CN115350330A - Application of electronegative small molecule regulated surface in protein differential adhesion - Google Patents

Application of electronegative small molecule regulated surface in protein differential adhesion Download PDF

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CN115350330A
CN115350330A CN202211063100.XA CN202211063100A CN115350330A CN 115350330 A CN115350330 A CN 115350330A CN 202211063100 A CN202211063100 A CN 202211063100A CN 115350330 A CN115350330 A CN 115350330A
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electronegative
adhesion
substrate
proteins
small molecule
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CN115350330B (en
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徐福建
杨雪
胡杨
付豪
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Beijing University of Chemical Technology
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    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61LMETHODS 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
    • A61L27/00Materials for grafts or prostheses or for coating grafts or prostheses
    • A61L27/14Macromolecular materials
    • A61L27/22Polypeptides or derivatives thereof, e.g. degradation products
    • A61L27/222Gelatin
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61LMETHODS 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
    • A61L27/00Materials for grafts or prostheses or for coating grafts or prostheses
    • A61L27/02Inorganic materials
    • A61L27/04Metals or alloys
    • A61L27/042Iron or iron alloys
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61LMETHODS 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
    • A61L27/00Materials for grafts or prostheses or for coating grafts or prostheses
    • A61L27/28Materials for coating prostheses
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61LMETHODS 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
    • A61L27/00Materials for grafts or prostheses or for coating grafts or prostheses
    • A61L27/28Materials for coating prostheses
    • A61L27/34Macromolecular materials
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61LMETHODS 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
    • A61L27/00Materials for grafts or prostheses or for coating grafts or prostheses
    • A61L27/50Materials characterised by their function or physical properties, e.g. injectable or lubricating compositions, shape-memory materials, surface modified materials
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61LMETHODS 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
    • A61L2400/00Materials characterised by their function or physical properties
    • A61L2400/18Modification of implant surfaces in order to improve biocompatibility, cell growth, fixation of biomolecules, e.g. plasma treatment
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61LMETHODS 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
    • A61L2420/00Materials or methods for coatings medical devices
    • A61L2420/02Methods for coating medical devices

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  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Dermatology (AREA)
  • Medicinal Chemistry (AREA)
  • Oral & Maxillofacial Surgery (AREA)
  • Transplantation (AREA)
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  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
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  • Inorganic Chemistry (AREA)
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Abstract

The invention discloses an application of a surface regulated by electronegative micromolecules in protein differential adhesion, wherein a substrate with positive ions on the surface is regulated by soaking electronegative micromolecule solution, so that the differential adhesion of different proteins on the surface of the substrate can be realized, and the specific steps are as follows: preparing electronegative small molecule solution; immersing a base material with positive ions on the surface into an electronegative micromolecule solution; washing and drying to obtain a modified base material; the substrates differentially adhere the proteins. The electronegativity of the cationic polymer on the surface of the substrate is regulated and controlled by electronegative micromolecules so as to regulate and control the adhesion acting force of the electropositive to electronegative protein, and the regulation and control of the protein adhesion amount and the differential adhesion of different proteins are realized.

Description

Application of electronegative small molecule regulated surface in protein differential adhesion
Technical Field
The invention belongs to the technical field of preparation of medical materials, and relates to application of a surface regulated and controlled by electronegative small molecules in differential adhesion of proteins.
Background
In the field of tissue engineering, the selective adhesion of cells on the surface of a material has very important significance, and the selective adhesion is favorable for simulating/remodeling the tissue structure of ordered combination of various types of cells in the original complex tissue of an organism. However, in the existing material preparation technology, cell selective adhesion mostly depends on preparing a material surface modified by a biofunctional molecule (such as RGD, VEGF, etc., noel s., et al. Acta biomatener.2016, 37, 69), and the action mechanism is that the biofunctional molecule can mediate differential adhesion with different cell surface protein receptors, but this method not only depends on expensive biofunctional molecule preparation and a biofunctional molecule surface immobilization process which is not beneficial to large-scale production, but also can only solve selective adhesion of a few cells with definite targets. Meanwhile, the polymer material is widely researched in various fields such as tissue engineering, drug carriers and the like due to flexible and various structural designs, and the differential adhesion of the proteins can be realized through the fine structural design, so that the material structure is expected to be further optimized, and the selective adhesion of cells is further realized. However, the current polymer material preparation technology mainly focuses on the research of cationic polymers (broad-spectrum enhanced protein/cell adhesion), and polyethylene glycol, electronegative polymers and zwitterionic polymers (significantly reduced protein/cell adhesion). Therefore, a preparation technology capable of simply and conveniently preparing a protein differential adhesion material is still lacked, and the development of a cell selective adhesion material in the field of tissue engineering is severely restricted.
Disclosure of Invention
In view of this, the present invention provides an application of a negatively charged small molecule-regulated surface to differential adhesion of proteins. The technical scheme is as follows: the application of the surface regulated by the electronegative micromolecules in protein differential adhesion is characterized in that a substrate with positive ions on the surface is regulated by soaking in electronegative micromolecule solution, so that differential adhesion of different proteins on the surface of the substrate can be realized, and the 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) Washing and drying to obtain a modified base material;
4) The substrates differentially adhere the proteins.
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, and the concentration of the electronegative micromolecule solution is 0.5-50mg/mL.
Further, the protein is albumin, globulin and fibrin.
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 chemically reacting a base material of which the surface does not contain cations with 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 base material 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 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).
Further, the base material of which the surface does not contain cations in the base material b is gelatin sponge, polyvinyl alcohol sponge, medical collagen sponge or gauze.
Further, the chemical reaction in the base material b is a quaternization reaction, and a ring opening reaction is carried out on hydroxyl, amino or carboxyl on the surface of the base material which does not contain cations on the surface of the base material and quaternary ammonium salt containing epoxy groups; the quaternary ammonium salt containing epoxy groups is 2, 3-epoxypropyl trimethyl ammonium chloride or a product obtained by the reaction of epoxy chloropropane and N, N-dimethyl X amine, and X is B, C and D.
Further, the preparation method is characterized in that after the gelatin modified by the 2, 3-epoxypropyl trimethyl quaternary ammonium salt and the sodium methyl sulfate are soaked, the high adhesion to fibrinogen and the moderate adhesion to albumin and globulin can be realized; 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 high-adhesion to globulin and the low-adhesion to fibrin can be realized.
The invention has the beneficial effects that: the invention prepares a protein differential adhesion surface material regulated by electronegative small molecules, and a part of counter anions (such as hydroxide radicals, chloride ions and the like) are converted into newly introduced electronegative small molecules through the competition effect of the electronegative small molecules and original counter anions of a cationic polymer, so that the strong electropositivity of the cationic polymer on the surface of a base material (and the accompanying strong binding capacity/adhesion acting force with electronegative proteins) are regulated, and finally the regulation of protein adhesion amount and the differential adhesion of different proteins are realized. Therefore, the invention realizes the polymer structure design and protein adhesion regulation relative to direct chemical synthesis (the chemical synthesis is often fine and tedious), and provides a simpler method for preparing protein differential adhesion materials.
Detailed Description
The preferred embodiments of the present invention will be described in detail.
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 10mg/mL sodium methyl sulfate aqueous solution 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 surface-equipped cationic base material was quaternized gelatin sponge, and the cationic polymer was quaternized gelatin and electronegative small-molecule sodium methyl sulfate.
Example 2
Soaking the quaternized gelatin sponge obtained in the step 1) in the example 1 in a 21mg/mL sodium methyl sulfate aqueous 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 concentration of electronegative small molecule sodium methylsulfate was different from that in example 1.
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. 1mg/mL poly (diallyldimethylammonium chloride) (PDADMAC) solution, 1mg/mL poly (sodium 4-styrenesulfonate) (PSS) solution was prepared with deionized water. 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 cationic polymer poly diallyl dimethyl ammonium chloride
2) Mixing the S-PP in 1) 4.5 Soaking in 0.1mg/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 cation immobilized substrate S-PP having a cation substrate on the surface thereof was prepared by alternately self-assembling 304 stainless steel sheets with poly (4-sodium 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
Unmodified gelatin sponge, designated Y2.
Comparative example 3
Unmodified 304 stainless steel sheet, designated Y3.
Test example 1 protein adhesion test
The prepared protein differential adhesion surface materials X1-X3 and the comparative examples Y1-Y3 are subjected to adhesion test contrast experiments of albumin, globulin and fibrinogen.
The test method comprises the following steps: taking a test method of human albumin as an example, 3mg of gelatin sponge series materials are added into a 2mL centrifuge tube, and a stainless steel sheet before and after modification is 1 multiplied by 1cm 2 Put into a 6-well plate. The human albumin is prepared into a PBS solution with the concentration of 10mg/mL, 50 mu L of protein solution is added on the material, and the material is incubated in a thermostat water bath kettle with the temperature of 37 ℃ for 30 minutes. The excess liquid was aspirated, gently washed with 200. Mu.L of PBS solution for 1 wash, the volume of the wash solution was adjusted to 500. Mu.L, 50. Mu.L of the wash solution was taken out and put into a 2mL centrifuge tube, 1mL of BCA working solution prepared in advance (reagent A: reagent B =50 (1 (v/v)) was added, and the mixture was incubated in a 37 ℃ thermostat water bath for 30 minutes, 100. Mu.L of the solution was added to a 96-well plate, and absorbance Abs at 562nm was measured.
Blank 50. Mu.L of protein solution was added to a 2mL centrifuge tube. The control group was material plus 50 μ L PBS.
Protein adhesion rate η% = (1- (Abs sample-Abs control)/Abs blank) × 100%
The albumin adhesion rates of the examples and comparative examples are shown in table 1:
TABLE 1 Albumin adhesion test results
Sample (I) X1 X2 Y1 Y2
η(%) 8.9 6.8 8.1 2.0
The globulin adhesion rates of the examples and comparative examples are shown in Table 2:
TABLE 2 globulin adherence test results
Sample(s) X1 X2 X3 Y1 Y2 Y3
η(%) 9.5 11.1 7.9 8.6 3.1 6.0
The fibrinogen adhesion rates of the examples and comparative examples are shown in table 3:
TABLE 3 fibrinogen adhesion test results
Sample (I) X1 X2 X3 Y1 Y2 Y3
η(%) 31.0 14.6 3.9 10.5 6.0 10.1
The protein adhesion rate is an important index for representing the protein adhesion effect on the surface of the material, and the larger the adhesion percentage is, the better the protein adhesion performance of the material is.
As can be seen from the data in tables 1-3, X1 of the gelatin sponges of examples 1-2 of the present invention (gelatin sponge material with 12% protein adhesion rate as high protein adhesion property) achieved high adhesion to fibrinogen, while moderate adhesion to albumin and globulin; x2 achieves high adhesion to fibrinogen, while moderate adhesion to albumin and globulin.
As can be seen from the data in tables 1 to 3, X3 of the stainless steel sheet of invention example 3 (the surface of the metal material had a 6% protein adhesion rate as a medium/acceptable protein adhesion property) achieved high adhesion to globulin while having low adhesion to fibrinogen.
Therefore, by adopting the preparation method, the electropositivity of the cationic polymer can be effectively adjusted by soaking electronegative micromolecules with different concentrations, and the adjustment of the protein adhesion amount and the selective adhesion of different proteins are realized by adjusting and controlling the strong adhesion acting force of the electropositive to electronegative proteins. The specific analysis is as follows:
the gelatin sponge of comparative example 1, the surface of which is fixed by the cationic polymer, has improved adhesion rate to three proteins compared with that of comparative example 2 (unmodified gelatin sponge), which shows that the cations adhere to the negatively charged proteins due to the positive electricity, and the sponge Y1 obtained by the comparative example has broad-spectrum high adhesion and no selectivity to the proteins.
The protein adhesion data of examples 1-2 and comparative example 1 (gelatin sponge with surface fixed by cationic polymer) show that when small molecules are added to form a complex system, the adhesion rate of sponge X1 to albumin and globulin is basically unchanged (the adhesion rates are respectively from 8.1% to 8.9% and from 8.6% to 9.5%), and the adhesion rate to fibrinogen is higher (the adhesion rate is increased from 10.5% to 31.0%); the adhesion rate of sponge X2 to albumin was low (the adhesion rate was reduced from 8.1% to 6.8%), and the adhesion rates to globulin and fibrinogen were high (the adhesion rates were increased from 8.6% to 11.1% and from 10.5% to 14.6%, respectively). Therefore, the sponge prepared by the invention can realize differential adhesion to protein.
The data of the protein adhesion rate of example 3 and comparative example 3 (unmodified 304 stainless steel sheet) show that the adhesion rate of X3 to globulin was high (the adhesion rate was increased from 6.0% to 7.9%) and the adhesion rate to fibrinogen was decreased (the adhesion rate was decreased from 10.1% to 3.9%) when a complex system was formed by adding small molecules and cationic polymer. Therefore, the membrane prepared by the invention can realize differential adhesion to protein.
Finally, it is noted that the above-mentioned preferred embodiments illustrate rather than limit the invention, and that, although 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. The application of the surface regulated by the electronegative micromolecules in protein differential adhesion is characterized in that a substrate with positive ions on the surface is soaked in an electronegative micromolecule solution for regulation, so that differential adhesion of different proteins on the surface of the substrate can be realized, and the 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) Washing and drying to obtain a modified base material;
4) The substrates differentially adhere the proteins.
2. The use of an electronegative small molecule to modulate surface adhesion difference between proteins as claimed in claim 1, wherein the electronegative small molecule in step 1) is one or more of sodium methylsulfate, sodium N-cyclohexylsulfamate, sodium morpholinoethanesulfonate monohydrate, sodium 3-N (-morpholino) propanesulfonate, sodium 3-morpholino-2-hydroxypropanesulfonate, and gluconic acid, and the concentration of the electronegative small molecule solution is 0.5-50mg/mL.
3. The use of a negatively charged small molecule modulated surface for differential adhesion of proteins according to claim 1, wherein said proteins are albumin, globulin and fibrin and the differential adhesion is the differential adhesion rate after isobaric contact.
4. The use of an electronegative, small molecule-mediated surface for differential adhesion of proteins as claimed in claim 1, wherein the cationic-surface substrates comprise three types:
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 chemically reacting a base material of which the surface does not contain cations with 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.
5. The use of an electronegative small molecule controlled surface for differential adhesion of proteins as claimed in claim 4, wherein the self-assembly in substrate a is to coat the cationic polymer and electronegative polymer on the surface by a layer-by-layer self-assembly method, and control the outermost layer to be the cationic polymer.
6. The use of the electronegative small molecule-mediated surface for differential adhesion of proteins as defined in claim 4, wherein the substrate that does not contain cations on its surface in substrate a is 304 stainless steel, titanium nail, silicon wafer, gelatin sponge, polyvinyl alcohol sponge, or collagen sponge for medical use.
7. The use of an electronegative small molecule controlled surface for differential adhesion of proteins as claimed in claim 4, wherein the cationic polymer in substrate a is one or more selected from 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 selected from poly (4-styrenesulfonate) and poly (methacrylic acid).
8. The use of an electronegative small molecule to modulate surface differential adhesion with proteins as claimed in claim 4, wherein the substrate that does not contain cations on its surface in substrate b is selected from the group consisting of gelatin sponge, polyvinyl alcohol sponge, medical collagen sponge, and gauze.
9. The use of an electronegative, small molecule-mediated surface for differential adhesion of proteins as claimed in claim 4, wherein the chemical reaction in substrate b is quaternization, which is a ring opening reaction of hydroxyl, amino, or carboxyl groups on the surface of the substrate without cations on its surface with quaternary ammonium salts containing epoxy groups; the quaternary ammonium salt containing epoxy group is 2, 3-epoxypropyl trimethyl ammonium chloride or a product obtained by the reaction of epoxy chloropropane and N, N-dimethyl X amine, and X is B, C and D.
10. The preparation method and the application of the protein differential adhesion surface regulated and controlled by the electronegative small molecules as claimed in claim 1, wherein after the gelatin modified by 2, 3-epoxypropyltrimethyl quaternary ammonium salt and the sodium methyl sulfate are soaked, differential adhesion of fibrinogen, albumin and globulin can be realized; after the cation immobilized 304 stainless steel surface obtained by alternating self-assembly modification of poly (4-sodium styrene sulfonate) and poly (diallyl dimethyl ammonium chloride) and sodium methyl sulfate are soaked, the surface can be differentially adhered to globulin and fibrinogen.
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