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Preparation method of multi-modified hyaluronic acid derivative

A technology of hyaluronic acid and its derivatives, which is applied in the field of biomedicine and can solve problems such as interfering with modification reactions and affecting the introduction of active groups

Pending Publication Date: 2022-07-08
BIOREGEN BIOMEDICAL (CHANGZHOU) CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, there are certain difficulties in modifying the side chains of hyaluronic acid to add different active functional groups, because the high-reactivity functional groups introduced first may interfere with the subsequent modification reactions and affect the subsequent modification reactions. Introduction of active groups

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0018] Sodium hyaluronate (molecular weight 1 million Daltons) 1g (2.5mmol) was dissolved in 500ml distilled water at room temperature, 1-hydroxybenzotriazole 0.667g (5.0mmol) was added, ethylenediamine 0.6g (10mmol) was added, and then the solution The pH value was adjusted to 4.75 with 0.5mol / L hydrochloric acid, 0.96g (5mmol) of 1-ethyl-3-(3-dimethylaminopropyl) carbodiimide hydrochloride was added, and 0.5mol / L hydrochloric acid was added. The pH of the solution was kept at 4.75 and the reaction was carried out at room temperature overnight. Then, 0.3 g (1.25 mmol) of dithiodipropionyl hydrazide was added to the above reaction solution, and 0.24 g (1.25 mmol) of 1-ethyl-3-(3-dimethylaminopropyl) carbodiimide hydrochloride was added. ), add 0.5mol / L hydrochloric acid to keep the pH value of the solution at 4.75, and react at room temperature for 4 hours. After the reaction, 1.43 g (5 mmol) of tris(2-carboxyethyl) phosphine hydrochloride was added to the post-reaction solut...

Embodiment 2

[0021]Sodium hyaluronate (molecular weight 200,000 Daltons) 1g (2.5mmol) was dissolved in 500ml of distilled water at room temperature, 1-hydroxybenzotriazole 0.667g (5.0mmol) was added, butanediamine 1.76g (20mmol) was added, and then the solution The pH value was adjusted to 4.75 with 0.5 mol / L hydrochloric acid, 0.96 g (5 mmol) of 1-ethyl-3-(3-dimethylaminopropyl) carbodiimide hydrochloride was added, and 0.5 mol / L hydrochloric acid was added. The pH of the solution was kept at 4.75, and the reaction was carried out at room temperature for 4 hours. Then, 0.3 g (1.25 mmol) of dithiodipropionyl hydrazide was added to the above reaction solution, and 0.12 g (0.625 mmol) of 1-ethyl-3-(3-dimethylaminopropyl) carbodiimide hydrochloride was added. ), add 0.5mol / L hydrochloric acid to keep the pH value of the solution at 4.75, and react at room temperature for 4 hours. After the reaction, 1.43 g (5 mmol) of tris(2-carboxyethyl) phosphine hydrochloride was added to the post-reactio...

Embodiment 3

[0024] 1g (2.5mmol) of sodium hyaluronate (molecular weight 500,000 Daltons) was dissolved in 500ml of distilled water at room temperature, 0.667g (5.0mmol) of 1-hydroxybenzotriazole was added, 1.48g (20mmol) of butanediamine was added, and then the solution The pH value was adjusted to 4.75 with 0.5 mol / L hydrochloric acid, 0.96 g (5 mmol) of 1-ethyl-3-(3-dimethylaminopropyl) carbodiimide hydrochloride was added, and 0.5 mol / L hydrochloric acid was added. The pH of the solution was kept at 4.75 and the reaction was carried out at room temperature overnight. Then, 0.33 g (1.25 mmol) of dithiodibutyric hydrazide was added to the above reaction solution, and 0.12 g (0.625 mmol) of 1-ethyl-3-(3-dimethylaminopropyl) carbodiimide hydrochloride was added. ), add 0.5mol / L hydrochloric acid to keep the pH value of the solution at 4.75, and react at room temperature for 4 hours. After the reaction, 1.43 g (5 mmol) of tris(2-carboxyethyl) phosphine hydrochloride was added to the post-r...

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Abstract

The invention discloses a preparation method of a multi-modified hyaluronic acid derivative, which can introduce amino and sulfydryl into the side chain of hyaluronic acid at the same time, effectively avoids the formation of a cross-linked structure, and has the characteristics of simple preparation process, small reagent dosage, suitability for industrial production and the like.

Description

technical field [0001] The invention relates to the field of biomedicine, in particular to a preparation method of multiple modified hyaluronic acid derivatives. Background technique [0002] Hyaluronic acid is an important component of cell matrix and various tissues, and has a variety of important physiological functions, such as: regulating cell proliferation, migration and differentiation, natural moisturizing effect, lubricating joints and protecting cartilage, regulating protein synthesis, regulating inflammatory response , regulate immune function, promote wound healing, etc. The unique viscoelasticity, biocompatibility and degradability of hyaluronic acid make it widely used in the biomedical field, including as an ophthalmic surgical adjuvant, post-surgical anti-adhesion, skin wound healing regeneration adjuvant, drug carrier , tissue engineering scaffolds, etc. [0003] However, hyaluronic acid is easily degraded and absorbed in the body and has a short residence...

Claims

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Application Information

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IPC IPC(8): C08B37/08
CPCC08B37/0072
Inventor 王云云宋文俊王昕宇张红晨王坤何志远舒晓正
Owner BIOREGEN BIOMEDICAL (CHANGZHOU) CO LTD