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A kind of monovalent copper metal complex and its preparation method and use

A technology of copper complexes and uses, applied in the preparation of monovalent copper metal complexes for the treatment of malignant tumor drugs, monovalent copper metal complexes and their preparation, can solve the problems of low biological potency, poor water solubility, and poor water solubility of DDTC, etc. problem, to achieve the effect of good water solubility and high anti-tumor activity

Inactive Publication Date: 2016-07-06
FUDAN UNIV SHANGHAI CANCER CENT
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although the complex formed by the direct combination of copper and disulfiram can inhibit proteasome activity and lead to tumor cell apoptosis, it still has defects such as poor water solubility and low biological potency.
Sodium diethyldithiocarbamate (DDTC) has a chemical group similar to that of disulfiram, and it can also react with copper ions. However, the water solubility of DDTC-Cu(Ⅱ) is still very poor. So far, there has been no report of its use in clinical treatment of tumors.

Method used

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  • A kind of monovalent copper metal complex and its preparation method and use
  • A kind of monovalent copper metal complex and its preparation method and use
  • A kind of monovalent copper metal complex and its preparation method and use

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] Embodiment 1 synthesizes monovalent copper complex

[0023] Sodium diethyldithiocarbamate (DDTC), copper chloride (CuCl 2 ), sodium sulfite (Na 2 SO 3 ) 50ml of the three solutions, the concentration is 200mM, airtight, and stored at 4°C, take a 500ml blue cap bottle, add 200ml deionized water and 200ml chloroform methanol mixed solvent, and then add the prepared DDTC, Na 2 SO 3 ,CuCl 2 Solution, mix well, the brownish-yellow product can be seen in the chloroform solution in the lower layer, after repeated washing with deionized water, separate with a separatory funnel, remove chloroform and methanol with a rotary evaporator at 50°C, obtain a dark brown crystalline powder, wash with n-hexane Three times, put it in a desiccator to dry.

[0024] According to mass spectrometry, its molecular weight is 422.22. Infrared spectrum data: 2981, 2929, 2869, 1506, 1436, 1377, 1353, 1301, 1274, 1208, 1148, 1097, 1073, 997, 914, 847, 778, 572.

Embodiment 2

[0025] Embodiment 2 synthesizes monovalent copper complex

[0026] Sodium diethyldithiocarbamate (DDTC), copper chloride (CuCl 2 ), sodium sulfite (Na 2 SO 3 ) 50ml of the three solutions, the concentration is 200mM, airtight, and stored at 4°C, take a 500ml blue cap bottle, add 200ml deionized water, add the above prepared DDTC, Na 2 SO 3 ,CuCl 2 Solution, mix well, then a brown complex is formed, settle naturally for 1 hour, absorb the supernatant, take the lower layer of suspension and centrifuge at 3000rpm, discard the supernatant, take the sedimented part, 0.45uM filter membrane + 2 layers of filter paper Vacuum pump negative pressure suction filtration, repeated washing with deionized water to remove salt, to obtain complex solids, and dry in a desiccator at room temperature.

[0027] Its molecular weight is 444.82 according to mass spectrometry, which is the molecular ion peak after adding a sodium, and its theoretical value is 444.90. After subtracting a sodium at...

Embodiment 3

[0028] Example 3 Determination of Antitumor Activity

[0029] drug preparation

[0030] Sodium diethyldithiocarbamate (DDTC), copper chloride (CuCl 2 ), sodium sulfite (Na 2 SO 3 ) three kinds of solutions, the concentration is 200mM, airtight, store at 4 ℃, spare.

[0031] Take a 15ml clean sterile centrifuge tube, first add 9ml sterilized deionized water, press DDTC:CuCl 2 :Na 2 SO 3 =2:2:1 Add 50ul, 50ul, and 25ul of three prepared reagent solutions with a concentration of 200mM, and shake well to obtain a brownish-yellow stable drug solution; take the prepared drug solution for cell experiments and animal experiments.

[0032] According to the monomer of the complex structure, that is, the equivalent concentration of DDTC-Cu is 1mM. Airtight, store at 4°C for later use.

[0033] cell experiment

[0034] Human pancreatic cancer SW1990, BXPC3, PANC-1 cells were cultured in 1640+10% FBS medium, 5% CO, 37°C for conventional culture. 96-well culture plate, implant 5000...

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Abstract

The invention belongs to the field of chemical medicines, and relates to metal complex anticancer drugs, in particular to a monovalent copper metal complex and its preparation method and application. The monovalent copper complex bis[diethyldithiocarbamate Copper (I)], through cell and animal anti-tumor experiments, the results confirmed that the monovalent copper complex has a significant inhibitory effect on tumor cells SW1990, BXPC3, PANC-1; animal experiments confirmed that the The monovalent copper complex can effectively inhibit the growth of transplanted tumors in animals within the safe dose range. The monovalent copper complex of the invention has good water solubility and higher antitumor activity. Medicines for clinical tumor treatment can be further prepared, especially medicines for treating malignant tumors.

Description

technical field [0001] The invention belongs to the field of chemical medicines and relates to metal complex anticancer drugs, in particular to a monovalent copper metal complex and its preparation method and use, especially the use of the monovalent copper metal complex in preparing medicines for treating malignant tumors. Background technique [0002] Tumor drug therapy is one of the three basic methods for treating malignant tumors. The prior art discloses that the metal complex cis-dichlorodiammine platinum (referred to as cisplatin) has anti-tumor activity since it was determined through experiments in Luxembourg in 1969, and was approved for clinical use in the treatment of testicular tumors and ovarian cancer in 1978. It is one of the three most widely used drugs to treat cancer in the world. The successful application of cisplatin has attracted great attention of scientists to platinum metal complex anticancer drugs, and a series of research results have been obtain...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C333/14A61P35/00
Inventor 韩尽斌刘鲁明
Owner FUDAN UNIV SHANGHAI CANCER CENT
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