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An amphiphilic four-armed star polymer and its shell-based reversible cross-linked micelle system, preparation method and application

A four-armed star-shaped, polymer technology, applied in the direction of non-active ingredient medical preparations, medical preparations containing active ingredients, drug combinations, etc., can solve the problems of reducing the therapeutic effect and hindering the release of inner core drugs, etc., to reduce the Burst release phenomenon, realization of application value, effect of improving load and release efficiency

Active Publication Date: 2019-01-15
SOUTH CHINA UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, when the micelles reach the tumor tissue, this irreversible chemically bonded and cross-linked structure will hinder the release of the core drug and reduce the therapeutic effect.

Method used

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  • An amphiphilic four-armed star polymer and its shell-based reversible cross-linked micelle system, preparation method and application
  • An amphiphilic four-armed star polymer and its shell-based reversible cross-linked micelle system, preparation method and application
  • An amphiphilic four-armed star polymer and its shell-based reversible cross-linked micelle system, preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0083] Example 1: Aldehyde functionalized monomer MAEBA

[0084] Take a 150mL clean three-necked flask, add a stirring bar, and under nitrogen protection, add p-(2-hydroxyethoxy)benzaldehyde (3.8g, 23mmol), triethylamine (2.33g, 23mmol) and 75mL di Chloromethane, ice bath, then slowly drop into 25mL dichloromethane containing methacryloyl chloride (7.2g, 69mmol), return to room temperature after stirring for 1h, continue to stir and react for 24h, pour into a separatory funnel, add H 2 O (100mL) extraction, then rinse the organic phase twice with NaCl (0.5M, 100mL) solution, then dry with anhydrous magnesium sulfate, filter, and remove the solvent by rotary evaporation, the obtained crude product is purified by silica gel column chromatography (eluent For n-hexane / ethyl acetate 4:1, R f value 0.4), and finally collect the target filtrate, and remove the solvent by rotary evaporation to obtain a white solid. The synthetic reaction formula is shown in formula (1). Analysis of...

Embodiment 2

[0086] Example 2: Aldehyde functionalized monomer MAEBA

[0087] Take a 150mL clean three-necked flask, add a stirring bar, and under nitrogen protection, add p-(2-hydroxyethoxy)benzaldehyde (3.8g, 23mmol), triethylamine (6.99g, 69mmol) and 75mL di Chloromethane, ice bath, then slowly drop into 25mL dichloromethane containing methacryloyl chloride (2.4g, 23mmol), return to room temperature after stirring for 5h, continue to stir and react for 12h, pour into a separatory funnel, add H 2 O (100mL) extraction, then rinse the organic phase twice with NaCl (0.5M, 100mL) solution, then dry with anhydrous magnesium sulfate, filter, and remove the solvent by rotary evaporation, the obtained crude product is purified by silica gel column chromatography (eluent For n-hexane / ethyl acetate 4:1, R f value 0.4), and finally collect the target filtrate, and remove the solvent by rotary evaporation to obtain a white solid.

Embodiment 3

[0088] Example 3: Preparation of amphiphilic four-arm star polymer (4-AS-PCL-P(PEGMA-co-MAEBA)) (x:y:z=12:9:9)

[0089] (1) Preparation of polycaprolactone-containing polymer 4-AS-PCL

[0090] Take a 50mL dry reaction bottle, put it into a stirring bar, then bake the reaction bottle with an alcohol lamp for 5min, add the initiator pentaerythritol (136mg, 1mmol) into the reaction bottle, and seal it with a rubber stopper. Vacuumize - pass argon three times, add monomer ε-CL (5.47g, 48mmol) under the protection of argon. Heating in the bath for 20min, adding Sn(Oct) 2 (11 mg), after 16 h of reaction, the reaction was terminated with liquid nitrogen. Add 50 mL of THF to dissolve the polymer, precipitate with 500 mL of cold methanol / water (1:1), and dry under vacuum at 45 °C and 35 mb. The synthetic reaction formula is shown in formula (2). Using NMR, infrared and GPC to analyze the molecular structure and composition, the results are shown in image 3 , Figure 4 with Fig...

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Abstract

The invention belongs to the technical field of biological medical macromolecule polymer materials, and discloses an amphipathic four-arm star-like polymer and a shell reversible crosslinked micelle system based on the same, and a preparation method and an application of the amphipathic four-arm star-like polymer. The polymer specifically has a structure shown by a formula (I) as shown in the specification, wherein x=10-30, y=5-20, and z=5-20. The invention also provides the shell reversible crosslinked micelle system based on the amphipathic four-arm star-like polymer. For the polymer disclosed by the invention, under the condition that the pH value is 6.5 and a catalyst namely aniline exists, an aldehyde group at a shell crosslinked site reacts with a crosslinking agent 3,3'-dithio-bis(propionic acid dihydrazide) to form a reversible crosslinked structure containing a disulfide bond and an acylhydrazone bond, and the reversible crosslinked structure has good stability and significantly-improved dilution resistance; and when the polymer is applied to loading water-insoluble medicines, controllable and rapid release of the water-insoluble medicines in different environments can be realized, efficient delivery release of medicines is realized, and the treatment efficiency of cancers is improved.

Description

technical field [0001] The invention belongs to the technical field of biomedical polymer materials, and in particular relates to an amphiphilic four-arm star polymer, a shell reversible cross-linked micelle system based on it, a preparation method and application thereof. Background technique [0002] At present, cancer has become one of the major factors threatening people's health. Traditional methods of treating cancer and tumors include physical radiation therapy and chemotherapy, and chemotherapy focuses on the delivery and release of anticancer drugs. With the development of nanotechnology, nano drug delivery system provides great convenience for the delivery and release of anticancer drugs, and plays an increasingly important role in the field of cancer treatment. Nano-drug delivery systems mainly include nanoparticles, vesicles, hydrogels, micelles, etc. Various carrier systems provide new means for cancer treatment, not only reducing the loss of drugs during deliv...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08F293/00C08F220/28C08F220/30C08G63/08A61K9/107A61K47/34A61K31/4745A61P35/00
CPCA61K9/1075A61K31/4745A61K47/34C08F220/28C08F220/286C08F220/30C08F220/302C08F293/00C08G63/08
Inventor 章莉娟熊迪姚娜钟曼丽
Owner SOUTH CHINA UNIV OF TECH
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