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A kind of mixed copper-based complex and its preparation method and application

A complex, copper-based technology, used in copper organic compounds, drug combinations, anti-tumor drugs, etc., can solve problems such as reducing tumor blood vessel density, and achieve the effect of inhibiting proliferation, low cytotoxicity and good effect.

Active Publication Date: 2020-05-12
GUILIN MEDICAL UNIVERSITY
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

In addition, copper, but not other metals, is closely related to angiogenesis. Vascular endothelial cells are particularly sensitive to copper, and the reduction of copper levels due to chelation effectively reduces the density of tumor blood vessels, while copper chelates themselves Effects on tumor angiogenesis are largely understudied

Method used

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  • A kind of mixed copper-based complex and its preparation method and application
  • A kind of mixed copper-based complex and its preparation method and application
  • A kind of mixed copper-based complex and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] Example 1 Mixed copper-based complexes [Cu(C 10 h 10 NO 5 SBr)(C 12 h 8 N 2 )]·CH 3 Preparation of OH

[0033] (1) Dissolve taurine (1.2514g, 10 mmol) and KOH (1.1220 g, 20 mmol) in 35 mL of anhydrous methanol, and then add 15 mL of 5-bromo-3-methoxy-salicylaldehyde dropwise (2.3104g, 10 mmol) in anhydrous methanol solution, stirred in a water bath at 50°C for 3 hours to obtain a yellow clear liquid; after vacuum distillation to remove most of the solvent, filtered and washed to obtain a yellow powder, dried in vacuum for 2 days, that is, to prepare Potassium K 2 C 10 h 10 NO 5 SBr;

[0034] (2) Weigh K 2 C 10 h 10 NO 5 SBr (0.0829 g, 0.2 mmol) and anhydrous copper sulfate (0.0527 g, 0.3 mmol) were added to 25 ml of a mixed solvent of methanol and water (V 甲醇 : V 水 = 24:1), placed in a 50°C water bath, heated and stirred to reflux to obtain a yellow-green clear liquid; after reflux for 20 minutes, add 1,10'-phenanthroline (0.0399 g, 0.2 mmol), and cont...

Embodiment 2

[0035]Embodiment 2 [Cu(C 10 h 10 NO 5 SBr)(C 12 h 8 N 2 )]·CH 3 OH in vitro cytotoxicity test

[0036] MTT method: Take tumor cells in the logarithmic growth phase and adjust the concentration of viable cells to 8×10 4 / ml was added to 96-well culture plate, 100 μl per well, cultured in the incubator for 12 h, and then added 100 μl of test samples of different concentrations diluted with serum-free culture, and each concentration of the sample addition group was set at 6 Multiple wells, and negative control at the same time, placed at 37 ° C, 5% CO 2 Incubate for 48 hours, then add 20 μl / well of MTT (5 mg / ml), 4 hours later use a micro-syringe to gently suck out the clear night, add 150 μl / well of dimethyl sulfoxide (DMSO), shake for about 10 minutes, and use a microplate reader The OD value was measured at a wavelength of 490 nm. Calculate the cell survival inhibition rate, and calculate its half inhibitory concentration IC by software 50 .

[0037] Inhibition rate...

Embodiment 3

[0041] Embodiment 3 flow cytometer measures [Cu(C 10 h 10 NO 5 SBr)(C 12 h 8 N 2 )]·CH 3 OH Induced Cell Apoptosis and Injury Experiment in Vitro

[0042] Apoptosis analysis kit Annexin V / PI was purchased from BD Bioscience, USA, and apoptosis detection was performed according to the instructions of the kit. cells (2×10 5 / well) were seeded in 12-well plates (Corning) for 12 h, and then treated with different concentrations of [Cu(C 10 h 10 NO 5 SBr)(C 12 h 8 N 2 )]·CH 3 OH was incubated with cells for a certain period of time (20 h and 40 h for C33A cells; 24 h for A549 / DDP; 24 h and 48 h for HUVECs). To detect early and late apoptosis, all suspended and adherent cells were collected, washed twice with 1×PBS, centrifuged at 1000 r / min for 5 minutes, and the supernatant was removed. Cells were resuspended in 100 µl Binding Buffer. Subsequently, cells were first stained with 5 µL Annexin-V, gently resuspended, and then stained with 5 µL PI. Gently resuspend cel...

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Abstract

The invention discloses a blended copper-based complex as well as a preparation method and application thereof. A structural formula of the blended copper-based complex is [Cu(C10H10NO5SBr)(C12H8N2)].CH3OH, wherein [Cu(C10H10NO5SBr)(C12H8N2)] is a coordination unit, C10H10NO5SBr is a schiff base anion ligand, and C12H8N2 is 1,10'-orthophenanthrolene as a neutral ligand. The preparation method comprises the following steps of mixing taurine and strong base, adding an organic solvent for dissolution with stirring, then adding 5-bromo-2-hydroxyl-3-methoxybenzaldehyde, performing constant-temperature stirring for 2-4h, and stopping reaction to obtain K2C10H10NO5SBr as potassium salt of a ligand; and then mixing the K2C10H10NO5SBr as the potassium salt of the ligand and copper salt, dissolvinga mixture into a methanol-water mixed solution, then adding the 1,10'-orthophenanthrolene, performing constant-temperature reaction for 8-20h, and obtaining the blended copper-based complex after reaction is finished. The blended copper-based complex is a candidate of an anti-tumor drug, is also a good tumor angiogenesis inhibitor and is a candidate of a novel dual-function anti-tumor drug.

Description

technical field [0001] The invention relates to a mixed metal-based complex, in particular to a mixed copper-based complex and its preparation method and application. Background technique [0002] Cancer treatment has always been facing severe challenges. Tumor growth, progression, invasion and metastasis are closely related to neovascularization. Malignant tumors can derive their own vasculature to obtain nutrition, and after tumor cells obtain nutrition, they can promote the formation of tumor blood vessels, which means that tumor blood vessels and tumor cells play a role of mutual promotion in the growth of tumors. In addition, inhibiting tumor angiogenesis while inducing tumor cell apoptosis can achieve a significant anti-tumor effect. It is of great significance to find anti-tumor drugs that have both the effect of inhibiting tumor angiogenesis and the dual function of killing tumor cells. [0003] Copper is a vital trace element in all living organisms and copper com...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F1/08A61P35/00
CPCA61P35/00C07F1/08
Inventor 秦秀英李付进刘丽梅王雅楠
Owner GUILIN MEDICAL UNIVERSITY
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