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Segmented copolymer and preparation method thereof, and temperature sensitive type hydrogel

A block copolymer and hydrogel technology, applied in the field of polyamino acids, can solve the problems of single adjustability, unfavorable human health, and inability to achieve long-term continuous drug delivery, and achieve good adjustability and good biocompatibility and the effect of biodegradability

Active Publication Date: 2013-03-27
CHANGZHOU INST OF ENERGY STORAGE MATERIALS &DEVICES
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  • Abstract
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Problems solved by technology

Among them, the aqueous solution of polyoxyethylene-polyoxypropylene condensate (also known as Poloxamer, Poloxamer) can be used as a temperature-sensitive injectable hydrogel, which is currently the most studied type for temperature-sensitive hydrogel. Glue polymer, but it can only exist in the body for a few days and is diluted by body fluids, it cannot achieve long-term continuous drug administration, and poloxamer cannot be biodegraded, which limits its application in the human body; subsequently, the development of A hydrogel of polyethylene glycol and poly(L-lactic acid) block copolymer (Jeong B, Bae YH, Lee DS, et al.Biodegradable block copolymers as injectable drug-delivery systems[J].Nature, 1997, 388:860~862.), it can be biodegraded, but the degradation products are small molecular compounds such as lactic acid, local excessive concentration of lactic acid will cause inflammation, which is not good for human health; with the deepening of research, researchers have prepared Hydrogels of polyoxyethylene-polyoxypropylene and polyalanine or polyalanine and phenylalanine random copolymers have been developed (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 polyphenylalanine Molecular weight to adjust the phase transition behavior of hydrogels, the adjustability is relatively simple, which is not conducive to the further application of temperature-sensitive hydrogels

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  • Segmented copolymer and preparation method thereof, and temperature sensitive type hydrogel
  • Segmented copolymer and preparation method thereof, and temperature sensitive type hydrogel
  • Segmented copolymer and preparation method thereof, and temperature sensitive type hydrogel

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preparation example Construction

[0046] The invention provides a kind of preparation method of block copolymer, comprises the following steps:

[0047] Aminated polyethylene glycol monomethyl ether with a structure of formula (IV) or aminated polyethylene glycol with a structure of formula (V) and γ-alkyl-L-glutamic acid ester-N-carboxyl The acid internal acid anhydride undergoes a polymerization reaction to obtain a block copolymer;

[0048]

[0049] Among them, m is the degree of polymerization, 10≤m≤227;

[0050] n is the degree of polymerization, 10≤n≤226.

[0051] 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:

[0052] Esterification of polyethylene glycol monomethyl ether or polyethylene glycol with triethylamine and methylsulfonyl chloride to obtain polyethylene glycol monomethyl ether methanesulfonate or...

Embodiment 1

[0086] Azeotrope 2.2 g of aminated polyethylene glycol monomethyl ether with a number average molecular weight of 550 and 60 mL of anhydrous toluene at 130° C. for 2 h to remove water, and then drain the remaining toluene under reduced pressure; dissolve the obtained solid In 20mL of dry N,N-dimethylformamide, the first solution was obtained; 3.74g of γ-methyl-L-glutamate-N-carboxylic acid internal anhydride was dissolved in 40mL of dry N,N - in dimethylformamide, the second solution is obtained; in a nitrogen atmosphere, the first solution is mixed with the second solution, stirred and reacted at room temperature and under nitrogen protection conditions for 24h; after the reaction is completed, the N , N-dimethylformamide, then the obtained solid was dissolved in chloroform, then settled with ether, suction filtered, and dried to obtain polyethylene glycol monomethyl ether-poly(γ-methyl-L-glutene Amino acid ester) block copolymers.

[0087] The obtained block copolymer is ca...

Embodiment 2

[0089] After azeotroping 2.2 g of aminated polyethylene glycol monomethyl ether with a number-average molecular weight of 550 and 60 mL of anhydrous toluene at 130 ° C for 2 h, the remaining toluene was drained under reduced pressure; the resulting solid was dissolved In 20mL of dry N,N-dimethylformamide, the first solution was obtained; 4.02g of γ-ethyl-L-glutamate-N-carboxylic acid internal anhydride was dissolved in 40mL of dry N,N - in dimethylformamide, the second solution was obtained; in a nitrogen atmosphere, the first solution was mixed with the second solution, and stirred and reacted for 24 hours at room temperature and under nitrogen protection conditions; after the reaction was completed, the N, N -Dimethylformamide, then the obtained solid is dissolved in chloroform, then precipitated with ether, filtered by suction, and dried to obtain polyethylene glycol monomethyl ether-poly(γ-ethyl-L-glutamic acid ester) block copolymers.

[0090] The obtained block copolyme...

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Abstract

The invention provides a segmented copolymer and a preparation method thereof, and a temperature sensitive type hydrogel. The segmented copolymer comprises a first segment formed by terminal aminated polyethylene glycol or terminal aminated polyethylene glycol monomethyl ether and a second segment formed by the poly (gamma-alkyl-L-glutamate), the side chain of the second segment contains alkyl substituent, segmented copolymers with different substituent side chains can be obtained by adjusting the types, structures or length of the carbon chain of substituent on the side chain, thereby the phase transition temperature of the formed temperature sensitive hydrogel can be adjusted, and the adjusting means of phase transition behaviors of the temperature sensitive type hydrogel are expanded, the segmented copolymer is in favor of further application of the temperature sensitive type hydrogel. The temperature sensitive type hydrogel has long degradation period, and is in favor of performing long drug effectiveness on the lesion location, the degradation products are amino acid and polyethylene glycol, and can be directly eliminated out of the body through kidney.

Description

technical field [0001] The invention relates to the technical field of polyamino acids, in particular to a block copolymer, its preparation method and temperature-sensitive hydrogel. Background technique [0002] Sustained and controlled release drug delivery system refers to a new class of drug delivery system in which the drug is released slowly from the preparation at a non-constant rate in the body, thereby prolonging the drug's action time. Compared with traditional pharmaceutical preparations, sustained and controlled release drug delivery systems have the characteristics of less dosage, less frequency of administration, high curative effect, and less toxic and side effects on normal cells and tissues. It has become a hot research topic in the field of pharmacy in the past 20 years. [0003] The temperature-sensitive hydrogel has unique solution-gel transition characteristics. By controlling its phase transition temperature to match the body temperature, a temperature-...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08G69/40C08J3/075A61K47/34A61L27/52A61L27/18
Inventor 贺超良成一龙肖春生丁建勋任凯旋庄秀丽陈学思
Owner CHANGZHOU INST OF ENERGY STORAGE MATERIALS &DEVICES
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