Cartilage targeting zwitterionic polymer, preparation method and application thereof

A zwitterion, polymer technology, used in prosthesis, tissue regeneration, medical science and other directions, can solve the problems of lack of long-term joint lubrication performance, no interaction, easy failure of polymers, and easy mass production and application. The effect of promotion, simple preparation process, simple operation and preparation process

Active Publication Date: 2021-12-14
SICHUAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0002] The polymers currently used for cartilage protection are mainly zwitterionic polymers, anionic / cationic polyelectrolytes or zwitterionic modified natural polysaccharide materials, however, these materials can only be used as lubricant supplements injected into the joint cavity, and cartilage There is no strong interaction between tissues, therefore, the polymers free in the joint cavity are easy to fail or be metabolized, and do not have long-term joint lubrication performance

Method used

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  • Cartilage targeting zwitterionic polymer, preparation method and application thereof
  • Cartilage targeting zwitterionic polymer, preparation method and application thereof
  • Cartilage targeting zwitterionic polymer, preparation method and application thereof

Examples

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Embodiment 1

[0043] In this embodiment, a method for preparing a cartilage-targeted zwitterionic polymer is provided, and the steps are as follows:

[0044] (1) Preparation of active ester monomer NHSMA

[0045] N-hydroxysuccinimide (NHS, 1.1736 g, 12 mmol) and triethylamine (1,650 μL, 12 mmol) were dissolved in 5 mL of chromatography-grade dichloromethane (DCM), stirred for 30 minutes under ice-bath conditions, and at the same time, Dissolve methacryloyl chloride (1 mL, 11 mmol) in 5 mL of chromatographic grade dichloromethane and add it dropwise to the previously prepared solution at a rate of 1 drop per 10 seconds. After the solution was added dropwise, the reaction system was gradually returned to room temperature and the reaction was continued for 12 h. After the reaction, wash with distilled water 3 times, 5 mL each time; then dry with anhydrous sodium sulfate, concentrate the resulting organic solution by rotary evaporation, and dissolve in ethyl acetate / n-hexane (1 / 3) mixed soluti...

Embodiment 2

[0056] In this embodiment, a method for preparing a cartilage-targeted zwitterionic polymer is provided, and the specific steps are as follows:

[0057] (1) Preparation of active ester monomer NHSMA

[0058] Its preparation process is consistent with embodiment 1.

[0059] (2) Synthesis of functional zwitterionic polymer pSBMA-pNHSMA by random copolymerization

[0060] Add [2-(methacryloyloxy)ethyl]dimethyl-(3-sulfonic acid propyl)ammonium hydroxide (SBMA), NHSMA, AIBN into the 25mL reaction flask according to the amount in Table 2, Then 10 mL of chromatographic grade DMF was added as a reaction solvent, and nitrogen gas was passed into the reaction bottle for 30 minutes, and then reacted at 70° C. for 24 h. After the reaction, the reaction solution was added dropwise into pre-cooled methanol to precipitate the polymer, and after repeated washing for 3 times, the obtained polymer was vacuum-dried to remove the organic solvent to obtain pSBMA-pNHSMA. Its reaction is shown in...

Embodiment 3

[0068] In this example, a preparation scheme for cartilage-targeting zwitterionic polymers is provided, and the specific steps are as follows:

[0069] (1) Preparation of active ester monomer NHSMA

[0070] Its preparation process is consistent with embodiment 1.

[0071] (2) Preparation of zwitterionic monomer [2-(methacryloyloxy) ethyl] dimethyl-(3-carboxylic acid ethyl) ammonium hydroxide (CBMA)

[0072] Mix 8.5mL of dimethylaminoethyl methacrylate (DMAEMA), 7mL of acrylic acid (AAc) and 0.01g of 4-methoxyphenol in an ice bath. After about 4 hours of reaction, the solution becomes thick; add 5mL of acetone Then continue to react for 24h. After the reaction was completed, the reaction solution was added dropwise into 25 mL of acetone to precipitate the product. After repeated precipitation for 3 times, the product CBMA was obtained by vacuum drying.

[0073]

[0074] (3) Synthesis of functional zwitterionic polymer pCBMA-pNHSMA by random copolymerization

[0075] Add ...

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Abstract

The invention belongs to the field of polymer functional materials, and specifically relates to a cartilage-targeting zwitterionic polymer and its preparation method and application. First, a methacryloyl chloride-modified N-hydroxysuccinimide monomer is synthesized for realizing High-efficiency chemical grafting of cartilage-targeting peptides; secondly, cartilage-targeting zwitterionic polymers were obtained by random copolymerization or RAFT polymerization. This polymer can be targeted to the surface of cartilage, enhance the lubricating properties of articular cartilage, and avoid wear during its movement. In addition, the "anti-fouling" performance provided by the zwitterionic unit can resist the damage of degrading enzymes to the cartilage matrix, thereby Achieve hose protection. This cartilage-targeting zwitterionic polymer has broad application prospects in bone tissue engineering.

Description

technical field [0001] The invention belongs to the field of polymer functional materials, and relates to a cartilage-targeting zwitterionic polymer and its preparation method and application, which can be used to enhance the lubricating performance of cartilage, weaken the damage of degrading enzymes to cartilage matrix, and protect joints Cartilage has a wide range of biological applications. Background technique [0002] The polymers currently used for cartilage protection are mainly zwitterionic polymers, anionic / cationic polyelectrolytes or zwitterionic modified natural polysaccharide materials, however, these materials can only be used as lubricant supplements injected into the joint cavity, and cartilage There is no strong interaction between tissues, therefore, the polymers free in the joint cavity are easy to fail or be metabolized, and do not have long-term joint lubrication performance. Contents of the invention [0003] The purpose of the present invention is ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08G81/02A61L27/26A61L27/50
CPCC08G81/02A61L27/26A61L27/50A61L2430/06C08L89/00C08L43/02
Inventor 谢婧李建树俞鹏孙辉任凯
Owner SICHUAN UNIV
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