CN114381083B - Antibacterial and antioxidant hydrogel for corneal contact lens and preparation method thereof - Google Patents
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Abstract
The invention belongs to the technical field of polymer hydrogel, and particularly relates to an antibacterial antioxidant hydrogel for a contact lens and a preparation method thereof, wherein the antibacterial antioxidant hydrogel comprises the following components in percentage by weight: 15 to 20 percent of acrylamide monomer, 1 to 1.5 percent of quaternized chitosan, 0.01 to 0.05 percent of cross-linking agent, 0.01 to 0.05 percent of initiator, 0.03 to 0.08 percent of accelerator and the balance of water. The antibacterial and antioxidant hydrogel disclosed by the invention has good light transmittance, mechanical property, antibacterial and antioxidant capacity and biocompatibility, and can be used as a hydrogel contact lens material for treating bacterial keratitis.
Description
Technical Field
The invention belongs to the technical field of polymer hydrogel, and particularly relates to an antibacterial and antioxidant hydrogel for a contact lens and a preparation method thereof.
Background
Bacterial keratitis is an eye disease caused by injury or bacterial infection of the cornea after wearing contact lenses, and can lead to complications such as corneal perforation and stroma damage. Currently, the eye drops containing broad-spectrum antibiotics are generally used clinically to treat bacterial keratitis. However, due to the limitation of the administration mode, the drug utilization rate of the antibiotic eye drops is low, and only less than 5 percent of the drug can really reach the infected area. In addition, bacterial infections are often accompanied by inflammation of the immune system and oxidative stress damage through reactive oxygen species. Excess reactive oxygen species can lead to impaired normal cell function and even cell death.
The antibacterial polymer shows remarkable selectivity for bacteria compared to other antibacterial agents, and is considered as a next-generation bactericide. Antimicrobial polymers can be classified into two groups according to their antimicrobial mechanism: contacting an active polymer, which is generally cationically charged, with a polymer that directly inhibits bacterial growth by interacting with negatively charged bacterial membranes, and releasing a biocide; the latter release bactericides to inactivate bacteria, such as antibiotics or other strong antimicrobial actives (e.g., metal nanoparticles).
Hydrogels are soft materials composed of crosslinked hydrophilic polymers and are widely used in tissue engineering and medical fields, such as artificial joints, corneal contact lenses, medical dressings, and the like, due to their high water content, adjustable mechanical properties, good biocompatibility, and the like. Hydrogels can be used as antimicrobial polymer carriers to load antibiotics or nanoparticles to inhibit bacterial infection by contacting or releasing a bactericide, for example, the drug-sustained-release hydrogel corneal contact lens disclosed in patent document CN 102316832B. However, sustained drug release of antibiotics in hydrogels still does not solve the problem of drug-resistant bacteria generation, and metal oxide nanoparticles have high cytotoxicity to mammalian cells. Therefore, an antimicrobial material that can inactivate bacteria merely by contact rather than release of a drug or nanoparticles would be safer and more reliable.
Disclosure of Invention
Based on the above disadvantages and shortcomings of the prior art, it is an object of the present invention to at least solve one or more of the above problems of the prior art, in other words, to provide an antibacterial and antioxidant hydrogel for a contact lens and a method for preparing the same, which satisfies one or more of the above requirements.
In order to achieve the purpose, the invention adopts the following technical scheme:
an antibacterial and antioxidant hydrogel for a contact lens comprises the following components in percentage by weight:
15 to 20 percent of acrylamide monomer, 1 to 1.5 percent of quaternized chitosan, 0.01 to 0.05 percent of cross-linking agent, 0.01 to 0.05 percent of initiator, 0.03 to 0.08 percent of accelerator and the balance of water.
As a preferable scheme, the antibacterial and antioxidant hydrogel also comprises the following components in percentage by weight: 0.001 to 1.5 percent of tannic acid.
The antibacterial and antioxidant hydrogel for the corneal contact lens takes polyacrylamide hydrogel as a matrix, and the quaternized chitosan and the tannic acid are introduced into a polyacrylamide hydrogel network to form a new physical cross-linking bond (hydrogen bond, pi-pi interaction and cation-pi interaction) to form a semi-interpenetrating network so as to enhance the mechanical strength. The quaternized chitosan mainly provides antibacterial performance, the tannic acid mainly provides antioxidant performance, and the two have cooperativity; by regulating the content of each component in the system, a series of hydrogel corneal contact lenses with antibacterial and antioxidant properties and capable of being used for treating bacterial keratitis are obtained.
Preferably, the acrylamide monomer is acrylamide, N-isopropylacrylamide or N, N-bis-methacrylamide.
Preferably, the structural formula of the quaternized chitosan is as follows:
wherein x/(x + y) is the quaternization ratio and is controlled to be 40-70%.
Preferably, the cross-linking agent is N, N-methylene bisacrylamide, the initiator is potassium persulfate or ammonium persulfate, and the accelerator is N, N, N ', N' -tetramethyl ethylenediamine.
The invention also provides a preparation method of the antibacterial and antioxidant hydrogel, which comprises the following steps:
(1) Adding quaternized chitosan and acrylamide monomers into water, and stirring until the quaternized chitosan and the acrylamide monomers are completely dissolved; then adding an initiator, a cross-linking agent and an accelerator in sequence, and uniformly stirring to form a reaction mixed solution;
(2) And transferring the reaction mixed solution into a mold for free radical polymerization reaction, taking the product out of the mold after the reaction is finished, and transferring the product into water to enable the gel to reach swelling balance, thereby obtaining the antibacterial antioxidant hydrogel.
The invention also provides a preparation method of the antibacterial and antioxidant hydrogel, which comprises the following steps:
(1) Adding quaternized chitosan and acrylamide monomers into water, and stirring until the quaternized chitosan and the acrylamide monomers are completely dissolved; then adding an initiator, a cross-linking agent and an accelerator in sequence, and uniformly stirring to form a reaction mixed solution;
(2) Transferring the reaction mixed solution into a mold for free radical polymerization reaction, taking the product out of the mold after the reaction is finished, and carrying out freeze drying treatment to obtain freeze-dried gel;
(3) And (3) immersing the freeze-dried gel into a tannic acid aqueous solution with the pH value of 2-3, adjusting the pH value of the tannic acid aqueous solution to be neutral after the immersion is finished, and transferring the gel into water to enable the gel to reach swelling balance, thereby obtaining the antibacterial and antioxidant hydrogel.
Preferably, the temperature of the free radical polymerization reaction is 20-35 ℃ and the time is 12-36 h.
Preferably, in the step (3), the soaking temperature is 60-75 ℃, and the soaking time is 10-24 h.
Preferably, in the step (3), the pH of the aqueous solution of tannic acid is adjusted to 2 to 3 with hydrochloric acid, and the pH of the aqueous solution of tannic acid is adjusted to neutral with sodium hydroxide.
Compared with the prior art, the invention has the beneficial effects that:
(1) The antibacterial and antioxidant hydrogel disclosed by the invention has high light transmittance and soft and tough mechanical properties, can be used as a corneal contact lens material, and meets the requirements of comfort and safety of a wearer;
(2) The antibacterial and antioxidant hydrogel disclosed by the invention has excellent antibacterial and antioxidant activities, and the antibacterial and antioxidant hydrogel and the antioxidant activities have a synergistic effect;
(3) The quaternized chitosan and the tannin of the antibacterial antioxidant hydrogel belong to natural biological compounds, the raw materials are cheap and easy to obtain, and the preparation cost of the hydrogel can be greatly reduced;
(4) The antibacterial and antioxidant hydrogel does not contain antibiotics and other medicines, and has no drug resistance problem;
(5) The antibacterial and antioxidant hydrogel disclosed by the invention has good biocompatibility;
(6) The antibacterial and antioxidant hydrogel can adjust the antibacterial and antioxidant performance by changing the content of each component, and the preparation process is simple and easy to control.
Drawings
FIG. 1 is a schematic route diagram of the synthesis of an antibacterial and antioxidant hydrogel according to an embodiment of the present invention;
FIG. 2 is a graph comparing light transmittance curves of the antibacterial and antioxidant hydrogels of examples 1-5 of the present invention;
FIG. 3 is a comparison graph of tensile stress-strain curves of the antibacterial and antioxidant hydrogels of examples 1-5 of the present invention;
FIG. 4 is a graph comparing the antioxidant properties of the antibacterial and antioxidant hydrogels of examples 1 to 5 and comparative examples 1 to 5 according to the present invention;
FIG. 5 is a graph showing the comparison of the antibacterial properties of the antibacterial and antioxidant hydrogels of examples 1 to 5 and comparative examples 1 to 5 according to the present invention;
FIG. 6 is a graph showing the comparison of cytotoxicity of the antibacterial and antioxidative hydrogels of examples 1 to 5 of the present invention.
Detailed Description
The technical solution of the present invention is further explained by the following specific examples.
The preparation method of the antibacterial and antioxidant hydrogel provided by the embodiment of the invention comprises the following steps:
(1) Adding 1-1.5 wt% of quaternized chitosan and 15-20 wt% of acrylamide monomer into water, and stirring until the quaternized chitosan and the acrylamide monomer are completely dissolved; then, 0.01 to 0.05 weight percent of initiator, 0.01 to 0.05 weight percent of cross-linking agent and 0.03 to 0.08 weight percent of accelerant are added in sequence and stirred evenly to form reaction mixed liquid;
(2) Transferring the reaction mixed solution into a mold, carrying out free radical polymerization reaction at 20-35 ℃, wherein the reaction time is 12-36 h, and taking out a product from the mold after the reaction is finished;
(3) Carrying out freeze drying treatment on the product taken out in the step (2) to obtain freeze-dried gel; then soaking the freeze-dried gel in Tannic Acid (TA) aqueous solutions with different concentrations and pH values of 2-3, which are adjusted by hydrochloric acid, and heating the gel in a water bath for 10-24 h at the temperature of 60-75 ℃;
(4) After the water bath heating is finished, adjusting the pH value of the tannic acid solution to be neutral by using sodium hydroxide;
(5) And (4) taking out the gel treated in the step (4), and soaking in water for 3 days to remove unreacted acrylamide monomers, quaternized chitosan, an initiator, an accelerator and tannic acid, so that the gel reaches swelling balance, and the hydrogel with antibacterial and antioxidant properties is obtained. Specifically, reference may be made to the synthesis principle of the antibacterial and antioxidant hydrogel shown in fig. 1.
Specifically, quaternized Chitosan (QCS) has the structural formula:
wherein x/(x + y) is the quaternization ratio and is controlled to be 40-70%.
The acrylamide monomer is acrylamide, N-isopropyl acrylamide or N, N-dimethylacrylamide, the crosslinking agent is N, N-methylene bisacrylamide, the initiator is potassium persulfate (KPS) or Ammonium Persulfate (APS), and the accelerator is N, N, N ', N' -tetramethyl ethylenediamine; the amount of water used was 6mL.
The differences between examples 1-9 and comparative examples 1-5 are shown in the formulation table and the preparation parameter table, and the specific preparation process can refer to the preparation method of the antibacterial and antioxidant hydrogel of the present invention, as shown in tables 1 and 2. In addition, if the antibacterial and antioxidant hydrogel does not contain tannic acid, the steps (3) to (4) are omitted, and the product of the step (2) is directly subjected to the step (5) to obtain the hydrogel.
TABLE 1 ingredient tables for examples 1 to 9 and comparative examples 1 to 5
Wherein, the acrylamide monomer in examples 1 to 7 and comparative examples 1 to 5 is acrylamide; the acrylamide-based monomer in example 8 is N-isopropylacrylamide; the acrylamide-based monomer in example 9 was N, N-bis-methacrylamide.
TABLE 2 preparation parameter tables for examples 1 to 9 and comparative examples 1 to 5
The hydrogels of examples 1 to 5 and comparative examples 1 to 5 were subjected to the following performance test:
1. and (3) testing light transmittance: the light transmittance of the contact lens is measured by an ultraviolet-visible spectrophotometer within the wavelength range of 450-800 nm.
2. And (3) testing mechanical properties: the hydrogel was cut into a dumbbell shape (length 16mm, width 4 mm) at room temperature and 50% humidity, and the tensile mechanical properties of the hydrogel contact lens were measured by fixing the tensile rate at 100mm/min using a universal tester.
3. And (3) oxidation resistance test: 10mg of hydrogel samples were added to 30mL each of freshly prepared 1,1-diphenyl-2-trinitrophenylhydrazine (DPPH) · ) Or 2,2' -azino-bis- (3-ethylbenzodihydropyrazoline-6-sulfonic Acid) (ABTS) ·+ ) In free radical solution, and mixingThe material was kept in the dark for 1h or 40min and then measured at 517nm (DPPH) using a UV-visible spectrophotometer · ) Or 752nm (ABTS) ·+ ) Absorbance of (d) in (d).
The radical clearance S is calculated as follows:
S＝[1-A i /A c ]*100％
wherein A is i And A c The absorbance of the free radical solution mixed with the hydrogel sample and the absorbance of the blank free radical solution at 517nm or 752nm, respectively.
4. And (3) testing antibacterial performance: samples were sterilized and placed in 48-well plates, then 200. Mu.L of bacterial suspension (1X 10) was added per well 5 CFU/mL). The selected bacteria are Escherichia coli (E.coli) or Staphylococcus aureus (S.aureus). After incubation for 8h in a shaker at 37 ℃, the bacteria were inoculated on Luria-Bertani (LB) agar plates and counted in bacterial concentration after 10-fold serial dilution. Finally, relative bacterial survival was calculated from the number of colonies before and after incubation.
5. In vitro cytotoxicity experiments: human Corneal Epithelial Cells (HCECs) were cultured in Ham's F12 complete medium (containing 10% FBS) for 2 to 3 days with proliferation, and then cultured at 1X 10/well 4 The concentration of each cell was transferred to a 96-well plate. After further culturing for 24h, cell adhesion was observed. After the HCECs reached 90% growth density, the 4mm diameter hydrogel was incubated with the cells for 10h. After removing the hydrogel, cell Counting Kit-8 (CCK-8) reagent was added to the well plate and incubated for 1-4 h. Finally, the Optical Density (OD) value at the wavelength of 450nm is measured by a microplate reader, so that the number of living cells can be indirectly quantified, and the activity of the cells is reflected.
As shown in FIG. 2, the hydrogels of examples 1 to 5 all had light transmittance of more than 80% in the visible wavelength range, demonstrating that the hydrogels of examples 1 to 5 have good light transmittance.
As shown in FIG. 3, the hydrogels of examples 1 to 5 all had good elongation at break and moderate tensile strength.
As shown in FIG. 4, the hydrogels of examples 1 to 5 and comparative examples 1 to 5 each had a certain oxidation resistance, and the oxidation resistance was enhanced as the content of tannic acid was increased.
As shown in fig. 5, the hydrogels of examples 1 to 5 have better bacteriostatic ability against staphylococcus aureus (s. Aureus) and escherichia coli (e. Coli), while the hydrogels of comparative examples 1 to 5 do not contain quaternized chitosan, and show poor antimicrobial effect.
As shown in FIG. 6, the hydrogels of examples 1-5 all have certain biocompatibility, and the survival rates of human corneal epithelial cells are 99%,95%,100%,82%, and 74%, respectively.
The experimental results show that the antibacterial and antioxidant hydrogel of each embodiment, especially the hydrogel of embodiment 3, has good light transmittance, certain mechanical properties, higher antibacterial and antioxidant capacity and excellent biocompatibility, and can be used as a hydrogel contact lens material for treating bacterial keratitis.
Because of numerous embodiments of the scheme of the invention, experimental data of each embodiment are huge and numerous, and the embodiment is not suitable for being enumerated and explained one by one, but the contents required to be verified and the obtained final conclusion of each embodiment are all close. Therefore, the contents of the verification of each example are not described one by one here, and only examples 1 to 5 are used as representatives to describe the excellent points of the present invention.
The foregoing has outlined rather broadly the preferred embodiments and principles of the present invention and it will be appreciated that those skilled in the art may devise variations of the present invention that are within the spirit and scope of the appended claims.
Claims (9)
1. The antibacterial and antioxidant hydrogel for the contact lens is characterized by comprising the following components in percentage by weight:
15 to 20 percent of acrylamide monomer, 1 to 1.5 percent of quaternized chitosan, 0.01 to 0.05 percent of cross-linking agent, 0.01 to 0.05 percent of initiator, 0.03 to 0.08 percent of accelerator and the balance of water.
2. An antibacterial and antioxidant hydrogel for a corneal contact lens is characterized by comprising the following components in percentage by weight:
15 to 20 percent of acrylamide monomer, 1 to 1.5 percent of quaternized chitosan, 0.01 to 0.05 percent of cross-linking agent, 0.01 to 0.05 percent of initiator, 0.03 to 0.08 percent of accelerator, 0.001 to 1.5 percent of tannic acid and the balance of water;
the preparation method of the antibacterial and antioxidant hydrogel comprises the following steps:
(1) Adding quaternized chitosan and acrylamide monomers into water, and stirring until the quaternized chitosan and the acrylamide monomers are completely dissolved; then adding an initiator, a cross-linking agent and an accelerator in sequence, and uniformly stirring to form a reaction mixed solution;
(2) Transferring the reaction mixed solution into a mold for free radical polymerization reaction, taking the product out of the mold after the reaction is finished, and carrying out freeze drying treatment to obtain freeze-dried gel;
(3) And (3) immersing the freeze-dried gel into a tannic acid aqueous solution with the pH value of 2-3, adjusting the pH value of the tannic acid aqueous solution to be neutral after the immersion is finished, and transferring the gel into water to enable the gel to reach swelling balance, thereby obtaining the antibacterial and antioxidant hydrogel.
3. The antibacterial and antioxidant hydrogel for a contact lens according to claim 2, wherein in the step (3), the soaking temperature is 60 to 75 ℃ and the soaking time is 10 to 24 hours.
4. The antimicrobial and antioxidant hydrogel for a contact lens as claimed in claim 2, wherein in the step (3), the pH of the aqueous solution of tannic acid is adjusted to 2-3 with hydrochloric acid, and the pH of the aqueous solution of tannic acid is adjusted to neutral with sodium hydroxide.
5. The antibacterial and antioxidant hydrogel for a contact lens according to claim 1 or 2, wherein the acrylamide monomer is acrylamide, N-isopropylacrylamide or N, N-bis-methacrylamide.
6. The antimicrobial and antioxidant hydrogel for a corneal contact lens according to claim 1 or 2, wherein the quaternization ratio of the quaternized chitosan is controlled to 40 to 70%.
7. The antibacterial and antioxidant hydrogel for a corneal contact lens according to claim 1 or 2, wherein the crosslinking agent is N, N-methylenebisacrylamide, the initiator is potassium persulfate or ammonium persulfate, and the accelerator is N, N, N ', N' -tetramethylethylenediamine.
8. The method for preparing the antibacterial and antioxidant hydrogel according to claim 1, comprising the steps of:
(1) Adding quaternized chitosan and acrylamide monomers into water, and stirring until the quaternized chitosan and the acrylamide monomers are completely dissolved; then adding an initiator, a cross-linking agent and an accelerator in sequence, and uniformly stirring to form a reaction mixed solution;
(2) And transferring the reaction mixed solution into a mold for free radical polymerization reaction, taking the product out of the mold after the reaction is finished, and transferring the product into water to ensure that the gel reaches swelling balance to obtain the antibacterial antioxidant hydrogel.
9. The method according to claim 8, wherein the temperature of the radical polymerization is 20 to 35 ℃ and the time is 12 to 36 hours.
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