Mononuclear copper complex and its preparation method and application

A copper complex and mononuclear technology, which is applied in the direction of copper organic compounds, drug combinations, antineoplastic drugs, etc., can solve the problems that the variety, quantity and function of natural nucleases cannot meet the needs of the market, and achieve good bonding and cleavage Effect, good anticancer activity, simple preparation method

Inactive Publication Date: 2016-05-25
NANKAI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the preparation of natural nucleases into anticancer drugs faces many problems, because the variety, quantity and function of natural nucleases are far from meeting the needs of the market.

Method used

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  • Mononuclear copper complex and its preparation method and application
  • Mononuclear copper complex and its preparation method and application
  • Mononuclear copper complex and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] Ligand L·2HClO 4 Synthesis:

[0031] Weigh 0.99g (5mmol) of dibenzylamine into a 50mL round bottom flask. Weigh 0.883g (5mmol) of 1-chloromethylnaphthalene, dissolve it in 20mL of acetone, and add it dropwise to dibenzylamine while stirring. Weigh 0.967g (7mmol) of K 2 CO 3 Particles were added to a round bottom flask to form a suspension. The reaction system was heated to reflux for 25h, and the material obtained by rotary evaporation was washed with H 2 O was dissolved and extracted with chloroform. The obtained extract was dried with MgSO4 and rotary evaporated to obtain 2.2723 g of the ligand product. Dissolve the oily liquid in 25mL of ethanol, then slowly add perchloric acid dropwise to produce a yellow-brown precipitate, filter it, and recrystallize it with absolute ethanol to obtain the ligand L 2HClO 4 The pale yellow powder 0.49g, yield 27.0%. Elemental analysis (%), theoretical value: (C 23 h 21 N 3 2HClO 4 ): C, 51.11; H, 3.89; N, 7.78. Experime...

Embodiment 2

[0033] Synthesis of mononuclear copper complex (1):

[0034] Weigh the ligand (2mmol) and dissolve it in 5mL ethanol, weigh copper trichloroacetate (2mmol), dissolve it with 5mL distilled water, add it to the reaction system, then add lithium hydroxide aqueous solution 5mL (5mmol), adjust the acidity of the system pH = 7. After stirring at room temperature for 4 hours, the reaction solution was filtered. After the filtrate was allowed to stand for 6 days, the precipitated crystals were the product, and the crystals were collected. Analyzed by X-ray single crystal diffractometer ( Figure 1a ) and elemental analysis, proved that the crystal is [CuLCl] (ClO4) (1). Determination of the percentage content of the corresponding elements (%): C, 51.43; H, 3.90; N, 7.86. The results are basically consistent with the theoretical values.

Embodiment 3

[0036] Synthesis of mononuclear copper complex (2):

[0037] Take the ligand (2mmol) prepared in Example 1 and dissolve it in 5mL ethanol, weigh Cu(acac) 2 / CH 2 Cl 2 (2mmol), dissolved in 5mL of distilled water, added to the reaction system, and then 5mL (5mmol) of lithium hydroxide aqueous solution was added to adjust the acidity of the system to pH=7. After stirring at room temperature for 2.5h, add KPF 6 (4mmol), stirred for another 2h, and the reaction solution was filtered. After the filtrate was allowed to stand for 7 days, the precipitated crystals were the product, and the crystals were collected. Analyzed by X-ray single crystal diffractometer ( Figure 1b) and elemental analysis, it was proved that the crystal was [CuL(acac)](PF 6 )(2). Determination of the percentage content of the corresponding elements (%): C, 52.03; H, 4.37; N, 6.51. The results are basically consistent with the theoretical values.

[0038] The structural parameters of the mononuclear c...

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Abstract

The invention relates to a mononuclear copper complex and a preparation method and application thereof. Chemical formulas of the mononuclear copper complex are respectively [CuLCl](ClO4)(1) and [CuL(acac)](PF6)(2), wherein L is N,N-(2-pyridyl)-1-(1-naphthyl) ethylamine, acac is acetylacetone, and PF6 is hexafluorophosphate radical. The complex (1) crystal is of an orthorhombic system, a space point group is Pbca, cell parameters are described in the specification; the complex (2) crystal is of a monoclinic system, a space point group is P2(1) / c, and cell parameters are described in the specification. A plurality of spectroscopic methods represent that the mononuclear copper complex has a strong bonding function for CT-DNA (Circulating Tumor-Desoxvribose Nucleic Acid); agar gel electrophoresis experiments prove that the mononuclear copper complex has a remarkable cutting effect on pBR322DNA by using an oxidation cutting principle; MTT (Methyl Thiazolyl Tetrazolium) experiments prove that the mononuclear copper complex has a better anti-tumor activity to multiple kinds of cells, and can be used as a potential anti-tumor medicine.

Description

technical field [0001] The invention relates to a mononuclear copper complex and its preparation method and application, in particular to its application in the fields of chemical nucleases and anticancer drugs. Background technique [0002] Cancer is a general term for a large class of malignant tumors and is one of the most important diseases threatening human life. In China, the annual number of abnormal deaths is about 8 million, of which about 1.6 million are due to cancer. With the development of biology and medicine, people have made great progress in the treatment of cancer, among which chemotherapy is an extremely important method, which has made extraordinary achievements. In the late 1960s, cisplatin, with its excellent anti-tumor effect, led the scientific community to further in-depth research on the pharmacological functions of metal complexes. Subsequently, many new metal complexes with high efficiency, low toxicity and anticancer properties have been contin...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F1/08A61P35/00
Inventor 周学拳孙倩田金磊阎世平
Owner NANKAI UNIV
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