention discloses an asymmetry oxamide fiber-bridged three-kernel copper complex as well as a preparation method and application thereof. The complex is generated from Cu<2+> and asymmetry oxamide ligand H3bdeox, perchlorate and 1,10-phenanthroline; the coordination polymer is of a trimetal central structure, and the molecular structure formula of the coordination polymer is [Cu3(bdeox)(phen)3(H2O)](ClO4)3?H2O, wherein Cu is bivalent copper ion, and H3bdeox is N-(2-carboxyl benzene)-N'-[(2-aminoethyl)ethyl] oxamide. The asymmetry oxamide fiber-bridged three-kernel copper complex disclosed by the invention is low in cost, the raw materials for synthesis is readily available, the product is separated out in a crystal mode, is large in purity and high in yield, and moreover, the coordination polymer is stable in a natural state, and is good in water solubility and grease solubility; in addition, the coordination polymer has an excellent inhibition function on various cancer cells of liver cancer, lymphatic leukemia and the like, and is wide in action spectrum and wide in application range.

Description

technical field [0001] The invention belongs to the technical field of complexes, and in particular relates to an unsymmetrical oxamide-bridged trinuclear copper complex and its preparation method and application. Background technique [0002] Copper is an important trace element, which plays an important role in the process of cell formation, participates in the activities of various enzymes and important life hormones in the human body, and is closely related to bone development and normal metabolism of the central nervous system. In recent years, copper complexes have aroused great interest among scholars at home and abroad because of their nuclease activity. Copper complexes containing aromatic ring structures can not only inhibit the activity of DNA and RNA polynucleases, but also in the presence of oxidants such as hydrogen peroxide and oxygen. DNA fragmentation can also be induced under certain conditions, and even some complexes can induce DNA fragmentation under the...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F1/08A61K31/555A61P35/00
Inventor 姜曼宣世英战淑慧周建华刘敏
Owner QINGDAO MUNICIPAL HOSPITAL
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