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Amino acid block copolymer and preparation method thereof and temperature-sensitive water gel

A block copolymer and hydrogel technology, applied in the field of polyamino acids, can solve the problems of unfavorable temperature-sensitive hydrogel application and single adjustability, and achieve good biodegradability, good adjustability, and good The effect of biocompatibility

Active Publication Date: 2017-05-17
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

The prior art discloses hydrogels of polyoxyethylene-polyoxypropylene and polyalanine or polyalanine and phenylalanine random copolymers (Macromalecule, 2008, 41:8204~8209, Biomacromolecules, 2009, 10: 2476~2481.), the biodegradation products of this type of hydrogel are amino acids, which have no harm to the human body, but the block copolymers that form hydrogels can only be changed by unilaterally changing the polyalanine block or polyphenylene acrylic acid. The molecular weight of amino acids is used to adjust the phase transition behavior of hydrogels, and the adjustability is relatively simple, which is not conducive to the further application of temperature-sensitive hydrogels.

Method used

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  • Amino acid block copolymer and preparation method thereof and temperature-sensitive water gel
  • Amino acid block copolymer and preparation method thereof and temperature-sensitive water gel
  • Amino acid block copolymer and preparation method thereof and temperature-sensitive water gel

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preparation example Construction

[0038] The invention provides a kind of preparation method of block copolymer, comprises the following steps:

[0039] Aminated polyethylene glycol monomethyl ether with a structure of formula IV or aminated polyethylene glycol with a structure of formula V, combined with a structure of formula VI γ-alkyl-L-ethyl glutamate-N- Carboxylic acid internal anhydride and amino acid derivative-N-carboxylic acid internal acid anhydride are polymerized and deprotected to obtain a block polymer;

[0040]

[0041] Among them, m is the degree of polymerization, 5≤m≤227;

[0042] n is the degree of polymerization, 5≤n≤226.

[0043] In the present invention, the aminated polyethylene glycol monomethyl ether having the structure of formula (IV) or the aminated polyethylene glycol having the structure of formula (V) is preferably prepared according to the following method:

[0044] Esterification of polyethylene glycol monomethyl ether or polyethylene glycol with potassium hydroxide and p...

Embodiment 1

[0091] Azeotrope 3.0 g of aminated polyethylene glycol monomethyl ether with a number average molecular weight of 2000 and 100 mL of toluene at 130 ° C for 2 h to remove water, and then drain the remaining toluene under reduced pressure; dissolve the obtained solid in 30 mL In dried N,N-dimethylformamide, the first solution was obtained; 4.52g of γ-ethyl-L-glutamic acid ester-N-carboxylic acid internal anhydride and 0.59g of γ-benzyl-L-glutamine Amino acid ester-N-carboxylic acid internal acid anhydride was dissolved in 60mL of dry N,N-dimethylformamide to obtain a second solution; in a nitrogen atmosphere, the first solution was mixed with the second solution, at room temperature . Stirring and reacting for 72 hours under nitrogen protection; after the reaction, drain N,N-dimethylformamide under reduced pressure, then dissolve the obtained solid in chloroform, settle with ether, filter with suction, and dry to obtain Polyethylene glycol monomethyl ether-polyamino acid ester b...

Embodiment 2

[0094] Azeotrope 3.0 g of aminated polyethylene glycol monomethyl ether with a number average molecular weight of 2000 and 100 mL of toluene at 130 ° C for 2 h to remove water, and then drain the remaining toluene under reduced pressure; dissolve the obtained solid in 30 mL In dried N,N-dimethylformamide, the first solution was obtained; 4.5g of γ-ethyl-L-glutamic acid ester-N-carboxylic acid internal anhydride and 1.18g of γ-benzyl-L-glutamine Amino acid ester-N-carboxylic acid internal acid anhydride was dissolved in 60mL of dry N,N-dimethylformamide to obtain a second solution; in a nitrogen atmosphere, the first solution was mixed with the second solution, at room temperature . Stirring and reacting for 72 hours under nitrogen protection; after the reaction, drain N,N-dimethylformamide under reduced pressure, then dissolve the obtained solid in chloroform, settle with ether, filter with suction, and dry to obtain Polyethylene glycol monomethyl ether-polyamino acid ester bl...

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Abstract

The invention provides a block copolymer. The block copolymer comprises a first block and a second block, wherein the first block is formed by terminal-aminated polyethylene glycol or terminal-aminated methoxy polyethylene glycol; the second block is of a structure shown in formula (III). The block copolymer has the advantages that the first block and the second block respectively have different polymerization degrees, and the ratio of the blocks, and the ratio of ethyl ester group to carboxyl or amino are adjusted, so as to obtain the block polymer with different structures, and water gel with different phase-transition temperatures; according to the block copolymer provided by the invention, multiple adjusting methods are provided, the adjustability of the formed temperature-sensitive water gel is good, the method of adjusting the phase-transition behavior of the temperature-sensitive water gel is expanded, and the further application of the temperature-sensitive water gel is facilitated.

Description

technical field [0001] The invention relates to the technical field of polyamino acid, in particular to an amino acid block copolymer, a preparation method thereof and a temperature-sensitive hydrogel. Background technique [0002] Injectable temperature-sensitive hydrogels are high-molecular aqueous solutions in vitro or at low temperatures, but when injected into the body, they can quickly transform into semi-solid gels, which is beneficial for such materials in drug delivery, Applications in tissue engineering, etc. At present, the research on local drug controlled release system based on injectable hydrogel has become one of the research hotspots in the field of drug controlled release. [0003] Polymers can form temperature-sensitive hydrogels, which has become one of the research hotspots in recent years. The prior art discloses hydrogels of polyoxyethylene-polyoxypropylene and polyalanine or polyalanine and phenylalanine random copolymers (Macromalecule, 2008, 41:82...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G69/40C08J3/075C08L77/00
CPCC08G69/40C08J3/075C08J2377/00
Inventor 贺超良于双江陈学思
Owner CHANGCHUN INST OF APPLIED CHEMISTRY - CHINESE ACAD OF SCI
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