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Preparation method and application of a kind of thiol/disulfide bond controllable self-crosslinking hyaluronic acid hydrogel

A hyaluronic acid and hydrogel technology, applied in medical science, prosthesis, etc., can solve the problems affecting the biocompatibility of hydrogel materials, achieve good water solubility, convenient gel method, and controllable physical properties Effect

Active Publication Date: 2017-12-08
SICHUAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Carboxyl, hydroxyl, amino and other chemically active functional groups are often used in chemical crosslinking reactions. Commonly used chemical crosslinking agents generally contain bifunctional groups, such as diamine, dihydrazine, dialdehyde, diol, etc., but these crosslinking agents Agents are usually cytotoxic, if residual will affect the biocompatibility of hydrogel materials

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  • Preparation method and application of a kind of thiol/disulfide bond controllable self-crosslinking hyaluronic acid hydrogel
  • Preparation method and application of a kind of thiol/disulfide bond controllable self-crosslinking hyaluronic acid hydrogel
  • Preparation method and application of a kind of thiol/disulfide bond controllable self-crosslinking hyaluronic acid hydrogel

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0061] (1) Dissolve 400mg of sodium hyaluronate in 100mL of deionized water, first add 230mg of N-succinimide (NHS), fully dissolve; then add 385mg of 1-ethyl-(3-dimethylaminopropyl) Carbodiimide hydrochloride (EDC·HCl) powder, adjust the pH=4.75 of the reaction solution with 1M NaOH and 1M HCl solution, and react for 2 hours; then add 10mL of 11.36mg / mL cysteine ​​( CSH·HCl) hydrochloride, react for 24 hours; finally adjust the pH of the reaction solution to 8.5 with 1M NaOH solution, add 10 mL of 46.5 mg / ml dithiothreitol (DTT) solution, and react for 12 hours.

[0062] (2) After the reaction, adjust the pH of the reaction solution to 3.0-3.5 with 1M HCl solution, dialyze in deionized water with pH=3.0-3.5 for 72 hours, and freeze-dry to obtain cysteine-modified hyaluronic acid.

[0063] Among them, the molecular weight of sodium hyaluronate is 0.1MDa, carboxyl group in sodium hyaluronate: N-succinimide: 1-ethyl-(3-dimethylaminopropyl) carbodiimide hydrochloride: half The m...

Embodiment 2

[0067] (1) Dissolve 400mg of sodium hyaluronate in 100mL of deionized water, first add 230mg of N-succinimide (NHS), fully dissolve; then add 575mg of 1-ethyl-(3-dimethylaminopropyl) Carbodiimide hydrochloride (EDC·HCl) powder, adjust the pH=4.75 of the reaction solution with 1M NaOH and 1M HCl solution, and react for 2 hours; then add 10mL of 22.72mg / mL cysteine ​​( CSH·HCl) hydrochloride, react for 24 hours; finally adjust the pH of the reaction solution to 8.5 with 1M NaOH solution, add 10 mL of 93.0 mg / ml dithiothreitol (DTT) solution, and react for 12 hours.

[0068] (2) After the reaction, adjust the pH of the reaction solution to 3.0-3.5 with 1M HCl solution, dialyze in deionized water with pH=3.0-3.5 for 72 hours, and freeze-dry to obtain cysteine-modified hyaluronic acid.

[0069] Among them, the molecular weight of sodium hyaluronate is 0.1MDa, carboxyl group in sodium hyaluronate: N-succinimide: 1-ethyl-(3-dimethylaminopropyl) carbodiimide hydrochloride: half The m...

Embodiment 3

[0073](1) Dissolve 400mg sodium hyaluronate in 100mL deionized water, first add 230mg N-succinimide (NHS), fully dissolve; then add 770mg 1-ethyl-(3-dimethylaminopropyl) Carbodiimide hydrochloride (EDC·HCl) powder, adjust the pH=4.75 of the reaction solution with 1M NaOH and 1M HCl solution, and react for 2 hours; then add 10mL45.44mg / mL of cysteine ​​( CSH·HCl) hydrochloride, react for 24 hours; finally adjust the pH of the reaction solution to 8.5 with 1M NaOH solution, add 10 mL of 186.0 mg / ml dithiothreitol (DTT) solution, and react for 12 hours.

[0074] (2) After the reaction, adjust the pH of the reaction solution to 3.0-3.5 with 1M HCl solution, dialyze in deionized water with pH=3.0-3.5 for 72 hours, and freeze-dry to obtain cysteine-modified hyaluronic acid.

[0075] Among them, the molecular weight of sodium hyaluronate is 0.1MDa, carboxyl group in sodium hyaluronate: N-succinimide: 1-ethyl-(3-dimethylaminopropyl) carbodiimide hydrochloride: half The mass ratio of ...

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Abstract

The invention discloses a preparation method and application of a hyaluronic acid hydrogel with controllable thiol / disulfide bond self-crosslinking, belonging to the field of biological materials. The hydrogel uses mercapto-hyaluronic acid compounds with free mercapto groups as raw materials, by adjusting the mercapto group density (10%-60%), gel temperature (4°C, 37°C) and molecular weight of hyaluronic acid (0.1M , 0.3M, 1M), using the redox transition characteristics between sulfhydryl and disulfide bonds to control the formation time, degradation time and mechanical properties of the gel, a controllable injectable gel with a good three-dimensional network cross-linked structure was constructed. Smart hydrogels. At the same time, this type of hydrogel has a single composition, no exogenous toxic substances are introduced before and after gelation, and has good biocompatibility and degradation performance. Based on the above findings, this type of controllable self-crosslinking polymer can be used for minimally invasive repair of in situ damage in tissue engineering and construction of intelligent and adjustable three-dimensional cell culture scaffolds.

Description

technical field [0001] The invention belongs to the field of biological materials, and in particular relates to a hyaluronic acid hydrogel with controllable self-crosslinking of thiol / disulfide bonds, a preparation method and application thereof. technical background [0002] Tissue engineering, also known as "regenerative medicine", refers to the technology of using biologically active substances to rebuild or repair organs and tissues through in vitro culture or construction. This concept was proposed by the National Science Foundation of the United States in 1987, and it was officially defined in 1988 as: applying the principles and technologies of life science and engineering to correctly understand the tissue structure and function of mammals in both normal and pathological states On the basis of the relationship between human beings, it is an emerging discipline to research and develop biological substitutes for repairing, maintaining, and promoting the functions and s...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08J3/075C08J3/24C08L5/08A61L27/20A61L27/58
Inventor 孙勇樊渝江边少荃曹万旭张兴栋
Owner SICHUAN UNIV
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