CN107626002B - Response type medical gel and preparation method and application thereof - Google Patents
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Abstract
The invention provides a responsive medical gel. Specifically, a functionalized hyperbranched polymer monomer (HB-PBAE) is synthesized through a Michael addition reaction among Dopamine (DOPA), polyethylene glycol diacrylate (PEGDA 700) and pentaerythritol triacrylate (PETA); HB-PBAE. Mixing solution of polyvinyl imidazole (PVI) and gelatin (Geln) in iron ion (Fe)3+) The solution forms a gel. The gel has soft and sticky property in the initial stage of gel formation, and is in the presence of zinc ion (Zn)2+) The gel adhesion after soaking in the solution is obviously reduced. The hydrogel has injectability, can be used as a surgical operation sealant or wound dressing, is coated on a tissue wound to avoid leakage of unfavorable liquid or gas, has ion responsiveness in the adhesion performance, can reduce secondary injury during dressing change, and can relieve wound pain.
Description
Technical Field
The invention relates to the field of medical instruments, in particular to a responsive medical gel and a preparation method and application thereof.
Background
A polymeric hydrogel may be defined as a crosslinked polymer that swells in water and retains a significant amount of water without being dissolved. Physical gels are gels formed by physical actions such as electrostatic interactions, hydrogen bonding, entanglement of chains, etc., which are non-permanent, and gels which can be converted to sols by heating, and are therefore also referred to as thermoreversible gels. Chemical gels are polymers with a three-dimensional network structure formed by cross-linking chemical bonds and are permanent, also known as true gels. The injectable gel is a novel hydrogel appearing in recent years, and the gel precursor with certain fluidity is implanted into the body in an injection mode, so that the gel can fill the whole defect part with irregular characters, and the surgical wound is small. The injectable hydrogel can be used as a tissue repair material and a wound surface sealant to close the wound surface and prevent liquid leakage and air leakage.
The intelligent high-molecular hydrogel is a high-molecular hydrogel which can generate sensitive response to external stimulation. According to the response condition to external stimuli, the intelligent polymer hydrogel is divided into temperature sensitive hydrogel, pH value sensitive hydrogel, photosensitive hydrogel, pressure sensitive hydrogel, biomolecule sensitive hydrogel, electric field sensitive hydrogel and the like. Ion-responsive hydrogels are one of the most studied and most valuable stimuli-responsive gels. The volume and form of the hydrogel are often controlled by changing the ionic strength and cooperate with other stimulation conditions to achieve various property transformations and functional applications. The change of the hydrogel volume is regulated and controlled through ionic strength, and the hydrogel crosslinked polymer network structure mainly contains a plurality of stimulation responsive groups, and the stimulation responsive groups can react with external stimulation ions, so that the molecular structure of a polymer chain is subjected to hydrophobic-hydrophilic substitution change, and rapid swelling or collapse is caused.
Hyperbranched polymer monomers are receiving more and more attention from researchers in the hydrogel community because hyperbranched structures can introduce many characteristic functional groups, thereby bringing more abundant performance to hydrogels.
Surgical sealants are products that close a wound of tissue by physical or chemical action, preventing the leakage of liquids or gases. A series of hydrogels with fast gel forming and excellent mechanical properties are used as Surgical sealants, such as hydrogel materials, for example, Progel sealant from Bard, Coseal sealant from Baxter, DuraSeal sealant from Confluent Surgical, Adheraus sealant and Ocueal sealant from HyperBranch Medical Technology, etc. The skin wound dressing is a covering or protection layer of a skin wound, can replace damaged skin to play a temporary protection role in the process of wound healing and treatment, avoids or controls wound infection, and provides a proper wound surface healing environment. The hydrogel can also be used as a dressing and applied to various skin wounds. The hydrogel adheres to the base of the wound, providing and maintaining a moist environment conducive to wound healing. The closed healing environment can promote the proliferation of capillary vessels and the formation of granulation tissues, thereby accelerating the healing of the wound surface. In addition, the skin wound dressing needs to be replaced regularly, and for large-area wounds, certain damage to new tissues can be caused during replacement, wound infection, healing delay and complications are caused, the adhesiveness of gel during dressing replacement is reduced as much as possible, and secondary damage is urgently reduced.
Therefore, the development of a responsive medical gel is urgent clinically.
Disclosure of Invention
The invention aims to overcome the defects of the prior art and provide a responsive medical gel product with adjustable and controllable adhesiveness.
The invention selects a hyperbranched polymer monomer (HP-PBAE) of dopamine and polyvinyl imidazole (PVI), and iron ions are used as a complexing agent to initiate gel, and the formed gel has injectability and self-repairing performance. Gelatin is added to increase the biocompatibility of the biomaterial, and is also capable of generating a coordination complex with iron ions. The zinc ions can be complexed with PVI in the interpenetrating grids to regulate and control the adhesive property of the gel.
The invention relates to a responsive medical gel product, which comprises the following components:
(1) a first liquid component: the liquid component is a mixed aqueous solution (HB-PBAE/PVI/Geln) of a functionalized hyperbranched polymer (HB-PBAE), polyvinyl imidazole (PVI) and gelatin (Geln), the concentration of the HB-PBAE in the aqueous solution is 5-10% (w/v), the concentration of the PVI in the aqueous solution is 5-10% (w/v), and the concentration of Geln in the aqueous solution is 1-10% (w/v);
(2) and a second liquid component: the liquid component is ferric chloride aqueous solution, and the concentration is 30-150 mM;
(3) and a third liquid component: the liquid component is zinc sulfate aqueous solution with the concentration of 30-150 mM.
When the response type medical gel product is used, the first liquid component and the second liquid component are mixed, quickly swirled, sucked into a syringe with a needle removed, quickly and uniformly pushed out in a gel form, and adhered to a wound surface of a tissue.
In the responsive medical gel product, the functionalized hyperbranched polymer (HB-PBAE) in the first component is synthesized by Michael addition reaction among Dopamine (DOPA), polyethylene glycol diacrylate (PEGDA 700) and pentaerythritol triacrylate (PETA). The first liquid component and the second liquid component are mixed to form a gel, and the gel has reduced adhesiveness and increased strength under the action of the third liquid component.
Another object of the present invention is to provide a method for preparing a responsive medical gel, comprising the steps of:
(1) and preparing a first liquid component: completely dissolving gelatin (Geln) in deionized water, wherein the temperature of a dissolving water bath is 40 ℃, and the concentration of Geln is 1-10% (w/v); adding HB-PBAE into the Geln aqueous solution, wherein the concentration of the HB-PBAE is 5-10% (w/v), and uniformly mixing at room temperature to obtain an HB-PBAE/Geln aqueous solution; adding PVI into an HB-PBAE/Geln aqueous solution, wherein the concentration of the PVI is 5-10% (w/v), and uniformly mixing at room temperature to obtain an HB-PBAE/PVI/Geln mixed solution;
(2) and preparing a second liquid component: dissolving ferric chloride in deionized water, wherein the concentration is 30-150 mM;
(3) and preparing a third liquid component: dissolving zinc sulfate in deionized water, wherein the concentration is 30-150 mM;
(4) mixing the first liquid component and the second liquid component, quickly swirling, sucking into the syringe with the needle removed, quickly and uniformly pushing out in a gel form, and coating the pushed hydrogel on the adhered substrate in any shape;
(5) and dropping a third liquid component on the surface of the gel, wherein the gel can be detached from the surface of the adhered substrate.
In the above method, the functionalized hyperbranched polymer (HB-PBAE) in the first component is synthesized by a michael addition reaction between Dopamine (DOPA), polyethylene glycol diacrylate (PEGDA 700) and pentaerythritol triacrylate (PETA). The first liquid component and the second liquid component are mixed to form a gel, and the gel has reduced adhesiveness and increased strength under the action of the third liquid component.
In the above production method, the concentration of the aqueous solution of ferric chloride is 30 to 150mM, preferably 100 mM. The volume of the added ferric chloride solution is 10-100% of the volume of the aqueous solution of the HB-PBAE/PVI/Geln mixture, and preferably 20-40%.
The invention provides a response type medical gel, which is based on an HB-PBAE/PVI/Geln mixed solution, and is physically crosslinked interpenetrating grid type hydrogel is obtained by complexing ferric ions and dopamine under the initiation of ferric chloride. Gelatin is added to increase the biocompatibility of the hydrogel, and can generate a coordination complex with iron ions. The PVI in the interpenetrating grids can be complexed with zinc ions to regulate and control the adhesion performance of the adhesive.
The hydrogel can be used for closing the wound surface of the tissue in thoracic surgery, neurosurgery, cardiovascular surgery, ophthalmology, general surgery, dermatology, burn department, plastic department and orthopedic surgery in medical science, reducing the leakage of gas or liquid, promoting wound healing and preventing tissue adhesion, for example, the hydrogel is used for reducing the leakage of gas after the suturing or stapling of lung tissue in the lung resection operation of the thoracic surgery; neurosurgery (in skull and spinal surgery) is used for sealing the dura mater in repair, and leakage of cerebrospinal fluid after the surgery is reduced; sealing of vascular reconstructive sites in cardiovascular surgery; sealing for lens perforation, eyelid surgery, lacrimal gland and conjunctival repair in ophthalmology; in surgery for sealing of anastomotic openings after intestinal anastomosis; fixing the hernia patch; adhesion prevention after operation; the closure of the wound surface of the dermatology or the burn department can promote the healing of the wound,
the medical gel of the present invention can be detected by the following method.
And (3) testing the compressive strength: the gel was sprayed into a mold to prepare a cylindrical gel sample having a diameter of 8mm and a height of 15mm, and the gel sample was tested in a universal testing machine (UTM, M350, Testometric Co., Ltd.) at a compression rate of 10 mm/min.
Adhesion test: reference YYT 0729.1-2009 tissue adhesive bond Performance test methods part 1: lap-shear tensile strength was measured on a universal testing machine (UTM, M350, Testometric ltd) in a lap-shear manner and calculated as the maximum load force divided by the overlap area of the respective samples. First, a method for preparing a tissue base: the casing was cut into a rectangle of 5.0 cm × 1.5 cm in size and soaked in PBS. The gel-forming precursor solution is applied to one tissue substrate and then immediately overlaid with another piece of tissue substrate. During the test, a force measuring sensor of 10 kgN is selected, and the stretching speed is 2 mm/min. The glass substrates were tested using 7.6 cm x 2.6 cm standard size glass slides and similar sampling, at a 5 mm/min pull rate.
Drawings
FIG. 1 is a schematic diagram of the synthesis of HP-PBAE.
FIG. 2 is a photograph of the HP-PBAE (20%)/PVI (10%)/Geln (5%) gel self-repair process.
FIG. 3 shows the strength change before and after soaking the HP-PBAE (20%)/PVI (10%)/Geln (5%) gel in zinc ions.
FIG. 4 shows the change in adhesion strength before and after soaking HP-PBAE (20%)/PVI (10%)/Geln (5%) gel in zinc ions.
Detailed description of the invention
The technical solutions of the present invention are further illustrated below with reference to specific examples, and the present invention is further illustrated below with reference to examples, but these examples are not intended to limit the present invention.
Example 1
A hyperbranched polymer monomer HB-PBAE (shown in figure 1) is synthesized by the Michael addition reaction of an amino group on Dopamine (DOPA) and double bonds on pentaerythritol triacrylate (PETA) and polyethylene glycol diacrylate (PEGDA 700). The molar ratio of active hydrogen of the amino group to carbon-carbon double bond in the reaction is 1.2:1, wherein PETA and PEGDA700 each provide half of the carbon-carbon double bonds.
The specific operation steps are as follows: weighing 6.6 g dopamine hydrochloride (DOPA. HCl), 6 g PETA, 21 g PEGDA700 and 80 g DMSO solvent, and fully mixing; adding Triethylamine (TEA) dropwise to adjust the pH value of the mixed solution to be about 8; heating the mixed solution in an oil bath for 2.5 h, setting the reaction time to 80 ℃, and carrying out light-proof treatment on the oil bath device because dopamine is easy to oxidize under illumination; naturally cooling to room temperature after the reaction is finished, purifying by using methyl tert-butyl ether, filtering by using a cotton-plugged funnel to remove separated unreacted DOPA.HCl, and purifying the filtrate twice by using methyl tert-butyl ether; and (3) suspending and steaming the obtained purified liquid, and removing residual purifying agent methyl tert-butyl ether to obtain a light yellow liquid product, namely the hyperbranched polymer monomer HB-PBAE.
Example 2
1-Vinyl Imidazole (VI) is used as a raw material, tetraethyl thiuram Disulfide (DS) is used as a chain transfer agent, and Azobisisobutyronitrile (AIBN) is used as an initiator to synthesize polyvinyl imidazole by a RAFT method. The molar ratio of DS, AIBN and 1-vinylimidazole in the reaction is 1:2: 50.
The specific operation steps are as follows: 23.53 g VI, 1.48 g DS, 1.64 g AIBN and 100 ml DMF solvent were mixed well; introducing nitrogen into the mixed solution for at least 30 min, and exhausting air; heating in oil bath, wherein the reaction time is 6 h, and the temperature is set to be 70 ℃; after the reaction is finished, naturally cooling the reaction solution to room temperature; the reaction solution was purified twice with 1000 ml of glacial ethyl ether, and then placed in a vacuum drying oven to volatilize and remove the residual anhydrous ethyl ether serving as a purifying agent, thereby obtaining a yellowish brown solid product, namely PVI.
Example 3
Dissolving 30 mg gelatin in 100 μ L PBS (pH 7.4) at 40 deg.C in a water bath, and making gelatin water solution with final concentration of 2% (w/v); and sequentially adding the HP-PBAE and the PVI solution into the gelatin aqueous solution, and uniformly mixing at room temperature to obtain an aqueous solution of a HP-PBAE/Geln/PVI mixture, wherein the HP-PBAE/Geln/PVI is in the aqueous solution of the mixture. Wherein the final concentration of HP-PBAE polymer monomer is 5% (w/v), and the final concentration of PVI is 2.5% (w/v); adding ferric chloride solution into the aqueous solution of the HP-PBAE/Geln/PVI mixture, quickly vortexing to obtain gel precursor solution, wherein the concentration of the added ferric chloride solution is 100mM, and the volume of the added ferric chloride solution is 20% of that of the aqueous solution of the HP-PBAE/Geln/PVI mixture; the gel precursor solution was drawn into the syringe from which the needle had been removed and rapidly and uniformly pushed out in the form of a gel.
Example 4
Dissolving 30 mg gelatin in 100 μ L PBS (pH 7.4) at 40 deg.C in a water bath to give a final gelatin solution concentration of 3% (w/v); and sequentially adding the HP-PBAE and the PVI solution into the gelatin aqueous solution, and uniformly mixing at room temperature to obtain an aqueous solution of a HP-PBAE/Geln/PVI mixture, wherein the HP-PBAE/Geln/PVI is in the aqueous solution of the mixture. Wherein the final concentration of HP-PBAE polymer monomer is 10% (w/v), and the final concentration of PVI is 5% (w/v); adding ferric chloride solution into the aqueous solution of the HP-PBAE/Geln/PVI mixture, quickly vortexing to obtain gel precursor solution, wherein the concentration of the added ferric chloride solution is 100mM, and the volume of the added ferric chloride solution is 20% of that of the aqueous solution of the HP-PBAE/Geln/PVI mixture; the gel precursor solution was drawn into the syringe from which the needle had been removed and rapidly and uniformly pushed out in the form of a gel.
Example 5
Dissolving 30 mg gelatin in 100 μ L PBS (pH 7.4) at 40 deg.C in a water bath to give a gelatin aqueous solution with a final concentration of 5% (w/v); and sequentially adding the HP-PBAE and the PVI solution into the gelatin aqueous solution, and uniformly mixing at room temperature to obtain an aqueous solution of a HP-PBAE/Geln/PVI mixture, wherein the HP-PBAE/Geln/PVI is in the aqueous solution of the mixture. Wherein the final concentration of HP-PBAE polymer monomer is 20% (w/v), and the final concentration of PVI is 10% (w/v); adding ferric chloride solution into the aqueous solution of the HP-PBAE/Geln/PVI mixture, quickly vortexing to obtain gel precursor solution, wherein the concentration of the added ferric chloride solution is 100mM, and the volume of the added ferric chloride solution is 25% of that of the aqueous solution of the HP-PBAE/Geln/PVI mixture; the gel precursor solution was drawn into the syringe from which the needle had been removed and rapidly and uniformly pushed out in the form of a gel.
The prepared gel is made into a strip shape, the strip shape is cut into four sections by a blade, the four sections of adhesives are spliced together again, after about 15 min, the four sections of adhesives are adhered to each other and can be clamped by forceps, and the gel realizes the self-repairing function (as shown in figure 2).
Aging the prepared gel for half an hour, dividing the gel into two groups, wherein each group has three samples, and one group of gel is not soaked with Zn2+Solution, one group soaked in 100 ml 100mM Zn2+In solution, soaked for 24h, followed by compression testing. The gel compressive strength increased from 13.31 + -1.40 kPa before soaking to 28.84 + -0.86 kPa after soaking (as shown in FIG. 3), and the gel compressive strength was responsive to zinc ions.
Aging the prepared gel for half an hour, soaking in 100 ml 100mM Zn2+Soaking in the solution for 10 min, 20 min and 30 min, and preparing sample for mechanical adhesion test. Soaking the gel in 100mM zinc ion solution for only 10 minThe maximum shear tensile strength is significantly reduced, and the maximum shear tensile strength is further reduced with the increase of the soaking time, but the reduction degree becomes gradually smaller (as shown in figure 4), and the shear-tensile strength of the gel has better responsiveness to zinc ions.
The invention has been described in an illustrative manner, and it is to be understood that any simple variations, modifications or other equivalent changes which can be made by one skilled in the art without departing from the spirit of the invention fall within the scope of the invention.
Claims (5)
1. A responsive medical gel product comprising the following components: (1) a first liquid component: the liquid component is a mixed aqueous solution (HB-PBAE/PVI/Geln) of a functionalized hyperbranched polymer monomer (HB-PBAE), polyvinyl imidazole (PVI) and gelatin (Geln), wherein the concentration of the HB-PBAE in the aqueous solution is 5-10% (w/v), the concentration of the PVI in the aqueous solution is 5-10% (w/v), and the concentration of the Geln in the aqueous solution is 1-10% (w/v); (2) and a second liquid component: the liquid component is ferric chloride aqueous solution, and the concentration is 30-150 mM; (3) and a third liquid component: the liquid component is zinc sulfate aqueous solution with the concentration of 30-150 mM;
the functionalized hyperbranched polymer monomer (HB-PBAE) in the first component is synthesized by the Michael addition reaction among Dopamine (DOPA), polyethylene glycol diacrylate (PEGDA 700) and pentaerythritol triacrylate (PETA);
when the response type medical gel product is used, the first liquid component and the second liquid component are mixed, quickly swirled and sucked into the syringe with the needle removed, quickly and uniformly pushed out in a gel form and adhered to a tissue wound surface;
the first liquid component and the second liquid component are mixed to form a gel, and the gel has reduced adhesiveness and increased compressive strength under the action of the third liquid component.
2. A method of preparing the responsive medical gel of claim 1, comprising the steps of: (1) and preparing a first liquid component: completely dissolving gelatin (Geln) in deionized water, wherein the temperature of a dissolving water bath is 40 ℃, and the concentration of Geln is 1-10% (w/v); adding HB-PBAE into the Geln aqueous solution, wherein the concentration of the HB-PBAE is 5-10% (w/v), and uniformly mixing at room temperature to obtain an HB-PBAE/Geln aqueous solution; adding PVI into an HB-PBAE/Geln aqueous solution, wherein the concentration of the PVI is 5-10% (w/v), and uniformly mixing at room temperature to obtain an HB-PBAE/PVI/Geln mixed solution; (2) and preparing a second liquid component: dissolving ferric chloride in deionized water with the concentration of 30-150 mM; (3) and preparing a third liquid component: dissolving zinc sulfate in deionized water at a concentration of 30-150 mM; (4) mixing the first liquid component and the second liquid component, quickly swirling, sucking into the syringe with the needle removed, quickly and uniformly pushing out in a gel form, and coating the pushed hydrogel on the adhered substrate in any shape; (5) and dropping a third liquid component on the surface of the gel, wherein the gel can be detached from the surface of the substrate to be adhered.
3. The method for preparing a responsive medical gel according to claim 2, wherein in the step (4), the gel is formed due to coordination crosslinking of iron ions, and has injectability and self-repairability; at the same time, the existence of PVI enables the gel to have zinc ions (Zn)2+) And (4) responsiveness.
4. A responsive medical gel product as claimed in claim 1 for use as a surgical sealant to avoid unwanted fluid or gas leakage.
5. A responsive medical gel product according to claim 1 for use as a wound dressing to reduce secondary trauma and reduce pain on the wound during dressing changes.
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| CN114573808B (en) * | 2022-03-17 | 2023-07-25 | 浙江大学杭州国际科创中心 | Terminal double bond ion response hyperbranched polymer and preparation method and application thereof |
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