CN112957516B - Polysaccharide-based tissue adhesive medical adhesive and application thereof - Google Patents

Polysaccharide-based tissue adhesive medical adhesive and application thereof Download PDF

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CN112957516B
CN112957516B CN202110160412.1A CN202110160412A CN112957516B CN 112957516 B CN112957516 B CN 112957516B CN 202110160412 A CN202110160412 A CN 202110160412A CN 112957516 B CN112957516 B CN 112957516B
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徐福建
李杨
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Wendexilin Hangzhou Biotechnology Co ltd
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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
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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
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Abstract

The invention discloses a polysaccharide-based tissue adhesive medical adhesive and application thereof, wherein the polysaccharide-based tissue adhesive medical adhesive consists of a polysaccharide derivative and a compound with at least two reaction functional groups, and the polysaccharide derivative and the compound with at least two reaction functional groups generate an adhesive effect through one or more of physical action or chemical reaction; the polysaccharide derivative is polysaccharide substituted by functional groups. The polysaccharide-based tissue adhesive medical adhesive can bear larger tensile force, has faster tissue adhesion time and higher tissue peeling force compared with cyanoacrylate medical adhesive, can realize the rapid adhesion and closure of wounds, has strong adhesion force with tissues after being applied, is not easy to peel, can be suitable for stretched wounds, and can realize effective closure.

Description

Polysaccharide-based tissue adhesive medical adhesive and application thereof
Technical Field
The invention belongs to the field of biomedical materials, and relates to polysaccharide-based tissue bonding medical glue and application thereof.
Background
The medical glue is a preparation, material or substance which can be adhered to the surface or cause the adhesion between the surfaces in medical application, is mainly used for local adhesion and repair of organs or tissues and replaces the traditional suture; or the combination and positioning of tissues and blood vessels for plugging and the like. Compared with the traditional methods such as suturing and nailing, the use of the medical adhesive can effectively shorten the operation time and obviously reduce the pain of patients. In tissue bonding, bonding generally involves the following aspects: 1. adhesion between living tissue internal activities; 2. adhesion between the organism and the medical glue; 3. adhesion between medical glues. The important component of the living tissue is protein, so the interaction between the medical glue and the protein is the main force for tissue adhesion. Cyanoacrylate medical adhesives have been rapidly developed and widely used in clinical practice in recent decades. However, the adhesive has the defects of poor impact resistance, low viscosity, poor gap filling performance on porous and rough surfaces, fast in-vivo degradation time, poor heat resistance, poor water resistance and the like, so that the application of the adhesive in medicine is limited to a certain extent.
The ideal medical glue should have the following properties: 1. safe use, asepsis, no toxicity, good biocompatibility, and no interference to the self healing of human tissues; 2. the adhesive can quickly adhere to tissues under physiological conditions, and has good adhesive strength and durability; 3. has certain functions of stopping bleeding and promoting tissue regeneration, and can inhibit bacterial infection; 4. can be degraded and absorbed by the organism within a reasonable time, and the degradation product has no toxic or side effect on the organism; 5. convenient use, easy storage, low price and easy obtainment of raw materials.
Disclosure of Invention
In view of the above, the present invention provides a polysaccharide-based tissue adhesive medical adhesive and applications thereof.
The invention specifically provides the following technical scheme:
1. the polysaccharide-based tissue-adhesive medical adhesive consists of a polysaccharide derivative and a compound with at least two reactive functional groups, wherein the polysaccharide derivative and the compound with at least two reactive functional groups generate an adhesive effect through one or more of physical action or chemical reaction; the polysaccharide derivative is polysaccharide substituted by functional groups.
Furthermore, the polysaccharide-based tissue bonding medical glue can bond tissues of organisms for 5-50 seconds, has a tissue peeling force of 240-400 g/cm and a tensile stress of 5-20 MPa, and can bear a tensile force of at least 500 g.
Further, the polysaccharide is one or more of chitosan, alginate, hyaluronate, starch, agar, cellulose, polyfructose, dextran, pullulan or chondroitin sulfate and derivatives thereof.
Further, the functional group is one or more of aldehyde group, ester group, amino group, imino group, amide group, imide group, sulfhydryl group, disulfide bond, carboxyl group, hydroxyl group, nitro group, alkenyl group, alkynyl group, azido group and halogen group.
Further, the functional group contained in the compound with at least two reactive functional groups is one or more of a halogen group functional group, an oxygen-containing functional group, a nitrogen-containing functional group, a phosphorus-containing functional group or a sulfur-containing functional group.
Further, the oxygen-containing functional group is a hydroxyl group, a carboxyl group, an ester group, an aldehyde group, a ketone group or an epoxy group, the nitrogen-containing functional group is an amino group, an imino group, an amide group, an azido group, an azo group, a cyanate group, an isocyanate group, a nitrate group, a nitrile group, a nitro group or a pyridyl group, the phosphorus-containing functional group is a phosphorus group, a phosphoric acid group or a phosphate group, and the sulfur-containing functional group is a mercapto group, a disulfide bond, a thiol group, a thioether group, a sulfone group or a sulfonic group.
Further, the degree of substitution of the functional group for the polysaccharide is 1% to 90%, and the molar ratio of the polysaccharide derivative to the compound having at least two reactive functional groups is 1: 0.01-1: 100.
further, the molar ratio of the polysaccharide derivative to the compound having at least two reactive functional groups is 1:0.2 to 1: 50.
Further, the polysaccharide derivative is one or more of N-hydroxysuccinimide ester modified glucan, oxidized sodium alginate, polyethylene glycol modified pullulan, oxidized hyaluronic acid, cystamine modified glucan or azide modified glucan; the structural formula of the N-hydroxysuccinimide ester modified glucan is as follows:
Figure BDA0002936342000000021
wherein m is 5-2000, n is 1-1800; the structural formula of the oxidized sodium alginate is as follows:
Figure BDA0002936342000000022
wherein m is 20-1000, and n is 1-900; the structural formula of the polyethylene glycol modified pullulan polysaccharide is as follows:
Figure BDA0002936342000000031
wherein m is 15-4000, and n is 1-3600; the oxidized hyaluronic acid has a structural formula:
Figure BDA0002936342000000032
wherein x is 1-4000, y is 1-3000, and z is 1-4000; the structural formula of the cystamine modified glucan is as follows:
Figure BDA0002936342000000033
wherein m is 5-2000, n is 1-1800; the structural formula of the azide-modified glucan is as follows:
Figure BDA0002936342000000034
wherein m is 5-2000, n is 1-1800; the compound with at least two reactive functional groups is one or more of branched polyethyleneimine, dopamine hydrochloride, cyclodextrin, amikacin sulfate, pentaerythritol tetrakis (3-mercaptopropionate), epichlorohydrin, sodium trimetaphosphate or pentaerythritol tetrapropargonate, and the structural formula of the pentaerythritol tetrapropargonate is as follows:
Figure BDA0002936342000000041
2. use of a polysaccharide-based tissue adhesive medical glue for the adhesion of wound tissue.
The invention has the beneficial effects that: the polysaccharide-based polymer has a molecular structure like a long line, has low strength and is easy to break without crosslinking and has no elasticity by virtue of the adhesive action generated by one or more of the physical action and the chemical action generated by the polysaccharide modified by the functional group and the compound with a plurality of reactive functional groups, and the adhesive action generated by one or more of the physical action and the chemical action generated by the compound with a plurality of reactive functional groups is the action force generated between linear molecules to connect the linear molecules together to form a net structure, so that the strength and the elasticity of the adhesive are improved, and the adhesive action has good biological safety and can be used for tissue adhesion. The powdered polysaccharide-based tissue adhesive medical colloid is fluffy, has good adhesiveness and is easy to use. The gel polysaccharide-based tissue adhesive medical adhesive is easy to use, has high biological safety and strong adhesion with human skin tissues. The polysaccharide-based tissue adhesive medical adhesive can bear larger tension (can bear 500g of tension under the optimized condition), has faster tissue adhesion time and higher tissue peeling force compared with cyanoacrylate medical adhesive, can realize the rapid adhesion and closure of wounds, has strong adhesion force with tissues after application, is not easy to peel, can be suitable for stretched wounds, and can realize effective closure.
Drawings
In order to make the purpose, technical scheme and beneficial effect of the invention more clear, the invention provides the following drawings:
figure 1 shows the application of a powdered polysaccharide-based tissue-adhesive medical glue 1 to fresh pig skin.
Fig. 2 shows the application of the gel-like polysaccharide-based tissue adhesive medical glue 2 to the back of the hands of volunteers.
Figure 3 is a tensile test after bonding of polysaccharide based tissue bonded medical glue 1.
Figure 4 is a polysaccharide-based tissue-adhesive medical glue 3 rat dorsal skin adhesion experiment.
Fig. 5 is a graph of the stress-strain mechanical property test of the polysaccharide-based tissue-adhesive medical glue.
Fig. 6 is a scanning electron microscope image of the cross-linked structure of the polysaccharide-based tissue-adhesive medical glue 5.
Fig. 7 is a gel-forming rheology diagram of polysaccharide-based tissue-adhesive medical gel 3.
Detailed Description
Preferred embodiments of the present invention will be described in detail below with reference to the accompanying drawings.
Example 1
Preparation of polysaccharide-based tissue-adhesive medical adhesive: 2g N-hydroxysuccinimide ester-modified dextran (structural formula:
Figure BDA0002936342000000051
wherein m is 5-2000, n is 1-1800, degree of substitution 90%) and 0.5g of branched polyethyleneimine are dissolved in 50mL of deionized water, and stirred for 6 hours. Purifying, drying and grinding the mixture by a conventional method to obtain powdery polysaccharide-based tissue adhesive medical glue 1,
example 2
Of polysaccharide-based tissue-adhesive medical gluesPreparation: 2g of oxidized sodium alginate powder (structural formula:
Figure BDA0002936342000000052
wherein m is 20-1000, n is 1-900, degree of substitution 70%) and 0.8g of dopamine hydrochloride powder to obtain the powdery polysaccharide-based tissue adhesive medical glue 2.
Example 3
Preparation of polysaccharide-based tissue-adhesive medical adhesive: 2g of polyethylene glycol-modified pullulan (structural formula:
Figure BDA0002936342000000053
wherein m is 15-4000, n is 1-3600, and the substitution degree is 5%) and 0.6g of alpha-cyclodextrin are dissolved in 60mL of deionized water and stirred for 3 hours. Purifying, drying and grinding the mixture by a conventional method to obtain the powdery polysaccharide-based tissue-adhesive medical adhesive 3.
Example 4
Preparation of polysaccharide-based tissue-adhesive medical adhesive: 1g of oxidized hyaluronic acid (structural formula:
Figure BDA0002936342000000061
wherein x is 1-4000, y is 1-3000, z is 1-4000, the substitution degree is 20 percent), 1g of chitosan and 0.2g of amikacin sulfate are dissolved in 30mL of deionized water to obtain the gelatinous polysaccharide-based tissue adhesive medical adhesive 4.
Example 5
Preparation of polysaccharide-based tissue-adhesive medical adhesive: 0.5g of cystamine-modified dextran (structural formula:
Figure BDA0002936342000000062
wherein m is 5 to 2000, n is 1 to 1800, degree of substitution 68%) and 0.5g of pentaerythritol tetra-3-mercaptopropionate are dissolved in 10mL of deionized water to obtain the gel-like polysaccharide-based tissue adhesive medical adhesive 5.
Example 6
Preparation of polysaccharide-based tissue-adhesive medical adhesive: 1g of azide-modified dextran (structural formula:
Figure BDA0002936342000000063
wherein m is 5 to 2000, n is 1 to 1800, degree of substitution 1%), 0.5g pentaerythritol tetrapropargonate (structural formula:
Figure BDA0002936342000000071
) And 2mg copper sulfate (catalyst) in 20mL DMSO, was routinely purified to give waxy polysaccharide-based tissue-binding medical gel 6.
Example 7
Preparation of polysaccharide-based tissue-adhesive medical adhesive: 1g of carboxymethyl chitosan (with a substitution degree of 35 percent) and 2g of epichlorohydrin are dissolved in 50mL of deionized water, heated at 50 ℃ for 12 hours, and subjected to conventional purification, drying and grinding to obtain powdery polysaccharide-based tissue adhesive medical adhesive 7.
Example 8
Preparation of polysaccharide-based tissue-adhesive medical adhesive: 1g hydroxyethyl starch (degree of substitution 18%), 1g sodium trimetaphosphate were dissolved in 50mL deionized water and purified, dried, and ground conventionally to give polysaccharide-based tissue-adhesive medical gel 8 in powder form.
Example 9
Each of the polysaccharide-based tissue-bonded medical adhesive 1-7 samples was applied between two fresh pigskins with a contact area of 2x2cm2, the bonded pigskin was picked up every 10 seconds and a weight of 50g was hung at one end, and the tissue bonding time was recorded as the time taken for the two pigskins to be fully bonded without slipping and able to withstand the weight of 50 g. After 10 minutes of bonding, the sample was peeled at a 90 ° angle and the tissue peel force was recorded in the tensile tester, yielding the data in table 1.
As can be seen from a comparison of the data in table 1: compared with cyanoacrylate medical adhesive, the polysaccharide-based tissue adhesive medical adhesive has the advantages of faster tissue adhesion time and higher tissue peeling force, can realize the rapid adhesion and closure of wounds, and has strong adhesion force with tissues after application and difficult peeling.
TABLE 1
Figure BDA0002936342000000072
Fig. 1 shows that the powdered polysaccharide-based tissue-adhesive medical gel 1 is applied to fresh pig skin, and it can be seen from fig. 1 that the powdered polysaccharide-based tissue-adhesive medical gel is fluffy, has good adhesiveness, and is easy to use.
Fig. 2 shows that the gel-like polysaccharide-based tissue adhesive medical glue 2 is applied to the back of the hand of a volunteer, and it can be seen from fig. 2 that the gel-like polysaccharide-based tissue adhesive medical glue is easy to use, has high biosafety and strong adhesion with human skin tissue.
Fig. 3 is a tensile test of the polysaccharide-based tissue adhesive medical glue 1 after adhesion, and it can be seen from fig. 3 that the polysaccharide-based tissue adhesive medical glue can bear 500g of tensile force, is suitable for a stretched wound, and can realize effective closure.
Fig. 4 is a polysaccharide-based tissue-adhesive medical adhesive 3 rat dorsal skin adhesion experiment, and it can be seen from fig. 4 that the polysaccharide-based tissue-adhesive medical adhesive can be widely used for closing wounds of biological tissues and has high biological safety.
Fig. 5 is a stress-strain mechanical property test of the polysaccharide-based tissue bonding medical adhesive, wherein curves 1 to 5 from left to right in the graph respectively represent stress-strain curves of the polysaccharide-based tissue bonding medical adhesive 6, the polysaccharide-based tissue bonding medical adhesive 4, the polysaccharide-based tissue bonding medical adhesive 7, the polysaccharide-based tissue bonding medical adhesive 8 and the polysaccharide-based tissue bonding medical adhesive 2, and can be seen from fig. 5: the polysaccharide-based tissue bonding medical adhesive has the tensile strength ranging from 5.8 MPa to 14.1MPa after bonding, which shows that the polysaccharide-based tissue bonding medical adhesive has higher tensile strength and can generate stronger bonding effect.
Fig. 6 is a scanning electron microscope image of the cross-linked structure of the polysaccharide-based tissue-adhesive medical glue 5. As can be seen from fig. 6, the polysaccharide-based tissue-binding medical glue allows linear molecules to be attached to each other to form a network structure, which improves the strength and elasticity of the adhesive.
Fig. 7 is a gel-forming rheology diagram of polysaccharide-based tissue-adhesive medical gel 3. It can be seen from fig. 7 that the faster gel time (only 30 seconds) of the powdered polysaccharide-based tissue-adhesive medical glue allows for rapid adhesion.
Finally, it is noted that the above-mentioned preferred embodiments illustrate rather than limit the invention, and that, although the invention has been described in detail with reference to the above-mentioned preferred embodiments, it will be understood by those skilled in the art that various changes in form and detail may be made therein without departing from the scope of the invention as defined by the appended claims.

Claims (2)

1. The polysaccharide-based tissue-adhesive medical adhesive is characterized by consisting of a polysaccharide derivative and a compound with at least two reactive functional groups, wherein the polysaccharide derivative and the compound with at least two reactive functional groups generate an adhesive effect through one or more of physical action or chemical reaction; the polysaccharide derivative is polysaccharide substituted by functional groups; the functional group is polyethylene glycol, the functional group is cyclodextrin, the tissue adhesion time of the polysaccharide-based tissue adhesion medical glue to an organism is 30 seconds, the tissue peeling force is 240.4g/cm, the polysaccharide derivative is polyethylene glycol modified pullulan, and the structural formula is as follows:
Figure FDA0003703682480000011
,
wherein m is 15-4000, n is 1-3600, the substitution degree is 5%, and the preparation of the polysaccharide-based tissue bonding medical adhesive comprises the following steps: dissolving 2g of polyethylene glycol modified pullulan and 0.6g of alpha-cyclodextrin in 60mL of deionized water, stirring for 3 hours, and conventionally purifying, drying and grinding to obtain powdery polysaccharide-based tissue adhesive medical adhesive.
2. Use of the polysaccharide-based tissue-adhesive medical glue according to claim 1 for the preparation of a wound tissue-adhesive material.
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