A kind of resveratrol polymer bonded drug and preparation method thereof

A technology of resveratrol and macromolecular polymer, which is used in pharmaceutical formulations, medical preparations with non-active ingredients, antibacterial drugs, etc., can solve the problem that the inclusion effect has a great influence, water solubility and stability are not involved, etc. problem, to achieve good hydrophilicity and biocompatibility, avoid phagocytosis, stability and water solubility improvement effect

Active Publication Date: 2017-10-13
BEIJING UNIV OF CHEM TECH
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The patent application number CN02144831.0 (hydroxypropyl-β-cyclodextrin inclusion complex of resveratrol and glucoside and derivatives and preparation method) discloses a method for preparing hydroxypropyl-β-cyclodextrin and Conjugates composed of resveratrol compounds, the main content of which discloses the preparation method of conjugates composed of resveratrol glycosides and cyclodextrins, but the temperature that has a greater impact on the inclusion effect is not involved
The application number is CN200610038491.4 (a class of resveratrol compounds with carboxyl substituents and its preparation method) to prepare new carboxyl substituted resveratrol compounds. The higher anti-tumor, cardiovascular protection or anti-oxidation activities of retrol, but not related to its water solubility and stability

Method used

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  • A kind of resveratrol polymer bonded drug and preparation method thereof
  • A kind of resveratrol polymer bonded drug and preparation method thereof
  • A kind of resveratrol polymer bonded drug and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0060] Add 1.9g of p-toluenesulfonyl chloride to a drying reactor with a water separator and a stirring device, pump argon 3 times, azeotropically remove water from anhydrous toluene, and after removing most of the toluene, change to a vacuum device for extraction The remaining toluene was dried under vacuum at 80°C for 6 hours. After returning to room temperature, add 3.00g of recrystallized resveratrol and 100ml of anhydrous acetone under the protection of inert gas, and add a small amount of NaHCO to the reaction. 3 , React under magnetic stirring at 25℃ for 18 hours. Filter the product to remove NaHCO 3 , The supernatant liquid was suspended and evaporated to a molten state to remove a large amount of acetone, the product was dissolved in appropriate dichloromethane, ether was settled, and dried in vacuo to obtain 4.10 g of a white powdery product with a yield of 83.7%.

[0061] The infrared spectrum of the obtained resveratrol derivatives can be seen figure 1 , NMR spectrum ...

Embodiment 2

[0065] Add 1.90g of p-toluenesulfonyl chloride to a drying reactor with a water separation device and a stirring device, pump argon 3 times, azeotropically remove water from anhydrous toluene, and after removing most of the toluene, change to a decompression device for extraction The remaining toluene was dried under vacuum at 80°C for 6 hours. After returning to room temperature, add 3.00g of recrystallized resveratrol and 100ml of anhydrous acetone under the protection of inert gas, while adding a small amount of NaHCO to the reaction 3 , React under magnetic stirring at 25℃ for 18 hours. Filter the product to remove NaHCO 3 , The supernatant liquid was suspended and evaporated to a molten state to remove a large amount of acetone, the product was dissolved in appropriate dichloromethane, ether was settled, and dried in vacuo to obtain 4.10 g of a white powdery product with a yield of 83.7%.

[0066] The infrared test results of the obtained synthetic product show that the prod...

Embodiment 3

[0069] Add 785 mg of acetyl chloride to a dry reactor with a water separation device and a stirring device, pump argon 3 times, soak the molecular sieve to remove water, after removing most of the water, change it to a decompression device to extract purified acetyl chloride. Under the protection of inert gas, add to 100ml of anhydrous acetone and add 3.00g of recrystallized resveratrol, while adding a small amount of NaHCO to the reaction 3 , React for 20 hours at 25℃ under magnetic stirring. Filter the product to remove NaHCO 3 , The supernatant liquid was suspended and evaporated to a molten state to remove a large amount of acetone, the product was dissolved in appropriate dichloromethane, ether was settled, and dried under vacuum to obtain 2.80 g of a white powdery product with a yield of 74.0%.

[0070] The infrared test result of the obtained synthetic product shows that the product contains both the resveratrol structure and the characteristic absorption peak of acetyl chl...

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Abstract

The invention discloses a polymer-resveratrol bonded drug and a preparation method thereof. The resveratrol polymer-bonded drug has the following general formula: P-RES'm wherein: P is a water-soluble polymer, m is an integer from 1 to 50; RES' is a resveratrol derivative , the resveratrol derivative is made of resveratrol and acid chloride. The polymer bonded drug of the present invention has good hydrophilicity and biocompatibility, can avoid human reticuloendothelial system phagocytosis in the blood circulation, and ensure sufficient time to reach the tumor site through the EPR effect, and then enter the cell through endocytosis , efficient targeting of experimental drugs.

Description

Technical field [0001] The invention relates to the field of medicine technology. More specifically, it relates to a resveratrol polymer bonded drug and a preparation method thereof. Background technique [0002] Resveratrol (resveratrol), a 1,2-stilbene derivative, its chemical name is 3,4',5-trihydroxy-trans-stilbene (3,4',5 -trihydroxy-stilbene), a colorless needle-like crystal, easily soluble in organic solvents such as ether, chloroform, methanol, ethanol, acetone, and ethyl acetate. Resveratrol is a kind of plant antitoxin produced by plants. It has a variety of physiological and pharmacological effects. It is the main active ingredient in grapes. Its structural formula is: [0003] [0004] Studies so far have shown that resveratrol has anti-tumor, anti-cardiovascular disease, anti-oxidation, and anti-bacterial effects. However, resveratrol is a polyphenol compound, which has the shortcomings of poor stability and insoluble in water, which limits its application and deve...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): A61K47/59A61K31/05A61K9/107A61P35/00A61P9/00A61P39/06A61P31/04
Inventor 乐园王文龙张亮杨小兰刘孟涛张德涛王洁欣陈建峰
Owner BEIJING UNIV OF CHEM TECH
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