CN113209356A - Preparation method of biological tissue adhesive and product thereof - Google Patents
Preparation method of biological tissue adhesive and product thereof Download PDFInfo
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- CN113209356A CN113209356A CN202110466327.8A CN202110466327A CN113209356A CN 113209356 A CN113209356 A CN 113209356A CN 202110466327 A CN202110466327 A CN 202110466327A CN 113209356 A CN113209356 A CN 113209356A
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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
- 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
- A61L24/0015—Medicaments; Biocides
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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
- A61L24/0042—Materials resorbable by the body
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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
- 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
- A61L2300/23—Carbohydrates
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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
- 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
- A61L2300/404—Biocides, antimicrobial agents, antiseptic agents
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Abstract
本发明公开了一种生物组织粘合剂的制备方法及其产品，生物组织粘合剂的制备方法，包括以下步骤：(1)在容器里加入γ‑聚谷氨酸和去离子水并在室温下进行搅拌，直至完全溶解；(2)待γ‑聚谷氨酸完全溶解后加入盐酸酪胺和单宁酸，继续搅拌得到A组分溶液；(3)用去离子水溶解4‑(4,6‑二甲氧基三嗪‑2‑基)‑4‑甲基吗啉盐酸盐，得到B组分溶液；(4)将A组分溶液和B组分溶液混合，搅拌均匀后得到生物组织粘合剂。还公开了由上述方法制备的生物组织粘合剂产品。本发明解决现有技术中市售医用组织粘合剂粘合度不高、机械强度差、不易生物降解以及降解产物的毒性和致癌性的缺点的问题。
The invention discloses a preparation method and a product of a biological tissue adhesive. The preparation method of the biological tissue adhesive comprises the following steps: (1) adding γ-polyglutamic acid and deionized water into a container and placing the Stir at room temperature until completely dissolved; (2) after γ-polyglutamic acid is completely dissolved, add tyramine hydrochloride and tannic acid, continue stirring to obtain A component solution; (3) dissolve 4-( 4,6-dimethoxytriazine-2-yl)-4-methylmorpholine hydrochloride to obtain B component solution; (4) mixing A component solution and B component solution, after stirring evenly Obtain biological tissue adhesive. Also disclosed are biological tissue adhesive products prepared by the above method. The invention solves the problems in the prior art that the commercial medical tissue adhesives have low adhesiveness, poor mechanical strength, difficult biodegradation, and the toxicity and carcinogenicity of degradation products.
Description
Technical Field
The invention relates to the technical field of biological tissue adhesives, in particular to a preparation method of a biological tissue adhesive and a product thereof.
Background
Tissue adhesives are increasingly preferred by patients and physicians during surgery to cover the entire wound area, eliminate the problem of stress localization associated with sutures, and have the advantages of being easy to apply, not requiring removal of the sutures, reducing procedure time, providing an aesthetic appearance, and reducing patient pain.
Currently, several types of commercial tissue adhesives used in many surgical procedures are largely classified as synthetic tissue adhesives or biological tissue adhesives. For example, cyanoacrylate, a representative synthetic tissue adhesive, undergoes rapid polymerization upon contact with anionic substances (including water and blood), and ensures highly stable adhesive strength on living tissues. However, a decisive disadvantage of cyanoacrylate-based tissue adhesives is the strong toxicity of formaldehyde, a degradation product thereof. Fibrin glue mimics the final phase of blood coagulation and has been successfully used as a novel biological tissue adhesive in almost all surgical fields due to its good biocompatibility. However, there are some disadvantages, such as weak tensile strength and adhesive strength, risk of viral contamination, etc., which limit the wider use of fibrin glue.
The most common method of developing optimal tissue adhesives is to use natural materials: chitosan, cellulose, alginate, hyaluronic acid, starch, chondroitin and the like, which have proven to be more biocompatible than synthetic materials. Polysaccharide adhesives have become important materials for tissue adhesion due to their advantages of degradability and biocompatibility, but they still have some disadvantages. Polysaccharides generally have the disadvantages of low solubility, poor adhesion to moist tissues, short degradation time, biological origin, and the like.
Disclosure of Invention
The invention mainly aims to provide a preparation method of a biological tissue adhesive and a product thereof, and aims to solve the problems that the medical tissue adhesive sold in the market in the prior art has the defects of poor mechanical strength, difficult biodegradation, and toxicity and carcinogenicity of degradation products.
In order to achieve the above object, according to one aspect of the present invention, there is provided a method for preparing a biological tissue adhesive, comprising the steps of:
(1) adding gamma-polyglutamic acid and deionized water into a container, and stirring at room temperature until the gamma-polyglutamic acid and the deionized water are completely dissolved;
(2) after the gamma-polyglutamic acid is completely dissolved, adding tyramine hydrochloride and tannic acid, and continuously stirring to obtain a component A solution;
(3) dissolving 4- (4, 6-dimethoxy triazine-2-yl) -4-methyl morpholine hydrochloride by deionized water to obtain a component B solution;
(4) and mixing the component solution A and the component solution B, and uniformly stirring to obtain the biological tissue adhesive.
Further, in the step (1), 0.3-0.5g of gamma-polyglutamic acid and 1.7mL of deionized water are added into a container and stirred at room temperature until the gamma-polyglutamic acid is completely dissolved;
step (2) after the gamma-polyglutamic acid is completely dissolved, adding 0.15-0.25g of tyramine hydrochloride and 0.025-0.0.075g of tannic acid, and continuously stirring to obtain a component A solution;
in the step (3), 0.2-0.3g of 4- (4, 6-dimethoxytriazin-2-yl) -4-methylmorpholine hydrochloride is dissolved in 0.5mL of deionized water to obtain a solution of the component B.
Further, the molecular weight of gamma-polyglutamic acid is 800 kDa.
According to another aspect of the present invention, there is provided a biological tissue adhesive prepared according to the above method.
Compared with the prior art, the invention has the beneficial effects that: the invention takes gamma-polyglutamic acid, tyramine hydrochloride, tannic acid, 4- (4, 6-dimethoxy triazine-2-yl) -4-methylmorpholine hydrochloride as raw materials, the polyglutamic acid is a natural polymer with good water solubility, moisture retention, adhesion, biodegradability and biocompatibility, and carboxyl on the structure can react with ferrous ions in blood to form blood clots to block wounds, thereby effectively stopping bleeding. The amide condensing agent 4- (4, 6-dimethoxytriazine-2-yl) -4-methylmorpholine hydrochloride (DMTMM) is used for crosslinking polyglutamic acid and tyramine hydrochloride, and tannic acid is added to crosslink with the polyglutamic acid through hydrogen bonds, so that the mechanical property of the hydrogel adhesive is enhanced, the adhesion strength is improved, and the tannic acid also has antibacterial and antioxidant effects. The biological adhesive synthesized by the invention is safe, nontoxic and easy to prepare, has better moisture-resistant adhesion capability and good biocompatibility, can be completely degraded after the tissue is healed by self-generation, and can be absorbed by the organism or discharged out of the body along with metabolism.
Compared with the prior art, the raw materials are cheap and easy to purchase, secondary treatment and processing are not needed, the preparation process is simplified, and the raw materials are prepared into A, B-component solution during actual production and sale and then are stored at normal temperature, and are storage-resistant and transport-resistant. Compared with the biological tissue adhesive in the prior art, the biological tissue adhesive can increase the shape of the well-adapted biological tissue and be attached to the surface of the biological tissue.
Therefore, the natural biological materials of polyglutamic acid, tyramine hydrochloride and tannic acid are used as raw materials to prepare the adhesive, and the synthesized biological adhesive is safe and non-toxic, has better moisture-resistant adhesion capability and good biocompatibility, can be completely degraded after the tissue is healed by self-generation, and can be absorbed by the organism or be discharged out of the body along with metabolism.
The invention is further described with reference to the following figures and detailed description. Additional aspects and advantages of the invention will be set forth in part in the description which follows and, in part, will be obvious from the description, or may be learned by practice of the invention.
Drawings
FIG. 1 is a graph showing the results of measuring the swelling ratio of the biological tissue adhesives prepared in examples 1 to 9 of the present invention.
Detailed Description
The invention will be described more fully hereinafter with reference to the accompanying drawings. Those skilled in the art will be able to implement the invention based on these teachings. Before the present invention is described in detail with reference to the accompanying drawings, it is to be noted that:
the technical solutions and features provided in the present invention in the respective sections including the following description may be combined with each other without conflict.
Moreover, the embodiments of the present invention described in the following description are generally only some embodiments of the present invention, and not all embodiments. Therefore, all other embodiments obtained by a person of ordinary skill in the art based on the embodiments of the present invention without any creative effort shall fall within the protection scope of the present invention.
With respect to terms and units in the present invention. The terms "comprising," "having," and any variations thereof in the description and claims of this invention and the related sections are intended to cover non-exclusive inclusions.
According to an aspect of the present invention, there is provided a method of preparing a biological tissue adhesive, comprising the steps of:
(1) adding gamma-polyglutamic acid and deionized water into a container, and stirring at room temperature until the gamma-polyglutamic acid and the deionized water are completely dissolved;
(2) after the gamma-polyglutamic acid is completely dissolved, adding tyramine hydrochloride and tannic acid, and continuously stirring to obtain a component A solution;
(3) dissolving 4- (4, 6-dimethoxy triazine-2-yl) -4-methyl morpholine hydrochloride by deionized water to obtain a component B solution;
(4) and mixing the component solution A and the component solution B, and uniformly stirring to obtain the biological tissue adhesive.
Further, in the step (1), 0.3-0.5g of gamma-polyglutamic acid and 1.7mL of deionized water are added into a container and stirred at room temperature until the gamma-polyglutamic acid is completely dissolved;
step (2) after the gamma-polyglutamic acid is completely dissolved, adding 0.15-0.25g of tyramine hydrochloride and 0.025-0.0.075g of tannic acid, and continuously stirring to obtain component A solution
In the step (3), 0.2-0.3g of 4- (4, 6-dimethoxytriazin-2-yl) -4-methylmorpholine hydrochloride is dissolved in 0.5mL of deionized water to obtain a solution of the component B.
Further, the molecular weight of gamma-polyglutamic acid is 800 kDa.
Further, the amide condensing agent is 4- (4, 6-dimethoxytriazin-2-yl) -4-methylmorpholine hydrochloride.
According to another aspect of the present invention, there is provided a biological tissue adhesive prepared according to the above method.
The invention is further illustrated by the following specific examples:
example 1
The embodiment of the invention provides a preparation method of a biological tissue adhesive with high adhesive strength and wet adhesion resistance, which comprises the following steps:
s1, adding 0.3g of gamma-polyglutamic acid and 1.7mL of deionized water into a beaker, and magnetically stirring at room temperature until the gamma-polyglutamic acid and the deionized water are completely dissolved;
s2, after the gamma-polyglutamic acid is completely dissolved, adding 0.15g of tyramine hydrochloride and 0.025g of tannic acid, and continuously stirring and dissolving uniformly to obtain a component A solution;
s3, dissolving 0.2g amide condensing agent 4- (4, 6-dimethoxytriazine-2-yl) -4-methylmorpholine hydrochloride by 0.5mL deionized water to obtain a component B solution;
and S4, mixing the component A and the component B, uniformly stirring, and gelling within 5min to obtain the biological tissue adhesive.
Examples 2 to 9
Examples 2 to 9 provide a method for preparing a high-adhesive-strength and wet-adhesion-resistant biological tissue adhesive, which is different from example 1 in that the mass of gamma-polyglutamic acid in step S1, the mass of tyramine hydrochloride and tannic acid in step S2, and the mass of 4- (4, 6-dimethoxytriazin-2-yl) -4-methylmorpholine hydrochloride in step S3 are changed, and the remaining steps are not changed, and the specific mixing ratio parameters of the relevant reactions in examples 2 to 9 are shown in table 1:
TABLE 1
| Examples | PGA(g) | Tyr·HCI(g) | TA(g) | DMTMM(g) |
| Example 2 | 0.3 | 0.2 | 0.05 | 0.25 |
| Example 3 | 0.3 | 0.25 | 0.075 | 0.3 |
| Example 4 | 0.4 | 0.15 | 0.50 | 0.3 |
| Example 5 | 0.4 | 0.2 | 0.075 | 0.2 |
| Example 6 | 0.4 | 0.25 | 0.025 | 0.25 |
| Example 7 | 0.5 | 0.15 | 0.075 | 0.25 |
| Example 8 | 0.5 | 0.2 | 0.025 | 0.3 |
| Example 9 | 0.5 | 0.25 | 0.05 | 0.2 |
The biological tissue adhesives prepared in examples 1 to 9 were tested for their shear adhesion strength to glass, rubber, PTFE, pigskin, rabbit skin, and sheep skin, and the results are shown in table 2:
TABLE 2
The biological tissue adhesives prepared in examples 1 to 9 were subjected to a swelling test in PBS, and the results are shown in fig. 1. The numbers of the curves in the figure correspond to the numbers of the examples, and it can be seen from FIG. 1 that the swelling ratio of example 4 is the lowest, the equilibrium swelling is about 9g/g, and the best adhesion effect of example 4 is shown; the highest value was found in example 9, and the equilibrium swelling ratio was about 30 g/g. All the biological tissue adhesives prepared in the examples show lower level of equilibrium swelling ratio, which shows that the biological tissue adhesives prepared by the invention have good bonding effect and high adhesive strength.
The heart, liver, spleen, lung and kidney tests of the rabbit with the biological tissue adhesives prepared in examples 1-9 show that the biological tissue adhesives prepared by the invention have good adhesion effect on various organs.
The biological tissue adhesives prepared in examples 1 to 9 were subjected to a test for bonding rabbit intestine, a 0.3cm wound was cut in the rabbit intestine, and the adhesive was bonded with the biological tissue adhesive prepared in example 4, which was placed under a tap and water was passed through, and the water flow smoothly passed through the rabbit intestine, and the biological tissue adhesive did not leak out of the wound and also did not fall off.
The biological tissue adhesives prepared in examples 1 to 9 were subjected to a test of bonding a rabbit stomach, a 1cm wound was cut in the middle of the stomach, and after bonding with the biological tissue adhesives prepared in examples 1 to 9, the stomach was filled with water and shaken, and no water was exuded from the wound and no detachment of the biological tissue adhesive occurred.
The contents of the present invention have been explained above. Those skilled in the art will be able to implement the invention based on these teachings. All other embodiments, which can be derived by a person skilled in the art from the above description without inventive step, shall fall within the scope of protection of the present invention.
Claims (4)
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN114344553A (en) * | 2022-03-01 | 2022-04-15 | 南京工业大学 | Polyglutamic acid gastric acid-resistant hemostatic adhesive |
| CN116327708A (en) * | 2023-03-31 | 2023-06-27 | 西南交通大学 | Preparation method of nanoparticles and preparation method of nano drug-loaded particles |
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| CN116327708A (en) * | 2023-03-31 | 2023-06-27 | 西南交通大学 | Preparation method of nanoparticles and preparation method of nano drug-loaded particles |
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