Phosphocholine monomer and polymer and application thereof

A technology of choline phosphoric acid and choline phosphoric ester, which is applied in the direction of phosphorus organic compounds, compounds of group 5/15 elements of the periodic table, medical preparations of non-active ingredients, etc., and can solve the problem of phosphatidylcholine groups Difficult synthesis, large-scale production, and functional modification, etc., to achieve excellent conjugation compatibility, high biomimeticity, and promote cell internalization

Pending Publication Date: 2021-09-03
CHANGCHUN INST OF APPLIED CHEMISTRY - CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the synthesis of phosphatidylcholine group monomers is difficult, and the core technology is in the hands of Japanese companies such as Shiseido Co., Ltd., and it is difficult to achieve large-scale production in China
In addition, the phosphatidylcholine group is difficult to functionalize because the phosphate group is connected to the polymer chain and the choline group is free, which reduces its functionality.

Method used

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  • Phosphocholine monomer and polymer and application thereof
  • Phosphocholine monomer and polymer and application thereof
  • Phosphocholine monomer and polymer and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0063] The preparation of embodiment 1 part acrylic acid choline phosphoric acid ester monomer

[0064] Triethylamine (51g, 0.51mol) and anhydrous methanol (16g, 0.5mol) were added to a branched flask containing 300mL of anhydrous tetrahydrofuran, stirred magnetically under nitrogen protection, cooled in an ice-water bath for 30 minutes, and then Add 2-chloro-2-oxo-dioxaphospholane (71g, 0.5mol) dropwise into the constant pressure dropping funnel. During the dropwise addition, the reaction system produces a large amount of white precipitate, and the dropwise addition is completed within 1 hour. After 2 hours of reaction in a water bath, slowly rise to room temperature, continue to react for 2 hours, filter, wash the filter cake twice with anhydrous tetrahydrofuran, collect the filtrate, remove the solvent under reduced pressure to obtain a crude product, and the crude product is subjected to short-neck distillation to obtain the pure product 2- Oxymethyl-2-oxo-dioxaphospholane...

Embodiment 2

[0078] Preparation of Functionalized Acrylic Phosphate Choline Monomer

[0079] Add triethylamine (51g, 0.51mol) and anhydrous acetylene butanol (35g, 0.5mol) into a branched flask containing 150mL of anhydrous tetrahydrofuran, stir magnetically under nitrogen protection, and cool in an ice-water bath for 30 minutes. 2-Chloro-2-oxo-dioxaphospholane (71g, 0.5mol) was added dropwise from the constant pressure dropping funnel. During the dropwise addition, the reaction system produced a large amount of white precipitate, and the dropwise addition was completed within 1 hour. Keep the reaction in ice-water bath for 2 hours, then slowly rise to room temperature, continue the reaction for 2 hours, filter, wash the filter cake twice with anhydrous tetrahydrofuran, collect the filtrate, remove the solvent under reduced pressure to obtain the crude product, and the crude product is subjected to short-neck distillation to obtain the pure product 44 g of 2-oxobutynyl-2-oxo-dioxaphosphola...

Embodiment 3

[0086] Preparation and performance characterization of embodiment 3 acrylic acid choline phosphate copolymer and its hydrogel

[0087] The initiator 2-bromo-2-methylpropionic acid 3-azidopropyl ester (2.5mg, 1mmol), 2,2-bipyridyl (0.312g, 2mmol), acryloyloxyethylcholine phosphoric acid ethyl ester (7.03g, 25mmol) was added to a Schlenk bottle containing 30mL of anhydrous methanol, and three times of freezing-thawing-deoxygenation were performed under nitrogen atmosphere, and cuprous bromide (143mg, 1mmol) was added under nitrogen protection. The reaction was carried out at room temperature. After 24 hours, the mixture was exposed to air to terminate the reaction, and then the mixture was dialyzed in deionized water (dialysis bag MWCO 2000). After 24 hours, the sample was freeze-dried to obtain the product PACP25. The product structure is as follows:

[0088]

[0089] 1 H-NMR (500MHz,D 2 O):4.64(t,-CH 2 O-CO-),4.29(t,-CH 2 OP), 3.86(m,-CH 2 N(CH 3 ) 2 -CH 2 -), 3.72...

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Abstract

The invention provides a phosphocholine monomer and a polymer and application thereof, and particularly provides a phosphocholine monomer with a structure as shown in a formula I. The phosphocholine monomer and polymer provided by the invention are used in the field of biomedical materials, can significantly improve the stability, biocompatibility, pollution resistance and long-acting antibacterial activity of the materials, improve the utilization rate of drug molecules, and have wide application prospects in multiple fields.

Description

technical field [0001] The invention relates to the technical field of biomedical materials, in particular to a phosphoric acid choline monomer and its polymer and application. Background technique [0002] With the continuous development of society, biomedical materials continue to emerge. Nanomaterials have received extensive attention in recent years. According to their unique properties, nanomaterials can improve the distribution of drugs in organisms, thereby enhancing the efficacy. Among them, the stability and targeting of nanoparticles are the two most important issues for their application in living organisms. Both issues need to be addressed by designing and modifying nanoparticles to make them stable and functional. Polyethylene glycol (PEG) is a very successful biomedical material in recent years. By conjugating polyethylene glycol to the surface of nanomaterials, the non-specific anti-protein adsorption properties (anti-pollution properties) of PEG are used t...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F9/6574C07F9/09C08F30/02C08F38/00C08F130/02C08F293/00C08F287/00C08F220/06C08F222/38A61K47/24A61K47/32A61L15/20A61L15/24A61L15/42A61L15/46A61L26/00A61L31/08A61L31/10A61L31/14A61L31/16
CPCC07F9/6574C07F9/091C08F30/02C08F38/00C08F130/02C08F293/005C08F287/00A61K47/24A61K47/32A61L26/008A61L26/0066A61L26/0014A61L26/00A61L26/0061A61L15/46A61L15/20A61L15/24A61L15/42A61L31/08A61L31/10A61L31/14A61L31/16C08F2438/01A61L2300/404A61L2300/602C08F220/06C08F222/385
Inventor 于喜飞梅韦康李晟冉刘三荣
Owner CHANGCHUN INST OF APPLIED CHEMISTRY - CHINESE ACAD OF SCI
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