Multi-armed polyglutamic acid taking beta-cyclodextrin as nucleus and injectable hydrogel and preparation method thereof

A polyglutamic acid, polyglutamic acid benzyl ester technology, applied in the field of injectable hydrogel and its preparation, multi-arm polyglutamic acid, can solve the problem of difficult hydrophobic drugs, etc., to achieve broad application prospects, good Effects of biodegradability and good biocompatibility

Active Publication Date: 2016-11-16
SHANGHAI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] Poly-L-glutamic acid is a polyamino acid with good biocompatibility, however poly-L-glutamic acid hydrogels are difficult to effectively load hydrophobic drugs due to their hydrophilicity

Method used

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  • Multi-armed polyglutamic acid taking beta-cyclodextrin as nucleus and injectable hydrogel and preparation method thereof
  • Multi-armed polyglutamic acid taking beta-cyclodextrin as nucleus and injectable hydrogel and preparation method thereof
  • Multi-armed polyglutamic acid taking beta-cyclodextrin as nucleus and injectable hydrogel and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] 1. Take a dry round-bottomed flask (100mL), add DMSO (20mL) and β-cyclodextrin (0.88 mmoL), stir well to dissolve, then add CDI (7.04mmoL), react under the protection of inert gas for 12~24h, Then add ethylenediamine (2.4mL) and continue to react for 12~24h. After pouring the reaction solution into excess absolute ethanol, a large amount of white matter is precipitated. The product is filtered and dried, dissolved in deionized water, and dialyzed with deionized water Freeze-drying can obtain about 0.5g of white product, which is polyamino β-cyclodextrin, and its structural formula is:

[0025]

[0026] Wherein the structural formula of R is:

[0027] .

[0028] 2. Put polyamino β-cyclodextrin (0.5g) in an anhydrous round bottom flask (100mL), add anhydrous DMSO (125mL), add L-glutamic acid-N-carboxylic acid anhydride ( 3.2g), vacuumize and blow nitrogen, and stir the reaction at room temperature for 72h. The reaction solution was poured into absolute ethanol (5...

Embodiment 2

[0044] The preparation of the aldylated multi-arm poly-L-glutamic acid in this example is basically the same as in Example 1, except that in step 2, polyamino β-cyclodextrin (1.0 g) was added, and DMSO was added (125mL), dissolved and added L-glutamic acid-N-carboxylic acid anhydride (3.2g). The multi-arm poly-L-glutamic acid finally obtained has an average molecular weight of about 2200 Daltons. The dosage and operating conditions of other reagents remained unchanged. The finally obtained injectable hydrogel had a gelation time of 81 s and a storage modulus of 81 Pa.

Embodiment 3

[0046] The preparation of the aldylated multi-arm poly-L-glutamic acid in this example is basically the same as that in Example 1, except that in step 2, polyamino β-cyclodextrin (0.25 g) was added and DMSO was added (125mL), dissolved and added L-glutamic acid-N-carboxylic acid anhydride (3.2g). The multi-arm poly-L-glutamic acid finally obtained has an average molecular weight of about 11,000 Daltons. The dosage and operating conditions of other reagents remained unchanged. The finally obtained injectable hydrogel had a gelation time of 86s and a storage modulus of 196Pa.

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Abstract

The invention relates to a multi-armed polyglutamic acid taking beta-cyclodextrin as a nucleus and an injectable hydrogel and a preparation method thereof. The method comprises the steps that multi-aminated beta-cyclodextrin is synthesized first, multiple grafting reaction initiating loci are introduced, L-glutamate-N-carboxylic acid anhydride ring opening polymerization is initiated, hydroformylation modification is conducted on the multi-armed poly(L-glutamic acid), and the obtained product serves as a first component of the hydrogel; meanwhile, the poly(L-glutamic acid) subjected to amination modification serves as a second component, the two components are mixed according to a certain proportion, and the glutamic acid-based hydrogel is obtained through crosslinking in a Schiff base reaction, wherein the gelation time ranges from 20 s to 400 s. The hydrogel has the advantages that the hydrogel has good biocompatibility and biodegradability and can adapt to different shapes; in addition, due to the fact that beta-cyclodextrin is introduced, crosslinking points can be increased, improvement of the mechanical strength of the hydrogel is promoted, and loading and release control can be conducted on hydrophobic drugs. Therefore, the hydrogel has wide application prospects in the fields of tissue engineering, regenerative medicine, controlled drug release and the like.

Description

technical field [0001] The invention relates to a polyglutamic acid with a multi-arm structure, an injectable hydrogel and a preparation method thereof, in particular to a multi-arm polyglutamic acid with a β-cyclodextrin as a core, an injectable hydrogel and its preparation method. Background technique [0002] Hydrogels are composed of three-dimensional network structure polymers and water molecules contained in them, which are formed by chemical or physical cross-linking and gelation, and have good biocompatibility and degradability. Among them, injectable hydrogels have received extensive attention in the field of tissue engineering. Injectable hydrogels can be used for controlled release of bioactive molecules, embedding cells, and as tissue scaffold materials. Injectable hydrogel fills the defect in the body by injection and solidifies in situ, which can avoid the high trauma of surgery, has the advantages of accelerating healing, reducing patient pain, and reducing m...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G69/08C08G69/50C08B37/16C08J3/075C08L77/02
CPCC08B37/0012C08G69/08C08G69/50C08J3/075C08L77/02C08L2201/06C08L2203/02C08L2205/025C08L2312/00
Inventor 颜世峰陈安尹静波
Owner SHANGHAI UNIV
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