CN113398310B - Chitosan catechol hemostatic gauze and preparation method thereof - Google Patents
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Abstract
The invention provides chitosan catechol hemostatic gauze and a preparation method thereof, and the preparation method comprises the following steps: s1, synthesizing a long-side alkenyl catechol compound through Suzuki coupling reaction; s2, immersing the chitosan hemostatic gauze into a sodium alginate solution, and then washing and drying to obtain the hemostatic gauze consisting of the 'skin-core' fiber of the chitosan coated by the sodium alginate; s3, carrying out corona treatment on the hemostatic gauze obtained in the step S2 to introduce free radicals; and S4, reacting the hemostatic gauze obtained in the step S3 with long-side alkenyl catechol compound synthesized in the step S1, and grafting the catechol compound on the surface of the hemostatic gauze to prepare the chitosan catechol hemostatic gauze. The invention has the advantages that: the chitosan catechol hemostatic gauze can be adhered to tissues to prevent blood from seeping outwards; the long alkyl hydrophobic function on the gauze can inhibit the absorption and diffusion of blood in the gauze, so that the gauze can realize the aim of rapid hemostasis; the chitosan can be degraded in vivo, so that it can be used as hemostatic material for human body.
Description
Technical Field
The invention belongs to the technical field of preparation of modified hemostatic gauze, and particularly relates to high-efficiency hemostatic gauze with chitosan modified by long-side alkenyl catechol compound capable of being degraded in vivo and a preparation method thereof.
Background
The chitosan is biodegradable natural polysaccharide with positive charges, and has the advantages of rich source, low cost, stable structure, biocompatibility, biodegradation, safety, no toxicity and the like. It is widely used as a raw material of hemostatic products due to cell, tissue, or mucosal adhesion caused by electrostatic attraction. Clinical hemostatic preparations based on chitosan include hemostatic powders such as Celox®And bandages such as HemCon®And so on. The chitosan hemostatic material can adsorb and gather red blood cells and platelets to form primary thrombus and play a role in hemostasis. The use of the chitosan hemostatic material can greatly improve the survival rate of trauma wounded persons under the condition of bleeding from trauma caused by daily accidents and battlefield injuries. However, the hemostasis mechanism of chitosan is pure physical occlusion hemostasis, so the hemostasis is slow, and is not suitable for hemostasis of a wound with heavy bleeding. Therefore, the improvement of the hemostatic efficiency of chitosan is an urgent need for medical care personnel and wounded persons.
Inspired by the strong adhesion of mussels, products such as adhesive gels, in which catechol groups are grafted onto chitosan molecules to enhance the adhesion of chitosan to tissues, thereby improving the wound sealing and hemostatic ability of the chitosan, have been reported in a great deal of research. In the research of this aspect, 3- (3, 4-dihydroxyphenyl) -propylamine or 3- (3, 4-dihydroxyphenyl) -propionic acid was generally used as a reaction substance to react with chitosan in a homogeneous aqueous solution to form catechol-grafted chitosan. The formed tissue adhesive gel is suitable for sealing hemostasis of small wounds. Gauze is a commonly used hemostatic dressing for large area bleeding wounds or heavy bleeding wounds because gauze is large in area, soft and shapeable to fit the shape of most wounds, and can be packed and pressed with force. Compared with cotton gauze which can not be biodegraded by human body, the chitosan hemostatic gauze has the advantage of being absorbed by human body, so that the chitosan hemostatic gauze can be used for hemostasis of internal wounds, and medical accidents caused by the fact that materials are kept in the body are reduced. However, no research report and patent application of catechol grafted chitosan hemostatic gauze has been found so far.
The applicant has invented urushiol cotton gauze (a preparation method of urushiol modified hemostatic gauze and urushiol modified hemostatic gauze, Liuhaiqing, Zhouyikang, Fangyan, Chinese patent ZL 2019102942289). It has excellent hemostatic performance on trauma. But the gauze cannot be absorbed by human body. In order to overcome the defects, the invention synthesizes the catechol compound with a long monoalkenyl side chain through a chemical reaction, and then the catechol compound is grafted on the surface of chitosan gauze to prepare the hemostatic gauze for human body absorption. Studies have shown that it is very difficult to graft catechol compounds to the surface of chitosan materials by heterogeneous reactions. This is because the amino group of chitosan and the aryl group of catechol compound form cation-pi action, and the amino group of chitosan and the aromatic hydroxyl group of catechol compound form hydrogen bond (as shown in fig. 1), so that the catechol group of catechol compound is adsorbed on the chitosan surface, and the long alkyl chain extends outside, thereby greatly reducing the adhesion of the catechol group on the modified chitosan material surface and the tissue surface, and weakening the hemostatic ability thereof.
Disclosure of Invention
In order to solve the problems in the prior art and prepare the high-efficiency chitosan hemostatic gauze capable of being degraded in vivo, the invention provides the high-efficiency hemostatic gauze (chitosan catechol hemostatic gauze for short) with long-side alkenyl catechol compound modified chitosan and the preparation method thereof. The invention originally utilizes the electrostatic attraction effect to coat a layer of sodium alginate on the surface of chitosan fiber, hides the amino group of chitosan to form composite fiber with chitosan as 'core' and sodium alginate as 'skin', then carries out corona treatment, introduces a reaction group on the surface of the composite fiber with 'core-skin', and carries out free radical grafting reaction with a long-side alkenyl catechol compound, thereby introducing not only a catechol group, but also hydrophobic alkyl (as shown in figure 2).
The invention is realized by the following technical scheme:
a preparation method of chitosan catechol hemostatic gauze comprises the following steps:
s1, synthesizing a long-side alkenyl catechol compound through Suzuki coupling reaction;
s2, immersing the chitosan gauze into a sodium alginate aqueous solution, and then washing and drying to obtain the hemostatic gauze consisting of the 'skin-core' fiber of the sodium alginate-coated chitosan;
s3, carrying out corona treatment on the hemostatic gauze obtained in the step S2 to introduce free radicals;
and S4, reacting the hemostatic gauze obtained in the step S3 with long-side alkenyl catechol compound synthesized in the step S1, and grafting the catechol compound on the surface of the hemostatic gauze to obtain the chitosan catechol hemostatic gauze.
Preferably, in step S1, the long-side alkenyl catechol compound is a monoalkenyl catechol compound having 5 to 14 carbon atoms.
Preferably, in step S2, the chitosan gauze is a woven or non-woven fabric composed of fibers.
Preferably, in step S2, the concentration of the sodium alginate aqueous solution is 0.1-1.0 wt%, and the immersion time is 10-180S.
Preferably, in step S2, the "sheath-core" fiber is a composite fiber with sodium alginate as the sheath and chitosan as the core, and the thickness of the sheath layer is 10-100 nm.
Preferably, in step S3, the corona treatment is performed in air at normal temperature and pressure for 30 to 180 seconds.
Preferably, in step S4, the reaction is carried out in a long-sided alkenyl catechol/ethanol solution. The concentration of the catechol compound in the long side alkenyl catechol/ethanol solution is 0.5-3.0 wt%, the reaction temperature is 50-80 ℃, and the reaction time is 0.5-3 h.
By adopting the technical scheme, the chitosan catechol hemostatic gauze can be adhered to tissues to prevent blood from seeping outwards, and the long alkyl hydrophobic function on the gauze can inhibit the absorption and diffusion of the blood in the gauze, so that the gauze can achieve the aim of rapid hemostasis.
Compared with the prior art, the invention also has the following beneficial effects:
1. the gauze has good in vivo biodegradation capacity.
2. The gauze has a skin-core structure with sodium alginate as the skin and chitosan as the core. The special structure can eliminate physical adsorption of chitosan amino on catechol compound.
3. The catechol compound is an artificially synthesized monoalkenyl catechol compound containing 5-14 carbon atoms, and the compound does not cause anaphylactic reaction of human body.
4. The corona treatment of the gauze is carried out in the air at normal temperature and normal pressure, and is simpler and more convenient than the plasma treatment under the vacuum condition.
5. The catechol group of the gauze has good adhesive capacity with wound tissues, and the gauze has a sealing and hemostatic function.
6. The hydroxyl-amino-carboxyl group and the porous structure of the gauze enable the gauze to have good hydrophilic and water-absorbing capacity, so that red blood cells, platelets and blood coagulation factors around wounds are concentrated, and the formation of thrombus is accelerated.
7. The hydrophobicity of the long alkyl chains on the surface of the gauze can inhibit blood flow and reduce blood loss.
8. Has more efficient hemostatic ability than urushiol cotton gauze.
Drawings
FIG. 1 is a schematic diagram showing the hydrogen bonding of the cation- π of the chitosan amino group with the catechol compound aryl group and the amino group with the catechol group;
FIG. 2 is a schematic diagram of a long-side-chain-alkyl catechol compound modified chitosan fiber to form a sheath-core structure;
FIG. 3 is a scanning electron microscope image of the surface topography of chitosan gauze, sodium alginate-coated chitosan core-skin gauze and chitosan catechol gauze prepared in comparative example 1 and example 2 of the present invention;
FIG. 4 is a graph showing the amount of bleeding from rat femoral artery wounds in chitosan catechol gauze, chitosan gauze and battle gauze prepared in examples 2, 3 and 4 of the present invention and comparative example 1;
FIG. 5 is a graph showing the amount of bleeding from wounds of rat hepatectomy model using chitosan catechol gauze, chitosan gauze and fighting gauze prepared in examples 2, 3 and 4 of the present invention and comparative example 1.
Detailed Description
The present invention will be described in detail with reference to specific examples. The following examples will assist those skilled in the art in further understanding the invention, but are not intended to limit the invention in any way. It should be noted that variations and modifications can be made by persons skilled in the art without departing from the spirit of the invention. All falling within the scope of the present invention.
Example 1
This example relates to the synthesis of a monoalkenylcatechol compound containing 11 carbon atoms, comprising the following steps:
dissolving 9-decene-1 alcohol and 3-4 dihydroxy benzoic acid in Tetrahydrofuran (THF) for reaction, taking 1, 3-Dicyclohexylcarbodiimide (DCC) as a dehydrating agent and 4-Dimethylaminopyridine (DMAP) as an esterification catalyst, and stirring at room temperature for reaction for 12 hours. After the reaction is finished, carrying out rotary evaporation treatment on the liquid to remove tetrahydrofuran, adding ethyl acetate, and carrying out vacuum filtration to remove solids. Pouring the solution into a separating funnel, adding saturated NaCl solution, shaking, standing for layering, taking the upper yellow transparent liquid, then adding the saturated NaCl solution again, and repeating the process for 4 times. Then adding anhydrous Na into the liquid2SO4Removing water from the liquid, adding silica gel, rotary evaporating, and dissolvingAfter the agent is completely volatilized, column chromatography treatment is carried out. Separating to obtain the target product 3, 4-dihydroxy-9-decene phenol ester.
Example 2
The embodiment relates to a preparation method of chitosan catechol hemostatic gauze, which comprises the following steps:
1. soaking chitosan gauze in 0.5 wt% sodium alginate solution for 30 min, taking out, washing with distilled water to remove free sodium alginate, and drying in a vacuum drying oven at 60 deg.C for 10 hr;
2. carrying out corona treatment (argon gas, 80 s) on the hemostatic gauze obtained in the step 1;
3. placing the hemostatic gauze obtained in the step 2 in a 1 wt% long-side alkenyl catechol compound/absolute ethyl alcohol solution for reflux reaction for 1 h, wherein the reaction temperature is 70 ℃;
4. and (4) washing the hemostatic gauze obtained in the step (3) with ethanol to obtain the chitosan hemostatic gauze modified by the long-side chain alkyl catechol compound.
The chitosan catechol hemostatic gauze prepared in this example was labeled as chitosan catechol gauze-1.
The surface topography of the chitosan hemostatic gauze is shown in fig. 3a and a-1. It can be seen that the hemostatic gauze is formed by random packing of fibers having a diameter of 20 microns. The shapes of the fibers of the chitosan-sodium alginate skin-core structure (figures 3b and b-1) and the fibers of the chitosan catechol gauze-1 (figures 3c and c-1) are basically the same as those of the chitosan gauze fibers, which indicates that the gauze surface modification chemical reaction does not have obvious influence on the shape of the gauze.
Example 3
The embodiment relates to a preparation method of chitosan catechol hemostatic gauze, which comprises the following steps:
1. soaking chitosan gauze in 0.5 wt% sodium alginate solution for 30 min, taking out, washing with distilled water to remove free sodium alginate, and drying in a vacuum drying oven at 60 deg.C for 10 h;
2. carrying out corona treatment (argon gas, 80 s) on the hemostatic gauze obtained in the step 1;
3. placing the hemostatic gauze obtained in the step 2 in a 1.5 wt% long side alkenyl catechol compound/absolute ethyl alcohol solution for reflux reaction for 1 h, wherein the reaction temperature is 70 ℃;
4. and (4) washing the hemostatic gauze obtained in the step (3) with ethanol to obtain the chitosan hemostatic gauze modified by the long-side chain alkyl catechol compound.
The chitosan catechol hemostatic gauze prepared in this example was labeled as chitosan catechol gauze-2.
Example 4
The embodiment relates to a preparation method of chitosan hemostatic gauze modified by a long-side alkenyl catechol compound, which comprises the following steps:
1. soaking chitosan gauze in 0.5 wt% sodium alginate solution for 30 min, taking out, washing with distilled water to remove free sodium alginate, and drying in a vacuum drying oven at 60 deg.C for 10 h;
2. carrying out corona treatment (argon gas, 80 s) on the hemostatic gauze obtained in the step 1;
3. placing the hemostatic gauze obtained in the step 2 in a 2 wt% long-side alkenyl catechol compound/absolute ethanol solution for reflux reaction for 1 h, wherein the reaction temperature is 70 ℃;
4. and (4) washing the hemostatic gauze obtained in the step (3) with ethanol to obtain the chitosan hemostatic gauze modified by the long-side chain alkyl catechol compound.
The chitosan catechol hemostatic gauze prepared in this example was labeled as chitosan catechol gauze-3.
Comparative example 1
This comparative example is gauze without modification of the long side alkenyl catechol compound and is reported as chitosan gauze.
Example 5
The embodiment relates to a hemostatic effect test of chitosan catechol hemostatic gauze, which comprises the following steps:
1. injecting 1 mL of 10% chloral hydrate into abdominal cavity of rat to make it narcotize;
2. a 1 cm x 0.5 cm incision was made in the right femoral artery;
3. immediately pressing chitosan catechol hemostatic gauze (chitosan catechol gauze-1, chitosan catechol gauze-2, chitosan catechol gauze-3, chitosan gauze) and combat gauze with known mass on femoral artery wound respectively;
4. pressing for 180 s, weighing, and calculating the amount of bleeding;
5. the amount of bleeding from the femoral wound on the thigh of the chitosan gauze control experiment, the battle gauze, and the chitosan catechol hemostatic gauze series used in this example is shown in fig. 4. The blood loss of chitosan catechol hemostatic gauze series samples is only 6 percent and 3.3 percent of the blood loss of chitosan gauze and fighting gauze of reference samples respectively. Demonstrating its excellent hemostatic ability on compressible wounds.
Example 6
The embodiment relates to a hemostatic effect test of chitosan catechol hemostatic gauze, which comprises the following steps:
1. injecting 1 mL of 10% chloral hydrate into abdominal cavity of rat to make it narcotize;
2. the chest is opened, and an incision of 1 cm × 0.5 cm is made on the right lobe;
3. immediately pressing chitosan hemostatic gauze (chitosan catechol gauze-1, chitosan catechol gauze-2, chitosan catechol gauze-3 and chitosan gauze) and fighting gauze with known mass on the liver cut wound of rat respectively;
4. pressing for 180 s, weighing, and calculating the amount of bleeding;
5. the amount of bleeding from the hepatectomy wounds for the blank control experiment, the battle gauze and the chitosan catechol hemostatic gauze series used in this example is shown in fig. 5. As can be seen from fig. 5, the blood loss of the chitosan catechol hemostatic gauze series samples was only 20% and 3% of the reference chitosan gauze and the battle gauze, respectively. Proves that the hemostatic powder also has excellent hemostatic capability on the liver incision wound which cannot be pressed.
The foregoing description of specific embodiments of the present invention has been presented. It is to be understood that the present invention is not limited to the specific embodiments described above, and that various changes and modifications may be made by one skilled in the art within the scope of the appended claims without departing from the spirit of the invention.
Claims (7)
1. The preparation method of the chitosan catechol hemostatic gauze is characterized by comprising the following steps:
s1, synthesizing a long-side alkenyl catechol compound through Suzuki coupling reaction, wherein the long-side alkenyl catechol compound is a mono-alkenyl catechol compound containing 5-14 carbon atoms;
s2, immersing the chitosan gauze into a sodium alginate aqueous solution, and then washing and drying to obtain the hemostatic gauze with the chitosan coated by the sodium alginate;
s3, carrying out corona treatment on the hemostatic gauze obtained in the step S2 to introduce free radicals;
and S4, reacting the hemostatic gauze obtained in the step S3 with long-side alkenyl catechol compound synthesized in the step S1, and grafting the catechol compound on the surface of the hemostatic gauze to obtain the chitosan catechol hemostatic gauze.
2. The method for preparing chitosan catechol hemostatic gauze according to claim 1, wherein in step S2, the chitosan gauze is woven or non-woven fabric composed of fibers.
3. The method for preparing chitosan catechol hemostatic gauze according to claim 1, wherein in the step S2, the concentration of the sodium alginate aqueous solution is 0.02-1.0 wt%, and the soaking time is 10-180S.
4. The method for preparing chitosan catechol hemostatic gauze according to claim 1, wherein in step S2, the thickness of the sodium alginate layer of the chitosan coated hemostatic gauze is 10-100 nm.
5. The method for preparing chitosan catechol hemostatic gauze according to claim 1, wherein in step S3, the corona treatment is performed in air at normal temperature and pressure for 30-180S.
6. The method for preparing chitosan catechol hemostatic gauze according to claim 1, wherein in step S4, the reaction is performed in a long-side alkenyl catechol/ethanol solution, the concentration of the catechol compound in the long-side alkenyl catechol/ethanol solution is 0.5-3.0 wt%, the reaction temperature is 50-80 ℃, and the reaction time is 0.5-3 h.
7. A chitosan catechol hemostatic gauze obtained by the preparation method of any one of claims 1 to 6.
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| CN117210969B (en) * | 2023-07-31 | 2024-06-25 | 山东艾文生物科技有限公司 | Chitosan/alginic acid skin-core structure composite fiber and preparation method thereof |
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| CN104013990A (en) * | 2014-06-18 | 2014-09-03 | 海南建科药业有限公司 | Modified chitosan having catechol group and biomedical material prepared from modified chitosan |
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