CN115926200A - Preparation method and application of enzyme-catalyzed double-crosslinked polymer composite hydrogel material - Google Patents
Preparation method and application of enzyme-catalyzed double-crosslinked polymer composite hydrogel material Download PDFInfo
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Abstract
The invention discloses a preparation method and application of an enzyme-catalyzed double-crosslinked polymer composite hydrogel material, and belongs to the technical field of biomedical materials. The technical scheme provided by the invention has the key points that: firstly, natural polymers and synthetic polymers with good biocompatibility are subjected to grafting modification, then a mild enzyme catalysis crosslinking and polymerization one-pot method is applied to prepare the double-crosslinking polymer composite hydrogel material, and grafted functional groups endow the hydrogel with excellent antibacterial and antioxidant properties and the like, and finally endow the hydrogel with application potential as a wound dressing. The hydrogel prepared by the invention has inherent multifunctionality, does not depend on traditional anti-inflammatory, antibiotic and other medicines, avoids the problems of drug resistance and the like brought by the traditional medicines, and has important biomedical application value in the aspect of promoting wound healing.
Description
Technical Field
The invention belongs to the technical field of biomedical gel materials, and particularly relates to a novel method for preparing a double-crosslinked polymer composite hydrogel material with inherent antibacterial and antioxidant functions through enzyme catalysis, and application of the double-crosslinked polymer composite hydrogel material serving as a dressing in promotion of skin wound tissue regeneration.
Background
The skin, the largest organ of the human body, plays a vital role in preventing the invasion of pathogens and maintaining normal physiological functions. Serious skin injury easily causes bacterial infection, the redox system is out of balance, further the excessive production of oxidation free radicals is caused, and some bioactive molecules are damaged, thereby delaying wound healing and even threatening the life safety of patients. Antibiotics and transition metal oxides in traditional active materials can be effectively used to treat bacterial infections, inflammation and relieve oxidative stress to promote wound healing. However, their practical use is hampered by their drug resistance and potential cytotoxicity. Therefore, it is very important to prepare a wound dressing with an inherent antibacterial and antioxidant function. Compared with the traditional dressing, the hydrogel has great application prospect, the hydrogel formed by the polymer has adjustable performance, and has multiple functions during wound healing, including isolating pathogens, maintaining a moist microenvironment, absorbing secretion, killing bacteria, removing oxidized species and the like. In addition, compared with the potential toxicity and other problems of the traditional strategy for preparing the polymer hydrogel by free radical polymerization and crosslinking, the mild enzyme-catalyzed crosslinking and polymerization strategy has great advantages.
Disclosure of Invention
The invention aims to provide a preparation method and application of an enzyme catalysis double-crosslinking polymer composite hydrogel material aiming at the defects of the existing hydrogel wound dressing, the method firstly carries out graft modification on natural polymers and synthetic polymer polyvinyl alcohol with good biocompatibility, then uses a mild enzyme catalysis crosslinking and polymerization one-pot method to prepare the double-crosslinking polymer composite hydrogel material, the grafting group quaternary ammonium salt gives excellent antibacterial property to the composite hydrogel, the grafted phenol group gives good oxidation resistance to the hydrogel, the inherent multifunctionality of the hydrogels does not depend on traditional anti-inflammatory, antibiotic and other medicines, and the hydrogel material has important biomedical application value in the aspect of promoting wound healing.
The invention adopts the following technical scheme for realizing the aim, and the preparation method of the enzyme catalysis double-crosslinking polymer composite hydrogel material is characterized by comprising the following specific steps of:
step S1: dissolving natural polysaccharide containing amino or carboxyl in deionized water, then adding glycidyl trimethyl ammonium chloride and glycidyl methacrylate, heating to react, filling a reaction solution into a dialysis bag, dialyzing in the deionized water, and freeze-drying to obtain trimethyl ammonium chloride and methacryloyl grafted aminopolysaccharide or trimethyl ammonium chloride and methacryloyl grafted carboxyl polysaccharide, dissolving trimethyl ammonium chloride and methacryloyl grafted aminopolysaccharide or trimethyl ammonium chloride and methacryloyl grafted carboxyl polysaccharide in the deionized water to obtain an intermediate amino macromolecular derivative solution or an intermediate carboxyl macromolecular derivative solution, wherein the natural polysaccharide containing amino is one or more of chitosan, carboxymethyl chitosan, carboxyethyl chitosan, hydroxyethyl chitosan or gelatin, and the polysaccharide containing carboxyl is one or more of sodium hyaluronate, sodium alginate, chondroitin sulfate, carboxymethyl cellulose, xanthan gum or gamma-polyglutamic acid;
step S2: adding p-hydroxybenzaldehyde into the intermediate amino polymer derivative solution obtained in the step S1, reacting at room temperature, adding sodium borohydride, continuously reacting, filling the reaction solution into a dialysis bag, dialyzing in deionized water, and freeze-drying to obtain the amino natural polymer derivative grafted with trimethyl ammonium chloride, methacryloyl and phenol groups; adding aminophenol and a catalyst into the intermediate carboxyl polymer derivative solution obtained in the step S1, reacting at room temperature, filling a reaction solution into a dialysis bag, dialyzing in deionized water, freeze-drying to obtain a carboxyl natural polymer derivative grafted with trimethyl ammonium chloride, methacryloyl and phenol groups, dissolving the amino natural polymer derivative or the carboxyl natural polymer derivative in deionized water to obtain a natural polymer derivative solution, wherein the aminophenol is one or more of tyramine, tyramine hydrochloride, tyrosine hydrochloride, dopamine or dopamine hydrochloride, and the catalyst is one or more of 1- (3-dimethylaminopropyl) -3-ethylcarbodiimide hydrochloride or 4- (4, 6-dimethoxytriazine) -4-methylmorpholine hydrochloride;
and step S3: dissolving dried polyvinyl alcohol in dimethyl sulfoxide, adding tert-butyl acetoacetate, stirring under a heating condition, reacting, filling a reaction solution into a dialysis bag, dialyzing in deionized water, freeze-drying to obtain acetoacetyl grafted polyvinyl alcohol, and dissolving the acetoacetyl grafted polyvinyl alcohol in the deionized water to obtain an acetoacetyl polyvinyl alcohol solution;
and step S4: and (3) uniformly mixing the natural polymer derivative solution obtained in the step (S2), the acetoacetyl polyvinyl alcohol solution obtained in the step (S3), a horseradish peroxidase solution and a hydrogen peroxide solution to obtain a gel-forming precursor solution, and standing at room temperature to obtain the enzyme-catalyzed double-crosslinked polymer composite hydrogel material.
Further limited, the concentration of the aminopolysaccharide solution or the carboxypolysaccharide solution in the step S1 is 2 to 100mg/mL, the molar ratio of the number of structural units of the aminopolysaccharide solution or the carboxypolysaccharide to the glycidyl trimethylammonium chloride and the glycidyl methacrylate is 0.1 to 5, the reaction temperature is 40 to 80 ℃, and the reaction time is 12 to 72h.
Further, the molar ratio of the number of the intermediate amino polymer derivative structural units in the step S2 to p-hydroxybenzaldehyde and sodium borohydride is 0.2 to 5.
The concentration of the polyvinyl alcohol solution in the step S3 is further limited to 10-300 mg/mL, the molar ratio of hydroxyl groups to acetoacetyl tert-butyl ester in the polyvinyl alcohol is 0.1-2, the reaction temperature is 80-150 ℃, and the reaction time is 2-12 h.
Further, the concentration of the natural polymer derivative solution in the step S4 is 20 to 100mg/mL, the concentration of the acetoacetyl polyvinyl alcohol solution is 50 to 300mg/mL, the concentration of horseradish peroxidase is 0.1 to 10mg/mL, the concentration of hydrogen peroxide is 0.01 to 1mol/L, the volume ratio of the natural polymer derivative solution, the acetoacetyl polyvinyl alcohol solution, the horseradish peroxidase solution and the hydrogen peroxide solution in the gel-forming precursor solution is 4.
The invention relates to application of an enzyme catalysis double-crosslinking polymer composite hydrogel material in preparation of biomedical dressings.
The invention relates to application of an enzyme catalysis double-crosslinking polymer composite hydrogel material in preparation of medical hydrogel wound dressing for promoting wound healing.
Compared with the prior art, the invention has the following advantages and beneficial effects: the double-crosslinking polymer composite hydrogel material with inherent antibacterial and antioxidant properties prepared by the invention uses natural polymers and synthetic polymers with good biocompatibility, enzyme catalysis polymerization and crosslinking are simultaneously realized by utilizing a mild enzyme catalysis one-pot method, the quaternary ammonium salt group provides excellent inherent antibacterial property, the phenol group provides excellent antioxidant property, the defect of drug resistance brought by drug use in the traditional therapy is avoided, and a long-term effective treatment protection is provided for wound healing.
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FIG. 1 is a scanning electron microscope (scale: 20 μm) of the lyophilized dual-crosslinked polymer composite hydrogel material with inherent antibacterial and antioxidant properties prepared in example 1 of the present invention, and a three-dimensional network gel skeleton structure can be observed.
FIG. 2 shows the result of the antibacterial performance test of the dual-crosslinked polymer hydrogel material with antibacterial and antioxidant properties prepared in example 1 of the present invention; the hydrogel group exhibited excellent antibacterial properties against escherichia coli and staphylococcus aureus compared to the blank group.
FIG. 3 shows the result of the scavenging test of nitrogen free radicals of the internal antibacterial and antioxidant double-crosslinked polymer composite hydrogel material prepared in example 1 of the present invention, and it can be seen from the figure that the hydrogel exhibits good scavenging ability to ABTS 8729and free radicals.
FIG. 4 is a HE staining pattern (scale bar: 100 μm) of wound tissue at day 14 of the full-thickness wound experiment on mouse skin for the internal antibacterial and antioxidant double-crosslinked polymer composite hydrogel material prepared in example 1 of the present invention, and it can be seen that the new skin of the gel group has relatively intact skin appendages, while the new skin of the blank group lacks corresponding skin appendages.
Detailed Description
The present invention is described in further detail below with reference to examples, but it should not be construed that the scope of the above subject matter of the present invention is limited to the following examples, and that all the technologies realized based on the above subject matter of the present invention belong to the scope of the present invention.
Example 1
Step S1: dissolving 4.4g of carboxymethyl chitosan in 100mL of deionized water, adding 0.7g and 0.67g of glycidol trimethyl ammonium chloride, reacting for 15 hours at 55 ℃, then filling the reaction solution into a dialysis bag, dialyzing for 3 days in the deionized water, and freeze-drying to obtain trimethyl ammonium chloride and methacryloyl grafted carboxymethyl chitosan, and then dissolving the trimethyl ammonium chloride and the methacryloyl grafted carboxymethyl chitosan in the deionized water to obtain an intermediate carboxymethyl chitosan derivative solution with the concentration of 10 mg/mL.
Step S2: adding 2.4g of p-hydroxybenzaldehyde into the intermediate carboxymethyl chitosan derivative solution obtained in the step S1, reacting for 1.5 hours at room temperature, then adding 1.45g of sodium borohydride, reacting for 3 hours at room temperature, filling the reaction solution into a dialysis bag, dialyzing for 3 days in deionized water, freeze-drying to obtain the carboxymethyl chitosan derivative grafted with trimethyl ammonium chloride, methacryloyl and phenol groups, and dissolving the carboxymethyl chitosan derivative in the deionized water to obtain a carboxymethyl chitosan derivative solution with the concentration of 40 mg/mL.
And step S3: dissolving 5.0g of polyvinyl alcohol in 50mL of dimethyl sulfoxide, adding 6.0g of tert-butyl acetoacetate, stirring and reacting at 110 ℃ for 6h, filling the reaction solution into a dialysis bag after the reaction is finished, dialyzing in deionized water for 3 days, freeze-drying to obtain an acetoacetyl grafted polyvinyl alcohol product, and dissolving the acetoacetyl grafted polyvinyl alcohol product in the deionized water to obtain an acetoacetyl polyvinyl alcohol solution with the concentration of 200 mg/mL.
Step S5: and (3) uniformly mixing 200 mu L of the carboxymethyl chitosan derivative solution obtained in the step (S2), 200 mu L of the acetoacetyl polyvinyl alcohol solution obtained in the step (S3), 50 mu L of a 5.0mg/mL horseradish peroxidase solution and 50 mu L of a 0.58mol/L hydrogen peroxide solution to obtain a gel-forming precursor solution, and standing at room temperature for 30min to obtain the double-crosslinked polymer composite hydrogel material with inherent antibacterial and antioxidant properties.
Example 2
Step S1: dissolving 2.0g of sodium hyaluronate in 80mL of deionized water, adding 0.76g and 0.71g of glycidol trimethyl ammonium chloride, reacting for 12 hours at 60 ℃, then filling the reaction solution into a dialysis bag, dialyzing in deionized water for 3 days, and freeze-drying to obtain trimethyl ammonium chloride and methacryloyl grafted sodium hyaluronate, and then dissolving trimethyl ammonium chloride and methacryloyl grafted carboxymethyl chitosan in deionized water to obtain an intermediate sodium hyaluronate derivative solution with the concentration of 20 mg/mL.
Step S2: adding 1.73g of tyramine hydrochloride and 2.76g of 4- (4, 6-dimethoxytriazine) -4-methylmorpholine hydrochloride into the intermediate sodium hyaluronate derivative solution obtained in the step S1, stirring and reacting for 24 hours at room temperature, filling the reaction solution into a dialysis bag, dialyzing for 3 days in deionized water, freeze-drying to obtain sodium hyaluronate derivatives grafted with trimethyl ammonium chloride, methacryloyl and phenol groups, and dissolving the sodium hyaluronate derivatives in the deionized water to obtain a sodium hyaluronate derivative solution with the concentration of 60 mg/mL.
And step S3: dissolving 5.0g of polyvinyl alcohol in 50mL of dimethyl sulfoxide, adding 8.0g of tert-butyl acetoacetate, stirring and reacting at 100 ℃ for 12 hours, filling the reaction solution into a dialysis bag after the reaction is finished, dialyzing in deionized water for 3 days, freeze-drying to obtain an acetoacetyl grafted polyvinyl alcohol product, and dissolving the acetoacetyl grafted polyvinyl alcohol product in the deionized water to obtain an acetoacetyl polyvinyl alcohol solution with the concentration of 150 mg/mL.
Step S5: and (3) uniformly mixing 200 mu L of the sodium hyaluronate derivative solution obtained in the step (S2), 200 mu L of the acetoacetyl polyvinyl alcohol solution obtained in the step (S3), 50 mu L of a 3.5mg/mL horseradish peroxidase solution and 50 mu L of a 0.45mol/L hydrogen peroxide solution to obtain a gel-forming precursor solution, and standing at room temperature for 60min to obtain the double-crosslinked polymer composite hydrogel material with inherent antibacterial and antioxidant properties.
In order to illustrate various properties of the hydrogel material prepared by the invention, the double-crosslinked composite hydrogel material with inherent antibacterial and antioxidant properties prepared in example 1 is tested, and the test results are shown in figures 1 to 4.
FIG. 1 is a scanning electron microscope (scale: 20 μm) of the lyophilized dual-crosslinked polymer composite hydrogel material with inherent antibacterial and antioxidant properties prepared in example 1 of the present invention, and a three-dimensional network gel skeleton structure can be observed.
Fig. 2 is a result of an antibacterial performance test of an intrinsic antibacterial and antioxidant double-crosslinked polymer composite hydrogel material prepared in example 1 of the present invention, and the hydrogel group exhibits excellent antibacterial performance against escherichia coli and staphylococcus aureus compared to a blank group.
FIG. 3 shows the result of the scavenging test of nitrogen free radicals of the internal antibacterial and antioxidant double-crosslinked polymer composite hydrogel material prepared in example 1 of the present invention, and it can be seen from the figure that the hydrogel exhibits good scavenging ability to ABTS 8729and free radicals.
FIG. 4 is a HE staining graph (scale bar: 100 μm) of wound tissues at day 14 of a full-thickness wound experiment on mouse skin of the intrinsic antibacterial and antioxidant double-crosslinked polymer composite hydrogel material prepared in example 1 of the present invention, and it can be seen that the gel group of the new skin has relatively intact skin appendages, while the blank group of the new skin lacks corresponding skin appendages.
In conclusion, the prepared double-crosslinking composite hydrogel material with inherent antibacterial and antioxidant properties shows good antibacterial and antioxidant properties, and can promote the regeneration of complete skin tissues and accessory organs thereof in a mouse skin full-thickness wound experiment so as to accelerate the healing of wounds.
While there have been shown and described the fundamental principles, principal features and advantages of the invention, various changes and modifications can be made therein without departing from the spirit and scope of the invention, which is intended to be covered thereby.
Claims (7)
1. A preparation method of an enzyme catalysis double-crosslinking polymer composite hydrogel material is characterized by comprising the following specific steps:
step S1: dissolving natural polysaccharide containing amino or carboxyl in deionized water, adding glycidol trimethyl ammonium chloride and glycidyl methacrylate, heating to react, filling the reaction solution into a dialysis bag, dialyzing in deionized water, and freeze-drying to obtain trimethyl ammonium chloride and methacryloyl grafted aminopolysaccharide or trimethyl ammonium chloride and methacryloyl grafted carboxyl polysaccharide, dissolving trimethyl ammonium chloride and methacryloyl grafted aminopolysaccharide or trimethyl ammonium chloride and methacryloyl grafted carboxyl polysaccharide in deionized water to obtain an intermediate amino macromolecule derivative solution or an intermediate carboxyl macromolecule derivative solution, wherein the natural polysaccharide containing amino is one or more of chitosan, carboxymethyl chitosan, carboxyethyl chitosan, hydroxyethyl chitosan or gelatin, and the polysaccharide containing carboxyl is one or more of sodium hyaluronate, sodium alginate, chondroitin sulfate, carboxymethyl cellulose, xanthan gum or gamma-polyglutamic acid;
step S2: adding p-hydroxybenzaldehyde into the intermediate amino polymer derivative solution obtained in the step S1, reacting at room temperature, adding sodium borohydride, continuously reacting, filling the reaction solution into a dialysis bag, dialyzing in deionized water, and freeze-drying to obtain the amino natural polymer derivative grafted with trimethyl ammonium chloride, methacryloyl and phenol groups; adding aminophenol and a catalyst into the intermediate carboxyl polymer derivative solution obtained in the step S1, reacting at room temperature, filling a reaction solution into a dialysis bag, dialyzing in deionized water, freeze-drying to obtain a carboxyl natural polymer derivative grafted with trimethyl ammonium chloride, methacryloyl and phenol groups, dissolving the amino natural polymer derivative or the carboxyl natural polymer derivative in deionized water to obtain a natural polymer derivative solution, wherein the aminophenol is one or more of tyramine, tyramine hydrochloride, tyrosine hydrochloride, dopamine or dopamine hydrochloride, and the catalyst is one or more of 1- (3-dimethylaminopropyl) -3-ethylcarbodiimide hydrochloride or 4- (4, 6-dimethoxytriazine) -4-methylmorpholine hydrochloride;
and step S3: dissolving dried polyvinyl alcohol in dimethyl sulfoxide, adding tert-butyl acetoacetate, stirring under a heating condition, reacting, filling a reaction solution into a dialysis bag, dialyzing in deionized water, freeze-drying to obtain acetoacetyl grafted polyvinyl alcohol, and dissolving the acetoacetyl grafted polyvinyl alcohol in the deionized water to obtain an acetoacetyl polyvinyl alcohol solution;
and step S4: and (3) uniformly mixing the natural polymer derivative solution obtained in the step (S2), the acetoacetyl polyvinyl alcohol solution obtained in the step (S3), a horseradish peroxidase solution and a hydrogen peroxide solution to obtain a gel-forming precursor solution, and standing at room temperature to obtain the enzyme-catalyzed double-crosslinked polymer composite hydrogel material.
2. The preparation method of the enzyme-catalyzed double-crosslinked polymer composite hydrogel material according to claim 1, wherein the preparation method comprises the following steps: the concentration of the aminopolysaccharide solution or the carboxyl polysaccharide solution in the step S1 is 2 to 100mg/mL, the molar ratio of the structural unit number of the aminopolysaccharide solution or the carboxyl polysaccharide to the glycidyl trimethylammonium chloride and the glycidyl methacrylate is 0.1 to 5, the reaction temperature is 40 to 80 ℃, and the reaction time is 12 to 72h.
3. The preparation method of the enzyme-catalyzed double-crosslinked polymer composite hydrogel material according to claim 1, wherein the preparation method comprises the following steps: the molar ratio of the number of the structural units of the intermediate amino macromolecule derivative in the step S2 to the p-hydroxybenzaldehyde and the sodium borohydride is 0.2 to 5, and the molar ratio of the number of the structural units of the carboxyl macromolecule derivative to the aminophenol and the catalyst is 0.5 to 2.
4. The preparation method of the enzyme-catalyzed double-crosslinked polymer composite hydrogel material according to claim 1, wherein the preparation method comprises the following steps: the concentration of the polyvinyl alcohol solution in the step S3 is 10-100 mg/mL, the mol of hydroxyl in the polyvinyl alcohol and the acetoacetyl tert-butyl ester is 0.1-2, the reaction temperature is 80-150 ℃, and the reaction time is 2-12 h.
5. The preparation method of the enzyme-catalyzed double-crosslinked polymer composite hydrogel material according to claim 1, wherein the preparation method comprises the following steps: the concentration of the natural polymer derivative solution in the step S4 is 20 to 100mg/mL, the concentration of the acetoacetyl polyvinyl alcohol solution is 50 to 300mg/mL, the concentration of horseradish peroxidase is 0.1 to 10mg/mL, the concentration of hydrogen peroxide is 0.01 to 1mol/L, the volume ratio of the natural polymer derivative solution, the acetoacetyl polyvinyl alcohol solution, the horseradish peroxidase solution and the hydrogen peroxide solution in the gel-forming precursor solution is 4.
6. The application of the enzyme-catalyzed double-crosslinked polymer composite hydrogel material prepared by the method of any one of claims 1 to 5 in preparation of biomedical dressings.
7. The application of the enzyme-catalyzed double-crosslinked polymer composite hydrogel material prepared by the method according to any one of claims 1 to 5 in preparing a hydrogel wound dressing for promoting wound healing.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN116462863A (en) * | 2023-06-15 | 2023-07-21 | 首都医科大学附属北京口腔医院 | Contains Mg 2+ Gallic acid grafted chitosan hydrogel of tannic acid microparticles, preparation method and application |
| CN116870241A (en) * | 2023-08-03 | 2023-10-13 | 海南大学 | In-situ formed double-network hydrogel dressing and preparation method and application thereof |
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN116462863A (en) * | 2023-06-15 | 2023-07-21 | 首都医科大学附属北京口腔医院 | Contains Mg 2+ Gallic acid grafted chitosan hydrogel of tannic acid microparticles, preparation method and application |
| CN116462863B (en) * | 2023-06-15 | 2023-09-01 | 首都医科大学附属北京口腔医院 | Contains Mg 2+ Gallic acid grafted chitosan hydrogel of tannic acid microparticles, preparation method and application |
| CN116870241A (en) * | 2023-08-03 | 2023-10-13 | 海南大学 | In-situ formed double-network hydrogel dressing and preparation method and application thereof |
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