CN115337444B - Preparation method of electronegative micromolecule-regulated procoagulant surface - Google Patents
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- CN115337444B CN115337444B CN202211065767.3A CN202211065767A CN115337444B CN 115337444 B CN115337444 B CN 115337444B CN 202211065767 A CN202211065767 A CN 202211065767A CN 115337444 B CN115337444 B CN 115337444B
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- 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
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- A61L24/001—Use of materials characterised by their function or physical properties
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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
- A61L24/06—Surgical adhesives or cements; Adhesives for colostomy devices containing macromolecular materials obtained by reactions only involving carbon-to-carbon unsaturated bonds
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- A61L2300/00—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices
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- A61L2300/418—Agents promoting blood coagulation, blood-clotting agents, embolising agents
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- A61L2400/00—Materials characterised by their function or physical properties
- A61L2400/18—Modification of implant surfaces in order to improve biocompatibility, cell growth, fixation of biomolecules, e.g. plasma treatment
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Abstract
The invention discloses a preparation method of a procoagulant surface regulated by electronegative micromolecules, which comprises the following steps of: preparing electronegative micromolecular solution; immersing a substrate with cations on the surface into electronegative micromolecular solution; washing and drying to obtain the electronegative micromolecular controlled procoagulant surface. The invention realizes the elimination of negative influence on endogenous coagulation pathway caused by the excessively high electropositivity of the cationic polymer, and improves the procoagulant performance of the substrate with the surface fixed with the cationic polymer through simple polymer structure regulation.
Description
Technical Field
The invention belongs to the field of medical hemostatic materials, and relates to a preparation method of a procoagulant surface regulated and controlled by electronegative micromolecules.
Background
The polymer material has flexible and various structural designs, and is widely studied in the fields of hemostasis, antibiosis, drug carriers and the like. The cationic polymer is favorable for aggregating electronegative proteins and cells and is used for developing various hemostatic materials, but the cationic polymer has a double-edged sword effect on blood coagulation, and the excessively high electropositivity of the cationic polymer can also influence an endogenous blood coagulation pathway and delay the generation of thrombin. It is therefore necessary to improve the procoagulant properties of cationic polymers by regulating their structure. Compared with the fine chemical modification reaction for regulating and controlling the cationic polymer structure, the method has the advantage that electronegative small molecules are introduced into the cationic polymer through small molecule exchange, so that simpler and more convenient regulation and control of the polymer structure can be expected to be realized. Based on the modified cationic polymer, the electronegativity of the cationic polymer is regulated and controlled through electronegative small molecules, and the surface of different cationic polymer substrates can be modified to obtain the procoagulant surface.
Disclosure of Invention
In view of this, the present invention provides a method for preparing a procoagulant surface regulated by electronegative small molecules. The technical scheme is specifically as follows:
a preparation method of a procoagulant surface regulated by electronegative micromolecules comprises the steps of modifying a substrate with cations on the surface by soaking electronegative micromolecule solution to obtain a hemostatic material with the procoagulant surface, wherein the preparation method comprises the following specific steps:
(1) Preparing electronegative micromolecular solution;
(2) Immersing the substrate with the cations on the surface into the solution in the step 1);
(3) Washing and drying to obtain the electronegative micromolecular controlled procoagulant surface.
Further, the electronegative micromolecules in the step 1) are one or more of sodium methyl sulfate, sodium methyl sulfonate, N-cyclohexyl sodium sulfamate, morpholine ethane sodium sulfonate monohydrate, 3-N (-morpholino) sodium propane sulfonate, 3-morpholine-2-hydroxy sodium propane sulfonate and gluconic acid, the concentration of the electronegative micromolecule solution is 0.5-50mg/mL, and the soaking process time in the step 2) is 0.5-10h.
Further, the substrates having cations on the surfaces thereof have three types:
the substrate a is a cation immobilization substrate obtained by self-assembling a substrate which does not contain cations on the surface and a cationic polymer;
the substrate b is a surface cation immobilization substrate obtained by chemical reaction of a substrate which does not contain cations on the surface and electropositive small molecules;
the substrate c is a substrate which contains a large amount of cationic groups on the surface, and the cationic groups are one or a combination of a plurality of guanidine groups, primary amines, quaternary amines or tertiary amines.
Further, the self-assembly in the substrate a is to coat the cationic polymer and the electronegative polymer on the surface by a layer-by-layer self-assembly method, and the outermost layer is controlled to be the cationic polymer.
Further, the substrate in the substrate a, which does not contain cations on the surface, is 304 stainless steel, metal titanium nails, silicon wafers, gelatin sponge, polyvinyl alcohol sponge or medical collagen sponge.
Further, the cationic polymer in the base material a is one or more of polydiallyl dimethyl ammonium chloride, poly (N, N-dimethylaminoethyl methacrylate), polylysine, polyhexamethylene biguanidine hydrochloride and polyhexamethylene monoguanidine hydrochloride, and the electronegative polymer is one or more of poly (4-sodium styrene sulfonate) and polymethacrylic acid.
Further, the substrate in the substrate b, which does not contain cations on the surface, is gelatin sponge, polyvinyl alcohol sponge, medical collagen sponge or gauze.
Further, the chemical reaction in the substrate b is a quaternization reaction, and a ring-opening reaction is performed between a hydroxyl group, an amino group or a carboxyl group on the substrate surface which does not contain a cation on the surface itself and a quaternary ammonium salt containing an epoxy group.
Further, the quaternary ammonium salt containing epoxy group is 2, 3-epoxypropyl trimethyl ammonium chloride or a product obtained by reacting epichlorohydrin with N, N-dimethyl X amine, and X is B, C, T, H, octyl, decyl, twelve and fourteen.
Further, characterized in that after 2, 3-epoxypropyl trimethyl quaternary ammonium salt modified gelatin and sodium methyl sulfate are soaked, a hemostatic material with a procoagulant surface can be obtained; the cationic immobilized 304 stainless steel surface obtained by alternately self-assembling and modifying poly (4-styrene sodium sulfonate) and poly (diallyl dimethyl ammonium chloride) and sodium methyl sulfate are soaked to obtain the hemostatic material with the procoagulant surface.
The invention has the beneficial effects that: according to the method for regulating and controlling the coagulation performance of the substrate with cations on the surface through the electronegative micromolecules, the cationic polymer in a surface fixing state is soaked in the electronegative micromolecule solution, so that the competing process of the electronegative micromolecules and the original counter anions of the cationic polymer can occur, and a part of counter anions (such as hydroxide ions, chloride ions and the like) are converted into newly introduced electronegative micromolecules, so that the strong electropositivity of the cationic polymer on the surface of the substrate and the accompanying strong binding capacity/adhesion force (generally causing the coagulation function to be reduced and the index of the endogenous coagulation time of blood plasma to be prolonged) of key coagulation factors/proteins in the coagulation process are regulated and controlled. The invention realizes the elimination of negative influence on endogenous coagulation pathway caused by the excessively high electropositivity of the cationic polymer, and improves the procoagulant performance of the substrate with the surface fixed with the cationic polymer through simple polymer structure regulation. Thus, the present invention provides a simpler method of preparing procoagulant surfaces relative to fine chemical modification synthetic reactions to modulate polymer structure to develop a (surface immobilized polymeric) substrate with procoagulant properties.
Detailed Description
Preferred embodiments of the present invention are described in detail below.
Example 1
1) 300mg of sodium hydroxide is dissolved in 10mL of deionized water, 1200mg of 2, 3-epoxypropyl trimethyl quaternary ammonium salt (GTA) is dissolved in 40mL of deionized water, the two are mixed to soak the gelatin sponge for 24 hours, the deionized water is washed for 3 times each for 10 minutes, and the Quaternized Gelatin Sponge (QGS) is obtained through freeze drying.
2) The quaternized gelatin sponge in the step 1) is soaked in 21mg/mL sodium methyl sulfate aqueous solution for 2 hours, washed with deionized water for 3 times each for 30 minutes, and freeze-dried to obtain hemostatic sponge X1.
In this embodiment, the substrate having cations on the surface is a quaternized gelatin sponge, the cationic polymer is a quaternized gelatin sponge, and the electronegative small molecule is sodium methyl sulfate.
Example 2
The quaternized gelatin sponge of step 1) in example 1 was soaked in 45mg/mL aqueous solution of sodium methylsulfonate for 2 hours, washed with deionized water 3 times for 30 minutes each time, and freeze-dried to obtain hemostatic sponge X2.
In this example, the substrate having cations on the surface is a quaternized gelatin sponge, the cationic polymer is a quaternized gelatin sponge, and the electronegative small molecule is sodium methylsulfonate.
Example 3
1) 304 stainless steel sheet (S for short) is cut into 1X 1cm 2 Continuously ultrasonic cleaning with isopropanol, ethanol and water, drying, and treating with oxygen plasma. Preparation of 1mg/mL Poly (diallyldimethylammonium chloride) with deionized water
(PDADMAC) solution, 1mg/mL poly (sodium 4-styrenesulfonate) (PSS) solution. Alternately soaking PDADMAC and PSS solution for 20min each time, washing with deionized water for 1min, and blowing nitrogen for 2min to obtain S-PP 4.5 (S-PP 4.5 The outermost layer is the cationic polymer polydiallyl dimethyl ammonium chloride).
2) S-PP as in 1) 4.5 Soaking in 1mg/mL sodium methyl sulfate aqueous solution for 1h, washing with deionized water for 1 time, each time for 1min, and drying with nitrogen to obtain hemostatic material X3.
In this embodiment, the surface hasThe base material for preparing the cations is cation immobilization base material S-PP obtained by alternately self-assembling 304 stainless steel sheets with poly (4-sodium styrene sulfonate) and poly (diallyl dimethyl ammonium chloride) 4.5 The cationic polymer is poly (diallyl dimethyl ammonium chloride), and the electronegative small molecule is sodium methyl sulfate.
Comparative example 1
The quaternized gelatin sponge obtained in step 1) of example 1 was designated Y1.
Comparative example 2
S-PP in step 1) in example 3 4.5 Designated Y2.
Comparative example 3
The quaternized gelatin sponge of step 1) in example 1 was immersed in 21mg/mL aqueous solution of sodium methylsulfonate for 2min, washed with deionized water 3 times for 30min each time, and freeze-dried to obtain hemostatic sponge Y3.
In this comparative example, the soaking time was only 2 minutes, which is much shorter than 2 hours of example 1.
Test example 1BCI
The prepared procoagulant surface hemostatic materials X1-X3 and comparative examples Y1-Y3 are subjected to in vitro coagulation effect comparative experiments.
The testing method comprises the following steps: the hemostatic sponge series is prepared by placing 5mg into 2mL plastic centrifuge tube, and stainless steel sheet is prepared by taking 1X 1cm 2 The mixture was placed in a 6-well plate. Fresh anticoagulation of 100. Mu.L SD rats was added to 10. Mu.L of calcium chloride solution (CaCl) 2 The method comprises the steps of carrying out a first treatment on the surface of the 0.2M) was mixed and immediately contacted with the pre-prepared material and incubated in a thermostatic water bath at 37 ℃ for 1 minute. Then 10mL deionized water was slowly added and incubation was continued for 3 minutes to allow the blood cells that did not form the blood clot to lyse sufficiently and release hemoglobin. After 3min, 100. Mu.L of the liquid was aspirated and added to a 96-well plate, and absorbance Abs at 545nm was measured with an ELISA to calculate hemoglobin content. The blank group was prepared by adding 100. Mu.L of fresh anticoagulant to 10mL of deionized water, incubating in a constant temperature water bath at 37℃for 3 minutes, and sucking 100. Mu.L of absorbance Abs at 545 nm. Finally, the coagulation index (BCI) is calculated by the following formula.
Coagulation index% (BCI) = (Abs) Sample of /Abs Blank space )×100％.................. A.
Wherein: abs Sample of Absorbance at 545nm for the experimental group; abs Blank space Is the absorbance of the blank at 545 nm. The BCI indexes of examples and comparative examples are shown in table 1:
TABLE 1 in vitro coagulation index test results
| Sample of | X1 | X2 | X3 | Y1 | Y2 | Y3 |
| BCI(％) | 42.0 | 38.1％ | 40.8 | 49.1 | 89.9 | 71.2 |
The in vitro coagulation index BCI is an important index for characterizing the in vitro procoagulant performance of the material and screening hemostatic materials, and the smaller the BCI value is, the better the in vitro procoagulant performance of the material is indicated. As can be seen from Table 1, the hemostatic materials X1 to X3 obtained in examples 1 to 3 of the present invention have BCI indexes significantly lower than those of the same materials as those of comparative examples Y1 to Y3. Therefore, by adopting the preparation method provided by the invention, the hemostatic material with excellent hemostatic performance can be obtained.
The electronegativity of the cationic polymer can be effectively regulated by soaking electronegative small molecules with different concentrations, the adverse effect on an endogenous coagulation pathway caused by the excessively strong electropositivity of the cationic polymer is eliminated, and the procoagulant performance of the cationic polymer can be effectively improved.
Comparative example 1 is that the quaternized gelatin sponge is modified without soaking electronegative small molecular sodium methyl sulfate, and the BCI of Y1 in table 1 is larger than that of examples 1 and 2, which indicates that the cationic polymer which is not subjected to electronegative small molecular regulation and control on electropositivity has a negative effect on the intrinsic coagulation pathway due to the excessively high electropositivity, so that the hemostatic performance of the hemostatic material cannot be effectively improved.
Comparative example 2 is that the stainless steel sheet coated with the cationic polymer coating is not soaked in sodium methyl sulfate for modification, and the BCI result of Y2 in table 1 is much larger than that of example 3, which indicates that the stainless steel surface of the cationic polymer which is not subjected to electronegative small molecule regulation and control on electropositivity has negative influence on the intrinsic coagulation pathway due to the excessively high electropositivity, so that the hemostatic performance of the hemostatic material cannot be effectively improved.
Comparative example 3 is that in the preparation step 2) of example 1, the quaternized gelatin sponge is soaked with sodium methylsulfonate with proper concentration, but the soaking time is too short to be beneficial to the effective exchange of counter ions, and the BCI of Y3 is larger than the BCI value of Y1, which indicates that the inappropriate electronegative small molecule regulation and control process is insufficient in positively shielding the cationic polymer, so that the electropositivity of the material is too strong, the endogenous coagulation pathway is negatively affected, and the hemostatic performance of the hemostatic material cannot be effectively improved.
Finally, it is noted that the above-mentioned preferred embodiments are only intended to illustrate rather than limit the invention, and that, although the invention has been described in detail by means of the above-mentioned preferred embodiments, it will be understood by those skilled in the art that various changes in form and details may be made therein without departing from the scope of the invention as defined by the appended claims.
Claims (8)
1. A preparation method of a procoagulant surface regulated by electronegative micromolecules is characterized in that a base material with cations on the surface is modified by soaking electronegative micromolecule solution to obtain a hemostatic material with the procoagulant surface, and the preparation method comprises the following specific steps:
(1) Preparing electronegative micromolecular solution;
(2) Immersing the substrate with the cations on the surface into the solution in the step 1);
(3) Washing and drying to obtain the procoagulant surface regulated by electronegative small molecules;
the electronegative micromolecules in the step 1) are one or more of sodium methyl sulfate, sodium methyl sulfonate, N-cyclohexylsulfamate, morpholine ethane sulfonic acid sodium salt monohydrate, 3-N (-morpholino) propane sulfonic acid sodium salt, 3-morpholine-2-hydroxy propane sulfonic acid sodium salt and gluconic acid, the concentration of the electronegative micromolecule solution is 0.5-50mg/mL, and the soaking process time in the step 2) is 0.5-10h.
2. The method for preparing a negative small molecule controlled procoagulant surface according to claim 1, wherein the substrate with cations on the surface comprises three kinds of substrates:
the substrate a is a cation immobilization substrate obtained by self-assembling a substrate which does not contain cations on the surface and a cationic polymer;
the substrate b is a surface cation immobilization substrate obtained by chemical reaction of a substrate which does not contain cations on the surface and electropositive small molecules;
the substrate c is a substrate itself having a cationic surface.
3. The method for preparing a negative small molecule controlled procoagulant surface according to claim 2, wherein the self-assembly in the substrate a is to coat the surface with a cationic polymer and a negative polymer by a layer-by-layer self-assembly method, and the outermost layer is controlled to be a cationic polymer.
4. The method for preparing the negative micromolecule controlled procoagulant surface according to claim 2, wherein the substrate in the substrate a does not contain cations on the surface is 304 stainless steel, metal titanium nails, silicon wafers, gelatin sponge, polyvinyl alcohol sponge or medical collagen sponge.
5. The method for preparing the negative small molecule controlled procoagulant surface according to claim 2, wherein the cationic polymer in the substrate a is one or more of polydiallyl dimethyl ammonium chloride, poly (N, N-dimethylaminoethyl methacrylate), polylysine, polyhexamethylene biguanide hydrochloride and polyhexamethylene monoguanidine hydrochloride, and the negative polymer is one or more of poly (sodium 4-styrene sulfonate) and polymethacrylic acid.
6. The method for preparing a negative small molecule controlled procoagulant surface according to claim 2, wherein the substrate of the substrate b which does not contain cations on its own surface is a gelatin sponge, a polyvinyl alcohol sponge, a medical collagen sponge or a gauze.
7. The method for preparing a negative small molecule controlled procoagulant surface according to claim 2, wherein the chemical reaction in the substrate b is a quaternization reaction, and the ring-opening reaction is carried out between hydroxyl, amino or carboxyl on the substrate surface which does not contain cations per se and quaternary ammonium salt containing epoxy groups.
8. The method for preparing a negative small molecule controlled procoagulant surface according to claim 7, wherein the quaternary ammonium salt containing epoxy group is 2, 3-epoxypropyl trimethyl ammonium chloride or a product obtained by reacting epichlorohydrin with N, N-dimethyl X amine, and X is twelve or fourteen.
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| JP4863655B2 (en) * | 2005-06-17 | 2012-01-25 | 国立大学法人 東京医科歯科大学 | Cell-containing sheet |
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| CN102492095A (en) * | 2011-12-08 | 2012-06-13 | 北京化工大学 | Construction of bio-reducible efficient cation gene vectors taking polysaccharides as frameworks with ATRP (Atom Transfer Radical Polymerization) method |
| CN102643374A (en) * | 2012-04-26 | 2012-08-22 | 北京化工大学 | High-performance cationic gene vectors with PGMA (polyglycidyl methacrylate) serving as framework constructed by ATRP (atom transfer radical polymerization) method |
| CN110683771A (en) * | 2019-11-12 | 2020-01-14 | 北京化工大学 | Preparation method of natural polymer and cationic polymer anti-algae coated glass and product thereof |
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