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Polyethylene glycol derivative and preparation method thereof, and polyethylene glycol hydrogel capable of rapidly generating cross-linking reaction

A polyethylene glycol and derivative technology, applied in the field of new biomedical materials, can solve the problems of slow gel formation, low mechanical strength, poor stability, etc., and achieves fast gel formation speed, fast reaction rate and good stability. Effect

Active Publication Date: 2020-07-24
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 polyethylene glycol hydrogel prepared by the prior art has slow gelation speed, poor stability, low mechanical strength, and the need to add toxic catalysts and other defects, which limit its application in the biomedical field

Method used

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  • Polyethylene glycol derivative and preparation method thereof, and polyethylene glycol hydrogel capable of rapidly generating cross-linking reaction
  • Polyethylene glycol derivative and preparation method thereof, and polyethylene glycol hydrogel capable of rapidly generating cross-linking reaction
  • Polyethylene glycol derivative and preparation method thereof, and polyethylene glycol hydrogel capable of rapidly generating cross-linking reaction

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preparation example Construction

[0065] The present invention also provides a kind of preparation method of above-mentioned polyethylene glycol derivative, comprises the following steps:

[0066] A) reacting 1,3-dimethoxy-1,3-dihydroisobenzofuran-5-carboxylic acid succinimide ester with polyethylene glycol whose end group is an amino group to obtain a reaction product;

[0067] B) Deprotecting the reaction product to obtain polyethylene glycol derivatives.

[0068] Wherein, the reaction process is as follows:

[0069]

[0070] In the present invention, 1,3-dimethoxy-1,3-dihydroisobenzofuran-5-carboxylic acid succinimide ester and polyethylene glycol whose end group is amino are dissolved in an organic solvent, Reaction in the presence of the agent, precipitation, to obtain the reaction product.

[0071] The molar equivalent of the 1,3-dimethoxy-1,3-dihydroisobenzofuran-5-carboxylic acid succinimide ester is 1.2 to 5 molar equivalents of the amino group in polyethylene glycol whose end group is an amino gro...

Embodiment 1

[0130] 3,4-Dimethylbenzoic acid (12g) and N-bromosuccinimide (57g) were dissolved in hot carbon tetrachloride (200mL), and then 1.6g of benzoyl peroxide was slowly added. The mixture was refluxed at 81°C for 15h. After filtration, the filter cake was washed by benzene (200 mL), diethyl ether (300 mL). All the filtrates were combined, concentrated by a rotary evaporator until the remaining liquid volume was 70 mL, and then dried by a vacuum pump to a solid. The resulting solid was recrystallized from acetonitrile to give 3,4-bis(dibromomethyl)benzoic acid (13 g, 35%).

Embodiment 2

[0132] The 3,4-bis(dibromomethyl)benzoic acid (13 g) prepared in Example 1 was dissolved in an aqueous sodium carbonate solution (130 mL) with a mass-volume concentration of 10%, and reacted at 70° C. for 4 h. The pH of the reaction solution was adjusted to 1 by concentrated hydrochloric acid, and extracted with ethyl acetate (4×60 mL). After the organic phases were combined, they were washed with saturated brine, dried over anhydrous sodium sulfate, filtered, and vacuum-dried to obtain 3,4-diformylbenzoic acid (2.8 g, 56%).

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Abstract

The invention provides a polyethylene glycol derivative, which comprises a repeating unit with a structure represented by a formula (I) and an end group with a structure represented by a formula (II).The polyethylene glycol derivative provided by the invention has good biocompatibility due to the repeating unit with the structure represented by the formula (I). Due to the fact that the o-phthalaldehyde terminal group with the structure represented by the formula (II) can react with various groups such as amino, (acyl) hydrazine, amido-oxy and the like, the reaction speed is high, and the reaction conditions are mild. The polyethylene glycol derivative provided by the invention and amino-terminated polyethylene glycol are mixed in an aqueous medium to quickly form a chemically cross-linkedhydrogel material, and the chemically cross-linked hydrogel material has the advantages of mild preparation conditions, high gelling speed, high mechanical strength and good stability. The polyethylene glycol hydrogel can be used as a drug sustained-release carrier or a tissue engineering scaffold and the like to be applied to the field of biomedical materials.

Description

technical field [0001] The invention belongs to the technical field of biomedical new materials, and in particular relates to a polyethylene glycol derivative, a preparation method thereof and a polyethylene glycol hydrogel capable of rapid cross-linking reaction. Background technique [0002] Hydrogel is a material with a three-dimensional network structure formed by certain cross-linking. Hydrogels are widely used in biomedical fields due to their similar physical and chemical properties to extracellular matrix and good biocompatibility. [0003] Polyethylene glycol is a common raw material for preparing hydrogels, including linear polyethylene glycol and multi-armed polyethylene glycol. Due to the low reactivity of the terminal hydroxyl groups of polyethylene glycol, it is usually necessary to derivatize polyethylene glycol to produce terminal groups with different functions, such as carboxyl, amino, mercapto, and aldehyde groups. Through the chemical reaction of the en...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G65/333C08J3/075C08L71/02C07D405/12A61K9/06A61K47/10A61K47/18A61L24/00A61L24/04A61L27/18A61L27/52
CPCC08G65/33337C08G65/33396C08J3/075C07D405/12A61K9/06A61K47/18A61K47/10A61L27/18A61L27/52A61L24/0031A61L24/046C08J2371/02C08G2650/04A61L2400/04C08L71/02C07C235/84C08G65/33327
Inventor 贺超良张震任慧陈学思
Owner CHANGCHUN INST OF APPLIED CHEMISTRY - CHINESE ACAD OF SCI
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