CN111744053A - Dual-network surgical adhesive and preparation method thereof - Google Patents
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- A—HUMAN NECESSITIES
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- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- 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
- A61L24/02—Surgical adhesives or cements; Adhesives for colostomy devices containing inorganic materials
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L24/00—Surgical adhesives or cements; Adhesives for colostomy devices
- A61L24/04—Surgical adhesives or cements; Adhesives for colostomy devices containing macromolecular materials
- A61L24/046—Surgical adhesives or cements; Adhesives for colostomy devices containing macromolecular materials obtained otherwise than 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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- 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
- C08B37/0084—Guluromannuronans, e.g. alginic acid, i.e. D-mannuronic acid and D-guluronic acid units linked with alternating alpha- and beta-1,4-glycosidic bonds; Derivatives thereof, e.g. alginates
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Abstract
The invention relates to the field of biological materials, and discloses a double-network medical surgical adhesive and a preparation method thereof. The medical surgical adhesive is in a liquid state at the initial mixing stage, can fill gaps of wound surfaces, is chemically crosslinked in a short time, is gelatinized by mixed solution, finally forms gel with good adhesion and filling on the wound surfaces, and effectively improves the adhesive property of the gel by adding a proper amount of hydroxyapatite.
Description
Technical Field
The invention relates to the field of biological materials, in particular to a dual-network medical surgical adhesive and a preparation method thereof.
Background
Suturing is the most common method of wound healing and repair after trauma or surgery, but this method has many disadvantages, such as further damage to the tissue, increased probability of infection, and leakage of body fluids and air. Surgical adhesives are gels that are cross-linkable in situ, are important materials for wound healing and tissue repair, and produce a mechanically strong adhesion between tissues and form a barrier at the wound site, as compared to conventional suturing methods. With the improvement of the requirements of operations and the requirements of wound closure and healing, the biological glue has a great application prospect.
The general purpose of a tissue sealant is to rapidly attach tissue to form a temporary barrier to prevent fluid leakage (e.g., blood, intestinal contents, cerebrospinal fluid) and gases (e.g., air) from a tissue wound following a surgical incision or resection. Tissue sealants may be used as an adjunct to conventional tissue closure methods (e.g., suturing or bonding), but they may also be used alone as a wound closure material.
Current commercial tissue sealants do not perform well in moist and highly dynamic environments, such as not providing good adhesion in the presence of blood. In addition, most clinically available adhesives and sealants do not provide elasticity and good adhesion. For example, cyanoacrylate adhesives are fast-adhering, strong but inelastic after curing, and polysaccharide adhesives have tissue-like elasticity but relatively weak adhesion. Thus, the clinical need for surgical sealants has not been met and there is still much room for growth in the bioadhesive market.
Disclosure of Invention
Aiming at the problems in the prior art, the invention provides a preparation method of a double-network medical surgical adhesive, and the adhesive prepared by the method has the elasticity similar to that of tissues, has strong adhesive force and still has good adhesive effect under the humid condition.
In order to achieve the purpose, the invention adopts the following technical scheme:
a preparation method of a double-network medical surgical adhesive comprises the following steps:
s1, dissolving the modified sodium alginate in a phosphate buffer solution to obtain a light yellow solution as a first solution; mixing the modified polyamino and carboxyl high molecular polymer and mesoporous hydroxyapatite in a phosphate buffer solution, and stirring until the mixture is clear and transparent to obtain a second solution;
s2, filling the first solution and the second solution into syringes with equal volumes, pushing the syringes in a duplex injection device, and mixing the solutions with equal volumes to form gel.
The modification method of the modified sodium alginate in the step S1 is to oxidize the hydroxyl group of the sodium alginate into aldehyde group by using an oxidant; the modification method of the modified polyamino and carboxyl high molecular polymer is that after carboxyl is activated by EDC and NHS, dopamine is added; the phosphate buffer solution is prepared from potassium dihydrogen phosphate, disodium hydrogen phosphate, sodium chloride and potassium chloride, and the pH value of the phosphate buffer solution is 7.4.
Preferably, the modified sodium alginate is obtained by reacting sodium alginate with an oxidant, wherein the oxidant is one or more of periodate, permanganate, hypochlorite, ozone, peroxide, hydroperoxide, persulfate and peroxyorganic acid.
More preferably, the oxidizing agent is sodium periodate, and the mass ratio of the sodium alginate to the sodium periodate is 1: 0.1-3; the modification process of the sodium alginate specifically comprises the following steps: dissolving sodium alginate in ultrapure water with the concentration of 5-10 wt%, adding sodium periodate, and reacting for 12-24h in a dark place.
Preferably, the aperture of the hydroxyapatite is 5-10nm, and the particle size is 100-300 nm; the preparation method of the hydroxyapatite can be chemical precipitation method, hydrothermal synthesis method, sol-gel method and simulated body fluid method, and more preferably, the hydroxyapatite prepared by the hydrothermal method has the best effect.
Preferably, the polyamino and carboxyl high molecular polymer is gelatin, and further, the modification method of gelatin specifically comprises: dissolving gelatin in ultrapure water at 35-50 ℃ to a concentration of 1-5 wt%, adding EDC and NHS, activating for 0.5-2h, and adding dopamine, wherein the mass ratio of gelatin to dopamine is 1:0.1-5, and the mass ratio of dopamine to EDC and NHS is 1:1-2: 0.8-1.5. More preferably, the method for modifying gelatin comprises the following steps: dissolving gelatin in ultrapure water at 40 ℃ to obtain a concentration of 1 wt%, adding EDC and NHS, activating for 0.5h, and adding dopamine, wherein the mass ratio of gelatin to dopamine is 1:1, and the mass ratio of dopamine to EDC and NHS is 1:1: 0.8.
Further, in the above technical scheme, the concentration of the modified sodium alginate in the first solution is 5-10 wt%, the concentration of the modified gelatin in the second solution is 10-20 wt%, and the concentration of the hydroxyapatite in the second solution is 0.005-1 wt%.
The invention has the beneficial effects that: the modified sodium alginate and the modified polyamino and carboxyl high molecular polymer form cross-linking points through dopamine self-polymerization and Schiff base reaction, and gel with a three-dimensional network structure is rapidly formed in situ, so that the gel is favorable for cell adhesion and tissue growth. And dopamine and aldehyde groups on the hydrogel network can react with amino or sulfydryl and other functional groups on tissues, so that better wet adhesion performance is provided. In addition, by adding hydroxyapatite, the adhesive force of the hydrogel is effectively improved while the good biocompatibility of the hydrogel is ensured.
Drawings
FIG. 1 is a graph of results of rheological property measurements of a dual-network medical surgical adhesive prepared according to the present invention;
FIG. 2 is a schematic illustration of the lap shear test method for detecting adhesive gel adhesion;
FIG. 3 is a surface SEM image of a dual-network medical surgical adhesive prepared according to example 2 of the present invention;
FIG. 4 is a SEM image of a cut surface of the dual-network medical surgical adhesive prepared in example 2 of the present invention;
FIG. 5 is a schematic diagram of gel formation in the present invention (left is in solution state, right is in gel state).
Detailed Description
The present invention will be described in detail with reference to examples, but those skilled in the art will appreciate that the following examples are only illustrative of the present invention and should not be construed as limiting the scope of the present invention. The examples, in which specific conditions are not specified, were conducted under conventional conditions or conditions recommended by the manufacturer. The reagents or instruments used are not indicated by the manufacturer, and are all conventional products available commercially.
In the description of the present invention, it should be noted that the terms "first", "second", and the like are used only for distinguishing the description, and are not intended to indicate or imply relative importance.
The following describes the dual-network medical surgical adhesive and the preparation method thereof in detail.
A preparation method of a double-network medical surgical adhesive comprises the following steps:
(1) dissolving the modified sodium alginate in a phosphate buffer solution, and uniformly stirring to obtain a light yellow solution as a first solution. Specifically, a manual stirring mode can be adopted, and the stirring time is 5-20 min.
Sodium alginate is a byproduct after iodine and mannitol are extracted from brown algae such as kelp or gulfweed, the molecule of the sodium alginate is formed by connecting beta-D-mannuronic acid (beta-D-mannuronic acid, M) and alpha-L-guluronic acid (alpha-L-guluronic acid, G) according to a (1 → 4) bond, and the sodium alginate is a natural polysaccharide and has stability, solubility, viscosity and safety required by pharmaceutical preparation auxiliary materials.
(2) Mixing hydroxyapatite and modified polyamino and carboxyl high molecular polymers in a phosphate buffer solution, and stirring until the mixture is clear and transparent to obtain a second solution; specifically, ultrasonic stirring is adopted for 5-20 min.
(3) The first solution and the second solution are filled into syringes with equal volume, and pushed and mixed in a duplex injection device to form gel.
The modification is to oxidize two adjacent hydroxyl groups of the sodium alginate into aldehyde groups, and the aldehyde groups react with the modified polyamino groups and the amino groups on the carboxyl high molecular polymer to generate Schiff base reaction to form a first network. The modified polyamino and carboxyl high molecular polymer uses EDC and NHS to activate carboxyl, reacts with amino on dopamine molecules, introduces dopamine, and enhances wet adhesion. At the same time, dopamine oxidizes and auto-polymerizes to form a second network.
Example 1
Weighing 1g of sodium alginate, dissolving in 50ml of water, adding 0.75g of sodium periodate, reacting for 24 hours in a dark place, dialyzing for three days, and freeze-drying to obtain the modified sodium alginate.
Gelatin was dissolved in ultrapure water at 40 ℃ at a concentration of 1 wt%, EDC and NHS were added, and after activation for 0.5h, dopamine was added. Wherein the mass ratio of the gelatin to the dopamine is 1:1, and the mass ratio of the dopamine to the EDC and the NHS is 1:1: 0.8.
0.1g of modified sodium alginate is weighed and dissolved in 1ml of phosphate solution, and stirred to be fully dissolved to obtain a light yellow solution as a first solution. Weighing 0.2g of modified gelatin, dissolving in 1ml of phosphate solution, adding 0.01g of hydroxyapatite (prepared by a hydrothermal method, the particle size of the hydroxyapatite is 100-300nm, and the pore diameter is 5-10nm), and ultrasonically stirring for 20 minutes to obtain a light yellow solution as a second solution.
1ml of the first solution and 1ml of the second solution were filled into a 1ml syringe and mixed into a gel by pushing in a duplex syringe.
Example 2
Weighing 1g of sodium alginate, dissolving in 50ml of water, adding 1g of sodium periodate, reacting for 24 hours in a dark place, dialyzing for three days, and freeze-drying to obtain the modified sodium alginate.
Gelatin was dissolved in ultrapure water at 40 ℃ at a concentration of 1 wt%, EDC and NHS were added, and after activation for 0.5h, dopamine was added. Wherein the mass ratio of the gelatin to the dopamine is 1:1, and the mass ratio of the dopamine to the EDC and NHS is 1:1:0.8, so as to obtain the modified gelatin.
0.1g of modified sodium alginate is weighed and dissolved in 1ml of phosphate solution, and the solution is fully dissolved by manual stirring to obtain a light yellow solution as a first solution. Weighing 0.2g of modified gelatin, dissolving in 1ml of phosphate solution, adding 0.01g of hydroxyapatite (prepared by a hydrothermal method, the particle size is 100-300nm, and the pore diameter is 5-10nm), and ultrasonically stirring for 20 minutes to obtain a light yellow solution as a second solution.
1ml of the first solution and 1ml of the second solution were filled into a 1ml syringe and mixed into a gel by pushing in a duplex syringe.
Comparative example 1
Weighing 1g of sodium alginate, dissolving in 50ml of water, adding 0.75g of sodium periodate, reacting for 24 hours in a dark place, dialyzing for three days, and freeze-drying to obtain the modified sodium alginate.
Gelatin was dissolved in ultrapure water at 40 ℃ at a concentration of 1 wt%, EDC and NHS were added, and after activation for 0.5h, dopamine was added. Wherein the mass ratio of the gelatin to the dopamine is 1:1, and the mass ratio of the dopamine to the EDC and NHS is 1:1:0.8, so as to obtain the modified gelatin.
0.1g of modified sodium alginate is weighed and dissolved in 1ml of phosphate solution, and the solution is fully dissolved by manual stirring to obtain a light yellow solution as a first solution. 0.2g of modified gelatin was weighed and dissolved in 1ml of phosphate solution to obtain a pale yellow solution as a second solution.
1ml of the first solution and 1ml of the second solution were filled into a 1ml syringe and mixed into a gel by pushing in a duplex syringe.
Comparative example 2
Weighing 1g of sodium alginate, dissolving in 50ml of water, adding 1g of sodium periodate, reacting for 24 hours in a dark place, dialyzing for three days, and freeze-drying.
Gelatin was dissolved in ultrapure water at 40 ℃ at a concentration of 1 wt%, EDC and NHS were added, and after activation for 0.5h, dopamine was added. Wherein the mass ratio of the gelatin to the dopamine is 1:1, and the mass ratio of the dopamine to the EDC and NHS is 1:1:0.8, so as to obtain the modified gelatin.
0.1g of modified sodium alginate is weighed and dissolved in 1ml of phosphate solution, and the solution is fully dissolved by manual stirring to obtain a light yellow solution as a first solution. 0.2g of modified gelatin was weighed and dissolved in 1ml of phosphate solution to obtain a pale yellow solution as a second solution.
1ml of the first solution and 1ml of the second solution were filled into a 1ml syringe and mixed into a gel by pushing in a duplex syringe.
The dual-network medical surgical adhesive prepared in the examples 1-2 and the comparative examples 1-2 is prepared into a test sample for rheological property detection, and the test process is as follows:
preparing hydrogel into gel samples with diameter of 26mm and height of 3mm, placing 5 gel samples on a plane aluminum plate with diameter of 26mm, and setting sample gaps3mm, the temperature of the sample is controlled by the rheometer system, the temperature is maintained at 37 ℃, and the relevant rheometer parameters are frequency: 0.1-10 rad · s-1The target value for deformation is 1%. The test results are shown in fig. 1. Wherein the results of example 1 are shown as S1; the results of example 2 are shown as S2; the result of comparative example 1 is shown as S3; the result of comparative example 2 is shown as S4.
As can be seen from FIG. 1, the dual-network medical surgical adhesive prepared in the examples 1-2 and the comparative examples 1-2 of the invention has higher storage modulus and loss modulus.
The dual network medical surgical adhesive prepared in examples 1 to 2 and comparative examples 1 to 2 was prepared as a test sample for adhesion test, and the test procedure was as follows:
cutting Corii Sus Domestica into strips with length of 10 cm and width of 2 cm, placing 1ml of the first solution and 1ml of the second solution into 1ml syringe, mixing by pushing in a duplex injection device, and coating onto the surface of Corii Sus Domestica with coating area of 4cm-1After coating, two pigskins are lapped, and the lapping area is 4cm-1. After 10 minutes, an adhesion test was carried out by means of a universal tensile machine (tensile rate of tensile tester 5 to 300 mm. min. -1), tensile rate of 10mm/min at room temperature, and adhesion was measured to give 32Kpa for example 1, 46Kpa for example 2, 15Kpa for comparative example 1 and 21Kpa for comparative example 2. The adhesive force of the examples 1 and 2 is greatly improved compared with that of the comparative example, which shows that the addition of the hydroxyapatite effectively improves the problem of poor adhesive force, and the reason is presumed to be that: the strength of the hydrogel is weaker than the adhesive strength, and the strength of the hydrogel is enhanced by adding the hydroxyapatite, so that the adhesive force is improved; the surface of the hydroxyapatite contains hydroxyl which can form hydrogen bond with tissues, thereby improving the adhesive strength. Also, example 2 has the highest adhesive force, and the maximum adhesive force to obtain an injectable adhesive is 46 Kpa. Example 2 the adhesion force was higher than that of example 1, which is presumed to be because: in example 2, sodium alginate has a higher degree of oxidation, contains more aldehyde groups, and serves as a reaction site, so that the bonding strength is higher. In experiments, the fact that the strength of the hydrogel is weakened and the adhesion force is weakened due to excessive addition of the hydroxyapatite is also found; particle sizeToo large will weaken the strength of the hydrogel and reduce adhesion.
The above description is only a preferred embodiment of the present invention and is not intended to limit the present invention, and various modifications and changes may be made by those skilled in the art. Any modification, equivalent replacement, or improvement made within the spirit and principle of the present invention should be included in the protection scope of the present invention.
Claims (9)
1. The preparation method of the double-network surgical adhesive is characterized by comprising the following steps:
s1, dissolving the modified sodium alginate in a phosphate buffer solution to serve as a first solution; mixing hydroxyapatite with modified polyamino and carboxyl high molecular polymer, and dissolving the mixture in a phosphate buffer solution to obtain a second solution;
s2, mixing the first solution and the second solution into gel in equal volume;
the modification method of the modified sodium alginate in the step S1 is to oxidize the hydroxyl group of the sodium alginate into aldehyde group by using an oxidant; the modification method of the modified polyamino and carboxyl high molecular polymer is to add dopamine after activating carboxyl by EDC and NHS.
2. The preparation method of the dual-network surgical adhesive according to claim 1, wherein the modified sodium alginate is obtained by reacting sodium alginate with an oxidant, wherein the oxidant is one or more of periodate, permanganate, hypochlorite, ozone, peroxide, hydroperoxide, persulfate and peroxyorganic acid.
3. The method for preparing the dual-network surgical adhesive as claimed in claim 2, wherein the oxidizing agent is sodium periodate, and the mass ratio of the sodium alginate to the sodium periodate is 1: 0.1-3.
4. The preparation method of the dual-network surgical adhesive according to claim 3, wherein the method for modifying sodium alginate by using the oxidant comprises the following steps: dissolving sodium alginate in ultrapure water with the concentration of 5-10 wt%, adding sodium periodate, and reacting for 12-24h in a dark place.
5. The method for preparing the dual-network surgical adhesive according to claim 1, wherein the pore size of the hydroxyapatite is 5-10nm, and the particle size is 100-300 nm.
6. The method of claim 1 wherein the polyamino and carboxyl polymers are gelatin.
7. The method for preparing the dual-network surgical adhesive according to claim 6, wherein the gelatin is modified by the following steps: dissolving gelatin in ultrapure water at 35-50 deg.C to a concentration of 1-5 wt%, adding EDC and NHS, activating for 0.5-2 hr, and adding dopamine. Wherein the mass ratio of the gelatin to the dopamine is 1:0.1-5, and the mass ratio of the dopamine to the EDC and the NHS is 1:1-2: 0.8-1.5.
8. The method for preparing the dual-network surgical adhesive according to claim 6, wherein the concentration of the modified sodium alginate in the first solution is 5-10 wt%, the concentration of the modified gelatin in the second solution is 10-20 wt%, and the concentration of the hydroxyapatite in the second solution is 0.005-1 wt%.
9. A surgical adhesive prepared by the process of any one of claims 1 to 8.
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| CN113524745A (en) * | 2021-07-01 | 2021-10-22 | 金塑企业集团（上海）有限公司 | High-strength polyolefin composite pipe and preparation method thereof |
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| CN113524745A (en) * | 2021-07-01 | 2021-10-22 | 金塑企业集团（上海）有限公司 | High-strength polyolefin composite pipe and preparation method thereof |
| CN113524745B (en) * | 2021-07-01 | 2022-05-20 | 金塑企业集团（上海）有限公司 | High-strength polyolefin composite pipe and preparation method thereof |
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