CN116747342A - Anti-inflammatory and easy-to-replace adhesive hydrogel adhesive bandage and preparation method thereof - Google Patents
Anti-inflammatory and easy-to-replace adhesive hydrogel adhesive bandage and preparation method thereof Download PDFInfo
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- CN116747342A CN116747342A CN202310682005.6A CN202310682005A CN116747342A CN 116747342 A CN116747342 A CN 116747342A CN 202310682005 A CN202310682005 A CN 202310682005A CN 116747342 A CN116747342 A CN 116747342A
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- 239000000017 hydrogel Substances 0.000 title claims abstract description 125
- 230000001070 adhesive effect Effects 0.000 title claims abstract description 64
- 239000000853 adhesive Substances 0.000 title claims abstract description 59
- 230000003110 anti-inflammatory effect Effects 0.000 title claims abstract description 30
- 238000002360 preparation method Methods 0.000 title claims abstract description 19
- 229960002663 thioctic acid Drugs 0.000 claims abstract description 34
- AGBQKNBQESQNJD-UHFFFAOYSA-M lipoate Chemical compound [O-]C(=O)CCCCC1CCSS1 AGBQKNBQESQNJD-UHFFFAOYSA-M 0.000 claims abstract description 17
- 235000019136 lipoic acid Nutrition 0.000 claims abstract description 17
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- 230000035876 healing Effects 0.000 claims abstract description 5
- 239000000243 solution Substances 0.000 claims description 52
- 208000027418 Wounds and injury Diseases 0.000 claims description 47
- 206010052428 Wound Diseases 0.000 claims description 46
- 238000006243 chemical reaction Methods 0.000 claims description 20
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 14
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 13
- 238000010438 heat treatment Methods 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 12
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 claims description 11
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 claims description 10
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 claims description 10
- 239000002243 precursor Substances 0.000 claims description 10
- OSSNTDFYBPYIEC-UHFFFAOYSA-N 1-ethenylimidazole Chemical compound C=CN1C=CN=C1 OSSNTDFYBPYIEC-UHFFFAOYSA-N 0.000 claims description 9
- 238000003756 stirring Methods 0.000 claims description 8
- -1 lipoyl imidazole Chemical compound 0.000 claims description 7
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 claims description 6
- KIUKXJAPPMFGSW-DNGZLQJQSA-N (2S,3S,4S,5R,6R)-6-[(2S,3R,4R,5S,6R)-3-Acetamido-2-[(2S,3S,4R,5R,6R)-6-[(2R,3R,4R,5S,6R)-3-acetamido-2,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-2-carboxy-4,5-dihydroxyoxan-3-yl]oxy-5-hydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-3,4,5-trihydroxyoxane-2-carboxylic acid Chemical compound CC(=O)N[C@H]1[C@H](O)O[C@H](CO)[C@@H](O)[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@H](O[C@H]2[C@@H]([C@@H](O[C@H]3[C@@H]([C@@H](O)[C@H](O)[C@H](O3)C(O)=O)O)[C@H](O)[C@@H](CO)O2)NC(C)=O)[C@@H](C(O)=O)O1 KIUKXJAPPMFGSW-DNGZLQJQSA-N 0.000 claims description 5
- 239000007864 aqueous solution Substances 0.000 claims description 5
- 229920002674 hyaluronan Polymers 0.000 claims description 5
- 229960003160 hyaluronic acid Drugs 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 206010072170 Skin wound Diseases 0.000 claims description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 3
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- 229910000402 monopotassium phosphate Inorganic materials 0.000 claims description 3
- 235000019796 monopotassium phosphate Nutrition 0.000 claims description 3
- 238000006386 neutralization reaction Methods 0.000 claims description 3
- 239000011505 plaster Substances 0.000 claims description 3
- 239000002904 solvent Substances 0.000 claims description 3
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- 238000004090 dissolution Methods 0.000 claims description 2
- PJNZPQUBCPKICU-UHFFFAOYSA-N phosphoric acid;potassium Chemical compound [K].OP(O)(O)=O PJNZPQUBCPKICU-UHFFFAOYSA-N 0.000 claims description 2
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- 230000002262 irrigation Effects 0.000 claims 1
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- 239000000463 material Substances 0.000 abstract description 3
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- WZUVPPKBWHMQCE-UHFFFAOYSA-N Haematoxylin Chemical compound C12=CC(O)=C(O)C=C2CC2(O)C1C1=CC=C(O)C(O)=C1OC2 WZUVPPKBWHMQCE-UHFFFAOYSA-N 0.000 description 2
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- YQGOJNYOYNNSMM-UHFFFAOYSA-N eosin Chemical compound [Na+].OC(=O)C1=CC=CC=C1C1=C2C=C(Br)C(=O)C(Br)=C2OC2=C(Br)C(O)=C(Br)C=C21 YQGOJNYOYNNSMM-UHFFFAOYSA-N 0.000 description 1
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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
- A61L15/00—Chemical aspects of, or use of materials for, bandages, dressings or absorbent pads
- A61L15/16—Bandages, dressings or absorbent pads for physiological fluids such as urine or blood, e.g. sanitary towels, tampons
- A61L15/22—Bandages, dressings or absorbent pads for physiological fluids such as urine or blood, e.g. sanitary towels, tampons containing macromolecular materials
- A61L15/28—Polysaccharides or their derivatives
-
- 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
- A61L15/00—Chemical aspects of, or use of materials for, bandages, dressings or absorbent pads
- A61L15/16—Bandages, dressings or absorbent pads for physiological fluids such as urine or blood, e.g. sanitary towels, tampons
- A61L15/20—Bandages, dressings or absorbent pads for physiological fluids such as urine or blood, e.g. sanitary towels, tampons containing organic 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
- A61L15/00—Chemical aspects of, or use of materials for, bandages, dressings or absorbent pads
- A61L15/16—Bandages, dressings or absorbent pads for physiological fluids such as urine or blood, e.g. sanitary towels, tampons
- A61L15/42—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
- A61L15/00—Chemical aspects of, or use of materials for, bandages, dressings or absorbent pads
- A61L15/16—Bandages, dressings or absorbent pads for physiological fluids such as urine or blood, e.g. sanitary towels, tampons
- A61L15/42—Use of materials characterised by their function or physical properties
- A61L15/44—Medicaments
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
- C08B37/00—Preparation of polysaccharides not provided for in groups C08B1/00 - C08B35/00; Derivatives thereof
- C08B37/006—Heteroglycans, i.e. polysaccharides having more than one sugar residue in the main chain in either alternating or less regular sequence; Gellans; Succinoglycans; Arabinogalactans; Tragacanth or gum tragacanth or traganth from Astragalus; Gum Karaya from Sterculia urens; Gum Ghatti from Anogeissus latifolia; Derivatives thereof
- C08B37/0063—Glycosaminoglycans or mucopolysaccharides, e.g. keratan sulfate; Derivatives thereof, e.g. fucoidan
- C08B37/0072—Hyaluronic acid, i.e. HA or hyaluronan; Derivatives thereof, e.g. crosslinked hyaluronic acid (hylan) or hyaluronates
-
- 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
- A61L2300/20—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices containing or releasing organic materials
- A61L2300/216—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices containing or releasing organic materials with other specific functional groups, e.g. aldehydes, ketones, phenols, quaternary phosphonium groups
-
- 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
- A61L2300/41—Anti-inflammatory agents, e.g. NSAIDs
-
- 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
- A61L2300/412—Tissue-regenerating or healing or proliferative agents
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- Hematology (AREA)
- Public Health (AREA)
- Epidemiology (AREA)
- Molecular Biology (AREA)
- Biochemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Materials For Medical Uses (AREA)
Abstract
The invention discloses an anti-inflammatory and easily-replaceable adhesive hydrogel adhesive bandage and a preparation method thereof, relates to the field of biomedical materials, and relates to an environment-friendly preparation method of the adhesive hydrogel adhesive bandage based on lipoic acid/hyaluronic acid-g-lipoic acid/cellulose nanocrystals, which has excellent adhesiveness, stretchability and reusability, has anti-inflammatory and wound repair promoting capabilities, can be easily removed through water flushing, has an on-demand removal function, and can be applied to the treatment and healing of emergency wound.
Description
Technical Field
The invention relates to the field of biomedical materials, in particular to an anti-inflammatory and easily-replaceable adhesive hydrogel adhesive bandage and a preparation method thereof.
Background
The wound dressing is a physical barrier for replacing normal skin to effectively resist external microorganism invasion, and is very important in providing good healing microenvironment for wounds, closing wounds, stopping bleeding in time, conforming to wound movement and the like. Traditional wound dressing, including gauze, cotton, sponge etc. can not close the surface of a wound in time effectively, prevent bleeding, and measures such as operation suture line, suturing nail can not be effectively deployed before the hospital. In the ambulation process of a patient, a wound part can frequently move, and the traditional hydrogel wound dressing can not meet the requirement of wound movement due to insufficient tissue adhesiveness and mechanical properties, and is often damaged or shifted, so that wound infection is caused. To address these urgent challenges, the development of a high strength, high adhesion anti-inflammatory wound dressing is critical for pre-hospital emergency.
At present, many strategies have been explored to prepare hydrogels with high adhesion and high strength. However, the preparation process is generally complicated, wherein the post-treatment process involved in the gel preparation process, including the removal of the initiator, the small molecule and the monomer, is unavoidable, and limits the application of the gel preparation process in biomedical engineering. Most importantly, in order to ensure the rapid healing of wounds, dressing needs to be frequently replaced within a certain time, and how to easily remove the high-adhesion hydrogel to avoid secondary injury to the wounds is a difficult problem to be solved by researchers. Therefore, the simple green synthesis of the hydrogel wound dressing with high performance and easy replacement has important significance and practical application value.
Disclosure of Invention
In order to solve the problems in the prior art, the invention aims to overcome the defects in the prior art and provide an anti-inflammatory and easily-replaced adhesive hydrogel adhesive bandage and a preparation method thereof.
The invention provides an anti-inflammatory and easily-replaceable adhesive hydrogel adhesive bandage, which has the following specific technical scheme:
an anti-inflammatory and easily replaceable adhesive hydrogel wound dressing, comprising the following components: hyaluronic acid-g-lipoic acid, cellulose nanocrystals, lipoic acid, tris (hydroxymethyl) aminomethane and 1-vinylimidazole.
The invention also provides a preparation method of the anti-inflammatory and easily-replaceable adhesive hydrogel adhesive bandage, which comprises the following steps of:
the preparation method of the anti-inflammatory and easy-to-replace adhesive hydrogel adhesive bandage comprises the following steps:
sequentially dissolving hyaluronic acid-G-lipoic acid, cellulose nanocrystalline and lipoic acid in an aqueous solution of tris (hydroxymethyl) aminomethane, performing a first heating reaction after the hyaluronic acid-G-lipoic acid, cellulose nanocrystalline and lipoic acid are fully and uniformly dissolved to obtain a precursor solution, dropwise adding 1-vinylimidazole into the precursor solution, uniformly mixing, performing a second heating reaction, and preparing G HC A hydrogel wound plaster.
Preferably, the preparation process of the hyaluronic acid-g-lipoic acid comprises the following steps:
dissolving hyaluronic acid in formamide, stirring at 95 ℃ until the hyaluronic acid is completely dissolved, continuing to cool to room temperature to obtain a second solution, and adding 4-dimethylaminopyridine into the second solution as a catalyst to obtain a third solution;
adding a lipoyl imidazole solution into the third solution, stirring at room temperature for reaction for 4 hours, and then adding a potassium dihydrogen phosphate solution for neutralization to obtain a fourth solution;
and (3) dialyzing and purifying the fourth solution to remove the solvent and impurities generated by the reaction, and then freeze-drying the fourth solution to collect a sample to obtain the hyaluronic acid-g-lipoic acid.
Further preferably, the preparation process of the lipoyl imidazole solution comprises the following steps:
dissolving lipoic acid in N, N-dimethylformamide at room temperature to prepare a first solution;
and adding N, N' -carbonyl diimidazole into the first solution, and stirring at room temperature to fully activate the carboxyl of the lipoic acid to obtain a lipoyl imidazole solution.
Preferably, the mass ratio of the hyaluronic acid-g-lipoic acid, the cellulose nanocrystalline and the lipoic acid is as follows: 2 (3-7): 40
Preferably, the hyaluronic acid-g-lipoic acid, the cellulose nanocrystals, and the lipoic acid are sequentially dissolved in an aqueous solution formed of tris (hydroxymethyl) aminomethane, and the dissolution is performed sufficiently using a shaker.
Preferably, the parameters of the first heating reaction are: the reaction is carried out for 30min under the heating condition of 70 ℃.
Preferably, the parameters of the second heating reaction are as follows: the reaction was carried out at 70℃for 6h.
The invention provides an application of an anti-inflammatory and easily-replaceable adhesive hydrogel adhesive bandage, which comprises the following specific technical scheme:
an anti-inflammatory and easily replaceable adhesive hydrogel adhesive bandage is applied to the treatment and healing of skin wounds.
Preferably, the anti-inflammatory, easily replaceable adhesive hydrogel wound covering is capable of being detached from the skin by a water rinse.
The fourth object of the present invention is to provide a hydrogel suitable for application in a wound dressing, which has the following structural formula:
wherein the "grey diamond" portion represents cellulose nanocrystals, the "… …" portion represents hydrogen bonds, and the "circular" portion represents 1-vinylimidazole.
Compared with the prior art, the invention has the beneficial effects that:
the invention provides a preparation method of an anti-inflammatory and easily-replaceable adhesive hydrogel adhesive bandage, which comprises the steps of dissolving HALA, CNC, LA and 1-vinyl imidazole in Tris Base solution in sequence, reacting for 6 hours at 70 ℃ to form a high-strength and high-adhesion anti-inflammatory hydrogel adhesive bandage, and applying the high-strength and high-adhesion anti-inflammatory hydrogel adhesive bandage to wound repair.
Drawings
FIG. 1 is a graph showing adhesive properties of hydrogels prepared in examples and comparative examples according to the present invention, wherein FIG. 1 (A) is a graph showing adhesive properties of hydrogels of example 2 to chicken soft tissues, FIG. 1 (B) is a graph showing adhesive properties of hydrogels of example 2 to pig skin surface, FIG. 1 (C) is a graph showing lap shear stress-tensile displacement of hydrogels prepared in examples and comparative examples, and FIG. 1 (D) is a graph showing shear modulus of hydrogels prepared in examples and comparative examples;
FIG. 2 is a cyclic strain diagram of the hydrogel of example 2 according to the present invention;
FIG. 3 is a graph showing burst pressure of hydrogels prepared according to examples and comparative examples of the present invention;
FIG. 4 shows the mechanical properties of hydrogels prepared according to examples and comparative examples of the present invention;
FIG. 5 is a graph showing the compressive stress-strain curves of hydrogels prepared according to examples and comparative examples of the present invention;
FIG. 6 shows the compressive modulus of hydrogels prepared according to examples and comparative examples of the present invention;
FIG. 7 is a graph showing the compression modulus of hydrogels prepared in examples and comparative examples according to the present invention;
FIG. 8 is a graph showing the repeated adhesion property test of the hydrogel of example 2 according to the present invention, wherein FIG. 8 (A) is a photograph of an experiment and FIG. 8 (B) is a graph showing the adhesion strength test data after repeated adhesion of the hydrogel;
FIG. 9 is a macroscopic photograph showing the effect of hydrogel in use and the natural recovery effect of a blank set according to example 2 of the present invention;
FIG. 10 is a photograph showing histological evaluation of the effect of hydrogel application and the natural recovery effect of the blank in example 2 of the present invention, wherein FIGS. 10 (A) and (C) correspond to the seventh and fourteenth days of recovery of the blank, respectively, and FIGS. 10 (B) and 10 (D) correspond to the following conditions, respectivelyBy G HC2 Seventh and fourteenth days of hydrogel recovery.
Detailed Description
The following description of the embodiments of the present invention will be made clearly and completely with reference to the accompanying drawings, in which it is apparent that the embodiments described are only some embodiments of the present invention, but not all embodiments. All other embodiments, which can be made by those skilled in the art based on the embodiments of the invention without making any inventive effort, are intended to be within the scope of the invention.
For ease of understanding, the english nouns mentioned below are first explained:
LA: lipoic acid;
tris Base: tris (hydroxymethyl) aminomethane;
CNC: cellulose nanocrystals;
DMF: n, N-dimethylformamide;
CDI: n, N' -carbonyldiimidazole;
LA-Im: lipoyl imidazole;
HA: hyaluronic acid;
DMAP: 4-dimethylaminopyridine.
HALA: hyaluronic acid-g-lipoic acid
An anti-inflammatory and easily-replaceable adhesive hydrogel adhesive bandage and a preparation method thereof, and the specific implementation mode is as follows:
example 1:
dissolving 0.62g of LA in 3mL of DMF at room temperature to prepare a first solution, adding 0.97g of CDI into the first solution, and stirring at room temperature for 1h to fully activate the carboxyl group of lipoic acid to obtain a LA-Im solution;
1.9g of HA is dissolved in 38mL of formamide, the mixture is stirred for 1h at 95 ℃, after the HA is completely dissolved, the mixture is continuously cooled to room temperature to obtain a second solution, and 0.62g of DMAP (dimethyl benzene) is added into the second solution as a catalyst to obtain a third solution;
adding the LA-Im solution into the third solution, stirring at room temperature for reaction for 4 hours, and then adding the monopotassium phosphate solution for neutralization to obtain a fourth solution;
dialyzing and purifying the fourth solution to remove the solvent and impurities generated by the reaction, then freeze-drying, and collecting a sample to obtain hyaluronic acid-g-lipoic acid, wherein the hyaluronic acid-g-lipoic acid is marked as HALA;
sequentially dissolving 20mg of HALA, 30mg of CNC and 400mg of LA in a Tris Base aqueous solution with the mass concentration of 16.67% +/-0.01%, fully and uniformly dissolving by using an oscillator, standing for 30min under the heating condition of 70 ℃ to obtain a precursor solution, dropwise adding 50 mu L of 1-vinylimidazole into the precursor solution, uniformly mixing, standing for 6h under the condition of 70 ℃ to prepare the G HC The hydrogel adhesive bandage is marked as follows: g HC1 。
Example 2:
substantially the same procedure as in example 1 except that the amount of CNC was changed from 30mg of example 1 to 50mg, G was prepared HC The hydrogel adhesive bandage is marked as follows: g HC2 。
Example 3:
substantially the same procedure as in example 1 was repeated except that the CNC was replaced with 70mg from 30mg in example 1, and a hydrogel wound dressing was prepared, labeled: g HC3 。
Comparative example 1:
sequentially dissolving 50mg of CNC and 400mg of LA in 200mL of Tris Base solution, fully and uniformly dissolving by using an oscillator, standing for reaction for 30min at 70 ℃ under heating, dropwise adding 50 mu L of 1-vinylimidazole into the solution, uniformly mixing, and standing for reaction for 6h at 70 ℃ to prepare the G HC The hydrogel adhesive bandage is marked as follows: g C 。
Comparative example 2:
substantially the same procedure as in example 1, except that the CNC was replaced with 0 from 30mg of example 1, a hydrogel wound dressing was prepared, labeled: g H 。
The structural formulas of the hydrogels prepared in examples 1 to 3 above are expressed as follows:
in the structural formula, a cross-linking agent HALA is introduced to cross-link with the polythiol and hydrogen bond, so that the cross-linking agent HALA has the forming capability, and CNC is introduced to form a plurality of binding sites with LA to generate strong hydrogen bond action.
Property testing of various hydrogel wound dressings prepared in the above examples and comparative examples was described as follows:
1. adhesive Strength test
In order to demonstrate that the prepared hydrogels are suitable for use on biological surfaces and have stable adhesive effects, several macroscopic experiments were performed, as shown in FIG. 1, G HC2 The hydrogel can adhere to the soft tissue of chicken (liver, kidney, heart, intestine, and pig skin in FIG. 1 (A)), and, as shown in FIG. 1 (B), when G HC2 When the hydrogel is adhered to the surface of the pigskin, the pigskin is greatly twisted, G HC2 The hydrogel still firmly adheres to the surface of the pigskin, so that the hydrogel has excellent adhesive capacity, can be directly adhered to the surface of a wound when being used for an adhesive bandage, is still stable in connection in a dynamic process, does not need to be covered on the wound part to fix the dressing like a traditional hydrogel dressing, and avoids the wound infection.
Lap shear tests were performed on examples 1 to 3 and comparative examples 1 and 2 using a universal tester, and shear modulus was further calculated as shown in fig. 1 (C) and 1 (D), G C 、G H 、G HC1 、G HC2 G HC3 The adhesive strength of the five hydrogel wound plaster samples reached 26.94kPa, 29.51kPa, 24.41kPa, 28.57kPa and 20.7kPa, respectively, and the shear moduli were 112.65 + -5.26 kPa, 105.23 + -7.67 kPa, 106.58 + -4.33 kPa, 114.39 + -9.38 kPa and 107.03 + -7.61 kPa, respectively, indicating that the prepared hydrogels all had excellent adhesive properties.
2. Self-healing Performance test
2.1 alternating Strain test
For G HC2 The hydrogel is subjected to low (1%) -high (500%) cyclic shear strain treatment, and as shown in fig. 2, under the low strain condition, the storage modulus of the system is larger than the loss modulus, and the system has good elasticity; and as the strain becomes 500%, the gel system breaks, the loss modulus is greater than the storage modulus, and the system shows obvious viscous behavior; when the initial strain value is recovered, the system is quickly recovered to the original state, and the storage modulus is not obviously reduced. This indicates that the adhesive hydrogels prepared based on lipoic acid have excellent self-healing properties.
2.2 burst pressure test
In order to study the ability of the hydrogel to withstand the impact of blood pressure and evaluate the sealing performance of the hydrogel on the skin, the test conditions of the hydrogel on the skin wound are simulated, and a layer of 0.05g/cm concentration is uniformly smeared around the notch of the rubber tube 3 After waiting for natural air drying, the prepared hydrogel is tightly attached to the notch and horizontally placed for 5min, and then the injector is slowly pushed to perform bursting pressure test. The hydrogel swells like a balloon, demonstrating the excellent properties of energy dissipation of the hydrogel. The peak pressure of the hydrogel before the pressure loss is taken as the burst pressure, as shown in FIG. 3, G C 、G H 、G HC1 、G HC2 G HC3 The maximum burst pressures to which the five hydrogel samples were subjected for the first time were 27.67.+ -. 1.53kPa, 21.67.+ -. 2.08kPa, 36.+ -. 2kPa, 35.83.+ -. 1.26kPa, and 47.+ -. 1kPa, respectively. These results indicate that the prepared hydrogel samples all have excellent adhesive strength. Five hydrogel samples were tested for secondary burst pressure due to their excellent adhesion and self-healing properties. After the first hydrogel breakage, the test device was placed horizontally for 10min to allow the hydrogel to reform the cross-linked network through the dynamic bonds, followed by a second burst test. Test results show that, compared with the result of the first explosion, G C 、G H 、G HC1 、G HC2 G HC3 The burst pressure values born by the five hydrogels are reduced by 23.33+ -1.53 kPa, 19.67+ -2.08 kPa, 29.67+ -1.53 kPa, 33.17+ -1.76 kPa and 42.67+ -1.53 kPa, respectively, and the results show that the hydrogelsThe adhesive can bear certain impact strength after self-healing, and can be used as an excellent sealing hemostatic patch.
3. Mechanical property test
3.1 frequency sweep vs. corresponding storage modulus, loss modulus
Adopting a rotary rheometer to perform G C 、G H 、G HC1 、G HC2 G HC3 Five hydrogel samples were tested for mechanical properties. As shown in fig. 4, the storage modulus (G') of the hydrogel was larger than the loss modulus (G ") when the oscillation frequency range of the hydrogel was observed at an oscillation frequency range of 0.1Hz to 100Hz under a strain of 1%. The results showed that the storage modulus was greater than the loss modulus, indicating that the five hydrogel samples were all elastic hydrogels. At the same time, find: g HC1 、G HC2 G HC3 Storage modulus of three hydrogels compared to G C 、G H There was a significant increase in storage modulus of the hydrogels with CNC addition at 1 Hz.
3.2 compression set test
Pair G using thermomechanical dynamic analyzer C 、G H 、G HC1 、G HC2 G HC3 Five hydrogel samples were tested for compression performance. As shown in FIG. 5, five samples were subjected to compressive stress of up to 450KPa, G C 、G H 、G HC1 、G HC2 G HC3 The deformation amounts of the hydrogels were 82.37%, 83.93%, 78.82%, 81.19% and 80.08%, respectively, and the hydrogels showed extremely strong toughness without breaking. FIG. 6 is G C 、G H 、G HC1 、G HC2 G HC3 The compressive modulus of (C) was calculated from the stress and strain ratios at 5% and 10% strain, and was 16.3.+ -. 0.85KPa, 11.43.+ -. 0.82KPa, 30.04.+ -. 0.93KPa, 29.96.+ -. 0.81KPa, and 29.24.+ -. 0.57KPa, respectively. G HC1 、G HC2 G HC3 Compression modulus of hydrogels compared to G C 、G H Are all significantly elevated.
3.3 tensile Property test
The universal testing machine pair G is adopted C 、G H 、G HC1 、G HC2 G HC3 Five hydrogel samples were subjected to cyclic tensile testing. As shown in FIG. 7, G C 、G H 、G HC1 、G HC2 G HC3 Stress-strain curves for cyclic stretching of hydrogels, showing that when the hydrogel is loaded to 200% strain, then immediately the external force is removed, a clear loop is observed in the cyclic stretching curves for all samples, but 50% strain fatigue is generated; the hysteresis energy of the five hydrogels was calculated using the loop area of the curve as: 57.15+ -4.17 kPa, 48.57+ -3.79 kPa, 45.38+ -2.76 kPa, 49.83+ -2.05 kPa, 67.06+ -2.73 kPa). This indicates that hydrogels can effectively dissipate energy under large deformation, exhibiting excellent toughness.
4. On demand debonding test
Will G HC1 、G HC2 G HC3 The three hydrogel samples are respectively adhered to the substrate, and the separation of the hydrogel and the substrate can be easily realized by hands by flushing the adhesive interface between the hydrogel and the substrate with water.
5. Repeated adhesion Performance test
G HC2 The hydrogel is adhered to a 100g weight, one end of the hydrogel is pinched and pulled upwards until the weight leaves the table top, then the hydrogel is washed by water to remove the viscosity, then the hydrogel is wiped dry, the hydrogel is placed for 10 minutes, then the hydrogel is adhered to the 100g weight again, and repeated tests are carried out again. As shown in FIG. 8 (A), in the first adhesion, G HC3 Hydrogels may be lightly loaded with a weight of 100 g; on the second adhesion, G HC3 The hydrogel can still bear a weight of 100g, but the adhesive force is reduced; lowering; in the third adhesion, the load is almost no longer 100g, and slippage occurs at the bonding interface; the fourth reattachment still allows a weight of 50g to be easily carried. The adhesive strength of the hydrogel at the time of repeated adhesion was tested by a universal tester, and as shown in fig. 8 (B), the repeated adhesive performance of the hydrogel was lowered with the increase of the number of adhesion, but the adhesive strength was still maintained to be large.
6. PH test
Pair G by pH meter C 、G H 、G HC1 、G HC2 G HC3 The precursor solutions in the preparation process of the five hydrogels and the soaking solutions obtained after the preparation process are soaked in 10mL of water for 5min respectively are subjected to pH test to analyze the safety of the hydrogels applied to wound dressings, and as shown in the table 1, the precursor solutions show weak alkalinity, but the test results of the soaked solutions after gel formation show that the pH value is close to neutral. The prepared hydrogel is not limited in application due to discomfort of acid and alkali, is prepared under green safety conditions, and can be applied as a wound dressing in the biological safety range. Meanwhile, LA is a small-molecule drug commonly used for treating diabetes clinically, has anti-inflammatory and antioxidant functions, so that LA is used as a monomer, and after polymerization, post-treatment such as dialysis is not needed, so that the LA has excellent biocompatibility.
Table 1 soaking solutions of five different hydrogel samples and pH values of their respective precursor solutions
Sample of | Precursor solution | Soaking solution of hydrogel |
G C | 8.5 | 7.4 |
G H | 8.2 | 7.2 |
G HC1 | 7.8 | 6.9 |
G HC2 | 7.8 | 6.9 |
G HC3 | 7.8 | 6.9 |
7. Rat wound repair
SD rat cut wound natural recovery (blank group) and G HC2 Hydrogel usage effect as shown in fig. 9, GHC2 hydrogel usage effect was significantly higher than untreated blank group, G at fourteen days HC2 The wound surface used by the hydrogel is completely closed, the repair is completed, and a blank group which is recovered naturally is arranged at the wound surface, and obvious incisions and scabs are arranged at the wound surface, which indicates G HC2 The hydrogel has good effect of promoting wound healing.
Further, to understand the effect of wound healing, the SD rat cut wound was naturally recovered and G was used HC2 Histological evaluation of skin tissue samples recovered from hydrogel, hematoxylin and eosin (H) was performed on incised skin tissue samples collected on the seventh and fourteenth days, respectively&E) Staining and then microscopic observation, as shown in fig. 10, at day seven, there was some defect in wound epidermis of blank group and dermis layer tissue structure was loose, in contrast to using G HC2 The epidermis of the sample is continuously adhered and the matrix deposition is dense; and G is used on fourteen days HC2 The epidermis of the sample is compact, the dermal tissue is perfect, the wound is obviously contracted, the growth of the skin appendages can be clearly observed, the blank group can still observe obvious skin defects, and the G is shown HC2 Hydrogel materials have a positive effect on promoting wound healing.
In conclusion, the hydrogel adhesive bandage prepared by the method provided by the invention has excellent tissue adhesiveness and higher mechanical properties, can be directly applied as the adhesive bandage, can be used for timely attaching the skins on two sides of a wound together, and can also serve as a temporary barrier for the skins to prevent microorganism invasion, so that wound healing is promoted.
Although embodiments of the present invention have been shown and described, it will be understood by those skilled in the art that various changes, modifications, substitutions and alterations can be made hereto without departing from the spirit and scope of the invention as defined by the appended embodiments and equivalents thereof.
Claims (10)
1. An anti-inflammatory, easily replaceable adhesive hydrogel wound dressing, comprising the following components: hyaluronic acid-g-lipoic acid, cellulose nanocrystals, lipoic acid, tris (hydroxymethyl) aminomethane and 1-vinylimidazole.
2. A process for preparing the adhesive hydrogel adhesive bandage with anti-inflammatory and easy replacement features that hyaluronic acid-G-lipoic acid, cellulose nano crystal and lipoic acid are sequentially dissolved in the aqueous solution of tris (hydroxymethyl) aminomethane, and after being fully dissolved uniformly, the first heating reaction is carried out to obtain the precursor solution, then 1-vinyl imidazole is dropped into the precursor solution, and the mixture is uniformly mixed, and the second heating reaction is carried out to obtain G HC A hydrogel wound plaster.
3. The method for preparing the anti-inflammatory and easily replaceable adhesive hydrogel wound dressing according to claim 2, wherein the preparation process of the hyaluronic acid-g-lipoic acid is as follows:
dissolving hyaluronic acid in formamide, stirring at 95 ℃ until the hyaluronic acid is completely dissolved, continuing to cool to room temperature to obtain a second solution, and adding 4-dimethylaminopyridine into the second solution as a catalyst to obtain a third solution;
adding a lipoyl imidazole solution into the third solution, stirring at room temperature for reaction for 4 hours, and then adding a potassium dihydrogen phosphate solution for neutralization to obtain a fourth solution;
and (3) dialyzing and purifying the fourth solution to remove the solvent and impurities generated by the reaction, and then freeze-drying the fourth solution to collect a sample to obtain the hyaluronic acid-g-lipoic acid.
4. The method for preparing an anti-inflammatory and easily replaceable adhesive hydrogel wound dressing according to claim 3, wherein the preparation process of the lipoyl imidazole solution is as follows:
dissolving lipoic acid in N, N-dimethylformamide at room temperature to prepare a first solution;
and adding N, N' -carbonyl diimidazole into the first solution, and stirring at room temperature to fully activate the carboxyl of the lipoic acid to obtain a lipoyl imidazole solution.
5. The method for preparing an anti-inflammatory and easily replaceable adhesive hydrogel wound dressing according to claim 2, wherein the mass ratio of the hyaluronic acid-g-lipoic acid, the cellulose nanocrystals and the lipoic acid is 2 (3-7): 40.
6. The method for producing an anti-inflammatory, easily replaceable, adhesive hydrogel wound dressing according to claim 2, wherein the hyaluronic acid-g-lipoic acid, the cellulose nanocrystals, and the lipoic acid are sequentially dissolved in an aqueous solution formed by the tris (hydroxymethyl) aminomethane, and the dissolution is performed sufficiently using an oscillator.
7. The method of preparing an anti-inflammatory, easily replaceable, adhesive hydrogel wound dressing of claim 2, wherein the parameters of the first heating reaction are: the reaction is carried out for 30min under the heating condition of 70 ℃, and the parameters of the second heating reaction are as follows: the reaction was carried out at 70℃for 6h.
8. The use of an anti-inflammatory, easily replaceable, adhesive hydrogel wound cover prepared by the method of preparing an anti-inflammatory, easily replaceable, adhesive hydrogel wound cover as claimed in any one of claims 2 to 7, wherein the anti-inflammatory, easily replaceable, adhesive hydrogel wound cover is used for the treatment and healing of skin wounds.
9. The use of an anti-inflammatory, easily replaceable, adhesive hydrogel wound covering of claim 8, wherein the adhesive hydrogel wound covering is capable of being detached from the skin by water irrigation.
10. A hydrogel suitable for use in a wound dressing application, the hydrogel having the following structural formula:
wherein the "grey diamond" portion represents cellulose nanocrystals, the "… …" portion represents hydrogen bonds, and the "circular" portion represents 1-vinylimidazole.
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