Acryloylphenylalanine-acrylate chiral copolymer macromolecular hydrogel, its preparation method and application

Abstract

The present invention discloses acryloylphenylalanine-acrylate chiral copolymer macromolecular hydrogels and their preparation methods and applications. The monomers acryloylphenylalanine and acrylate monomers (dimethylaminoethyl methacrylamide, 2-hydroxyethyl methacrylate, diethylaminoethyl methacrylate) are dissolved in a 1-methylpyrrolidone solution containing 1% polyethyleneimine, and a photoinitiator and a crosslinking agent are added. The carbon-carbon double bonds of the monomers are initiated by ultraviolet light for free radical polymerization. The polymeric macromolecular hydrogel ((L / D)APhe-co-DMAEMA) of the present invention can form a uniform and stable hydrogel film. Moreover, the preparation method of this hydrogel is simple, and the gels of L and D chirality have similar mechanical properties, good film-forming properties and biocompatibility, which is convenient for exploring the influence of chiral gels on cell culture.

Description

Technical Field

[0001] The present invention relates to a chiral macromolecular gel material for regulating cell adhesion and proliferation. Specifically, it relates to a preparation technology of a chiral macromolecular gel derived from phenylalanine and the regulation of cell adhesion and proliferation based on this material, belonging to the field of biomedical tissue engineering. Background Art

[0002] The interaction between cells and biomaterials at the interface is an important aspect determining their biomedical and bioengineering applications. If cells are exposed to the material surface, they are regulated not only by extracellular matrix (ECM) proteins but also by the surface chemistry and physical properties of the material. Chirality, as a fundamental property of nature, widely exists and greatly affects the physiological processes of organisms for materials. Therefore, chiral materials can regulate cell behavior. Hydrogels can mimic the natural extracellular matrix (ECM), have a mechanical structure similar to many soft tissues, can support cell adhesion and protein isolation, and provide tools for the amplification and directed differentiation of various cell types in a way that cannot be achieved by traditional culture matrices, and have become the most promising choice for cell culture. [2] Therefore, introducing chirality into hydrogels has practical significance for the research of cell culture and the study of the influence of chiral interfaces on cell behavior.

[0003] Chiral gels are gels prepared from chiral materials or gels prepared by making materials helical through asymmetric polymerization and other methods using achiral materials. Currently, chiral gels mainly include chiral supramolecular gels and chiral macromolecular gels. Chiral supramolecular gels are gels formed by non-covalent interactions between molecules, such as hydrogen bonds, coordination interactions, hydrophobic interactions, etc. However, due to the instability of non-covalent interactions and their weak interaction strength, chiral supramolecular gels often exhibit disadvantages such as easy dispersion, instability, and great susceptibility to the environment, which are exactly the advantages of chiral macromolecular gels. Macromolecular gels are gels formed by covalent cross-linking between molecules. Currently, the research on chiral macromolecular gels is relatively lacking, and due to the increase in molecular weight after polymerization, the chiral characterization of macromolecular gels is more complex. Therefore, the research on chiral macromolecules often focuses on chiral polymers, and there is little research on chiral gel materials. In view of the problems such as uncontrollable assembly structure and easy disintegration of supramolecular gels, the present invention synthesizes a chiral macromolecular gel material. Chiral macromolecular gels have characteristics such as high water content and an extracellular matrix-like environment, solving the current dilemma that the research on macromolecular chirality is limited to chiral polymers, and providing a method for studying the influence of macromolecular chiral gels on cell behavior. Summary of the Invention

[0004] The aim is to provide a chiral copolymer hydrogel film of acryloylphenylalanine and acrylate monomers.

[0005] The object of the present invention is achieved by the following technical solutions.

[0006] The present invention provides a method for preparing a copolymer hydrogel based on acryloylphenylalanine and acrylate monomers, comprising the following steps:

[0007] 1) Dissolve (L / D)phenylalanine in 1M NaOH solution. Under stirring in an ice-water bath, slowly dropwise add acryloyl chloride, and keep the solution pH around 10 by adding 2M NaOH. After the dropwise addition, maintain the ice-water bath for 30 min, react at room temperature for 3 h, and acidify the solution pH to 2-3 with 2M HCl. Precipitate white precipitate and stir for 30 min to make it fully uniform. Filter the turbid liquid by suction filtration and wash it with deionized water. Then extract the solid with ethyl acetate three times, separate the ethyl acetate solution and dry the ethyl acetate solution with anhydrous magnesium sulfate. Filter the anhydrous magnesium sulfate to obtain a clear solution, place it in a rotary evaporator, evaporate most of the solvent, and then dry it in a vacuum oven to obtain (L / D)acryloylphenylalanine.

[0008] 2) Using an N-methylpyrrolidone solution containing 1% polyethyleneimine as the solvent, uniformly mix the prepared (L / D)acryloylphenylalanine monomer (Phe-A), acrylate monomer, photoinitiator, and crosslinker. Pipette an appropriate amount (2 μl) of the mixed monomer solution onto a glass slide treated with a silane coupling agent, cover the glass slide with a PET film, and initiate a free radical polymerization reaction under 365 nm ultraviolet light irradiation for 1 h.

[0009] 3) After the reaction, place the gel in an oven at 50 °C for 4-8 h, then use tweezers to tear the PET film to obtain an acryloylphenylalanine-acrylate monomer copolymer hydrogel film. Rinse it three times with water / ethanol / acetone in sequence. After natural drying, soak it in PBS buffer solution for storage, and sterilize it with an ultraviolet lamp for 1 h.

[0010] Further, in step (1), the molar ratio of the added amounts of phenylalanine and acryloyl chloride is 1:1.5-2.2.

[0011] Further, in step (2), the molar ratio of (L / D)acryloylphenylalanine to acrylate monomer is 1.5-8:1.

[0012] Further, the acrylate monomer is one of dimethylaminoethyl methacrylamide, 2-hydroxyethyl methacrylate, and diethylaminoethyl methacrylate. Preferably, the acrylate monomer is dimethylaminoethyl methacrylamide.

[0013] Further, in step (2), the photoinitiator is selected as hydroxycyclohexyl phenyl ketone, and the dosage of the photoinitiator is 3% - 5% of the sum of the masses of the two monomers. The crosslinking agent is N,N-methylenebisacrylamide, and the dosage of the crosslinking agent is 8% - 12% of the sum of the masses of the two monomers. The polymerization initiation temperature is room temperature of 20 - 25 °C, and the polymerization reaction time is 1 h.

[0014] Further, the total mass of the monomer acryloyl phenylalanine and the acrylate monomer in the solution with an N-methylpyrrolidone solution containing 1% polyethyleneimine as the solvent has a solid content of 25% - 35% (the solid content is the proportion of the total mass of the monomer acryloyl phenylalanine and dimethylaminoethyl methacrylate in the total mass of the solvent).

[0015] Application of acryloyl-(L / D)-phenylalanine / dimethylaminoethyl methacrylate chiral copolymer hydrogel as a biomaterial.

[0016] Further, application of acryloyl-(L / D)-phenylalanine / dimethylaminoethyl methacrylate chiral copolymer hydrogel in cell culture materials.

[0017] Compared with the prior art, the excellent effects of the present invention are as follows:

[0018] The present invention provides a preparation method of a chiral gel film to study the influence of the chiral interface on cell behavior. Compared with the prior art, the chiral gel film can better simulate the biophysical conditions required for tissue engineering and has a chiral interface with certain mechanical properties and uniform stability compared with the commonly used polymer chiral interfaces, and inherits the advantages that the composition and function of the polymer chiral interface are easy to adjust, and the perfect control of the surface properties can be achieved. Therefore, it is considered that this method can be used as an alternative to the polymer chiral interface, providing a method for controlling the surface properties of chiral interface functional materials to regulate the behavior of cells and other biomolecules. Description of the Drawings

[0019] Figure 1 It is the reaction equation and structural formula of the chiral (L / D)APhe-co-DMAEMA copolymer gel prepared by the present invention.

[0020] Figure 2 It is the nuclear magnetic resonance hydrogen spectrum of L / D acryloyl phenylalanine (APhe) prepared by the present invention.

[0021] Figure 3 It is the circular dichroism CD curve of the chiral polymer (L / D)APhe-co-DMAEMA prepared by the present invention.

[0022] Figure 4 It is the morphology observed by scanning electron microscopy (SEM) after freeze-drying of the chiral (L / D)APhe-co-DMAEMA copolymer gel prepared by the present invention.

[0023] Figure 5 It is the rheological analysis of the chiral (L / D) APhe-co-DMAEMA copolymer gel prepared by the present invention. Figures A and B are respectively the strain tests of the gels of Example 2 (L / D), Figures C and D are respectively the frequency tests of the gels of Example 3 (L / D), and Figures E and F are respectively the frequency tests of the gels of Example 3 (L / D). Figures G and H are respectively the frequency tests of the gels of Example 4 (L / D).

[0024] Figure 6 It is the cell viability measured after culturing mouse fibroblasts (L929) for 48 h with the chiral (L / D) APhe-co-DMAEMA copolymer gel prepared by the present invention. Among them, L2 / D2, L4 / D4, and L6 / D6 respectively correspond to the cell viabilities of the gel films of Example 3, Example 2, and Example 4.

[0025] Figure 7 It is the cell viability measured by culturing mouse fibroblasts (L929) with the chiral (L / D) APhe-co-DMAEMA copolymer gel film prepared in Example 2 of the present invention.

[0026] Figure 8 It is the live-dead staining map of the chiral (L / D) APhe-co-DMAEMA copolymer gel film prepared by the present invention after culturing mouse fibroblasts (L929) for 48 h. A, B, and C are respectively the live cell stainings of the L-type, D-type, and blank gel films, and E, F, and G are respectively the dead cell stainings of the L-type, D-type, and blank gel films. Detailed implementation manners

[0027] The technical solutions of the present invention will be further described below through specific examples. For the experimental methods without specific conditions noted in the examples, they are usually carried out according to the conventional conditions and the conditions described in the manuals, or according to the conditions recommended by the manufacturers; for the general equipment, materials, reagents, etc. used, unless otherwise specified, they can all be obtained through commercial channels

[0028] Example 1

[0029] Preparation and characterization of acryloylphenylalanine

[0030] Dissolve 3.3 g of L-phenylalanine or D-phenylalanine in 40 mL of 1 M NaOH solution. Under stirring in an ice-water bath, slowly add dropwise 3.98 g of acryloyl chloride, and continuously add 2 M NaOH to keep the pH of the solution around 10. After the addition is complete, maintain the ice-water bath for 30 min, react at room temperature for 3 h, acidify the solution to pH 2 - 3 with 2 M HCl, precipitate a white solid and stir for 30 min to make it fully homogeneous. Filter the turbid liquid by suction filtration and wash it with deionized water. Then, extract the solid with ethyl acetate three times. Separate the ethyl acetate solution and dry the ethyl acetate solution with anhydrous magnesium sulfate. Filter the anhydrous magnesium sulfate to obtain a clear solution, place it in a rotary evaporator, evaporate most of the solvent, and then dry it in a vacuum oven to obtain the L-acryloylphenylalanine monomer or D-acryloylphenylalanine monomer APhe.

[0031] Figure 2 It is the 1H NMR spectrum of the L / D-acryloylphenylalanine (APhe) prepared above.

[0032] 1H NMR of APhe monomer 1 1H NMR analysis.

[0033] Weigh 3 - 5 mg of the prepared (L / D)-acryloylphenylalanine (APhe) monomer and dissolve it in 0.5 mL of deuterated dimethyl sulfoxide (DMSO-d6) for 1 1H NMR analysis. As can be seen from Figure 2 the content, the characteristic peaks of acryloyl and phenylalanine can be observed. These include -NH- (b, δ = 8.43 ppm) and -CH=CH2 (d and e, δ = 6.25 ppm and δ = 5.56 - 6.06 ppm) on acryloyl, -COOH (a, δ = 12.78), phenyl (c, δ = 7.23), and the methyl groups of -NH-CH-CH2 (f and g, δ = 4.53 and δ = 2.89 - 3.08) on phenylalanine. This indicates the successful synthesis of (L / D)-acryloylphenylalanine (APhe).

[0034] Example 2

[0035] Dissolve 0.438 g of (L / D)-acryloylphenylalanine (APhe) monomer, 0.079 g of monomer dimethylaminoethyl methacrylate (DMAEMA), 0.020 g of photoinitiator hydroxycyclohexyl phenyl ketone (I184), and 0.039 g of crosslinking agent N,N'-methylenebisacrylamide (MBA) in 1.6 mL of a 1% (by mass) polyethyleneimine (PEI) solution in N-methylpyrrolidone (NMP), stir evenly. Pipette 2 μL of the mixed monomer solution onto a cover glass treated with a silane coupling agent, cover the cover glass with a PET film, and initiate a free radical polymerization reaction under 365 nm ultraviolet light irradiation for 1 h. After the reaction, place the gel in an oven at 50 °C for 8 - 12 h, then use tweezers to tear off the PET film to obtain a (L / D)-acryloylphenylalanine-dimethylaminoethyl methacrylate copolymer hydrogel film. Rinse it 3 times with water / ethanol / acetone in sequence. After natural drying, soak it in PBS buffer solution for preservation, and sterilize it with an ultraviolet lamp for 1 h, namely L-APhe-co-DMAEMA copolymer gel or D-APhe-co-DMAEMA copolymer gel.

[0036] Example 3

[0037] Dissolve 0.5 g of monomer (L / D)-acryloylphenylalanine (APhe), 0.18 g of monomer dimethylaminoethyl methacrylate (DMAEMA), 0.027 g of photoinitiator hydroxycyclohexyl phenyl ketone (I184), and 0.053 g of crosslinking agent N,N'-methylenebisacrylamide (MBA) in 2.2 mL of a 1% polyethyleneimine (PEI) solution in N-methylpyrrolidone (NMP), stir evenly to obtain a mixed solution of acryloylphenylalanine and dimethylaminoethyl methacrylate. Pipette 2 μL of the mixed monomer solution onto a cover glass treated with a silane coupling agent, cover the cover glass with a PET film, and initiate a free radical polymerization reaction under 365 nm ultraviolet light irradiation for 1 h. After the reaction, place the gel in an oven at 50 °C for 8 - 12 h, then use tweezers to tear off the PET film to obtain a (L / D)-acryloylphenylalanine-dimethylaminoethyl methacrylate copolymer hydrogel film. Rinse it 3 times with water / ethanol / acetone in sequence. After natural drying, soak it in PBS buffer solution for preservation.

[0038] Example 4

[0039] Dissolve 1 g of the prepared monomer (L / D) acryloylphenylalanine (APhe), 0.119 g of the monomer dimethylaminoethyl methacrylate (DMAEMA), 0.043 g of the photoinitiator hydroxycyclohexyl phenyl ketone (I184), and 0.084 g of the crosslinking agent N,N'-methylenebisacrylamide (MBA) in 3.7 mL of a 1% polyethyleneimine (PEI) solution in N-methylpyrrolidone (NMP), and stir evenly to obtain a mixed solution of acryloylphenylalanine and dimethylaminoethyl methacrylate. Pipette 2 μL of the mixed monomer solution onto a cover glass treated with a silane coupling agent, cover the PET film on the cover glass, and initiate a free radical polymerization reaction under 365 nm ultraviolet light irradiation for 1 h. After the reaction, place the gel in an oven at 50 °C for 8 - 12 h, then use tweezers to tear the PET film to obtain an (L / D) acryloylphenylalanine-dimethylaminoethyl methacrylate chiral copolymer hydrogel film. Rinse it 3 times with water / ethanol / acetone in sequence. After natural drying, soak it in PBS buffer for storage, and sterilize it with an ultraviolet lamp for 1 h.

[0040] Example 5

[0041] Compared with the example, replace the dimethylaminoethyl methacrylamide therein with methylacryloyloxyethyl trimethylammonium chloride, 2-hydroxyethyl methacrylate, N,N-diethyl-dipropenamide, N-vinylpyrrolidone, and keep other operations the same. Study the influence of acrylate monomers on the chiral copolymer hydrogel film. After research, it is found that dimethylaminoethyl methacrylamide is most suitable compared with gels copolymerized with other monomers, having a lower swelling ratio and better film-forming property.

[0042] Table 1 records the swelling ratios of the gels after copolymerization of acryloylphenylalanine and acrylates (2-hydroxyethyl methacrylate and dimethylaminoethyl methacrylamide). Among the two monomers, the acryloyl-dimethylaminoethyl methacrylate gel has a swelling ratio of only about 10, obviously having a lower swelling ratio. In addition, due to the too high swelling ratio caused by the 2-hydroxyethyl methacrylate monomer during the film preparation process, the silanized cover glass is difficult to bind the gel, resulting in its detachment in the solution. Therefore, it is not suitable as the monomer for the film of the present invention.

[0043] Table 1 is the swelling ratio of the copolymer gel of acryloylphenylalanine and acrylates (2-hydroxyethyl methacrylate and dimethylaminoethyl methacrylate).

[0044] Table 1

[0045]

[0046] UV test and circular dichroism CD curve analysis of the (L / D) APhe-co-DMAEMA copolymer prepared in Example 2

[0047] To study the chirality of copolymer gels, the chirality of the synthesized (L / D)APhe-co-DMAEMA after copolymerization was tested by UV and CD. The results are as follows Figure 3 shown. LAPhe-co-DMAEMA and DAPhe-co-DMAEMA show completely opposite chiral signals. The maximum positive Cotton effect peak is at 225 nm, and the maximum negative Cotton effect peak is also at 225 nm. The absolute values of the peaks are basically the same. From the UV spectrum, it can be seen that the (L / D)APhe-co-DMAEMA copolymer has a characteristic peak of phenylalanine at 216 nm. This indicates that the chirality of APhe-co-DMAEMA exists at the phenylalanine site after copolymerization and shows a good chiral mirror image relationship at the characteristic peak of phenylalanine.

[0048] Rheological analysis of Ahe-co-DMAEMA copolymer gels.

[0049] To study the rheological properties of the gels, a rotational rheometer was used to perform rheological tests on the gels. A flat plate with a diameter of 25 mm was used. At room temperature, dynamic strain tests were carried out at a frequency of 10 rad / s in the stress range of 0.1% - 1000%, and dynamic frequency tests were carried out at a stress of 1% in the frequency range of 0.1 rad / s - 100 rad / s.

[0050] The results are as follows Figure 5 shown. A and B are the strain tests of the L-APhe-co-DMAEMA and D-APhe-co-DMAEMA copolymer gels prepared in Example 2, respectively. The figure shows that the strengths of the elastic modulus and loss modulus of L-APhe-co-DMAEMA and D-APhe-co-DMAEMA are basically consistent with the strain. Among them, the elastic modulus (G’) of the gel reaches 400 Pa, and the loss modulus (G”) reaches 20 Pa. Before the stress reaches 50%, the elastic modulus (G’) is always greater than the loss modulus (G”), indicating that the gel shows a quasi-solid state. As the stress increases, G’ and G” deviate from linearity until the stress reaches 50%, where G’ and G” intersect, and then G” is shown to be greater than G’. At this time, the gel shows a quasi-liquid state, indicating that the gel undergoes a gel-to-sol transition. Figures C and D are the dynamic frequency tests of the L-APhe-co-DMAEMA ( Figure 5 C), D-APhe-co-DMAEMA ( Figure 5 D) copolymer gels prepared in Example 2. In the figure, the elastic modulus and storage modulus are basically stable, indicating that the gel has good strength and stable performance. Figures E, F, G, and H are the dynamic frequency tests of the (L / D) gels in Examples 3 and 4. Compared with Example 2, the modulus changes of the gels in Examples 3 and 4 are larger, and the frequency is relatively unstable.

[0051] (L / D)APhe-co-DMAEMA Copolymer Gel Scanning Electron Microscopy (SEM) Analysis

[0052] To observe the surface morphology of the gel, a field emission scanning electron microscope (SEM) from FEI Company, USA was used to characterize the (L / D)APhe-co-DMAEMA copolymer gel. The results are as follows Figure 4 shown. A and B are the surface morphologies of the L gel and D gel films respectively, and C and D are the morphologies of the gel cross-sections. It can be seen from the figure that the morphological structures of the L / D gel films from the surface and cross-section are basically the same. From Figures A and B, it can be seen that the surface of the gel film is a uniform, stable and continuous gel layer, and there are no pores large enough to support cell adhesion on the surface. From Figures C and D, it can be seen that the gel cross-section presents a porous structure with a continuous diameter in the range of 20 - 100 μm. This indicates the stability of the gel cross-linking and the presence of an environment containing a large amount of water during swelling, which is beneficial for cell culture.

[0053] (L / D)APhe-co-DMAEMA Copolymer Gel Cell Culture

[0054] To study the effect of the chiral gel on cell culture, (L929) mouse fibroblasts were used to conduct cell culture on the (L / D)APhe-co-DMAEMA copolymer gel film respectively, and the cell growth conditions within 24 h and 48 h were observed. As shown in Figure 6, L2 / D2, L4 / D4, and L6 / D6 correspond to the cell activities after culturing on the gel films of Example 3, Example 2, and Example 4 for 48 h respectively. Among them, the difference in L / D cell activities in Example 2 is the largest, the chiral difference is the most obvious, and the rheological properties are the most stable. Therefore, the subsequent tests will give priority to Example 2.

[0055] To improve the cell adhesion ability of the gel film to enhance cell activity, but due to the cytotoxicity of PEI itself, it is necessary to control the concentration of PEI added to the solution. The cytotoxicity of the gel film PEI concentration was tested with (L929) mouse fibroblasts. The results showed that when the PEI concentration was between 1% - 1.5%, the gel film had good cell activity, and there were obvious differences in cell activity between the L / D films. Therefore, N-methylpyrrolidone with a 1% concentration of PEI was selected as the solvent for the gel reaction solution.

[0056] Cells grow better on the D-type gel prepared in Example 2 than on the L-type gel ( Figure 7) After 24 h of cell culture, the cell survival rates were 81.48% and 92.66% respectively. The difference in cell survival rate at the L / D gel interface was small, indicating that chirality had no obvious effect on cell adhesion and proliferation in the short term. After 48 h of cell culture, chirally modified gels had a greater impact on cell proliferation. The cell survival rates were 86.67% and 113.35% respectively, and it was found that cell proliferation on the D-type gel film was significantly higher than that on the L-type gel film.

[0057] Live / dead staining was performed on cells after 48 h of cell culture as Figure 8 shown. It was clearly observed that the proliferation density and fluorescence intensity of live cells on the D-type gel film in Figure B were better than those on the L-type gel film in Figure A, and the cell spreading on the D-type gel film was better. As shown in Figures E, F, and G, dead cells were stained. It was observed that there were basically no dead cells on the L / D gel films in Figures E and F, which was basically the same as that in the control group G, indicating that the gel films had low toxicity. According to the above gel characterization, except for the chirality difference, the physical and chemical properties of the L / D gels were basically the same. Therefore, it can be concluded that the difference in cell proliferation was caused by the chirality of the gels, and cell proliferation on the D-type gel was better than that on the L-type gel.

Claims

1. A method for preparing an acryloylphenylalanine-acrylate chiral copolymer macromolecular hydrogel, characterized in that: (1) Using phenylalanine and acryloyl chloride as raw materials, acryloylphenylalanine is prepared; the phenylalanine is L-phenylalanine or D-phenylalanine; (2) Using an N-methylpyrrolidone solution containing polyethyleneimine as a solvent, the acryloylphenylalanine monomer, acrylate monomer, initiator, and crosslinking agent are uniformly mixed to obtain a mixed monomer. The mixed monomer solution is sucked and placed on a substrate, and the film is covered, and a free radical polymerization reaction is initiated under ultraviolet light irradiation; (3) After the reaction, the gel is placed in an oven for drying to obtain an acryloylphenylalanine-acrylate chiral copolymer macromolecular hydrogel film. After washing and drying, it is soaked and stored in PBS buffer solution and sterilized with an ultraviolet lamp.

2. The preparation method of the acryloylphenylalanine-acrylate chiral copolymer macromolecular hydrogel according to claim 1, characterized in that: The molar ratio of the addition amounts of phenylalanine and acryloyl chloride is 1:1.5 - 2.2; the acryloylphenylalanine is L-acryloylphenylalanine or D-acryloylphenylalanine.

3. The preparation method of the acryloylphenylalanine-acrylate chiral copolymer macromolecular hydrogel according to claim 1, wherein: The molar ratio of the acryloylphenylalanine monomer to the acrylate monomer is 1.5 - 8:

1.

4. The preparation method of the acryloylphenylalanine-acrylate chiral copolymer macromolecular hydrogel according to claim 1, characterized in that: The initiator selected is hydroxycyclohexanone phenyl ketone, and the dosage of the initiator is 3% - 5% of the sum of the masses of the two monomers; the crosslinking agent is N,N-methylenebisacrylamide, and the dosage of the crosslinking agent is 8% - 12% of the sum of the masses of the two monomers; the polymerization reaction temperature is 20 - 25 °C, and the polymerization reaction time is 1 h.

5. The preparation method of the acryloylphenylalanine-acrylate chiral copolymer macromolecular hydrogel according to claim 1, wherein: The mass ratio of the sum of the masses of the two monomers to the mass of the solvent is 1:2.5 - 4; the mass fraction of polyethyleneimine in the solvent is 1%.

6. The preparation method of the acryloylphenylalanine-acrylate chiral copolymer macromolecular hydrogel according to claim 1, characterized in that: The acrylate monomer is one of dimethylaminoethyl methacrylamide, 2-hydroxyethyl methacrylate, and diethylaminoethyl methacrylate.

7. The preparation method of the acryloylphenylalanine-acrylate chiral copolymer macromolecular hydrogel according to claim 6, characterized in that: The acrylate monomer is dimethylaminoethyl methacrylamide.

8. An acryloylphenylalanine-acrylate chiral copolymer macromolecular hydrogel prepared by the method according to any one of claims 1 - 7.

9. Use of an acryloylphenylalanine-acrylate chiral copolymer macromolecular hydrogel prepared by the method according to any one of claims 1 - 7 as a biomaterial.

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