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Quadrivalent platinum prodrug bendazac platinum, preparation thereof, and preparation methods and applications of prodrug and preparation

A technology of platinum-bendazine and drug-bendaxate, which is applied in the field of medicine, can solve problems such as poor tumor accumulation capacity, lack of tumor targeting, and short blood circulation time, and achieve increased uptake capacity and good anti-tumor effects , anti-tumor synergistic effect

Active Publication Date: 2021-06-15
山东省第二人民医院(山东省耳鼻喉医院、山东省耳鼻喉研究所)
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] Although tetravalent platinum prodrugs can reduce the toxicity of divalent platinum to a certain extent, they still have the disadvantages of small molecule drugs, such as short blood circulation time, poor accumulation in tumor sites, low drug utilization, and lack of tumor targeting Wait

Method used

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  • Quadrivalent platinum prodrug bendazac platinum, preparation thereof, and preparation methods and applications of prodrug and preparation
  • Quadrivalent platinum prodrug bendazac platinum, preparation thereof, and preparation methods and applications of prodrug and preparation
  • Quadrivalent platinum prodrug bendazac platinum, preparation thereof, and preparation methods and applications of prodrug and preparation

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0043] Accurately weigh 200mg (0.67mmol) cisplatin with an analytical balance in a round bottom flask, slowly add 3mL of 30wt% hydrogen peroxide at a mass concentration, protect the round bottom flask from light with tinfoil, and reflux at 70°C for 5 hours. After the reaction is complete, put Place the round bottom flask in a refrigerator at 4°C for static crystallization, transfer to an EP tube and centrifuge, wash the centrifuged solid twice with distilled water, ethanol, and ether, and dry the solid in a vacuum oven overnight to obtain a light yellow solid hydroxyl platinum.

[0044] Accurately weigh 100mg (0.3mmol) of hydroxyplatinum in a round bottom flask with an analytical balance, add anhydrous DMF to dissolve it, accurately weigh 254.07mg (0.9mmol) of benzalic acid, 130μL (0.9mmol) of triethylamine, 288mg of TBTU ( 0.9mmol) were dissolved in anhydrous DMF, and added to the round bottom flask while stirring, triethylamine and TBTU were catalysts. The round-bottomed fl...

Embodiment 2

[0046] Precisely weigh 200 mg (0.67 mmol) of cisplatin with an analytical balance in a round-bottomed flask, slowly add 0.35 mL of 30 wt % hydrogen peroxide, protect the round-bottomed flask from light with tinfoil, and reflux at 100° C. for 1 hour. After the reaction is complete, Place the round-bottomed flask in a refrigerator at 10°C for static crystallization, transfer to an EP tube and centrifuge, wash the centrifuged solid twice with distilled water, ethanol, and ether, and dry the solid in a vacuum oven overnight to obtain a light yellow solid Hydroxyplatinum.

[0047] Precisely weigh 100mg (0.3mmol) of hydroxyplatinum in a round-bottomed flask with an analytical balance, add anhydrous DMF to dissolve it, and accurately weigh 762.21mg (2.7mmol) of bentacic acid, 390μL (2.7mmol) of triethylamine, and 864mg of TBTU (2.7mmol) were dissolved in anhydrous DMF, and added to the round bottom flask while stirring. The round-bottomed flask was protected from light with tinfoil,...

Embodiment 3

[0049] Accurately weigh 200 mg (0.67 mmol) cisplatin with an analytical balance in a round bottom flask, slowly add 13 mL of 30 wt % hydrogen peroxide, protect the round bottom flask from light with tinfoil, and reflux at 40 ° C for 10 hours. After the reaction is complete, put Place the round bottom flask in a refrigerator at 0°C for static crystallization, transfer to an EP tube and centrifuge, wash the centrifuged solid twice with distilled water, ethanol, and ether, and dry the solid in a vacuum oven overnight to obtain a light yellow solid hydroxyl platinum.

[0050] Precisely weigh 100mg (0.3mmol) of hydroxyplatinum in a round bottom flask with an analytical balance, add anhydrous DMF to dissolve it, and accurately weigh 84.7mg (0.3mmol) of benzaxacid, 43.3μL (0.3mmol) of triethylamine, and 96mg of TBTU (0.3mmol) were dissolved in anhydrous DMF, and added to the round bottom flask while stirring. The round-bottomed flask was protected from light with tinfoil, evacuated,...

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Abstract

The invention belongs to the technical field of medicines, and particularly relates to a tetravalent platinum prodrug bendazac platinum, a preparation thereof, and preparation methods and applications of the prodrug and the preparation. The structural formula of the prodrug is shown in the specification. The preparation method of the prodrug comprises the following steps: (1) synthesizing hydroxyl platinum; (2) synthesizing bendazac platinum; and (3) purifying the bendazac platinum. The preparation method of the nano preparation comprises the following steps: (1) preparing a bendazac platinum solution; and (2) preparing the nano preparation by taking bovine serum albumin as a carrier. The tetravalent platinum prodrug bendazac platinum and the nano preparation thereof provided by the invention are good in water solubility, small in toxic and side effects and high in anti-tumor efficacy, can be passively targeted to a tumor site, can increase the drug uptake ability of tumor cells, and show a good anti-tumor effect, and the inhibition rates of the tetravalent platinum prodrug bendazac platinum to various tumors can be higher than 90%.

Description

technical field [0001] The invention belongs to the technical field of medicines, and in particular relates to a tetravalent platinum prodrug, platinum bendaxate, a preparation, a preparation method and an application thereof. Background technique [0002] Cancer is one of the major diseases causing human death worldwide. Among cancer-related deaths, about 90% of cancer patients die from metastasis of malignant tumors. Studies have found that tumor growth and metastasis are the combined results of multiple factors such as immunosuppression in the tumor microenvironment, epithelial-mesenchymal transition, and neovascularization. Cyclooxygenase (COX) is the rate-limiting enzyme for the synthesis of prostaglandins (PGs) in the human body. Cyclooxygenase mainly includes two subtypes: COX-1 and COX-2, of which COX-2 is an inducible cyclooxygenase, which is expressed at a low level in normal tissue cells, but can be inhibited by inflammatory factors, cancer Induced expression o...

Claims

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Application Information

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IPC IPC(8): C07F15/00A61K31/555A61K9/08A61K47/42A61P35/00
CPCC07F15/0093A61K31/555A61K9/08A61K47/42A61P35/00
Inventor 吴记勇张荻王冬博聂晶孙磊
Owner 山东省第二人民医院(山东省耳鼻喉医院、山东省耳鼻喉研究所)
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