CN113144278A - Injectable and degradable antibacterial PEG hydrogel wound repair dressing material and preparation method and application thereof - Google Patents
Injectable and degradable antibacterial PEG hydrogel wound repair dressing material and preparation method and application thereof Download PDFInfo
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- CN113144278A CN113144278A CN202110199078.0A CN202110199078A CN113144278A CN 113144278 A CN113144278 A CN 113144278A CN 202110199078 A CN202110199078 A CN 202110199078A CN 113144278 A CN113144278 A CN 113144278A
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L26/00—Chemical aspects of, or use of materials for, wound dressings or bandages in liquid, gel or powder form
- A61L26/0061—Use of materials characterised by their function or physical properties
- A61L26/008—Hydrogels or hydrocolloids
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L26/00—Chemical aspects of, or use of materials for, wound dressings or bandages in liquid, gel or powder form
- A61L26/0061—Use of materials characterised by their function or physical properties
- A61L26/0066—Medicaments; Biocides
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L26/00—Chemical aspects of, or use of materials for, wound dressings or bandages in liquid, gel or powder form
- A61L26/0061—Use of materials characterised by their function or physical properties
- A61L26/009—Materials resorbable by the body
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J3/00—Processes of treating or compounding macromolecular substances
- C08J3/24—Crosslinking, e.g. vulcanising, of macromolecules
- C08J3/243—Two or more independent types of crosslinking for one or more polymers
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L2300/00—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices
- A61L2300/40—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices characterised by a specific therapeutic activity or mode of action
- A61L2300/404—Biocides, antimicrobial agents, antiseptic agents
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L2400/00—Materials characterised by their function or physical properties
- A61L2400/06—Flowable or injectable implant compositions
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2371/00—Characterised by the use of polyethers obtained by reactions forming an ether link in the main chain; Derivatives of such polymers
- C08J2371/02—Polyalkylene oxides
Abstract
The invention relates to an injectable and degradable antibacterial PEG hydrogel wound repair dressing material and a preparation method and application thereof, wherein the method comprises the following steps: carrying out Michael addition reaction on a non-degradable crosslinking agent, a hydrolyzable degradable crosslinking agent and a crosslinking monomer 4-arm-PEG-MAL in a solvent at a reaction temperature to prepare an injectable and degradable PEG hydrogel; the PEG hydrogel is injectable, can be hydrolyzed and degraded, has a certain antibacterial property, can reduce inflammatory reaction near a wound surface, and can promote angiogenesis around the wound surface. The PEG hydrogel disclosed by the invention has the advantages of uniform pore structure, good biocompatibility, high gelling speed, good mechanical property, no toxicity, capability of promoting cell proliferation and migration, good bacteriostatic action, capability of reducing inflammatory reaction near a wound surface and promoting angiogenesis around the wound surface, and capability of being used as a wound surface repair material.
Description
Technical Field
The invention relates to the field of biomedical polymer materials, in particular to an injectable and degradable antibacterial PEG hydrogel wound repair dressing material and a preparation method and application thereof.
Background
Currently, there are two main types of wound therapy: one is a non-surgical treatment and the other is a surgical treatment. Non-surgical treatment tends to make wounds difficult to heal, and patients need to be faced with longer medical intervention. Surgical treatments such as flap transplantation can cause some degree of damage to healthy tissue in the vicinity of the patient's donor flap. In addition, both non-surgical and surgical treatments need to face problems such as wound infection. An ideal surgical wound dressing should have antimicrobial properties. To date, most of the antimicrobial properties of wound dressings have been provided by silver compounds, antibiotics, iodine, benzalkonium chloride, and other drug carriers. However, the safety of silver compounds used in biomedicine is still a serious problem. In addition, the most commonly used antibiotic formulations lack broad spectrum antimicrobial activity and typically exhibit burst release in an initial state when combined with a dressing. In contrast, dressing materials with inherent antimicrobial properties are more attractive. In order to overcome the above disadvantages, methods for regenerating tissues by using scaffold materials related to tissue engineering have been developed.
Tissue engineering has attracted considerable attention over the past decade as an alternative to traditional tissue regeneration methods, and there have been great attempts in the field to synthesize and manufacture scaffolds that can improve tissue regeneration. A hydrogel is a hydrophilic polymeric material with a lightly crosslinked three-dimensional network structure that is known to absorb and retain large amounts of water while maintaining its own structure insoluble in water. Hydrogels have been widely used as tissue engineering scaffold materials, especially in wound healing applications, due to their excellent properties, such as excellent water absorption and retention, good biocompatibility, and drug loading without loss of activity. For wound healing, hydrogels can provide a moist environment for the wound site, absorb exudates, and clean up the local environment to accelerate healing without causing toxicity. Polyethylene glycol (PEG) is one of the most important raw materials for preparing hydrogels. It has the characteristics of no toxicity, low immunogenicity, good biocompatibility and the like, and can be excreted by the kidney without accumulating in the body. In tissue engineering, scaffolds that are degraded and remodeled as cells migrate and synthesize new extracellular matrix are thought to be more favorable for long-term tissue regeneration. The degradation characteristics of hydrogels can generally be achieved by introducing hydrolytically or enzymatically degradable groups into the hydrogel host structure.
Disclosure of Invention
Aiming at the problems of the hydrogel, the invention provides the hydrogel wound repair dressing material which has the advantages of good biocompatibility, no cytotoxicity, capability of promoting cell proliferation and migration, certain antibacterial effect, quick gelling, good mechanical property gel and hydrolytic degradation.
The specific technical scheme is as follows:
the preparation method of the injectable degradable antibacterial PEG hydrogel wound repair dressing material comprises the following steps: the injectable degradable antibacterial PEG hydrogel wound repair dressing material is prepared by carrying out Michael addition reaction on a non-degradable cross-linking agent HS-PEG-SH and a hydrolyzable degradable cross-linking agent PEG-ester-dithiol and a cross-linking monomer 4-arm-PEG-MAL at a reaction temperature in a solvent, wherein the degradation time of hydrogel is regulated and controlled by the content of the hydrolyzable degradable cross-linking agent PEG-ester-dithiol.
Furthermore, the content of the hydrolytic degradation crosslinking agent PEG-ester-dithiol is 1 percent to 100 percent.
Further, the molar ratio of the functional group-MAL in the 4-arm-PEG-MAL to the functional group-SH in the cross-linking agent is 1: 1.
Further, the specific steps also comprise that the cross-linking agent formed by mixing the cross-linking monomer 4-arm-PEG-MAL, PEG-dithiol and PEG-ester-dithiol is respectively dissolved in PBS buffer solution containing 4mM TEA.
Further, the reaction temperature is 37 ℃, and the crosslinking time is 1-10 min.
The injectable and degradable antibacterial PEG hydrogel wound repair dressing material is applied as a dressing material for promoting wound repair.
The injectable and degradable antibacterial PEG hydrogel wound repair dressing material is prepared by the preparation method.
The beneficial effect of above-mentioned scheme is:
1) the PEG hydrogel wound repair dressing material has the advantages of uniform pore structure, good biocompatibility, no cytotoxicity, quick gelling and good mechanical property;
2) the PEG hydrogel wound repair dressing material has the function of promoting cell proliferation and migration;
3) the PEG hydrogel wound repair dressing material has the antibacterial property;
4) the PEG hydrogel wound repair dressing material can reduce inflammatory reaction near the wound and promote angiogenesis around the wound;
5) the PEG hydrogel wound repair dressing material can regulate and control the degradation period of hydrogel by regulating the degradation rate of the hydrogel.
Drawings
FIG. 1 is a graph of the gel-forming effect of PEG hydrogels provided in examples of the present invention;
FIG. 2 is an Ellman experimental plot of a PEG hydrogel provided in an example of the invention;
FIG. 3 is a rheology test plot of a PEG hydrogel provided in an example of the invention;
FIG. 4 is an infrared spectrum of a PEG hydrogel provided in an embodiment of the present invention;
FIG. 5 is a scanning electron micrograph of a PEG hydrogel and its degradation provided in an embodiment of the present invention;
FIG. 6 is a line graph of in vitro degradation rates for PEG hydrogels provided in examples of the invention;
FIG. 7 is an experimental graph of the in vitro biocompatibility of a PEG hydrogel provided in an example of the present invention;
FIG. 8 is a graph of a scratch healing experiment for a PEG hydrogel provided in an example of the present invention;
FIG. 9 is a graph showing the effect of an antibacterial test on a PEG hydrogel provided in an example of the present invention;
FIG. 10 is a graph of wound healing experiments in mice with PEG hydrogels provided in the examples of the present invention;
fig. 11 is a graph of HE staining and Masson staining of tissue sections of PEG hydrogels provided in examples of the invention;
fig. 12 is a photograph of immunofluorescence staining of PEG hydrogels provided in examples of the invention.
Detailed Description
The technical solutions in the embodiments of the present invention will be clearly and completely described below with reference to the drawings in the embodiments of the present invention, and it is obvious that the described embodiments are only a part of the embodiments of the present invention, and not all of the embodiments. All other embodiments, which can be obtained by a person skilled in the art without any inventive step based on the embodiments of the present invention, are within the scope of the present invention.
It should be noted that the embodiments and features of the embodiments may be combined with each other without conflict.
The invention is further described with reference to the following drawings and specific examples, which are not intended to be limiting.
An injectable and degradable antibacterial PEG hydrogel wound repair dressing material, the preparation method comprises the following steps: commercially available crosslinking monomer 4-arm-PEG-MAL and a crosslinking agent (formed by mixing PEG-dithiol and PEG-diesel-dithiol, wherein the molar ratio of the functional group-MAL to the functional group-SH is 1:1) are respectively dissolved in PBS buffer solution containing 4mM TEA to be fully and uniformly mixed, and then the crosslinking agent and the triethanolamine solution of the crosslinking monomer are transferred into a 500-mu-L mould to react in a 37 ℃ biochemical incubator for 10min to obtain the injectable and degradable antibacterial PEG hydrogel.
The parameters of examples 1 to 3 of the present invention and comparative examples are shown in the following table:
in the invention, the mass percentage of PEG-ester-dithiol in the cross-linking agent can be 1-100%, and the degradation time of the hydrogel can be adjusted by adjusting the proportion of the degradable cross-linking agent and the non-degradable cross-linking agent. When the hydrogel is used as a wound dressing, different proportions of degradable cross-linking agents and non-degradable cross-linking agents can be selected according to the approximate healing time of the wound, generally speaking, the hydrogel can be selected from the embodiment 1 for chronic wounds such as diabetes and the like, the hydrogel can be selected from the embodiment 3 for acute wounds such as knife wound and gunshot wound and the like, and if no special requirements exist, the hydrogel can be directly selected from the embodiment 2, and the structure and the performance of the hydrogel can be researched by taking the embodiment 2 as an example.
The structure and properties of the sample were examined in example 2.
The gel formation process begins immediately after mixing the crosslinking agent and crosslinking monomer, as shown in fig. 1, and does not flow with gravity about mid-tenth, as further demonstrated by the Ellman test results of fig. 2 and the rheological test results shown in fig. 3. In FIG. 2, the free thiol content of the system decreases very rapidly by the tenth minute of mixing the crosslinking agent and the crosslinking monomer and stabilizes by 60 minutes. The results of the rheological experiments shown in figure 3 also show that the storage modulus of the hydrogel reaches a maximum around one hour.
FIG. 4 shows the IR spectra of the raw materials and PEG hydrogel, the IR results show complete reaction and sufficient crosslinking of the hydrogel.
FIG. 5 shows scanning electron microscope images of hydrogels and their degradation products at 7 th, 14 th and 21 th days, and it shows that the PEG hydrogels provided by the present invention are all porous sponge-like structures, and have uniform and uniform pore sizes, average pore size of 10-30 μm, and relatively large porosity.
The degradation curve is shown in FIG. 6, and the degradation experimental procedure is as follows: freeze-drying PEG hydrogel, accurately weighing the weight of the PEG hydrogel, adding the dried hydrogel into a complete culture medium, placing the culture medium in a constant-temperature shaking table with the rotating speed of 200R/min at 37 ℃, taking out the culture medium at a set time point, rinsing the culture medium with distilled water, freeze-drying and weighing, calculating the cumulative degradation percentage (%) of each group of hydrogel in the solution (the weight of the hydrogel before degradation-the mass of the hydrogel after degradation)/the weight of the hydrogel before degradation multiplied by 100 percent, taking 3 test samples from each group of hydrogel in order to ensure the accuracy of the experiment, and taking the average value of the three test samples.
As shown in FIG. 7, the present invention adopts human immortalized keratinocytes and adopts leaching liquor toxicity experiments to study the biocompatibility of PEG hydrogel raw materials, materials and degradation products according to the method recommended by the national standard, wherein, negative control group polypropylene (PP) and positive control group Phenol (Phenol) are arranged.
As shown in fig. 8, the effect of the PEG hydrogel provided by the present invention on cell migration was studied through a scratch healing experiment, and the result shows that the hydrogel can significantly promote the migration of human immortalized keratinocytes.
The results of the antibacterial experiments are shown in fig. 9, and the area within the blue dotted circle is the inhibition zone. In this experiment, a PEG hydrogel loaded with gentamicin (40000U/mL) was set as an experimental group, and the antibacterial ability of the drug loaded PEG hydrogel was further studied. The result shows that the PEG hydrogel without antibiotic load has certain antibacterial capacity and obvious inhibition effect on common gram-negative bacteria and gram-negative bacteria, and compared with a positive control group which is covered with antibiotic filter paper, the PEG hydrogel without antibiotic load shows inhibition effect on escherichia coli and staphylococcus aureus, and the antibacterial efficiency is 64.1% and 93.5% respectively. The experimental result also shows that after the gentamicin is loaded, the antibacterial capacity of the hydrogel is obviously enhanced, the antibacterial ring is larger, the antibacterial time is longer, and meanwhile, after the gentamicin is loaded into the PEG hydrogel, the function and the activity of the gentamicin are not influenced. From the results, the PEG hydrogel can be used as a wound dressing material which can carry the medicine and has certain antibacterial ability, and the structure and the function of the medicine cannot be adversely affected in the process of carrying the medicine.
In vivo experiments are carried out by taking SD rats as wound healing models to further discuss the influence of the PEG hydrogel on wound healing. As shown in fig. 10, wound areas covered with PEG hydrogel and gentamicin-loaded PEG hydrogel were smaller than those covered with PBS at 7, 10 and 14 days after incision, and some of the rat wounds covered with PEG hydrogel were completely healed at 14 days after surgery, while none of the control groups were completely healed. The in vivo experiment result shows that whether the gentamicin is loaded or not, the PEG hydrogel can play a role in promoting the wound healing.
Fig. 11 shows H & E staining (a) and Masson staining (B) images of tissue sections near the rat wound, and histological analysis showed that the re-epithelialization process of the rat wound was significantly improved after treatment with PEG hydrogel and gentamicin-loaded PEG hydrogel, and that inflammatory cell infiltration in the rat wound was less after treatment with PEG hydrogel or gentamicin-loaded PEG hydrogel compared to the control group. The Masson staining result shows that after the PEG hydrogel or the PEG hydrogel loaded with gentamicin is used for treating, more collagen is deposited in the wound area of the rat, and the collagen is also another most important index for promoting the wound healing.
Inflammatory responses and angiogenesis were studied near the wound area by immunofluorescent staining analysis, and an immunofluorescent stained image is shown in fig. 12. Among them, tumor necrosis factor alpha (TNF-alpha) was selected as a marker to study inflammatory response. As shown in the figure, the red fluorescence is TNF-alpha, the blue fluorescence (DAPI) is cell nucleus, and the fluorescence intensity of TNF-alpha in the control group is higher than that of the PEG group and gentamicin-PEG group, which shows that the PEG hydrogel can reduce the inflammatory reaction degree around the wound surface. Meanwhile, Vascular Endothelial Growth Factor (VEGF) is selected as a marker to analyze the angiogenesis condition near the wound surface, as shown in the figure, the red fluorescence is VEGF, the blue fluorescence (DAPI) is cell nucleus, and compared with a control group, the VEGF can be obviously observed to have higher-level expression in a PEG group and a gentamicin-PEG group, so that the PEG hydrogel can be further shown to promote the expression of the VEGF near the wound surface and promote the growth and recovery of tissues near the wound surface.
While the invention has been described with reference to a preferred embodiment, it will be understood by those skilled in the art that various changes in form and detail may be made therein without departing from the spirit and scope of the invention.
Claims (7)
1. The preparation method of the injectable degradable antibacterial PEG hydrogel wound repair dressing material is characterized by comprising the following steps: carrying out Michael addition reaction on a non-degradable cross-linking agent HS-PEG-SH and a hydrolysable degradable cross-linking agent PEG-ester-dithiol and a cross-linking monomer 4-arm-PEG-MAL in a solvent at a reaction temperature to prepare the injectable degradable antibacterial PEG hydrogel wound repair dressing material, wherein the degradation time of the hydrogel is regulated and controlled by the content of the hydrolysable degradable cross-linking agent PEG-ester-dithiol.
2. The preparation method of the injectable degradable antibacterial PEG hydrogel wound repair dressing material according to claim 1, characterized in that the content of the hydrolytic degradable crosslinking agent PEG-ester-dithiol is 1% -100%.
3. The preparation method of the injectable degradable antibacterial PEG hydrogel wound repair dressing material according to claim 1, characterized in that the molar ratio of the functional group-MAL in 4-arm-PEG-MAL to the functional group-SH in the cross-linking agent is 1: 1.
4. The preparation method of the injectable degradable antibacterial PEG hydrogel wound repair dressing material according to claim 1, characterized by further comprising the step of respectively dissolving a cross-linking agent formed by mixing a cross-linking monomer 4-arm-PEG-MAL with PEG-dithiol and PEG-ester-dithiol in PBS buffer containing 4mM TEA.
5. The preparation method of the injectable degradable antibacterial PEG hydrogel wound repair dressing material according to claim 1, characterized in that the reaction temperature is 37 ℃ and the crosslinking time is 1-10 min.
6. An injectable and degradable antibacterial PEG hydrogel wound repair dressing material, which is characterized by being prepared by the preparation method of any one of claims 1 to 5.
7. Use of an injectable and degradable antibacterial PEG hydrogel wound repair dressing material according to claim 6 as a dressing material for promoting wound repair.
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Cited By (1)
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| WO2024081793A1 (en) * | 2022-10-12 | 2024-04-18 | Massachusetts Institute Of Technology | Ingestible in vivo-assembling drug release formulations and methods |
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Application publication date: 20210723 |