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Method for preparing temperature-responsive adhesive injectable hydrogel

A technology of temperature response and adhesion, which is applied in the field of preparation of adhesive injectable hydrogels, can solve the problems of weak strength, regulation, and inability to effectively regulate the structure and adhesion of hydrogels, and achieve control structure and strength, good biocompatibility, and the effect of rapid in-situ injection molding

Active Publication Date: 2018-12-04
NANCHANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, such adhesive hydrogels prepared by dynamic covalent bonds or Michael addition reactions are usually weak, and cannot effectively regulate the structure and adhesion of hydrogels.
[0004] The adhesion of currently reported mussel-like adhesive hydrogels depends on the density of residual dopamine groups on the surface of the hydrogel, and it is difficult to effectively regulate its adhesion through other environmental stimuli (such as temperature, pH, etc.) sex

Method used

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  • Method for preparing temperature-responsive adhesive injectable hydrogel
  • Method for preparing temperature-responsive adhesive injectable hydrogel
  • Method for preparing temperature-responsive adhesive injectable hydrogel

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] The preparation of embodiment 1 dopamine methacrylamide (DMA)

[0030] 8g NaHCO 3 and 20g Na 2 B 4 o 7 10H 2Dissolve O in 200mL of distilled water, remove oxygen by bubbling with nitrogen for 30 minutes, add 10g of dopamine hydrochloride, stir to dissolve, take 9.4mL of methacrylic anhydride, dissolve in 50mL of tetrahydrofuran, and add dropwise to the above mixture with a constant pressure funnel , adjust the pH of the mixture to >8 with 1M NaOH, stir the reaction at room temperature for 16 hours and filter with suction to remove insoluble NaHCO 3 and Na 2 B 4 o 7 10H 2 O, the filtrate was washed with 100mL ethyl acetate, and adjusted to pH4 Dry overnight, filter to remove MgSO 4 , concentrated by rotary evaporation to about 50 mL, recrystallized drop by drop into 450 mL of ice n-hexane under vigorous stirring, filtered by suction, and dried in vacuum to obtain dopamine methacrylamide;

Embodiment 2

[0031] The preparation of the temperature-responsive polymer of embodiment 2 different dopamine group contents

[0032] (1) Preparation of polymer PMOD-1: 2-(2-methoxyethoxy)ethyl methacrylate (3.00mL, 16.3mmol), oligo(ethylene glycol) methyl ether methacrylic acid Ester (2.51mL, 5.43mmol), dopamine methacrylamide (0.4803g, 2.17mmol) prepared in Example 1 and azobisisobutyronitrile (0.0589g, 0.358mmol) were added to a 15mL N, N - Dimethylformamide was stirred in a round-bottomed flask to fully dissolve it, bubbled with nitrogen for 30 minutes to remove oxygen, and continued to react in an oil bath at 65°C for 5 hours. The reaction solution was dissolved / precipitated three times with tetrahydrofuran / glacial ether, After vacuum drying at room temperature for 48 hours, the polymer PMOD-1 was obtained.

[0033] Polymer PMOD-1 measures the degree of polymerization of each structural unit by proton nuclear magnetic spectrum: x=77.4, y=22.6, z=8.8, gel permeation chromatography dete...

Embodiment 3

[0038] Example 3 Polymer temperature responsiveness measurement

[0039] Each polymer prepared in Example 2 was dissolved in a PBS buffer solution of 7.4, and its concentration was fixed at 5 mg / mL. Pipette 3 mL of the solution into a quartz cuvette and seal it, and keep the solution temperature at the set temperature value for 10 min. , through the UV-3100 ultraviolet-visible spectrophotometer equipped with a constant temperature water bath circulation device to record the light transmittance at 600nm at each temperature, and determine the change of the light transmittance of the polymer solution with temperature. Among them, the lower critical solution temperature (LCST) is defined as the temperature at which the light transmittance drops to 50% of the initial value. See the test results figure 1 .

[0040] From figure 1 It can be obtained that the LCST of the polymers PMOD-1, PMOD-2 and PMOD-3 are 38.4°C, 39.6°C and 40.7°C, respectively.

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Abstract

The invention provides a method for preparing a temperature-responsive adhesive injectable hydrogel. The method comprises the following steps: synthesizing a temperature-responsive polymer with different dopamine contents from dopamine methacrylamide used as an adhesive monomer and ethyl 2-(2-methoxyethoxy)methacrylate and oligo(ethylene glycol)methyl ether methacrylate as temperature-sensitive monomers, and carrying out enzyme catalytic crosslinking on the polymer and a dopamine group under the catalysis of horseradish peroxidase and hydrogen peroxide to prepare the temperature-responsive adhesive hydrogel. The hydrogel prepared in the invention has the characteristics of fastness in gel formation, realization of in-situ injection molding, realization of regulating the gelation time and the gel strength by regulating the concentrations of the polymer, horseradish peroxidase and hydrogen peroxide, and convenience in use; and the adhesion strength of the hydrogel is enhanced with the rising of the temperature, so the temperature-responsive characteristic makes the obtained hydrogel applied to fields of tissue adhesives, wound dressings, cell culture media and drug controlled releasecarriers.

Description

technical field [0001] The invention belongs to the field of biomedical hydrogel preparation, in particular to a method for preparing a temperature-responsive adhesive injectable hydrogel. Background technique [0002] Marine biological mussels can secrete dopamine-rich proteins, which can firmly adhere to the surface of various materials in a humid environment, and have excellent adhesion properties. Mussel biomimetic adhesion hydrogel refers to imitating the adhesion characteristics of marine organisms, mussels, and combining the excellent performance of hydrogel with the structure of imitation mussel adhesion protein dopamine, which is a newly developed kind of outstanding adhesion performance, biological Hydrogel material with good compatibility. Mussel biomimetic adhesive hydrogel has the characteristics of excellent biocompatibility, tissue adhesion, safety and harmlessness, and has great application value in the fields of skin repair, tissue adhesion, wound healing a...

Claims

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Application Information

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IPC IPC(8): C08F283/06C08F220/28C08F220/58A61L24/00A61L24/06A61L26/00A61K9/06A61K47/32
CPCA61K9/0019A61K9/06A61K47/32A61L24/001A61L24/0031A61L24/06A61L26/0014A61L26/0061A61L26/008A61L2400/06C08F220/28C08F220/282C08F283/065C08L51/08C08F220/286C08F220/58
Inventor 彭志平朱和康杨越王吉方倩
Owner NANCHANG UNIV
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