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Amino acid block copolymer, its preparation method and temperature-sensitive hydrogel

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: 2019-03-08
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, its preparation method and temperature-sensitive hydrogel
  • Amino acid block copolymer, its preparation method and temperature-sensitive hydrogel
  • Amino acid block copolymer, its preparation method and temperature-sensitive hydrogel

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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 block copolymer provided by the present invention comprises a first block formed of aminated polyethylene glycol or aminated polyethylene glycol monomethyl ether and a second block having a structure of formula (III). The first block and the second block of the block copolymer of the present invention all have different degrees of polymerization, and block ratios with different structures can be obtained by adjusting the ratio of blocks and the ratio of ethyl ester groups to carboxyl groups or amino groups. Segment polymers, and hydrogels with different phase transition temperatures. The block polymer provided by the present invention has a variety of adjustment means, so that the temperature-sensitive hydrogel formed has good adjustability, expands the adjustment means for the phase transition behavior of the temperature-sensitive hydrogel, and is beneficial to this type of temperature Sensitive hydrogels for further applications.

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 Patents(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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