A kind of polyethylene glycol derivative, its preparation method and polyethylene glycol hydrogel capable of rapid cross-linking reaction

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

Active Publication Date: 2022-02-22
长春赛诺海思生物医用材料有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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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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  • A kind of polyethylene glycol derivative, its preparation method and polyethylene glycol hydrogel capable of rapid cross-linking reaction
  • A kind of polyethylene glycol derivative, its preparation method and polyethylene glycol hydrogel capable of rapid cross-linking reaction
  • A kind of polyethylene glycol derivative, its preparation method and polyethylene glycol hydrogel capable of rapid 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 15 h. 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 present invention provides a polyethylene glycol derivative, comprising a repeating unit having a structure of formula (I) and an end group having a structure of formula (II). The polyethylene glycol derivative provided by the present invention has good biocompatibility due to the repeating unit of the structure of formula (I). Because the end group of o-phthalaldehyde having the structure of formula (II) can react with various groups such as amino group, (hydrazine) group, aminooxy group, etc., the reaction rate is fast and the reaction conditions are mild. Mixing the polyethylene glycol derivative provided by the invention with the polyethylene glycol containing amino groups at the end group in an aqueous medium can quickly form a chemically cross-linked hydrogel material, which has mild preparation conditions, fast gelation speed, and high mechanical strength. High, good stability. The polyethylene glycol hydrogel can be used in the field of biomedical materials as a slow-release drug carrier or a tissue engineering scaffold.

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 Patents(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 长春赛诺海思生物医用材料有限公司
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