CN115337444A - Preparation method of negative-charged small molecule regulated procoagulant surface - Google Patents
Preparation method of negative-charged small molecule regulated procoagulant surface Download PDFInfo
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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
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- A—HUMAN NECESSITIES
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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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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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- 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
- A61L2300/418—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 modifying a base material with cations on the surface by soaking electronegative micromolecule solution to obtain a hemostatic material with the procoagulant surface: preparing electronegative small molecule solution; immersing a base material with positive ions on the surface into an electronegative micromolecule solution; and washing and drying to obtain the procoagulant surface regulated by electronegative micromolecules. The invention eliminates the negative influence of intrinsic coagulation path caused by overhigh electropositivity of the cationic polymer, and improves the procoagulant performance of the base material with the cationic polymer fixed on the surface through simple and convenient regulation and control of the polymer structure.
Description
Technical Field
The invention belongs to the field of medical hemostatic materials, and relates to a preparation method of a procoagulant surface regulated by electronegative small molecules.
Background
The polymer material has flexible and various structural designs, and is widely researched 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 action of the cationic polymer on blood coagulation is a double-edged sword, and the excessively high electropositivity of the cationic polymer can also influence the intrinsic coagulation pathway and delay the generation of thrombin. It is therefore necessary to modify the structure of the cationic polymer to improve its procoagulant properties. Compared with the fine chemical modification reaction for regulating the structure of the cationic polymer, the electronegative micromolecules are introduced on the cationic polymer through micromolecule exchange, and the simpler regulation of the polymer structure is expected to be realized. Based on the method, the electropositivity of the cationic polymer is regulated and controlled by electronegative micromolecules, and the surfaces of different cationic polymer substrates can be modified to obtain the procoagulant surface.
Disclosure of Invention
In view of the above, the present invention provides a method for preparing a procoagulant surface regulated by electronegative small molecules. The technical scheme is as follows:
a preparation method of a procoagulant surface regulated by electronegative micromolecules is characterized in that a substrate with positive ions on the surface is soaked in an electronegative micromolecule solution for modification to obtain a hemostatic material with the procoagulant surface, and the preparation method comprises the following specific steps:
(1) Preparing electronegative small molecule solution;
(2) Immersing a base material with cations on the surface into the solution in the step 1);
(3) And washing and drying to obtain the procoagulant surface regulated by electronegative micromolecules.
Further, the electronegative micromolecules in the step 1) are one or more of sodium methyl sulfate, sodium methyl sulfonate, N-cyclohexyl sodium sulfamate, morpholine ethanesulfonic acid sodium salt monohydrate, 3-N (-morpholinyl) sodium propane sulfonate, 3-morpholine-2-hydroxypropanesulfonic acid sodium salt and gluconic acid, the concentration of the electronegative micromolecule solution is 0.5-50mg/mL, and the soaking time in the step 2) is 0.5-10h.
Further, the base material having cations on the surface has three types:
the base material a is a cation immobilized base material obtained by self-assembling a base material of which the surface does not contain cations and a cationic polymer;
the base material b is a surface cation immobilized base material obtained by the chemical reaction of a base material the surface of which does not contain cations and electropositive micromolecules;
the substrate c is a substrate with a large number of cationic groups on the surface, and the cationic groups are one or more combinations of guanidino, primary amine, quaternary ammonium or tertiary amine.
Further, the self-assembly described in the substrate a is to coat the surface with the cationic polymer and the electronegative polymer by a layer-by-layer self-assembly method, and control the outermost layer to be the cationic polymer.
Further, the base material of which the surface does not contain cations in the base material a is 304 stainless steel, a metal titanium nail, a silicon wafer, gelatin sponge, polyvinyl alcohol sponge or medical collagen sponge.
Further, the cationic polymer in the base material a is one or more of poly (diallyldimethylammonium chloride), poly (N, N-dimethylaminoethyl methacrylate), polylysine, poly (hexamethylene biguanide hydrochloride) and poly (hexamethylene biguanide hydrochloride), and the electronegative polymer is one or more of poly (4-styrene sodium sulfonate) and poly (methacrylic acid).
Furthermore, the base material which does not contain cations on the surface in the base material b is gelatin sponge, polyvinyl alcohol sponge, medical collagen sponge or gauze.
Further, the chemical reaction described in the base material b is a quaternization reaction in which a hydroxyl group, an amino group, or a carboxyl group on the surface of the base material, the surface of which does not contain cations, and a quaternary ammonium salt containing an epoxy group undergo a ring-opening reaction.
<xnotran> , 5363 zxft 5363- N, N- X , X , , , , , , , . </xnotran>
Further, the hemostatic material is characterized in that the hemostatic material with the procoagulant surface can be obtained by soaking 2,3-epoxypropyl trimethyl quaternary ammonium salt modified gelatin and sodium methyl sulfate; the hemostatic material with the procoagulant surface can be obtained after the cation immobilized 304 stainless steel surface obtained by the alternating self-assembly modification of poly (4-sodium styrene sulfonate) and poly (diallyl dimethyl ammonium chloride) is soaked with sodium methyl sulfate.
The invention has the beneficial effects that: the invention provides a method for regulating and controlling the coagulation performance of a base material with cations on the surface through electronegative small molecules, which is characterized in that a cationic polymer in a surface fixing state is soaked in an electronegative small molecule solution, so that a competition process of the electronegative small molecules and original counter anions of the cationic polymer can be generated, and a part of counter anions (such as hydroxide, chloride ions and the like) are converted into newly introduced electronegative small molecules, so that the strong electropositivity of the cationic polymer on the surface of the base material and the accompanying strong binding capacity/adhesion acting force with key coagulation factors/proteins in a coagulation process (generally, the indexes of coagulation function reduction and plasma endogenous coagulation time are prolonged) are regulated and controlled. The invention eliminates the negative influence of intrinsic coagulation path caused by overhigh electropositivity of the cationic polymer, and improves the procoagulant performance of the base material with the cationic polymer fixed on the surface through simple and convenient regulation and control of the polymer structure. Therefore, the invention provides a simpler method for preparing the procoagulant surface compared with the method for regulating the polymer structure by fine chemical modification synthesis reaction to develop a substrate (surface fixing macromolecule) with procoagulant performance.
Detailed Description
The following describes in detail preferred embodiments of the present invention.
Example 1
1) 300mg of sodium hydroxide is dissolved in 10mL of deionized water, 1200mg of 2, 3-epoxypropyltrimethyl quaternary ammonium salt (GTA) is dissolved in 40mL of deionized water, the two are mixed and soaked in the gelatin sponge for 24 hours, the gelatin sponge is washed by the deionized water for 3 times, 10min each time, and the mixture is frozen and dried to obtain the Quaternized Gelatin Sponge (QGS).
2) Soaking the quaternized gelatin sponge in the step 1) in a sodium methyl sulfate aqueous solution of 21mg/mL for 2h, washing with deionized water for 3 times, each time for 30min, and freeze-drying to obtain the hemostatic sponge X1.
In this example, the base material having cations on the surface was a quaternized gelatin sponge, the cationic polymer was a quaternized gelatin sponge, and the electronegative small molecule was sodium methyl sulfate.
Example 2
Soaking the quaternized gelatin sponge obtained in the step 1) in the example 1 in a 45mg/mL sodium methanesulfonate water solution for 2h, washing with deionized water for 3 times, 30min each time, and freeze-drying to obtain the hemostatic sponge X2.
In this example, the base material having cations on the surface is quaternized gelfoam, the cationic polymer is quaternized gelfoam, and the electronegative small molecule is sodium methanesulfonate.
Example 3
1) Cutting 304 stainless steel sheet (S) into 1 × 1cm 2 Continuously ultrasonically cleaning the mixture by using isopropanol, ethanol and water, drying the mixture, and then treating the dried mixture by using 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 a cationic polymer poly (diallyldimethylammonium chloride).
2) The S-PP 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 example, the base material having cations on the surface was a cation-immobilized base material S-PP obtained by alternately self-assembling 304 stainless steel sheet with poly (sodium 4-styrenesulfonate) and poly (diallyldimethylammonium chloride) 4.5 The cationic polymer is poly (diallyl dimethyl ammonium chloride), and the electronegative micromolecule is sodium methyl sulfate.
Comparative example 1
The quaternized gelatin sponge obtained in step 1) of example 1 was designated as Y1.
Comparative example 2
S-PP in step 1) of example 3 4.5 And is named as Y2.
Comparative example 3
Soaking the quaternized gelatin sponge obtained in the step 1) in the example 1 in a 21mg/mL sodium methanesulfonate aqueous solution for 2min, washing with deionized water for 3 times, 30min each time, and freeze-drying to obtain the hemostatic sponge Y3.
In this comparative example, the soaking time was only 2 minutes, which is much shorter than 2 hours for example 1.
Test example 1BCI
The prepared procoagulant surface hemostatic materials X1-X3 and the comparative examples Y1-Y3 are used for carrying out in vitro blood coagulation effect comparison experiments.
The test method comprises the following steps: the hemostatic sponge series is prepared by placing 5mg into 2mL plastic centrifuge tube, and taking 1 × 1cm stainless steel sheet 2 Put into 6-well plate. mu.L of fresh anticoagulated blood from SD rats was added to 10. Mu.L of calcium chloride solution (CaCl) 2 (ii) a 0.2M), immediately brought into contact with the pre-prepared material and incubated for 1 minute at 37 ℃ in a thermostated water bath. Then 10mL of deionized water was slowly added and incubation was continued for 3 minutes to fully lyse the blood cells that did not form clots and release hemoglobin. After 3min, 100 mu L of liquid is sucked and added into a 96-well plate, and the absorbance Abs at 545nm is tested by an enzyme linked immunosorbent assay instrument to calculate the hemoglobin content. Blank set was prepared by taking 100. Mu.L of fresh anticoagulated blood, adding 10mL of deionized water, incubating for 3 minutes in a thermostatted water bath at 37 ℃ and pipetting 100. Mu.L of absorbance Abs at 545nm for the test. Finally, the Blood Coagulation Index (BCI) was calculated by the following formula.
Blood coagulation index% (BCI) = (Abs) Sample (I) /Abs Blank space ) The
In the formula: abs Sample (I) Is the absorbance at 545nm of the experimental group; abs Blank space Is the absorbance of the blank at 545 nm. The BCI indices of the examples and comparative examples are shown in table 1:
table 1 in vitro coagulation index test results
| Sample(s) | X1 | X2 | X3 | Y1 | Y2 | Y3 |
| BCI(％) | 42.0 | 38.1％ | 40.8 | 49.1 | 89.9 | 71.2 |
The in vitro blood coagulation index BCI is an important index for characterizing the in vitro procoagulant performance of the material and screening the hemostatic material, and the smaller the BCI value is, the better the in vitro procoagulant performance of the material is. As can be seen from Table 1, the BCI index of the hemostatic materials X1-X3 obtained in examples 1-3 of the present invention is significantly lower than that of the same type of materials in comparative examples Y1-Y3. Therefore, the preparation method of the invention can obtain the hemostatic material with excellent hemostatic performance.
By soaking electronegative micromolecules with different concentrations, the electropositivity of the cationic polymer can be effectively adjusted, the adverse effect on an endogenous blood coagulation path 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 quaternized gelatin sponge is not soaked in electronegative micromolecule sodium methyl sulfate for modification, the BCI of Y1 in Table 1 is larger than that of examples 1 and 2, which shows that cationic polymer which is not subjected to electronegative micromolecule regulation and control of electropositivity has negative influence on endogenous blood coagulation path due to too 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 with sodium methyl sulfate for modification, and the BCI result of Y2 in table 1 is much larger than that of example 3, which shows that the surface of the stainless steel without the cationic polymer with electronegativity controlled by small molecules has negative influence on the endogenous blood 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, sodium methanesulfonate with a proper soaking concentration is soaked in the quaternized gelatin sponge, but the soaking time is too short, so that effective exchange of counter ions is not facilitated, and the BCI of Y3 is greater than the BCI value of Y1, so that the unsuitable electronegative small molecule regulation and control process has insufficient electropositive shielding on the cationic polymer, so that the electropositivity of the material is too strong, and the endogenous blood coagulation pathway is negatively affected, so that the hemostatic performance of the hemostatic material cannot be effectively improved.
Finally, it is noted that the above-mentioned preferred embodiments illustrate rather than limit the invention, and that, while 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 (10)
1. A preparation method of a procoagulant surface regulated by electronegative micromolecules is characterized in that a substrate with cations on the surface is soaked in an electronegative micromolecule solution for modification to obtain a hemostatic material with the procoagulant surface, and the preparation method comprises the following specific steps:
(1) Preparing electronegative small molecule solution;
(2) Immersing a base material with cations on the surface into the solution in the step 1);
(3) And washing and drying to obtain the coagulation promoting surface regulated by the electronegative micromolecules.
2. The method for preparing the procoagulant surface according to claim 1, wherein the electronegative small molecules in step 1) are one or more of sodium methyl sulfate, sodium methyl sulfonate, sodium N-cyclohexylsulfamate, sodium morpholine ethanesulfonate monohydrate, sodium 3-N (-morpholino) propanesulfonate, sodium 3-morpholino-2-hydroxypropanesulfonate and gluconic acid, the concentration of the electronegative small molecule solution is 0.5-50mg/mL, and the soaking time in step 2) is 0.5-10h.
3. The method of claim 1, wherein the cationic surface-bearing substrate comprises three types of substrates:
the base material a is a cation immobilized base material obtained by self-assembling a base material the surface of which does not contain cations and a cationic polymer;
the base material b is a surface cation immobilized base material obtained by the chemical reaction of a base material the surface of which does not contain cations and electropositive micromolecules;
the substrate c is a substrate with a large number of cationic groups on the surface, and the cationic groups are one or more combinations of guanidino, primary amine, quaternary ammonium or tertiary amine.
4. The method for preparing the electronegative small molecule regulated procoagulant surface according to claim 3, wherein 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.
5. The method for preparing the electronegative small molecule regulated procoagulant surface according to claim 3, wherein the substrate which does not contain cations on the surface is 304 stainless steel, metal titanium nails, silicon wafers, gelatin sponges, polyvinyl alcohol sponges or medical collagen sponges.
6. The method for preparing an electronegative small molecule regulated procoagulant surface according to claim 3, wherein the cationic polymer in the substrate a is one or more of poly (diallyldimethylammonium chloride), poly (N, N-dimethylaminoethyl methacrylate), polylysine, poly (hexamethylene biguanide hydrochloride) and poly (hexamethylene monoguanidine hydrochloride), and the electronegative polymer is one or more of poly (4-sodium styrene sulfonate) and poly (methacrylic acid).
7. The method for preparing an electronegative small molecule regulated procoagulant surface according to claim 3, wherein the substrate b which does not contain cations on the surface is gelatin sponge, polyvinyl alcohol sponge, medical collagen sponge or gauze.
8. The method of claim 3, wherein the chemical reaction in the substrate b is a quaternization reaction, and the hydroxyl, amino or carboxyl groups on the surface of the substrate, which does not contain cations on its surface, undergo a ring-opening reaction with the quaternary ammonium salt containing epoxy groups.
9. <xnotran> 8 , , 5363 zxft 5363- N, N- X , X , , , , , , , . </xnotran>
10. The method for preparing the electronegative small molecule regulated protein differential adhesion surface and the application thereof according to claim 1, wherein the hemostatic material with the procoagulant surface can be obtained by soaking 2,3-epoxypropyl trimethyl quaternary ammonium salt modified gelatin and methyl sodium sulfate; the hemostatic material with the procoagulant surface can be obtained after the cation immobilized 304 stainless steel surface obtained by the alternating self-assembly modification of poly (4-sodium styrene sulfonate) and poly (diallyl dimethyl ammonium chloride) is soaked with sodium methyl sulfate.
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| CN117567790A (en) * | 2024-01-15 | 2024-02-20 | 四川大学 | Medical polyurethane foam with procoagulant inner surface and anticoagulant outer surface and preparation method thereof |
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| CN117567790A (en) * | 2024-01-15 | 2024-02-20 | 四川大学 | Medical polyurethane foam with procoagulant inner surface and anticoagulant outer surface and preparation method thereof |
| CN117567790B (en) * | 2024-01-15 | 2024-03-26 | 四川大学 | Medical polyurethane foam with procoagulant inner surface and anticoagulant outer surface and preparation method thereof |
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