CN115350330B - Application of electronegative micromolecule regulated surface in protein differential adhesion - Google Patents
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- A61L27/222—Gelatin
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- A61L2420/02—Methods for coating medical devices
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Abstract
The invention discloses an application of a surface regulated by electronegative micromolecules to protein differential adhesion, which is characterized in that a substrate with cations on the surface is regulated by soaking electronegative micromolecule solution, so that differential adhesion of the surface of the substrate to different proteins can be realized, and the specific steps are as follows: preparing electronegative micromolecular solution; immersing a substrate with cations on the surface into electronegative micromolecular solution; washing and drying to obtain a modified substrate; the substrate differentially adheres to the protein. The electropositivity of the cationic polymer on the surface of the substrate is regulated and controlled through electronegative micromolecules so as to regulate and control the adhesion force of electropositive to electronegative proteins and realize regulation and control of protein adhesion amount and differential adhesion of different proteins.
Description
Technical Field
The invention belongs to the technical field of preparation of medical materials, and relates to application of a electronegative micromolecule regulated surface to protein differential adhesion.
Background
In the field of tissue engineering, the selective adhesion of cells on the surface of a material has a very important meaning, and the selective adhesion is beneficial to simulating/remodelling the tissue structure of ordered combination of multiple types of cells in the original complex tissues of an organism. However, in the existing material preparation technology, cell selective adhesion depends on the preparation of material surfaces modified by biofunctional molecules (such as RGD, VEGF, and the like, nool s., et al acta biomatter.2016, 37,69), and the mechanism of action is that biofunctional molecules can mediate differential adhesion with different cell surface protein receptors, but the method depends on expensive biofunctional molecule preparation and biofunctional molecule surface fixing process which is unfavorable for mass production, and can only solve selective adhesion of a few cells with definite targets. Meanwhile, the high polymer material is flexible and various in structural design, is widely studied in the fields of tissue engineering, drug carriers and the like, can realize protein differential adhesion through fine structural design, and is also expected to further optimize the material structure so as to realize selective adhesion of cells. However, the current polymer material preparation technology is mainly focused on the research of cationic polymers (broad-spectrum enhanced protein/cell adhesion) and two materials of polyethylene glycol, electronegative polymers and zwitterionic polymers (obviously reduced protein/cell adhesion). Therefore, the preparation technology for simply and conveniently preparing the protein differential adhesion material is still lacking, and the development of the cell selective adhesion material in the field of tissue engineering is severely restricted.
Disclosure of Invention
In view of the above, the invention provides an application of electronegative small molecule controlled surface in differential adhesion of proteins. The technical scheme is specifically as follows: the application of the surface regulated by electronegative small molecules on the protein differential adhesion regulates and controls a substrate with cations on the surface by soaking electronegative small molecule solution, so that the differential adhesion of the surface of the substrate to different proteins can be realized, and the specific steps are as follows:
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 a modified substrate;
4) The substrate differentially adheres to the protein.
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 sulfonic acid sodium salt monohydrate, 3-N (-morpholino) propane sulfonic acid sodium, 3-morpholine-2-hydroxy propane sulfonic acid sodium and gluconic acid, and the concentration of the electronegative micromolecule solution is 0.5-50mg/mL.
Further, the proteins are albumin, globulin and fibrin.
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 carried out between hydroxyl, amino or carboxyl on the substrate surface without cations on the substrate surface and the quaternary ammonium salt containing epoxy groups; the quaternary ammonium salt containing epoxy group is 2, 3-epoxypropyl trimethyl ammonium chloride or a product obtained by reacting epoxy chloropropane with N, N-dimethyl X amine, and X is B, C and T.
Further, the method is characterized in that after 2, 3-epoxypropyl trimethyl quaternary ammonium salt modified gelatin and sodium methyl sulfate are soaked, the gelatin can be used for high adhesion of fibrinogen, albumin, globulin and the like; 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 can be used for high adhesion to globulin and low adhesion to fibrin after being soaked.
The invention has the beneficial effects that: according to the protein differential adhesion surface material regulated by electronegative micromolecules, a part of counter anions (such as hydroxide, chloride ions and the like) are converted into newly introduced electronegative micromolecules through the competitive action of the electronegative micromolecules and the original counter anions of the cationic polymer, so that the ferroelectric property (and the accompanying strong binding capacity/adhesion force with electronegative proteins) of the cationic polymer on the surface of a substrate is regulated, and finally the regulation of the protein adhesion amount and the differential adhesion of different proteins are realized. Therefore, compared with the direct chemical synthesis, the invention realizes the polymer structure design and the protein adhesion regulation (the chemical synthesis is often fine but complicated), and provides a simpler and more convenient method for preparing the protein differential adhesion material.
Detailed Description
A preferred embodiment 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-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 10mg/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 example, the surface is provided with a cationic substrate which is a quaternized gelatin sponge, and the cationic polymer is a quaternized gelatin, and the electronegative small molecule is sodium methyl sulfate.
Example 2
The quaternized gelatin sponge in the step 1) in the example 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 X2.
In this example, the concentration of electronegative small molecule sodium methyl sulfate was different from that in example 1.
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. 1mg/mL of poly (diallyldimethylammonium chloride) (PDADMAC) solution and 1mg/mL of poly (sodium 4-styrenesulfonate) (PSS) solution were 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 the cationic polymer polydiallyl dimethyl ammonium chloride
2) S-PP as 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 surface provided with the cationic substrate was a cationic immobilized substrate S-PP obtained by alternately self-assembling a 304 stainless steel sheet with poly (4-styrenesulfonate sodium) and poly (diallyldimethylammonium 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
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 and comparative experiments of albumin, globulin and fibrinogen.
The testing method comprises the following steps: taking a test method of human albumin as an example, adding 3mg of gelatin sponge series materials into a 2mL centrifuge tube, and taking 1X 1cm stainless steel sheets before and after modification 2 The mixture was placed in a 6-well plate. Human albumin was prepared as a 10mg/mL PBS solution, 50. Mu.L of the protein solution was added to the material and incubated in a constant temperature water bath at 37℃for 30 minutes. Excess liquid was aspirated off, and 200. Mu.L PBS was usedThe solution is lightly washed for 1 washing, the volume of the washing solution is fixed to 500 mu L, 50 mu L of the washing solution is taken in a 2mL centrifuge tube, 1mL of BCA working solution (reagent A: reagent B=50:1 (v/v)) prepared in advance is added, the solution is placed in a constant temperature water bath at 37 ℃ for incubation for 30 minutes, 100 mu L of the solution is taken and added into a 96-well plate, and absorbance Abs at 562nm is tested.
Blank 50. Mu.L of protein solution was added to a 2mL centrifuge tube. The control group was material plus 50 μl 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 of | 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 results of globulin adhesion Rate test
| Sample of | 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 of | 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 of tables 1 to 3, the gelatin sponge of examples 1 to 2 of the present invention (gelatin sponge material having a 12% protein adhesion rate as high protein adhesion property) X1 achieves high adhesion to fibrinogen while moderate adhesion to albumin and globulin; x2 achieves high adhesion to fibrinogen while medium adhesion to albumin and globulin.
As can be seen from the data of tables 1 to 3, the stainless steel sheet of inventive example 3 (the surface of the metal material had a protein adhesion rate of 6% as a medium/acceptable protein adhesion property) X3 achieved high adhesion to globulin while the adhesion to fibrinogen was low.
Therefore, by adopting the preparation method, the electropositivity of the cationic polymer can be effectively regulated by soaking electronegative small molecules with different concentrations, and the regulation of the protein adhesion amount and the selective adhesion of different proteins can be realized by regulating and controlling the strong adhesion acting force of the electropositivity to electronegative proteins. The specific analysis is as follows:
comparative example 1 is a gelatin sponge with a surface immobilized with a cationic polymer, and the adhesion rate to all three proteins is improved compared with comparative example 2 (unmodified gelatin sponge), which shows that the positive ion is positively adhered to negative protein, and the sponge Y1 obtained in comparative example is broad-spectrum and high-adhesion without selectivity to protein.
The protein adhesion rate data of examples 1-2 and comparative example 1 (gelatin sponge with surface immobilized with cationic polymer) shows that the adhesion rate of sponge X1 to albumin and globulin is substantially unchanged (adhesion rates from 8.1% to 8.9%, from 8.6% to 9.5%, respectively) and the adhesion rate to fibrinogen is increased (adhesion rate increases from 10.5% to 31.0%) when small molecules are added to form a complex system; the adhesion rate of sponge X2 to albumin was low (adhesion rate was reduced from 8.1% to 6.8%) and to globulin and fibrinogen was high (adhesion rates were increased from 8.6% to 11.1% and from 10.5% to 14.6%, respectively). Thus, the sponge prepared by the invention can realize differential adhesion to protein.
The protein adhesion rate data of example 3 and comparative example 3 (unmodified 304 stainless steel sheet) shows that the adhesion rate of stainless steel sheet X3 to globulin becomes high (the adhesion rate increases from 6.0% to 7.9%) and the adhesion rate to fibrinogen decreases (the adhesion rate decreases from 10.1% to 3.9%) when a composite system is formed by adding small molecules and cationic polymer. Thus, the membrane prepared by the invention can realize differential adhesion to protein.
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 (7)
1. The application of the surface regulated by electronegative small molecules on the protein differential adhesion is characterized in that the substrate with cations on the surface is regulated by soaking electronegative small molecule solution, so that the differential adhesion of the substrate surface to different proteins can be realized, and the specific steps are as follows:
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 a modified substrate;
4) The base material carries out differential adhesion on the protein;
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, and the concentration of the electronegative micromolecule solution is 0.5-50 mg/mL;
the proteins are albumin, globulin and fibrin, and the differential adhesion is different adhesion rates after the mass contact;
the base material with cations on the surface has 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.
2. The application of the electronegative small molecule controlled surface to protein differential adhesion according to claim 1, wherein the self-assembly in the substrate a is to coat the surface with a cationic polymer and an electronegative polymer by a layer-by-layer self-assembly method, and the outermost layer is controlled to be the cationic polymer.
3. The application of the electronegative micromolecule controlled surface to protein differential adhesion according to claim 1, wherein 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.
4. The application of the electronegative small molecule controlled surface to protein differential adhesion 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 electronegative polymer is one or more of poly (4-sodium styrene sulfonate) and polymethacrylic acid.
5. The application of the electronegative micromolecule controlled surface to protein differential adhesion according to claim 1, wherein the substrate which does not contain cations on the surface of the substrate b is gelatin sponge, polyvinyl alcohol sponge, medical collagen sponge or gauze.
6. The application of the electronegative small molecule controlled surface to the differential adhesion of proteins according to claim 1, 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 without cations on the substrate surface and the quaternary ammonium salt containing epoxy groups; the quaternary ammonium salt containing epoxy group is 2, 3-epoxypropyl trimethyl ammonium chloride or a product obtained by reacting epoxy chloropropane with N, N-dimethyl X amine, and X is B, C and T.
7. The application of the electronegative micromolecule controlled surface to protein differential adhesion according to claim 1, wherein the application is characterized in that the differential adhesion to fibrinogen, albumin and globulin can be realized after 2, 3-epoxypropyl trimethyl quaternary ammonium salt modified gelatin and sodium methyl sulfate are soaked; after the cationic immobilized 304 stainless steel surface obtained by alternately self-assembling and modifying the poly (4-styrene sodium sulfonate) and the poly (diallyl dimethyl ammonium chloride) and the sodium methyl sulfate are soaked, the differential adhesion of the globulin and the fibrinogen can be realized.
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