CN116650704A - Polysaccharide-based conductive injectable bioactive hydrogel wound dressing and preparation method thereof - Google Patents
Polysaccharide-based conductive injectable bioactive hydrogel wound dressing and preparation method thereof Download PDFInfo
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- CN116650704A CN116650704A CN202210153137.5A CN202210153137A CN116650704A CN 116650704 A CN116650704 A CN 116650704A CN 202210153137 A CN202210153137 A CN 202210153137A CN 116650704 A CN116650704 A CN 116650704A
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- derivative
- hydrogel
- polysaccharide
- chitosan
- polydopamine
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Classifications
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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
- A61L26/0009—Chemical aspects of, or use of materials for, wound dressings or bandages in liquid, gel or powder form containing macromolecular materials
- A61L26/0023—Polysaccharides
-
- 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
- A61L26/0004—Chemical aspects of, or use of materials for, wound dressings or bandages in liquid, gel or powder form containing inorganic materials
-
- 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
- A61L26/0009—Chemical aspects of, or use of materials for, wound dressings or bandages in liquid, gel or powder form containing macromolecular materials
- A61L26/0019—Chemical aspects of, or use of materials for, wound dressings or bandages in liquid, gel or powder form containing macromolecular materials obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
-
- 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
-
- 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
- A61L26/008—Hydrogels or hydrocolloids
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- A—HUMAN NECESSITIES
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- 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
- A61L2300/10—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices containing or releasing inorganic materials
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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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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
- Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Materials Engineering (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Inorganic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Dispersion Chemistry (AREA)
- Materials For Medical Uses (AREA)
Abstract
The application discloses a composition for synthesizing polysaccharide-based conductive injectable bioactive hydrogel, and further discloses a synthesis method of the hydrogel. The hydrogel provided by the application can be directly delivered to a target site, is beneficial to filling irregular shapes and deep wounds, has easily-adjustable modulus, and can be matched with the requirements of different tissue defects; the hydrogel provided by the application can promote tissue reconstruction; the dispersibility in water is strong, and the tissue adhesiveness is strong; the raw materials are completely based on natural polysaccharide, so that the natural polysaccharide has rich natural content and is easy to industrialize; the preparation method has excellent biocompatibility, can remarkably promote skin wound healing, and has wide application prospect in the field of biology; the material has adjustable elastic modulus and good self-repairing performance, can be suitable for biological 3D printing technology, and can be applied to tissue engineering.
Description
Technical Field
The application relates to polysaccharide-based conductive injectable bioactive hydrogel, in particular to diversification of gel performance realized by doping multidimensional carbon materials and application thereof in the field of skin repair, and belongs to the field of high polymer materials.
Background
The skin is used as an important natural barrier for human body, is often damaged by the outside, and can be severely wounded by burns, corrosion, trauma and the like. Wound healing is a complex process involving several stages of inflammation, cell proliferation, tissue formation and remodeling, and therefore repair of skin wounds remains a significant clinical challenge. Traditional wound dressing mainly has materials such as gauze, bandage, through covering wound defect position, isolated external environment absorbs the exudation and the secretion in the open wound, protects the wound from infection, has advantages such as with low costs, easy and simple to handle, but need often change in order to prevent bacterial growth. Excessive interstitial fluid and blood exudation at the wound site can form blood clot adhesion, secondary damage is caused during replacement, wound healing is not facilitated, in addition, the dressing itself has no biological activity, and the healing effect depends on the regeneration capacity of the patient. In addition, the skin is one of the electric signal sensitive tissues, the electric conductivity can reach 10 < -4 > to 2.6mS/cm, wherein the dermis is about 2.2mS/cm, the epidermis is about 0.26mS/cm, and the introduction of the electroactive substances can promote the adhesion, proliferation, migration and differentiation of cells. Development of medical materials with multifunctional properties is important, which can protect wounds from external forces, prevent the wounds from being infected by bacteria, viruses and the like.
The physical structure of the hydrogel is most similar to the extracellular matrix of human tissue, and the high water content provides a gentle and moist microenvironment for wound healing; the hydrogel network consists of polymer chains and various hydrophilic groups, and has good water absorption and retention properties; and most of the hydrogel wound dressing has lower modulus and can be matched with the modulus of human skin tissues, so that the research on the injectable hydrogel wound dressing capable of promoting wound healing has good prospect. The natural polysaccharide is used as a polymer material widely existing in the nature, and is modified by chemical modification due to the advantages of various structures, wide distribution, good biocompatibility and the like, and the polysaccharide-based hydrogel wound dressing is obtained by realizing functionalization through the regulation and control of a network structure. However, most hydrogel wound dressings have single functions at present, can not well fill deep or irregular tissue defects, have contact gaps with tissue parts, have no conductive performance, and greatly reduce the capability of stimulating wound regeneration and repair.
Disclosure of Invention
Studies have shown that conductive biomaterials have the effect of promoting tissue regeneration during the wound healing process. Graphene is a promising candidate material due to its excellent conductivity, biocompatibility, high surface area and mechanical strength, but the disadvantage of poor dispersibility limits the application of graphene. Therefore, the carbon-based conductive material is combined with the polysaccharide hydrogel to prepare the multifunctional bioactive injectable hydrogel wound dressing, and the promotion of wound regeneration and repair is particularly important.
According to one aspect of the present application, there is provided a composition for synthesizing a hydrogel having biological activity.
A composition for synthesizing a polysaccharide-based electrically conductive injectable bioactive hydrogel, characterized in that the composition comprises, by mass:
0.5 to 15 percent of natural polysaccharide derivative
0.5 to 1.5 percent of chitosan derivative
0.05% -2% of reduced graphene oxide-polydopamine nano-sheet.
Alternatively, the derivative of the natural polysaccharide may comprise any value or range of values comprised of any two values in the range of 0.5, 1, 3, 5, 7, 9, 11, 13, 15wt% of the composition.
Optionally, the derivative of chitosan comprises any value or range of values comprising any two values in 0.5, 0.7, 0.9, 1.1, 1.3, 1.5wt% of the composition.
Optionally, the derivative of natural polysaccharide comprises at least one of dextran derivative, xyloglucan derivative, hyaluronic acid derivative and sodium alginate derivative.
Optionally, the chitosan derivative is a methacrylated chitosan;
the deacetylation degree of the chitosan of the methacryloylated chitosan is 75-100%;
preferably, the viscosity of the chitosan is > 400 mPa.S or the viscosity is < 200 mPa.S.
In a second aspect of the present application, there is provided a method of synthesizing a hydrogel using the above composition.
A method of synthesizing a hydrogel using the composition of any one of claims 1-3, the method comprising the steps of:
(1) Obtaining a derivative of natural polysaccharide and a derivative of chitosan;
(2) Obtaining a dispersion liquid of the reduced graphene oxide-polydopamine nanosheets;
(3) Dissolving the chitosan derivative obtained in the step (1) and a catalyst in water, and treating to obtain a prepolymer solution A;
(4) Mixing the natural polysaccharide derivative obtained in the step (1) with the dispersion liquid of the reduced graphene oxide-polydopamine nano-sheets obtained in the step (2) to obtain a pre-polymerization liquid B;
(5) And (3) mixing the prepolymer A obtained in the step (3) with the prepolymer B obtained in the step (4) for reaction to obtain the hydrogel.
Optionally, the preparation method of the reduced graphene oxide-polydopamine nanosheet dispersion liquid in the step (2) comprises the following steps:
(2-1) dissolving dopamine in a buffer solution, and polymerizing to obtain a polydopamine solution;
and (2-2) adding graphene oxide into the polydopamine solution obtained in the step (1), mixing and reacting to obtain the reduced graphene oxide-polydopamine nanosheet dispersion liquid.
Optionally, the mixing of step (2-2) is performed under the following conditions: ice bath ultrasonic treatment is carried out for 60-180min;
the reaction in the step (2-2) is carried out under the conditions that the reaction temperature is 60-70 ℃ and the reaction time is 24-48h.
Optionally, in the step (2-1), the concentration of dopamine in the buffer is any value or a range of values consisting of any two values of 0.02, 0.04, 0.06, 0.08, 0.1 wt%;
the buffer substance is at least one selected from Tris-HCl, phosphate buffer solution and acetate buffer solution.
Optionally, in the step (4), the concentration of the chitosan derivative in the prepolymer liquid a is 1, 1.2, 1.4, 1.6, 1.8, 2, 2.2, 2.4, 2.6, 2.8, 3wt% or a range of values consisting of any number or any two; the concentration of the natural polysaccharide derivative in the prepolymer liquid B is any value or a range of values consisting of any two values in 1, 3, 5, 7, 9, 11, 13, 15, 17, 19, 21, 23, 25, 27, 29 and 30 weight percent;
optionally, in the step (3), the treatment is light-shielding treatment, and the catalyst is a photoinitiator;
the photoinitiator is at least one selected from 405nm blue light initiation, phenyl-2, 4, 6-trimethyl benzoyl lithium phosphonate (LAP), 365nm external light initiation, 2-hydroxy-2-methyl-1-phenyl acetone (1173), 2-hydroxy-2-methyl-1- [4- (2-hydroxy ethoxy) phenyl ] -1-acetone (2959), 2' -azo bis [ 2-methyl-N- (2-hydroxyethyl) propionamide ] (VA-086).
In a third aspect the application provides an injectable wound filler.
An injectable wound filler, the injectable wound filler being a hydrogel obtained by the method described above.
Aiming at the defect of single function of the current injectable hydrogel wound dressing, the application provides a polysaccharide-based conductive injectable bioactive hydrogel wound dressing and a preparation method thereof. The application takes natural polysaccharide as a material basis, carries out aldehyde modification on the natural polysaccharide through oxidization, and carries out double bond modification on chitosan through amidation reaction. The aldehyde group and the amino group can react rapidly to form a dynamic amide bond, a dynamic covalent network is constructed, the gel is in a weak crosslinking state at the moment, gel-sol conversion can be generated under the action of shearing force, and the gel-sol conversion injection has good injectability. And the gel state can be recovered after the shearing force is removed, so that the wound of the irregular geometric shape and deep anatomical part can be completely sealed in a minimally invasive injection mode, and the wound is fully fused with surrounding tissues. In addition, double bond polymerization is initiated under illumination, so that the regulation and control of the modulus of the injectable hydrogel are further realized, and the application of different wound positions can be satisfied. Due to the existence of bioelectricity of human tissues, the external electric signals can stimulate cell regeneration and reconstruction in the wound healing process, graphene is oxidized by a chemical method to obtain Graphene Oxide (GO) with hydrophilic groups such as hydroxyl, epoxy, carboxyl and the like, and the dispersibility of the carbon material in water is improved. In order to ensure the conductivity, the graphene oxide is reduced by the dopamine to obtain a series of reduced graphene oxide (rGO), and a hydrophilic polydopamine coating is generated on the surface so as to enhance the water dispersibility of the polydopamine. Thus preparing the bioactive carbon-based material with good conductivity, tissue adhesion and photo-thermal antibacterial performance. Further, the dopamine reduction graphene oxide is dispersed in the polysaccharide pre-polymerization liquid, and the high-viscosity polysaccharide solution is favorable for uniform dispersion of rGO. Thus obtaining the multifunctional polysaccharide-based conductive injectable bioactive hydrogel wound dressing.
The application has the beneficial effects that:
1) The hydrogel provided by the application can be directly delivered to a target site, is beneficial to filling irregular shapes and deep wounds, has easily-adjustable modulus, and can be matched with the requirements of different tissue defects;
2) The hydrogel provided by the application has conductive performance, and the external electrical signal can stimulate cell regeneration in the wound healing process, so that tissue reconstruction is promoted;
3) The hydrogel provided by the application has strong dispersibility in water and strong tissue adhesiveness; the raw materials are completely based on natural polysaccharide, the natural content is rich, and the industrialization is easy;
4) The hydrogel provided by the application has excellent biocompatibility, can remarkably promote skin wound healing, and has wide application prospects in the field of biology;
5) The hydrogel provided by the application has adjustable elastic modulus and good self-repairing performance, can be suitable for biological 3D printing technology, and can be applied to tissue engineering.
Drawings
Fig. 1 is a schematic structural diagram of dopamine-reduced graphene oxide in embodiment 1 of the present application.
FIG. 2 is a schematic diagram of the structures of methacryloylated chitosan and oxidized dextran in example 1 of the present application.
Fig. 3 is a graph of a sample of a material rheology test of example 1 of the present application (a) time sweep (b) frequency sweep (c) strain sweep (d) alternating strain sweep.
FIG. 4 is a graph showing the adhesion performance test sample of the material of example 1 of the present application to pigskin.
FIG. 5 is a graph showing a sample of a cytotoxicity test of CCK-8 in example 1 of the present application, NIH/3T3 cells were cultured by a leaching solution method for 24 hours, 48 hours, and sampled
FIG. 6 is a chart showing the sample of the material of example 1 of the present application, which was cultured for 24 hours by NIH/3T3 cells, stained with Calcein/PI kit, and observed by fluorescence confocal.
Fig. 7 is a sample graph of the hydrogel prepared in example 1 of the present application as a wound dressing to promote regeneration and repair of the whole skin of mice.
Detailed Description
The present application is described in detail below with reference to examples, but the present application is not limited to these examples.
Unless otherwise specified, the starting materials and catalysts in the examples of the present application were all purchased commercially, with dextran, xyloglucan, hyaluronic acid, sodium alginate, chitosan (viscosity > 400mpa·s), chitosan (viscosity < 200mpa·s), chitosan (degree of deacetylation=75%), chitosan (degree of deacetylation=95%), sodium periodate, dopamine hydrochloride, graphene oxide, tris-HCl buffer, phosphoric acid buffer (ph=8.5), acetic acid buffer (ph=8.5) methacrylic anhydride, glacial acetic acid, sodium bicarbonate, ethylene glycol, phenyl-2, 4, 6-trimethylbenzoyl lithium phosphonate (LAP), 2-hydroxy-2-methyl-1-phenylpropion (1173), 2-hydroxy-2-methyl-1- [4- (2-hydroxyethoxy) phenyl ] -1-propanone (2959), 2' -azobis [ 2-methyl-N- (2-hydroxyethyl) propionamide ] (VA-086) available from ala Ding Yaopin limited. CCK-8 kit and live and dead staining kit were purchased from Biyun Tian Biotechnology Co.
The analysis method in the embodiment of the application is as follows:
in embodiments of the present application, the rheological properties of the materials were analyzed by using a rheometer (TA Instruments, DHR-3, USA), including specifically time-sweep, frequency-sweep, strain-sweep, alternating strain-sweep. The analysis conditions were: at 37 ℃, a 60mm flat plate is selected for testing, the time scanning condition is that the strain is 1%, the frequency is 10rad/s, and the time is 180s; the condition of frequency scanning is that the strain is 1%, and the frequency is 0.1-100 rad/s; the condition of amplitude scanning is that the frequency is 10rad/s, the strain is 1-1000%, the condition of alternate strain scanning is that the frequency is 10rad/s, the strain is 1% -500% and four cycles are alternate, and each cycle is 120s.
In the embodiment of the application, the resistivity of five points in the hydrogel sample is tested at room temperature by using a four-probe resistance meter (Cresbox, suzhou Laser Company, china), the conductivity of the corresponding test point is converted by taking the reciprocal of the resistivity, and the conductivity result of the final hydrogel is averaged.
In the embodiment of the application, the adhesion performance of the gel and the pigskin is detected by a lap shear test method, and the gel and the pigskin are tested by the lap shear test method, wherein a testing instrument is a universal material tester (Instron 5567, U.S.) and the testing condition is that the uniaxial stretching speed is 100mm/min.
In the embodiment of the application, in-vitro cytotoxicity detection is carried out by CCK-8 kit and live-dead staining experiment, and the material is verified to have good biocompatibility.
In the embodiment of the application, the polysaccharide-based conductive injectable hydrogel wound dressing has the effect of promoting wound regeneration and repair by constructing a full-layer skin wound model of a mouse.
In one embodiment of the application:
(1) Preparation of natural polysaccharide derivatives:
the natural polysaccharide is dissolved in deionized water, sodium periodate is added, the reaction is carried out for 4 hours in a dark place, and the reaction is stopped by introducing glycol. And (3) putting the reaction solution into a 3500D dialysis bag for dialysis for 3-5 days, removing impurities, and freeze-drying to obtain the natural polysaccharide derivative.
(2) Preparation of methacryloylated chitosan:
firstly, uniformly dispersing chitosan in water, adding glacial acetic acid, and stirring until the chitosan is completely dissolved. Methacrylic anhydride was slowly added to the reaction solution, reacted, and 10% NaHCO was used 3 The pH of the reaction solution was adjusted to about 6.5, and the whole process was slowly performed. And dialyzing the crude product for 5-7 days, and freeze-drying to obtain the methacrylated chitosan.
(3) Preparation of reduced graphene oxide:
dispersing Dopamine (DA) in a buffer solution, polymerizing to form Polydopamine (PDA) solution, adding GO, performing ice bath ultrasound for 60-180min, and stirring at 60-70 ℃ for 24-48h to obtain PDA-rGO nano-sheet dispersion.
(4) Preparation of a prepolymerization solution A, B:
sterilizing the material, dissolving the methacryloylated chitosan in deionized water completely, dissolving a photoinitiator in the solution, and performing light-shielding treatment (obtaining a prepolymer A); and (3) dissolving the natural polysaccharide derivative in the PDA-rGO nano-sheet dispersion liquid (marked as B solution) in a certain proportion to obtain two uniform A, B prepolymer liquids.
(5) Preparation of multifunctional polysaccharide-based conductive injectable hydrogels:
mixing the two pre-polymerization solutions A and B according to the volume ratio of 1:1, quickly reacting amino and aldehyde groups to form Schiff base bonds, injecting gel at a target position, and then initiating double bond polymerization on chitosan in situ by utilizing illumination to form a covalent network, so as to obtain the multifunctional polysaccharide-based conductive injectable hydrogel.
Example 1
Step 1: and (3) carrying out oxidative modification on natural polysaccharide, dissolving glucan in deionized water, adding a certain proportion of sodium periodate, carrying out light-shielding reaction for 4 hours, and adding glycol to terminate the reaction. And (3) putting the reaction solution into a 3500D dialysis bag for dialysis for 3-5 days to remove impurities, and freeze-drying to obtain the aldehyde group modified glucan.
The contents of the substances are as follows:
dextran 5.0wt%
Sodium periodate 0.5wt%
Ethylene glycol 1.0ml
200ml of deionized water
Step 2: the double bond modification of chitosan, firstly, uniformly dispersing chitosan (deacetylation degree 95%) in water, adding glacial acetic acid, and stirring until the chitosan is completely dissolved. Slowly adding methacrylic anhydride into the reaction solution, reacting for 24-48h at 60 ℃ and utilizing 10% NaHCO 3 The solution was adjusted to a pH of about 6.5 and the entire process was carried out slowly to avoid substantial foam formation. The crude product is dialyzed for 5 to 7 days and then freeze-dried to obtain the methacrylated Chitosan (CHMA).
The contents of the substances are as follows:
1.0wt% chitosan (degree of deacetylation 95%)
Glacial acetic acid 4.0ml
Methacrylic anhydride 1.0ml
300ml of deionized water
Step 3: reduced graphene oxide (rGO): dispersing Dopamine (DA) in Tris-HCl buffer solution, polymerizing DA to form PDA solution, adding GO, ice-bath ultrasound for 60-180min, and stirring at 60-70 ℃ for 24-48h to obtain PDA-rGO nano-sheet dispersion.
The contents of the substances are as follows:
dopamine 0.08wt%
Graphene oxide 0.2wt%
Tris-HCl 10mmol/L
Deionized water 10ml
Step 4: after sterilizing the material, CHMA was completely dissolved in deionized water, LAP photoinitiator was dissolved in CHMA aqueous solution and subjected to light-shielding treatment (designated as solution a). The formylated glucan is dissolved in the PDA-rGO nano-sheet dispersion liquid (marked as B solution) in the step 3 according to a certain proportion, so that two uniform A and B prepolymerization liquids are obtained.
The contents of the substances are as follows:
methacrylated Chitosan (degree of deacetylation 95%) CHMA1.0wt%
LAP photoinitiator 0.2wt%
15wt% of aldehyde dextran
Deionized water 10ml
PDA-rGO nano-sheet dispersion liquid 10ml
Step 5: mixing the two pre-polymerization solutions A and B according to the volume ratio of 1:1, quickly reacting amino and aldehyde groups to form Schiff base bonds, injecting gel at a target position, and then initiating double bond polymerization on chitosan in situ under the irradiation of 405nm blue light to form a covalent network, thereby obtaining the multifunctional polysaccharide-based conductive injectable hydrogel.
The results of the rheological property analysis, the in vitro cytotoxicity test, the electrical property and adhesion property test, and the wound regeneration and repair effect test of the multifunctional polysaccharide-based conductive injectable hydrogel obtained in example 1 are shown in table 1.
TABLE 1
The procedure used in examples 2-20 was the same as in example 1, but with the reactants and reaction conditions used being shown in Table 2, in Table 3, in Table 4, in Table 5; the results of the rheological property analysis, the in vitro cytotoxicity test, the electrical property and adhesion property test, and the wound regeneration and repair effect test of the multifunctional polysaccharide-based conductive injectable hydrogels obtained in examples 2 to 20 are shown in Table 6. TABLE 2
TABLE 3 Table 3
TABLE 4 Table 4
TABLE 5
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TABLE 6
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While the application has been described in terms of preferred embodiments, it will be understood by those skilled in the art that various changes and modifications can be made without departing from the scope of the application, and it is intended that the application is not limited to the specific embodiments disclosed.
Claims (10)
1. A composition for synthesizing a polysaccharide-based electrically conductive injectable bioactive hydrogel, characterized in that the composition comprises, by mass:
0.5 to 15 percent of natural polysaccharide derivative
0.5 to 1.5 percent of chitosan derivative
0.05% -2% of reduced graphene oxide-polydopamine nano-sheet.
2. The composition for synthesizing a polysaccharide-based conductive injectable bioactive hydrogel of claim 1, wherein the derivative of natural polysaccharide comprises at least one of a derivative of dextran, a derivative of xyloglucan, a derivative of hyaluronic acid, a derivative of sodium alginate.
3. The composition for synthesizing a polysaccharide-based conductive injectable bioactive hydrogel of claim 1, wherein the chitosan derivative is a methacrylated chitosan;
the deacetylation degree of the chitosan ranges from 75% to 100%;
preferably, the methacrylated chitosan is at least one selected from the group consisting of viscosity > 400 mPa.S and viscosity < 200 mPa.S.
4. A method of synthesizing a hydrogel using the composition of any one of claims 1-3, the method comprising the steps of:
(1) Obtaining a dispersion liquid of the reduced graphene oxide-polydopamine nanosheets;
(2) Dissolving a chitosan derivative and a catalyst in water, and treating to obtain a prepolymer solution A;
(3) Mixing a natural polysaccharide derivative with the reduced graphene oxide-polydopamine nanosheet dispersion liquid obtained in the step (1) to obtain a prepolymer liquid B;
(4) And (3) mixing the prepolymer A obtained in the step (2) with the prepolymer B obtained in the step (3) and reacting to obtain the hydrogel.
5. The method according to claim 4, wherein the preparation method of the reduced graphene oxide-polydopamine nanoplatelet dispersion in the step (1) comprises the following steps:
dissolving dopamine in a buffer solution, and polymerizing to obtain a polydopamine solution;
(1-2) adding graphene oxide into the polydopamine solution obtained in the step (1-1), mixing, and reacting to obtain the reduced graphene oxide-polydopamine nanosheet dispersion liquid.
6. The method of claim 5, wherein the mixing of step (2-2) is performed under conditions of: ice bath ultrasonic treatment is carried out for 60-180min;
the reaction in the step (2-2) is carried out under the conditions that the reaction temperature is 60-70 ℃ and the reaction time is 24-48h.
7. The method according to claim 5, wherein in the step (2-1), the concentration of dopamine in the buffer is 0.02-1wt%;
the buffer substance is at least one selected from Tris-HCl, phosphate buffer solution and acetate buffer solution.
8. The method according to claim 4, wherein in the step (4), the concentration of the chitosan derivative in the prepolymer liquid A is 1 to 3wt%;
in the prepolymer solution B, the concentration of the natural polysaccharide derivative is 1-30wt%.
9. The method according to claim 4, wherein in the step (3), the treatment is a light shielding treatment, and the catalyst is a photoinitiator;
preferably, the photoinitiator is selected from at least one of phenyl-2, 4, 6-trimethylbenzoyl lithium phosphonate, 2-hydroxy-2-methyl-1-phenylpropionic acid, 2-hydroxy-2-methyl-1- [4- (2-hydroxyethoxy) phenyl ] -1-propanone, 2' -azobis [ 2-methyl-N- (2-hydroxyethyl) propionamide ].
10. An injectable wound filler, characterized in that it comprises a hydrogel obtained by the method according to any one of claims 4-9.
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