CN115068684A - Curcumin-loaded hydrogel for repairing chronic wounds of diabetes and preparation method thereof - Google Patents
Curcumin-loaded hydrogel for repairing chronic wounds of diabetes and preparation method thereof Download PDFInfo
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- CN115068684A CN115068684A CN202210754943.8A CN202210754943A CN115068684A CN 115068684 A CN115068684 A CN 115068684A CN 202210754943 A CN202210754943 A CN 202210754943A CN 115068684 A CN115068684 A CN 115068684A
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- VFLDPWHFBUODDF-FCXRPNKRSA-N curcumin Chemical compound C1=C(O)C(OC)=CC(\C=C\C(=O)CC(=O)\C=C\C=2C=C(OC)C(O)=CC=2)=C1 VFLDPWHFBUODDF-FCXRPNKRSA-N 0.000 title claims abstract description 142
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Abstract
The invention discloses a curcumin-loaded hydrogel for repairing a chronic wound surface of diabetes and a preparation method thereof. The preparation method of the curcumin-loaded hydrogel comprises the following steps: 1) preparing phenylboronic acid modified gelatin; 2) preparing oxidized hyaluronic acid; 3) solubilization of curcumin by phenylboronic acid-modified gelatin; 4) and (3) preparing curcumin-loaded dynamic hydrogel. The hydrogel has good self-healing performance, is easy for tissue adhesion, has excellent biocompatibility, and can slowly release curcumin so as to weaken inflammatory reaction at a wound surface, thereby achieving the effect of repairing a chronic wound surface.
Description
Technical Field
The invention relates to the technical field of biomedical materials and tissue engineering, in particular to curcumin-loaded hydrogel for repairing chronic wounds of diabetes and a preparation method thereof.
Background
The skin is the largest organ of the human body, which contains a complex network structure. The skin maintains the normal physiological environment of the human body and is also an important barrier to prevent the human body from being invaded by foreign objects. The skin of a normal organism can be spontaneously and orderly unfolded and repaired according to four stages of a hemostasis stage, an inflammation stage, a proliferation stage and a tissue remodeling stage after being damaged in a small range, the healing period of the properly treated wound surface is short, and no other complications are generated. Chronic diseases such as diabetes, pressure sores and the like cause local blood supply insufficiency due to damaged tissues of patients, the inflammatory reaction at wound surfaces is serious, the healing process is disordered, the skin healing period is prolonged or not healed, and the life of the patients is endangered finally.
At present, the common modes for clinically treating the chronic wound surface are vacuum-assisted closed negative pressure drainage and wet dressings, wherein the wet dressings such as multifunctional hydrogel dressings and the like are the most economical and simple modes for treating the chronic wound surface. The hydrogel system is constructed by adopting natural macromolecules, so that excellent biocompatibility of the material is ensured, and corresponding functions can be endowed to the hydrogel system by carrying out special group modification on the natural macromolecules. The multifunctional hydrogel system regulates the progress of four stages of wound healing by directly or indirectly regulating signal channels of various cells, up-regulating the expression level of growth factors and the like, thereby promoting the normal healing of the wound. For chronic wounds, the wound is difficult to close, bacteria at the wound grow, and excessive accumulated Reactive Oxygen Species (ROS) further damage cells and trigger more serious inflammatory reaction, so that for chronic wound repair, the design of a hydrogel system needs to start from antibiosis, anti-inflammation and excessive ROS removal to promote the normal progress of the wound healing process.
Curcumin (Cur) is a natural compound with excellent anti-inflammatory and antioxidant properties, has been widely used for treating various skin diseases, but has the defects of poor water solubility, poor stability and the like. To improve the pharmaceutical stability of Cur, researchers have explored a number of systems in which hydrogels are considered good carriers. More researches adopt micelle or nano particle loaded Cur to improve the water solubility and stability of the material, but the preparation process is complicated, the cost is high and the like.
Disclosure of Invention
The invention aims to overcome the defects of the prior art and provide curcumin-loaded hydrogel for repairing chronic wounds of diabetes and a preparation method thereof, wherein the curcumin-loaded hydrogel is prepared by adopting phenylboronic acid-modified gelatin and oxidized hyaluronic acid as main materials and combining Schiff base and phenylboronic acid ester bonds to form dynamic response hydrogel; phenyl boric acid ester bond formed by reaction of phenyl boric acid and diketone on curcumin combines curcumin and gelatin modified by phenyl boric acid to achieve the purpose of solubilizing curcumin; in the hyperglycemia and acidic environment of chronic wounds, particularly diabetic chronic wounds, curcumin can be released in the dynamic hydrogel, and the chronic wounds can be effectively treated.
In order to achieve the purpose, the technical scheme provided by the invention is as follows: a preparation method of curcumin-loaded hydrogel for repairing diabetic chronic wounds comprises the following steps:
preparation of phenylboronic acid modified gelatin: fully heating gelatin to dissolve in 2-equilin ethanesulfonic acid (MES) buffer aqueous solution, cooling to room temperature, adding EDC/NHS, then adding 3-aminophenylboronic acid, stirring at room temperature for reaction to obtain reaction liquid A, placing the reaction liquid A in a dialysis bag for dialysis, and freeze-drying to obtain flocculent material, namely phenylboronic acid modified gelatin;
preparation of oxidized hyaluronic acid: stirring hyaluronic acid with molecular weight of 100-150W overnight for dissolving, adding sodium periodate, stirring for reaction in a dark place, finally adding ethylene glycol for reaction under stirring to obtain a reaction liquid B, placing the reaction liquid B in a dialysis bag for dialysis, and freeze-drying to obtain a flocculent material, namely oxidized hyaluronic acid;
solubilization of curcumin by phenylboronic acid-modified gelatin: dissolving curcumin in an ethanol solution for later use, dissolving phenylboronic acid modified gelatin in 1xPBS for later use, and dropwise adding the ethanol solution of curcumin into a PBS solution in which the modified gelatin is dissolved to obtain a solution C; wherein, phenylboronic acid groups on the phenylboronic acid modified gelatin polymer material can be complexed with an o-diketone structure of curcumin to form phenylboronic acid ester dynamic bonds, so that the aim of solubilizing the curcumin is fulfilled;
preparation of curcumin-loaded dynamic hydrogel: oxidized hyaluronic acid was added to 1xPBS to be sufficiently dissolved, and then mixed with solution C and stirred until hydrogel was formed.
Further, in the preparation of the phenylboronic acid modified gelatin, the mass ratio of the gelatin to the 3-aminophenylboronic acid is 5: EDC at 9.6mg/ml and NHS at 2.3 mg/ml.
Further, in the preparation of oxidized hyaluronic acid, hyaluronic acid and sodium periodate were added in amounts of 6mg/ml each.
Further, in the preparation of the oxidized hyaluronic acid, the mass ratio of the added glycol to the added sodium periodate is 1: 1.
further, in the solubilization of curcumin by phenylboronic acid modified gelatin, the concentration of curcumin in the solution C is 0.2-1 mg/ml.
Further, in the preparation of the curcumin-loaded dynamic hydrogel, the mass ratio of the phenylboronic acid modified gelatin to the oxidized hyaluronic acid is 2: 1.
the invention also provides the curcumin-loaded hydrogel for repairing the chronic wound surface of the diabetes, which is prepared by the method.
Compared with the prior art, the invention has the following advantages and beneficial effects:
according to the invention, the gelatin modified by phenylboronic acid and oxidized hyaluronic acid are used as main materials of the hydrogel, the main raw materials of the gelatin and oxidized hyaluronic acid are main components of an extracellular matrix, the biocompatibility is excellent, the gelatin and oxidized hyaluronic acid are formed through dynamic covalent bonds of Schiff base and phenylboronic acid ester, the environment responsiveness is excellent, the hydrogel can be slowly broken in an acidic environment of a chronic wound surface, and the drug-loading system is good. Meanwhile, the dynamic hydrogel can better adapt to the complex wound shape of the chronic wound surface and can be used for carrying out full filling treatment on the complex wound surface. Curcumin is a natural bioactive polyphenol, has the effects of scavenging free radicals, resisting oxidation, resisting inflammation, regulating immunity and the like, and is applied to various skin wounds. In recent years, many researches show that curcumin can play a role in treating diabetic wounds by regulating and controlling various cell signal pathways, but curcumin has the defects of low stability, extremely low water solubility and the like, and further application of curcumin in skin tissue engineering is hindered. Most hydrogel systems improve the solubility of curcumin in aqueous solution by loading curcumin through micelles or nanoparticles, but the operation undoubtedly complicates the material system, and the invention adopts the gelatin modified by single phenylboronic acid to load curcumin, so that the operation is simple and easy. The dynamic hydrogel loaded with curcumin slowly releases curcumin at the chronic wound to play a role in continuously and effectively repairing the chronic wound.
Drawings
FIG. 1 is a schematic diagram of the formation of a hydrogel according to the present invention.
Fig. 2 is a graph of the compression modulus of hydrogels loaded with different concentrations of curcumin in example 1, example 2, example 3, and example 4.
Fig. 3 is a graph of the pigskin shear-pulling modulus of hydrogels loaded with different concentrations of curcumin in example 1, example 2, example 3 and example 4.
Fig. 4 is a diagram for evaluating the cell compatibility of the hydrogels loaded with curcumin at different concentrations in example 1, example 2, example 3, and example 4.
Detailed Description
The present invention will be described in further detail with reference to the drawings and examples, but the embodiments of the present invention are not limited thereto. Unless otherwise specified, the technical means used in the examples are conventional means well known to those skilled in the art.
Example 1
1) Heating and stirring gelatin at a concentration of 10mg/mL, dissolving the gelatin in MES buffer solution with pH of 5.5, cooling to room temperature after the gelatin is fully dissolved, then adding 4.8g of EDC and 1.15g of NHS, adding 2g of 3-aminophenylboronic acid after the gelatin is fully dissolved by stirring, continuing stirring for reaction for 48 hours to obtain reaction liquid A1, placing the reaction liquid A1 in an 8K-14K dialysis bag, dialyzing in a deionized water environment, and freeze-drying to obtain a polymer material, namely the phenylboronic acid modified gelatin.
2)3g of sodium hyaluronate is fully stirred in 500ml of deionized water, 3g of sodium periodate is added after the sodium hyaluronate is completely dissolved, the sodium periodate is continuously stirred for 8 hours in a dark place, finally 3ml of ethylene glycol is added, the stirring is carried out for 1 hour, the reaction is stopped, reaction liquid B1 is obtained, the reaction liquid B1 is placed in a 3k dialysis bag, the dialysis is carried out in a deionized environment, and the polymer material, namely the oxidized hyaluronic acid, is obtained by freeze-drying.
3) The phenylboronic acid modified gelatin was dissolved in 500ul of 1xPBS to obtain solution C1, ensuring that the final mass fraction was 30%.
4) Dissolving oxidized hyaluronic acid in 500ul of 1xPBS at a mass fraction of 15%, mixing and stirring the oxidized hyaluronic acid with the solution C1 in the step 3) until gelling occurs, so as to obtain the dynamic hydrogel (GOHA), wherein the gelling schematic diagram is shown in figure 1.
Example 2
1) Heating and stirring gelatin at a concentration of 10mg/mL, dissolving the gelatin in MES buffer solution with pH of 5.5, cooling to room temperature after the gelatin is fully dissolved, then adding 4.8g of EDC and 1.15g of NHS, adding 2g of 3-aminophenylboronic acid after the gelatin is fully dissolved by stirring, continuing stirring for reaction for 48 hours to obtain reaction liquid A2, placing the reaction liquid A2 in an 8K-14K dialysis bag, dialyzing in a deionized water environment, and freeze-drying to obtain a polymer material, namely the phenylboronic acid modified gelatin.
2)3g of sodium hyaluronate is fully stirred in 500ml of deionized water, 3g of sodium periodate is added after the sodium hyaluronate is completely dissolved, the sodium periodate is continuously stirred for 8 hours in a dark place, finally 3ml of ethylene glycol is added, the stirring is carried out for 1 hour, the reaction is stopped, reaction liquid B2 is obtained, the reaction liquid B2 is placed in a 3k dialysis bag, the dialysis is carried out in a deionized environment, and the polymer material, namely the oxidized hyaluronic acid, is obtained by freeze-drying.
3) Preparing 4mg/ml ethanol solution of curcumin for later use. Dissolving phenylboronic acid modified gelatin in 500ul of 1xPBS to ensure that the final mass fraction is 30%, adding 25ul of the ethanol solution of curcumin (the concentration of curcumin in the mixed solution is 0.2mg/ml) to obtain solution C2, and stirring uniformly for later use.
4) Dissolving oxidized hyaluronic acid in 500ul of 1xPBS by mass percent of 15%, mixing and stirring the oxidized hyaluronic acid and the solution C2 in the step 3) until gelling occurs, and obtaining the hydrogel (GOHA-Cur0.1) loaded with 0.1mg of curcumin. The compressive modulus of hydrogels with different curcumin contents is shown in figure 2. The hydrogel of all groups is soft and glutinous in texture, low in compression modulus and capable of being well attached to the wound surface.
Example 3
1) Heating and stirring gelatin at a concentration of 10mg/mL, dissolving the gelatin in MES buffer solution with pH of 5.5, cooling to room temperature after the gelatin is fully dissolved, then adding 4.8g of EDC and 1.15g of NHS, adding 2g of 3-aminophenylboronic acid after the gelatin is fully dissolved by stirring, continuing stirring for reaction for 48 hours to obtain reaction liquid A3, placing the reaction liquid A3 in an 8K-14K dialysis bag, dialyzing in a deionized water environment, and freeze-drying to obtain a polymer material, namely the phenylboronic acid modified gelatin.
2)3g of sodium hyaluronate is fully stirred in 500ml of deionized water, 3g of sodium periodate is added after the sodium hyaluronate is completely dissolved, the sodium periodate is continuously stirred for 8 hours in a dark place, finally 3ml of ethylene glycol is added, the stirring is carried out for 1 hour, the reaction is stopped, reaction liquid B3 is obtained, the reaction liquid B3 is placed in a 3k dialysis bag, the dialysis is carried out in a deionized environment, and the polymer material, namely the oxidized hyaluronic acid, is obtained by freeze-drying.
3) Preparing 4mg/ml ethanol solution of curcumin for later use. Dissolving phenylboronic acid modified gelatin in 500ul of 1xPBS to ensure that the final mass fraction is 30%, adding 75ul of the ethanol solution of the curcumin (the concentration of the curcumin in the mixed solution is 0.6mg/ml) to obtain a solution C3, and uniformly stirring for later use.
4) Dissolving oxidized hyaluronic acid in 1xPBS of 500ul by mass percent, mixing and stirring the oxidized hyaluronic acid and the solution C3 in the step 3) until a gelling phenomenon occurs, and obtaining the hydrogel (GOHA-Cur0.3) loaded with 0.3mg of curcumin. The shear tensile modulus of the hydrogel with different curcumin contents on the pigskin is shown in figure 3, and the hydrogel loaded with curcumin has good adhesion to tissues, is beneficial to covering wound surfaces for a long time and then continuously administering, and has the effects of sterilization and inflammation diminishing.
Example 4
1) Heating and stirring gelatin at a concentration of 10mg/mL, dissolving the gelatin in MES buffer solution with pH of 5.5, cooling to room temperature after the gelatin is fully dissolved, then adding 4.8g of EDC and 1.15g of NHS, adding 2g of 3-aminophenylboronic acid after the gelatin is fully dissolved by stirring, continuing stirring for reaction for 48 hours to obtain reaction liquid A4, placing the reaction liquid A4 in an 8K-14K dialysis bag, dialyzing in a deionized water environment, and freeze-drying to obtain a polymer material, namely the phenylboronic acid modified gelatin.
2)3g of sodium hyaluronate is fully stirred in 500ml of deionized water, 3g of sodium periodate is added after the sodium hyaluronate is completely dissolved, the sodium periodate is continuously stirred for 8 hours in a dark place, finally 3ml of ethylene glycol is added, the reaction is stopped for 1 hour, reaction liquid B4 is obtained, the reaction liquid B4 is placed in a 3k dialysis bag and dialyzed in a deionized environment, and the polymer material, namely the oxidized hyaluronic acid, is obtained through freeze-drying.
3) Preparing 4mg/ml ethanol solution of curcumin for standby. Dissolving phenylboronic acid modified gelatin in 500ul of 1xPBS to ensure that the final mass fraction is 30%, adding 125ul of the ethanol solution of the curcumin (the concentration of the curcumin in the mixed solution is 1mg/ml) to obtain a solution C4, and uniformly stirring for later use.
4) Dissolving oxidized hyaluronic acid in 500ul of 1xPBS by mass percent of 15%, mixing and stirring the oxidized hyaluronic acid and the solution C4 in the step 3) until gelling occurs, and obtaining the hydrogel (GOHA-Cur0.5) loaded with 0.5mg of curcumin. The hydrogel with different curcumin content has excellent biocompatibility. As shown in fig. 4, the fibroblasts NIH-3T3 and hydrogels with different curcumin contents showed better proliferation tendency after co-culture for 1, 2 and 3 days, indicating that all the groups of hydrogels have good biosafety.
The examples of the present invention are given for clarity of illustration only, and are not intended to limit the embodiments of the present invention. Other variants and modifications of the embodiments described above will be obvious to those skilled in the art, and it is not necessary or exhaustive for all embodiments to be considered. Any modification, equivalent replacement, and improvement made within the spirit and principle of the present invention should be included in the protection scope of the claims of the present invention.
Claims (7)
1. The preparation method of the curcumin-loaded hydrogel for repairing the chronic wound surface of the diabetes is characterized by comprising the following steps of:
preparation of phenylboronic acid modified gelatin: fully heating gelatin to dissolve in 2-equilin ethanesulfonic acid (MES) buffer aqueous solution, cooling to room temperature, adding EDC/NHS, then adding 3-aminophenylboronic acid, stirring at room temperature for reaction to obtain reaction liquid A, placing the reaction liquid A in a dialysis bag for dialysis, and freeze-drying to obtain flocculent material, namely phenylboronic acid modified gelatin;
preparation of oxidized hyaluronic acid: stirring hyaluronic acid with molecular weight of 100-150W overnight for dissolving, adding sodium periodate, stirring for reaction in a dark place, finally adding ethylene glycol for reaction under stirring to obtain a reaction liquid B, placing the reaction liquid B in a dialysis bag for dialysis, and freeze-drying to obtain a flocculent material, namely oxidized hyaluronic acid;
solubilization of curcumin by phenylboronic acid-modified gelatin: dissolving curcumin in an ethanol solution for later use, dissolving phenylboronic acid modified gelatin in 1xPBS for later use, and dropwise adding the ethanol solution of curcumin into a PBS solution in which the modified gelatin is dissolved to obtain a solution C; wherein, phenylboronic acid groups on the phenylboronic acid modified gelatin polymer material can be complexed with an o-diketone structure of curcumin to form phenylboronic acid ester dynamic bonds, so that the aim of solubilizing the curcumin is fulfilled;
preparation of curcumin-loaded dynamic hydrogel: oxidized hyaluronic acid was added to 1xPBS to be sufficiently dissolved, and then mixed with solution C and stirred until hydrogel was formed.
2. The method for preparing the curcumin-loaded hydrogel for diabetic chronic wound repair according to claim 1, wherein in the preparation of the phenylboronic acid-modified gelatin, the mass ratio of the gelatin to the 3-aminophenylboronic acid is 5: EDC at 9.6mg/ml and NHS at 2.3 mg/ml.
3. The method for preparing curcumin-loaded hydrogel for diabetic chronic wound repair according to claim 1, wherein hyaluronic acid and sodium periodate are added in an amount of 6mg/ml in the preparation of oxidized hyaluronic acid.
4. The method for preparing the curcumin-loaded hydrogel for diabetic chronic wound repair according to claim 1, wherein in the preparation of the oxidized hyaluronic acid, the mass ratio of the added glycol to the added sodium periodate is 1: 1.
5. the preparation method of the curcumin-loaded hydrogel for diabetic chronic wound repair according to claim 1, wherein the concentration of curcumin in the solution C is 0.2-1 mg/ml in the solubilization of curcumin by phenylboronic acid modified gelatin.
6. The preparation method of the curcumin-loaded hydrogel for chronic wound repair of diabetes according to claim 1, wherein in the preparation of the curcumin-loaded dynamic hydrogel, the mass ratio of the phenylboronic acid modified gelatin to the oxidized hyaluronic acid is 2: 1.
7. a curcumin-loaded hydrogel for diabetic chronic wound repair prepared by the preparation method of any one of claims 1 to 6.
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