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Anti-cancer tetravalent platinum complex capable of inhibiting inflammation and immune escape and preparation method thereof

A technology for immune escape and anti-inflammation, applied in the field of biomedicine, which can solve the problems of low selectivity and high systemic toxicity

Inactive Publication Date: 2020-10-30
NANJING UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, platinum-based antineoplastic drugs still face some challenges, such as high systemic toxicity, drug resistance, and low selectivity. analogues, so these problems have not been fundamentally resolved

Method used

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  • Anti-cancer tetravalent platinum complex capable of inhibiting inflammation and immune escape and preparation method thereof
  • Anti-cancer tetravalent platinum complex capable of inhibiting inflammation and immune escape and preparation method thereof
  • Anti-cancer tetravalent platinum complex capable of inhibiting inflammation and immune escape and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] Synthesis of Tetravalent Platinum Complexes

[0033]

[0034] S1. Add hydrogen peroxide (30wt%, 20mL) dropwise into an aqueous solution (12mL) of cisplatin (CDDP, 400mg, 1.33mmol), and stir under reflux at 60°C for 4h. Cool overnight to obtain pale yellow crystals, filter and wash with ice water, and dry in vacuo to obtain tetravalent Oxoplatin yellow powder product;

[0035] S2, combine oxoplatin (100mg, 0.30mmol) with (NPX, 207.23 mg, 0.90 mmol), TEA (125 μL, 0.90 mmol) and TBTU (288.99 mg, 0.90 mmol) were mixed in DMF (15 mL), and stirred for 48 h in the dark.

[0036] S3. After the reaction is completed, a mixture of ethanol and water is added to the mixture, and a yellow crude product is precipitated. The precipitate was dissolved in methanol, washed several times with ether, and dried in vacuum to obtain a light yellow powder with a yield of about 65%.

Embodiment 2

[0037] The cytotoxic activity test of embodiment 2 compound

[0038] The compounds prepared in Example 1 of the present invention were tested for their cytotoxic activity, using breast cancer cells (MFC-7, MDA-MB-231, MDA-MB-435), ovarian cancer cells (Caov-3) and cervical cancer cells ( HeLa) as a model, with the compound synthesized in Example 1 and cisplatin as the test substance, after the test substance acts on the cells, observe the survival situation of the cells, test the cell survival rate with the thiazolyl blue (MTT) method, The specific operation steps are as follows:

[0039] S1. Collect the above-mentioned logarithmic phase cells, adjust the concentration of the cell suspension, add them to a 96-well plate, and the number of cells per well is about 5000;

[0040] S2. Place the above experimental cells at 37°C, 5% CO 2 Cultivated in a cell culture incubator for 18h;

[0041] S3. Compounds or cisplatin solutions with different concentration gradients were prepar...

Embodiment 3

[0050] Anti-inflammatory ability detection of the compound of embodiment 3

[0051] The anti-inflammatory ability of the compound prepared in Example 1 of the present invention was tested, mouse macrophage RAW264.7 and human breast cancer cell MCF-7 were selected as models, and the compound synthesized in Example 1 and cisplatin were used as the substances to be detected , after the substances to be detected acted on the cells, the relative content of inflammatory factors IL-6 and IL-1β in the RAW264.7 cell supernatant was detected by ELISA kit, and the COX- 2 The change of protein and the relative content of PGE2 in the cell supernatant, the specific operation steps are as follows:

[0052] S1. Collect the above logarithmic phase cells and adjust the concentration of the cell suspension to 2×10 cells per well. 5 cells at a density of 6 wells;

[0053] S2. Place the above experimental cells at 37°C, 5% CO 2 Cultivated in a cell culture incubator for 18 hours;

[0054] S3. ...

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Abstract

The invention provides an anti-cancer tetravalent platinum complex capable of inhibiting inflammation and immune escape and a preparation method, and particularly relates to the field of biological medicine. The molecular structure of the anti-cancer tetravalent platinum complex is as follows: S1, reacting a divalent platinum complex with hydrogen peroxide H2O2 to obtain a tetravalent platinum complex; S2, mixing the tetravalent platinum complex obtained in the step S1 with O-benzotriazole-N, N, N ', N'-tetramethylurea tetrafluoroboric acid (TBTU) and triethylamine (TEA) in an N, N-dimethylformamide (DMF) solution, and uniformly stirring and mixing; S3, after the reaction is finished, collecting a filtrate, concentrating the filtrate to 0.5-5mL, dropwise adding a mixture of ethanol and water, and centrifugally collecting precipitates; and dissolving the precipitate in methanol, washing the precipitate with diethyl ether for three times, and carrying out vacuum drying to obtain the target product. The tetravalent platinum complex disclosed by the invention not only has very strong toxic activity to tumor cells, but also inhibits inflammation and immune escape through a plurality ofaction targets, and shows an excellent anti-tumor effect in vivo.

Description

technical field [0001] The invention belongs to the field of biomedicine, and in particular relates to an anticancer tetravalent platinum complex capable of inhibiting inflammation and immune escape and a preparation method thereof. Background technique [0002] Platinum antineoplastic drugs have become the most widely used metal drugs in clinical practice. Since the first generation of platinum antineoplastic drugs represented by cisplatin (CDDP) was approved by the FDA for the treatment of testicular cancer and ovarian cancer, its It plays a leading role in the treatment of various solid tumors such as carcinoma and malignant pleural mesothelioma. However, due to the strong cytotoxicity of cisplatin, serious side effects may occur during treatment. In order to overcome this defect and reduce the systemic toxicity of cisplatin, the second-generation platinum-based antineoplastic drugs carboplatin (1989) and nedaplatin (Japan) and the third-generation platinum-based anti-tu...

Claims

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Application Information

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IPC IPC(8): C07F15/00A61K31/282A61P35/00A61P29/00A61P37/02
CPCC07F15/0093A61P35/00A61P29/00A61P37/02
Inventor 王晓勇金素星郭子建
Owner NANJING UNIV
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