CN112898598B - Tissue adhesion hydrogel and preparation method and application thereof - Google Patents

Tissue adhesion hydrogel and preparation method and application thereof Download PDF

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CN112898598B
CN112898598B CN202110093102.2A CN202110093102A CN112898598B CN 112898598 B CN112898598 B CN 112898598B CN 202110093102 A CN202110093102 A CN 202110093102A CN 112898598 B CN112898598 B CN 112898598B
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hydrogel
dopa
dissolving
grafted
photoinitiator
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CN112898598A (en
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蒋玉仁
张承良
吴启瑶
杨顺
杨婷婷
韩婷
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Central South University
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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J3/00—Processes of treating or compounding macromolecular substances
    • C08J3/02—Making solutions, dispersions, lattices or gels by other methods than by solution, emulsion or suspension polymerisation techniques
    • C08J3/03—Making solutions, dispersions, lattices or gels by other methods than by solution, emulsion or suspension polymerisation techniques in aqueous media
    • C08J3/075—Macromolecular gels
    • 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
    • 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
    • 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
    • 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
    • A61L24/08—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
    • 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
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F251/00—Macromolecular compounds obtained by polymerising monomers on to polysaccharides or derivatives thereof
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F289/00—Macromolecular compounds obtained by polymerising monomers on to macromolecular compounds not provided for in groups C08F251/00 - C08F287/00
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • 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
    • 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

Abstract

The invention discloses a tissue adhesion hydrogel and a preparation method and application thereof. The hydrogel component comprises dopa grafted two polymers containing aldehyde groups and amino groups respectively, acrylic acid, N-hydroxysuccinimide acrylic ester and a photoinitiator, and the two polymers are mixed and fully polymerized by ultraviolet irradiation to obtain the hydrogel material. Wherein, the aldehyde-containing macromolecule grafted by dopa and the amino-containing macromolecule grafted by dopa react to form Schiff base, the acrylic acid and the N-hydroxysuccinimide acrylic ester polymerize to form a copolymer under the action of a photoinitiator, and meanwhile, the active ester group of the N-hydroxysuccinimide acrylic ester can chemically react with the amino-containing macromolecule grafted by dopa, so that the hydrogel has higher crosslinking density. The hydrogel has good skin affinity and high tissue adhesion strength.

Description

Tissue adhesion hydrogel and preparation method and application thereof
Technical Field
The invention relates to a tissue adhesion hydrogel, a preparation method and application thereof, and belongs to the field of functional polymer materials.
Background
For the wound closing treatment of human tissues, the traditional treatment method mainly comprises the steps of surgical line suturing and rivet mechanical fixation, but the method has complicated operation and can cause infection due to the fact that the wound is not tightly sealed. Another material for wound treatment follows: a viscous hydrogel. The adhesive is easy and quick to operate, only needs to be smeared on a wound, does not need to be sutured or unraveled, does not hurt tissues around the wound, has a much better wound sealing effect than the traditional method, can effectively prevent body fluid and air from leaking, and prevents wound infection.
The high polymer materials such as sodium alginate, chitosan, gelatin and the like have good biocompatibility and are common materials in human tissue engineering. However, since such natural polymer materials are used alone, their adhesive ability often does not meet the expectations of people when they are used as the main component of hydrogels. As in the patent of 2015199554. X, a medical adhesive and a preparation method thereof are disclosed, wherein the preparation method comprises the steps of mixing an equal volume of aldehyde sodium alginate solution with the concentration of 10-50% (w/v) with an amino carboxymethyl chitosan solution with the concentration of 1-6% (w/v), and reacting Schiff base to form hydrogel, wherein the pigskin adhesive strength of the hydrogel is 10-30 gfcm -2 The adhesion strength is not outstanding enough.
In the patent application No. 201810746272.4, an antibacterial adhesive injectable hydrogel dressing, and its preparation method and application are disclosed, wherein the antibacterial adhesive injectable hydrogel dressing is prepared by capping quaternized chitosan polymer and aldehyde group
Figure GDA0004185646930000011
F127 polymer is respectively prepared into solutions, and the solutions are subjected to crosslinking reaction for 5-400 s at 20-45 ℃ to prepare the antibacterial adhesive injectable hydrogel dressing, wherein the quaternized chitosan polymer and aldehyde group end-capped->
Figure GDA0004185646930000012
Figure GDA0004185646930000013
The mass ratio of F127 polymer is (1-20) (50-200). The modification described in this invention->
Figure GDA0004185646930000014
The aldehyde group of the F127 polymer has a certain adhesive property together with the chemical action of tissues and the electrostatic action and the hydrophobic action of chitosan. However, the hydrogel has a strength of 4.4kPa to 6.1kPa, and has a disadvantage of insufficient adhesive ability. In addition, two components are preparedAcetone and methylene dichloride used in the method are toxic and harmful substances, so that toxic effects on organisms are easily caused by incomplete purification in the actual application process.
Therefore, the tissue adhesive hydrogel which has strong tissue adhesive property, simple preparation, low cost and quick operation is clinically needed.
Disclosure of Invention
The invention aims to provide the tissue adhesion hydrogel which has strong tissue adhesion performance, simple preparation, low cost and quick operation.
The invention provides a tissue adhesion hydrogel, which is characterized in that: a hydrogel having the structure of formula (1).
Figure GDA0004185646930000021
In the structure of the formula (I), G 1 Is one of oxidized sodium alginate, oxidized dextran and oxidized cellulose, G 2 Is one of chitosan, gelatin and chitosan.
In the structure of the formula (I), G 1 The molecular weight of (2) is 10000-200000, the oxidation degree is 30% -80%; g 1 The content of the grafted dopa is 0.1 mmol/g-1 mmol/g.
In the structure of the formula (I), G 2 The molecular weight of (2) is 10000-200000; g 2 The content of the grafted dopa is 0.001 mmol/g-0.02 mmol/g.
In the structure of the formula (I), G 1 And G 2 The mass ratio of (1-5) is (1-5);
in the structure of the formula (I), m and N are respectively the polymerization degree of N-hydroxysuccinimide acrylate and acrylic acid;
in the structure of the formula (I), G 1 、G 2 The mass ratio of the polyacrylic acid to the poly N-hydroxysuccinimide acrylic ester is (1-10), the mass ratio of the polyacrylic acid to the poly N-hydroxysuccinimide acrylic ester is (2-15), the mass ratio of the polyacrylic acid to the poly N-hydroxysuccinimide acrylic ester is (50-200), and the mass ratio of the polyacrylic acid to the poly N-hydroxysuccinimide acrylic ester is (1-10).
The invention also provides a preparation method of the tissue adhesion hydrogel, which comprises the following preparation steps:
(1) Will G 1 And G 2 Adding the mixture into distilled water according to a certain proportion, and fully mixing and dissolving;
g added 1 And G 2 The total volume concentration in water is 15-45 mg/ml;
(2) Then adding acrylic acid and N-hydroxysuccinimide acrylate, mixing, stirring and dissolving;
(3) And adding a photoinitiator, stirring and dissolving, and irradiating under an ultraviolet lamp to perform polymerization reaction to obtain the tissue adhesion hydrogel.
The photoinitiator is one of 2-hydroxy-methyl phenyl propane-1-ketone, 1-hydroxy cyclohexyl phenyl ketone, 2-methyl-1- (4-methylthiophenyl) -2-morpholinyl-1-acetone, methyl o-benzoyl benzoate, 2-hydroxy-4' - (2-hydroxyethoxy) -2-methyl propiophenone and alpha-ketoglutaric acid.
G 1 、G 2 The mass ratio of the sum of the masses of (2) to the mass ratio 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 certain mechanical properties through polymerization under the action of a photoinitiator, contains a large number of carboxyl groups, can form a large number of hydrogen bonds with tissues, has good skin-friendly property, and has certain adhesion capability;
g in the invention 1 And G 2 Crosslinking is carried out through Schiff base reaction, acrylic acid and N-hydroxysuccinimide acrylic ester are subjected to free radical polymerization under the action of a photoinitiator, and meanwhile, the active ester group of the N-hydroxysuccinimide acrylic ester can be reacted with G 2 The amino groups of the hydrogel are chemically crosslinked, so that the hydrogel has a multi-dimensional crosslinking mode with high crosslinking density, and further the hydrogel can be ensured to have higher mechanical strength and adhesive strength;
according to the invention, the dynamic Schiff base generated by the reaction of aldehyde groups and amino groups enables the hydrogel to have certain self-healing capacity, and can be used for adhering tissues for a long time;
in the tissue-adhering hydrogel of the present inventionG of (2) 1 And G 2 All contain a certain dopa group, and the group can form a large number of hydrogen bonds with tissues, so that the hydrogen bond density of the hydrogel is increased, and the adhesive strength of the hydrogel is further increased;
the tissue adhesion hydrogel disclosed by the invention has the advantages of low-cost and easily available raw materials, simplicity in preparation and short period, and can be directly used when being used for wound surfaces.
Detailed Description
The technical scheme of the present invention is further described below with reference to specific examples, but the present invention is not limited in any way by these examples. Unless otherwise specified, the examples are conventional reagents and conventional methods.
Example 1
Adding 4mg of dopa grafted oxidized sodium alginate (with relative molecular weight of 10000-200000, oxidation degree of 54.48 percent, grafted dopa content of 0.72 mmol/g) and 20mg of dopa grafted gelatin (with relative molecular weight of 10000-200000, grafted dopa content of 0.013 mmol/g) into 1.6ml of distilled water, mixing and ultrasonically dissolving, continuously stirring 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 mixture into a mold, and polymerizing under an ultraviolet lamp for 3 hours to obtain the tissue adhesive hydrogel.
Example 2
8mg of dopa grafted oxidized sodium alginate (relative molecular weight is 10000-200000, oxidation degree is 54.48%, content of grafted dopa is 0.72 mmol/g) and 40mg of dopa grafted gelatin (relative molecular weight is 10000-200000, content of grafted dopa is 0.013 mmol/g) are added into 1.6ml of distilled water, mixed and ultrasonically dissolved, stirring is continued for 10 minutes after dissolving, 420mg of acrylic acid and 20mg of N-hydroxysuccinimide acrylate are added, mixed and stirred for dissolving, 20mg of 2-hydroxy-4' - (2-hydroxyethoxy) -2-methyl propiophenone are added, mixed and stirred for dissolving, the mixed solution is placed into a mould, and polymerized under an ultraviolet lamp for 3 hours, thus obtaining the tissue adhesion hydrogel.
Example 3
Adding 12mg of dopa grafted oxidized sodium alginate (with the relative molecular weight of 10000-200000, the oxidation degree of 54.48 percent, the content of grafted dopa of 0.72 mmol/g) and 60mg of dopa grafted gelatin (with the relative molecular weight of 10000-200000, the content of grafted dopa of 0.013 mmol/g) into 1.6ml of distilled water, mixing and ultrasonically dissolving, continuously stirring for 10 minutes after dissolving, adding 420mg of acrylic acid and 20mg of N-hydroxysuccinimide acrylate, mixing and stirring for dissolving, adding 20mg of 2-hydroxy-4' - (2-hydroxyethoxy) -2-methyl propiophenone, mixing and stirring for dissolving, placing the mixture into a mold, and polymerizing under an ultraviolet lamp for 3 hours to obtain the tissue adhesion hydrogel.
Performance testing
The hydrogels prepared in examples 1 to 3 were applied to the surfaces of pigskins, respectively, with a sizing area of 15mm×15mm and a sizing thickness of 1mm, and after two pigskins were bonded, they were pressed by hand for 20 seconds, and then shear strength test was performed using a universal tester, and the shear strength results of the test are shown in the following table.
Experimental example Shear strength
Example 1 1.73kPa
Example 2 3.16kPa
Example 3 7.57kPa

Claims (3)

1. A tissue adhering hydrogel, characterized in that: the preparation method comprises the following steps:
(1) Will G 1 And G 2 Adding the mixture into distilled water according to a certain proportion, and fully mixing and dissolving;
(2) Then adding acrylic acid and N-hydroxysuccinimide acrylate, mixing, stirring and dissolving;
(3) Adding a photoinitiator, stirring and dissolving, and then irradiating under an ultraviolet lamp to perform polymerization reaction to obtain tissue-adhering hydrogel;
wherein:
the G is 1 Is one of oxidized sodium alginate, oxidized dextran and oxidized cellulose;
the G is 2 Is one of chitosan, gelatin and chitosan;
the G is 1 The molecular weight of (2) is 10000-200000, the oxidation degree is 30% -80%; g 1 The dopa is grafted, and the content of the dopa is 0.1 mmol/g-1 mmol/g;
the G is 2 The molecular weight of (2) is 10000-200000; g 2 The content of the dopa grafted is 0.001 mmol/g-0.02 mmol/g;
the G is 1 And G 2 The mass ratio of (1-5) is (1-5);
the G is 1 、G 2 The mass ratio of the acrylic acid to the N-hydroxysuccinimide acrylic ester is (1-10), 2-15, 50-200 and 1-10.
2. A method of making the tissue-adhesive hydrogel of claim 1, wherein: the preparation method comprises the following steps:
(1) Will G 1 And G 2 Adding the mixture into distilled water according to a certain proportion, and fully mixing and dissolving;
g added 1 And G 2 The total volume concentration in water is 15-45 mg/ml;
(2) Then adding acrylic acid and N-hydroxysuccinimide acrylate, mixing, stirring and dissolving;
(3) Adding a photoinitiator, stirring and dissolving, and then irradiating under an ultraviolet lamp to perform polymerization reaction to obtain tissue-adhering hydrogel;
the photoinitiator is one of 2-hydroxy-methyl phenyl propane-1-ketone, 1-hydroxy cyclohexyl phenyl ketone, 2-methyl-1- (4-methylthiophenyl) -2-morpholinyl-1-acetone, methyl o-benzoyl benzoate, 2-hydroxy-4' - (2-hydroxyethoxy) -2-methyl propiophenone and alpha-ketoglutaric acid;
G 1 、G 2 the mass ratio of the sum of the masses of (2) to the mass ratio of the added photoinitiator is (6-18): 5.
3. Use of the tissue-adhesive hydrogel of claim 1 in the preparation of a medical adhesive.
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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
CN114887110B (en) * 2022-04-20 2023-04-11 华中科技大学 Hemostatic material capable of quickly stopping bleeding and preparation method 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
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