CN112898598A - Tissue adhesion hydrogel and preparation method and application thereof - Google Patents
Tissue adhesion hydrogel and preparation method and application thereof Download PDFInfo
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- A61L24/00—Surgical adhesives or cements; Adhesives for colostomy devices
- A61L24/001—Use of materials characterised by their function or physical properties
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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
- A61L24/00—Surgical adhesives or cements; Adhesives for colostomy devices
- A61L24/001—Use of materials characterised by their function or physical properties
- A61L24/0031—Hydrogels or hydrocolloids
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L24/00—Surgical adhesives or cements; Adhesives for colostomy devices
- A61L24/04—Surgical adhesives or cements; Adhesives for colostomy devices containing macromolecular materials
- A61L24/06—Surgical adhesives or cements; Adhesives for colostomy devices containing macromolecular materials obtained by reactions only involving carbon-to-carbon unsaturated bonds
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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- A61L24/00—Surgical adhesives or cements; Adhesives for colostomy devices
- A61L24/04—Surgical adhesives or cements; Adhesives for colostomy devices containing macromolecular materials
- A61L24/08—Polysaccharides
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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
- A61L24/00—Surgical adhesives or cements; Adhesives for colostomy devices
- A61L24/04—Surgical adhesives or cements; Adhesives for colostomy devices containing macromolecular materials
- A61L24/10—Polypeptides; Proteins
- A61L24/104—Gelatin
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- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
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- C08J2351/00—Characterised by the use of graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Derivatives of such polymers
- C08J2351/02—Characterised by the use of graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Derivatives of such polymers grafted on to polysaccharides
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Abstract
The invention discloses a tissue adhesion hydrogel and a preparation method and application thereof. The hydrogel component comprises two macromolecules which are grafted by dopa and respectively contain aldehyde group and amino group, acrylic acid, N-hydroxysuccinimide acrylate and a photoinitiator, and the two macromolecules are mixed and then fully polymerized by ultraviolet irradiation to obtain the hydrogel material. The dopa grafted aldehyde-containing polymer and the dopa grafted amino-containing polymer react to form Schiff base, acrylic acid and N-hydroxysuccinimide acrylate are polymerized to form a copolymer under the action of a photoinitiator, and meanwhile, an active ester group of the N-hydroxysuccinimide acrylate can chemically react with the dopa grafted amino-containing polymer, so that the hydrogel has higher crosslinking density. The hydrogel has good skin affinity and high tissue adhesion strength.
Description
Technical Field
The invention relates to a tissue adhesion hydrogel and a preparation method and application thereof, belonging to the field of functional polymer materials.
Background
Aiming at the closing treatment of human tissue wounds, the traditional treatment methods mainly comprise surgical suture and rivet mechanical fixation, but the methods are complicated to operate and can cause infection due to the fact that the wounds are not tightly sealed. Another material for treating wounds has emerged: an adhesive hydrogel. The adhesive is simple and quick to operate, only needs to be coated on a wound without sewing and stitches removing, does not hurt tissues around the wound, has a wound sealing effect which is much better than that of the traditional method, and can effectively prevent body fluid and air from leaking and prevent wound infection.
High molecular materials such as sodium alginate, chitosan, gelatin and the like have good biocompatibility and are common materials in human tissue engineering. However, because of the use of such natural polymer materials alone, their binding ability as the main component of hydrogels is often not as desired. For example, in the invention patent with the application number of 201510891554.X, a medical adhesive and a preparation method thereof are disclosed, the preparation method comprises the steps of mixing an aldehydic sodium alginate solution with the concentration of 10-50% (w/v) and an aminated carboxymethyl chitosan solution with the concentration of 1-6% (w/v) which have the same volume, and carrying out Schiff base reaction to form hydrogel, wherein the pigskin bonding strength of the hydrogel is 10-30 gfcm-2The adhesive strength is not sufficiently outstanding.
In the invention patent with the application number of 201810746272.4, an antibacterial adhesive injectable hydrogel dressing is disclosed, and a preparation method and application thereof, wherein the preparation method of the antibacterial adhesive injectable hydrogel dressing is that quaternary ammonium chitosan polymer and chitosan polymer are mixedEnd-capped with aldehyde groupsRespectively preparing the F127 polymer into solutions, and performing crosslinking reaction for 5-400 s at the temperature of 20-45 ℃ to prepare the antibacterial adhesive injectable hydrogel dressing, wherein the quaternized chitosan polymer and the aldehyde group end-cappedThe mass ratio of the F127 polymer is (1-20) to (50-200). Modification of the inventionThe aldehyde group of the F127 polymer has chemical action with tissues and electrostatic action and hydrophobic action of chitosan, and the actions jointly enable the hydrogel to have certain adhesive property. However, this hydrogel had a drawback that its adhesive strength was 4.4kPa to 6.1kPa, and its adhesive ability was insufficient. In addition, acetone and dichloromethane used in the preparation of the two components are toxic and harmful substances, so that the acetone and the dichloromethane are easy to cause toxic action to organisms due to incomplete purification in the actual application process.
Therefore, clinically, the tissue adhesion hydrogel which is strong in tissue adhesion performance, simple to prepare, low in cost and fast to operate is needed.
Disclosure of Invention
The invention aims to provide the tissue adhesion hydrogel which has the advantages of strong tissue adhesion performance, simple preparation, low cost and quick operation.
The present invention provides a tissue-adhesive hydrogel characterized in that: a hydrogel having the following structure.
In the structure of the formula (I), G1Is one of oxidized sodium alginate, oxidized dextran and oxidized cellulose, G2Is one of chitosan, gelatin and chitosan.
In the structure of the formula (I), G1Is divided intoThe molecular weight is 10000-200000, and the oxidation degree is 30% -80%; g1Dopa is grafted, and the content of the dopa is 0.1mmol/g to 1 mmol/g.
In the structure of the formula (I), G2The molecular weight of (A) is 10000-200000; g2Dopa is grafted, and the content of the dopa is 0.001mmol/g to 0.02 mmol/g.
In the structure of the formula (I), G1And G2The mass ratio of (1-5) to (1-5);
in the structure of the formula (I), m and N are respectively the polymerization degrees of acrylic acid and N-hydroxysuccinimide acrylate;
in the structure of the formula (I), G1、G2The mass ratio of the polyacrylic acid to the poly-N-hydroxysuccinimide acrylate is (1-10) to (2-15) to (50-200) to (1-10).
The invention also provides a preparation method of the tissue adhesion hydrogel, which comprises the following steps:
(1) g is to be1And G2Adding into distilled water according to a certain proportion, mixing and dissolving;
added G1And G2The total volume concentration in water is 15-45 mg/ml;
(2) adding acrylic acid and N-hydroxysuccinimide acrylate, mixing, stirring and dissolving;
(3) adding photoinitiator, stirring for dissolving, and irradiating under an ultraviolet lamp for polymerization reaction to obtain the tissue adhesive hydrogel.
The photoinitiator is one of 2-hydroxy-methyl phenyl propane-1-ketone, 1-hydroxycyclohexyl phenyl ketone, 2-methyl-1- (4-methylthiophenyl) -2-morpholinyl-1-acetone, methyl o-benzoylbenzoate, 2-hydroxy-4' - (2-hydroxyethoxy) -2-methyl propiophenone and alpha-ketoglutaric acid.
G1、G2The mass ratio of the sum of the mass of (1) to the mass of the added photoinitiator is (6-18): 5.
Compared with the prior art, the invention has the advantages that:
the tissue adhesion hydrogel disclosed by the invention takes acrylic acid as a main component, can ensure a certain mechanical property by polymerization under the action of a photoinitiator, contains a large number of carboxyl groups, can form a large number of hydrogen bonds with tissues, and has good skin-friendly property, so that the gel has a certain adhesion capability;
in the invention G1And G2Performing Schiff base reaction to perform crosslinking reaction, performing free radical polymerization on acrylic acid and N-hydroxysuccinimide acrylate under the action of a photoinitiator, and simultaneously enabling active ester groups of the N-hydroxysuccinimide acrylate and G2The amino group is chemically crosslinked, so that the hydrogel has a multi-dimensional crosslinking mode with high crosslinking density, and the hydrogel can have higher mechanical strength and adhesive strength;
the hydrogel has certain self-healing capability due to the dynamic Schiff base generated by the reaction of aldehyde group and amino group, and can adhere to the tissue for a long time;
g1 and G2 in the tissue adhesion hydrogel disclosed by the invention both contain certain dopa groups, and the groups can form a large number of hydrogen bonds with tissues, so that the hydrogen bond density of the hydrogel is increased, and the adhesion strength of the hydrogel is further increased;
the tissue adhesion hydrogel has the advantages of cheap and easily obtained raw materials, simple preparation and short period, and can be directly used when being used for wound surface.
Detailed Description
The technical solution of the present invention is further described with reference to the following specific examples, which are not intended to limit the present invention in any way. In the examples, unless otherwise specified, conventional reagents and conventional methods were used.
Example 1
Adding 4mg of dopa-grafted oxidized sodium alginate (with the relative molecular mass of 10000-200000, the degree of oxidation of 54.48% and the grafted dopa content of 0.72mmol/g) and 20mg of dopa-grafted gelatin (with the relative molecular mass of 10000-200000 and the grafted dopa content of 0.013mmol/g) into 1.6ml of distilled water, mixing and ultrasonically dissolving, continuing to stir for 10 minutes after dissolving, adding 420mg of acrylic acid and 20mg of N-hydroxysuccinimide acrylate, mixing and stirring for dissolving, adding 0.118mmol of 2-hydroxy-4' - (2-hydroxyethoxy) -2-methyl propiophenone, mixing and stirring for dissolving, placing the mixed solution into a mold, and polymerizing for 3 hours under an ultraviolet lamp to obtain the tissue adhesion hydrogel.
Example 2
Adding 8mg of dopa-grafted oxidized sodium alginate (with the relative molecular mass of 10000-200000, the degree of oxidation of 54.48% and the grafted dopa content of 0.72mmol/g) and 40mg of dopa-grafted gelatin (with the relative molecular mass of 10000-200000 and the grafted dopa content of 0.013mmol/g) into 1.6ml of distilled water, mixing and ultrasonically dissolving, continuing to stir for 10 minutes after dissolving, adding 420mg of acrylic acid and 20mg of N-hydroxysuccinimide acrylate, mixing, stirring and dissolving, adding 20mg of 2-hydroxy-4' - (2-hydroxyethoxy) -2-methyl propiophenone, mixing, stirring and dissolving, placing the mixed solution into a mold, and polymerizing for 3 hours under an ultraviolet lamp to obtain the tissue adhesive hydrogel.
Example 3
Adding 12mg of dopa-grafted oxidized sodium alginate (with the relative molecular mass of 10000-200000, the degree of oxidation of 54.48% and the grafted dopa content of 0.72mmol/g) and 60mg of dopa-grafted gelatin (with the relative molecular mass of 10000-200000 and the grafted dopa content of 0.013mmol/g) into 1.6ml of distilled water, mixing and ultrasonically dissolving, continuing to stir for 10 minutes after dissolving, adding 420mg of acrylic acid and 20mg of N-hydroxysuccinimide acrylate, mixing, stirring and dissolving, adding 20mg of 2-hydroxy-4' - (2-hydroxyethoxy) -2-methyl propiophenone, mixing, stirring and dissolving, placing the mixed solution into a mold, and polymerizing for 3 hours under an ultraviolet lamp to obtain the tissue adhesive hydrogel.
Performance testing
The hydrogels prepared in examples 1 to 3 were applied to the surface of pigskins, respectively, the size application area was 15mm x 15mm, the size application thickness was 1mm, two pigskins were bonded and then pressed by hand for 20 seconds, and then a shear strength test was performed using a universal tester, and the results of the shear strength test are shown in the following table.
Examples of the experiments | Shear strength |
Example 1 | 1.73kPa |
Example 2 | 3.16kPa |
Example 3 | 7.57kPa |
Claims (3)
1. A tissue adherent hydrogel, comprising: a hydrogel having the structure of formula (I);
in the structure of the formula (I), G1Is one of oxidized sodium alginate, oxidized dextran and oxidized cellulose, G2Is one of chitosan, gelatin and chitosan;
in the structure of the formula (I), G1The molecular weight of (A) is 10000-200000, and the oxidation degree is 30% -80%; g1Dopa is grafted, and the content of the dopa is 0.1mmol/g to 1 mmol/g;
in the structure of the formula (I), G2The molecular weight of (A) is 10000-200000; g2Dopa is grafted, and the content of the dopa is 0.001mmol/g to 0.02 mmol/g;
in the structure of the formula (I), G1And G2The mass ratio of (1-5) to (1-5);
in the structure of the formula (I), m and N are respectively the polymerization degrees of acrylic acid and N-hydroxysuccinimide acrylate;
in the structure of the formula (I), G1、G2The mass ratio of the polyacrylic acid to the poly-N-hydroxysuccinimide acrylate is (1-10) to (2-15) to (50-200) to (1-10).
2. A method of preparing the tissue-adhesive hydrogel of claim 1, wherein: the preparation method comprises the following steps:
(1) g is to be1And G2Adding into distilled water according to a certain proportion, mixing and dissolving;
added G1And G2The total volume concentration in water is 15-45 mg/ml;
(2) adding acrylic acid and N-hydroxysuccinimide acrylate, mixing, stirring and dissolving;
(3) adding photoinitiator, stirring for dissolving, and irradiating under an ultraviolet lamp for polymerization reaction to obtain the tissue adhesive hydrogel.
The photoinitiator is one of 2-hydroxy-methyl phenyl propane-1-ketone, 1-hydroxycyclohexyl phenyl ketone, 2-methyl-1- (4-methylthiophenyl) -2-morpholinyl-1-acetone, methyl o-benzoylbenzoate, 2-hydroxy-4' - (2-hydroxyethoxy) -2-methyl propiophenone and alpha-ketoglutaric acid,
G1、G2the mass ratio of the sum of the mass of (1) to the mass of the added photoinitiator is (6-18): 5.
3. Use of a tissue adhesive hydrogel according to claim 1 in a medical adhesive.
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Cited By (7)
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CN114272427A (en) * | 2021-12-31 | 2022-04-05 | 山东大学 | Preparation method of multifunctional colloid patch capable of being pasted with wet surface |
CN114712550A (en) * | 2022-04-20 | 2022-07-08 | 华中科技大学 | Hydrogel adhesive capable of being injected for rapid hemostasis and preparation method and application thereof |
CN114767919A (en) * | 2022-04-20 | 2022-07-22 | 华中科技大学 | Hydrogel powder for rapid hemostasis and preparation method and application thereof |
CN114887110A (en) * | 2022-04-20 | 2022-08-12 | 华中科技大学 | Hemostatic material capable of rapidly stopping bleeding and preparation method thereof |
CN115109367A (en) * | 2022-07-22 | 2022-09-27 | 苏州凝智新材料发展有限公司 | Injectable hydrogel and preparation method and application thereof |
CN115708892A (en) * | 2022-11-15 | 2023-02-24 | 中国科学技术大学 | Hydrogel tissue adhesive of sand tower worm-imitating glue and preparation method and application thereof |
CN117679555A (en) * | 2024-02-04 | 2024-03-12 | 吉林农业科技学院 | Larch cellulose hydrogel, preparation method thereof and application of larch cellulose hydrogel in promoting bone repair |
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CN114272427A (en) * | 2021-12-31 | 2022-04-05 | 山东大学 | Preparation method of multifunctional colloid patch capable of being pasted with wet surface |
CN114712550A (en) * | 2022-04-20 | 2022-07-08 | 华中科技大学 | Hydrogel adhesive capable of being injected for rapid hemostasis and preparation method and application thereof |
CN114767919A (en) * | 2022-04-20 | 2022-07-22 | 华中科技大学 | Hydrogel powder for rapid hemostasis and preparation method and application thereof |
CN114887110A (en) * | 2022-04-20 | 2022-08-12 | 华中科技大学 | Hemostatic material capable of rapidly stopping bleeding and preparation method thereof |
CN114712550B (en) * | 2022-04-20 | 2023-02-14 | 华中科技大学 | Hydrogel adhesive capable of being injected for rapid hemostasis and preparation method and application thereof |
CN114767919B (en) * | 2022-04-20 | 2023-08-25 | 华中科技大学 | Hydrogel powder for rapid hemostasis as well as preparation method and application thereof |
CN115109367A (en) * | 2022-07-22 | 2022-09-27 | 苏州凝智新材料发展有限公司 | Injectable hydrogel and preparation method and application thereof |
CN115109367B (en) * | 2022-07-22 | 2023-11-24 | 苏州凝智新材料发展有限公司 | Injectable hydrogel and preparation method and application thereof |
CN115708892A (en) * | 2022-11-15 | 2023-02-24 | 中国科学技术大学 | Hydrogel tissue adhesive of sand tower worm-imitating glue and preparation method and application thereof |
CN115708892B (en) * | 2022-11-15 | 2024-04-26 | 中国科学技术大学 | Hydrogel tissue adhesive imitating vermicular worm gum in sand tower, and preparation method and application thereof |
CN117679555A (en) * | 2024-02-04 | 2024-03-12 | 吉林农业科技学院 | Larch cellulose hydrogel, preparation method thereof and application of larch cellulose hydrogel in promoting bone repair |
CN117679555B (en) * | 2024-02-04 | 2024-04-12 | 吉林农业科技学院 | Larch cellulose hydrogel, preparation method thereof and application of larch cellulose hydrogel in promoting bone repair |
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