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Macromolecule thiolated modified derivatives and cross-linking material thereof

A polymer compound and polymer technology, applied in the field of compounds, can solve the problems of ineffective biomedical applications, poor chemical reaction performance, restricted collision probability, etc., to achieve adjustable performance, high yield, side chain chemistry, etc. Flexible and changeable structure

Active Publication Date: 2008-06-18
BIOREGEN BIOMEDICAL (CHANGZHOU) CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the polymer thiol-modified derivatives of these two structures have a single side chain structure and performance, which cannot effectively meet various biomedical applications.
At the same time, the side chains of the polymer thiol-modified derivatives of these two structures are relatively short, which restricts the collision probability of thiol groups with other chemical functional groups during further chemical modification and crosslinking, and the chemical reaction performance is not good.

Method used

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  • Macromolecule thiolated modified derivatives and cross-linking material thereof
  • Macromolecule thiolated modified derivatives and cross-linking material thereof
  • Macromolecule thiolated modified derivatives and cross-linking material thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0081] Example 1. Synthesis of dithiodipropionic acid bisacylglycine dihydrazide (abbreviated as DGDTPDH)

[0082] Add 10 g of dithiodipropionic acid (Aldrich, USA) and 50 ml of anhydrous dimethylformamide into a 1000 ml beaker. After stirring and dissolving at room temperature, 17.0 g of carbonyldiimidazole (Aldrich, USA) was added. At this time, the solution produced a large number of carbon dioxide bubbles and white precipitates. Reaction under reduced pressure at room temperature for 3 hours. Then 14.7 g of glycine ethyl ester hydrochloride (Aldrich, USA) was added, and the reaction was stirred for 1 hour. Then 500 ml of ether was added, and the mixture was allowed to stand still for 1 hour. Carefully pour off the upper organic phase, then add 100 mL of ethanol and 10 mL of hydrazine hydrate. After stirring overnight at room temperature, the precipitated product was collected by filtration. The precipitate was rinsed twice with 200 ml of absolute ethanol, and then dri...

Embodiment 2

[0083] Example 2. Synthesis of low-substituted DGDTPDH modified hyaluronic acid mercapto derivatives (HA-DGDTPDH)

[0084] Dissolve 1 g of sodium hyaluronate (molecular weight: 620,000 to 1,150,000, NovaMatrix FMC BIOPOLYMER, USA) in 200 ml of distilled water to obtain a clear and transparent solution. Add 1.32 g of DGDTPDH prepared in Example 1 to the above solution, and stir to dissolve. Then the pH value of the solution was adjusted to 4.75 with 0.1 mol / L hydrochloric acid, 0.36 g of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (Aldrich, USA) was added, and electromagnetically stirred. An appropriate amount of 0.1 mol / L hydrochloric acid was continuously added to the above solution to keep the pH value of the solution at 4.75. The viscosity of the solution continued to increase and formed a gel in about 15 minutes. After the gel was formed, the reaction was left at room temperature for 2 hours. Then 10 g of dithiothreitol (Diagnostic Chemical Limited, USA)...

Embodiment 3

[0085] Example 3. Synthesis of highly substituted DGDTPDH modified hyaluronic acid mercapto derivatives (HA-DGDTPDH)

[0086] Dissolve 1 g of sodium hyaluronate (molecular weight: 620,000 to 1,150,000, NovaMatrix FMC BIOPOLYMER, USA) in 200 ml of distilled water to obtain a clear and transparent solution. Add 2.64 g of DGDTPDH prepared in Example 1 to the above solution, and stir to dissolve. Then the pH value of the solution was adjusted to 4.75 with 0.1 mol / L hydrochloric acid, 0.96 g of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (Aldrich, USA) was added, and electromagnetically stirred. An appropriate amount of 0.1 mol / L hydrochloric acid was continuously added to the above solution to keep the pH value of the solution at 4.75. The viscosity of the solution continued to increase, and a gel formed in about 10 minutes. After the gel was formed, the reaction was left at room temperature for 2 hours. Then 20 g of dithiothreitol (Diagnostic Chemical Limited, ...

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Abstract

The present invention discloses a macromolecular sulfydryl modified derivative with general formula (I) or (II) as well as corresponding dithio-bond cross-linking material and corresponding cross-linking material of sulfydryl reaction active cross linker. Wherein, R1 and R2 include alkylidene, substituted alkylidene, aromatic base, polyether polyols, etc. and R1 and R2 can have the same or different chemical structure; P refers to macromolecular compound residue including carboxyl in the side chain and the molecular weight of the macromolecular sulfydryl modified derivative is 10 to 5 million. The side-chain chemical structure of the macromolecular sulfydryl modified derivative with general formula (I) or (II) is flexible and changeable with notable advantages of adjustable performance, mild preparation conditions, high production rate, high modification and controllability. The cross-linking material of the macromolecular sulfydryl modified derivative provided by the present invention can be used to inhibit the attachment of cells and used as the matrix for cell adhesion and growth.

Description

technical field [0001] The present invention relates to compounds, in particular to macromolecule mercapto-modified derivatives; in addition, the present invention also relates to the corresponding disulfide bond cross-linking materials and mercapto-reactive cross-linking agent cross-linking materials of the macromolecule mercapto-modified derivatives. Background technique [0002] Polymer thiol-modified derivatives have many important biomedical applications, such as chemically active modification of various small molecule drugs and polypeptide protein drugs, preparation of various cross-linked polymer materials, and so on. These new materials can be used as cell growth matrix, wound repair regeneration matrix, drug sustained release carrier, wound dressing, in situ embedding cell matrix, etc., and have important uses in the field of biomedicine. However, so far, there are few types of such thiol-modified polymer derivatives, and only the polymer mercapto-modified derivativ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08B37/00C08F20/06C08F8/34C08J3/24C08K3/36C08L89/00C08H99/00
CPCC08H1/00C07B43/06C07K1/1077C08B37/0075C08B37/003C08B37/0045C07C323/41C08B37/0072C08B11/15C08B37/0084C08B37/0069C07C323/60
Inventor 宋婵舒晓正
Owner BIOREGEN BIOMEDICAL (CHANGZHOU) CO LTD
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