CN116606517A - Biocompatible degradable interpenetrating network hydrogel and preparation method thereof - Google Patents
Biocompatible degradable interpenetrating network hydrogel and preparation method thereof Download PDFInfo
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- 229920006237 degradable polymer Polymers 0.000 claims abstract description 11
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- 239000003999 initiator Substances 0.000 claims abstract description 8
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- ROOXNKNUYICQNP-UHFFFAOYSA-N ammonium persulfate Chemical compound [NH4+].[NH4+].[O-]S(=O)(=O)OOS([O-])(=O)=O ROOXNKNUYICQNP-UHFFFAOYSA-N 0.000 claims description 10
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- RHQDFWAXVIIEBN-UHFFFAOYSA-N Trifluoroethanol Chemical compound OCC(F)(F)F RHQDFWAXVIIEBN-UHFFFAOYSA-N 0.000 claims description 7
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- 239000004632 polycaprolactone Substances 0.000 claims description 7
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- 229910001870 ammonium persulfate Inorganic materials 0.000 claims description 5
- 238000010438 heat treatment Methods 0.000 claims description 5
- 230000004083 survival effect Effects 0.000 claims description 4
- 229920002818 (Hydroxyethyl)methacrylate Polymers 0.000 claims description 3
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- QZPSOSOOLFHYRR-UHFFFAOYSA-N 3-hydroxypropyl prop-2-enoate Chemical compound OCCCOC(=O)C=C QZPSOSOOLFHYRR-UHFFFAOYSA-N 0.000 claims description 3
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- USHAGKDGDHPEEY-UHFFFAOYSA-L potassium persulfate Chemical compound [K+].[K+].[O-]S(=O)(=O)OOS([O-])(=O)=O USHAGKDGDHPEEY-UHFFFAOYSA-L 0.000 claims description 2
- 239000003814 drug Substances 0.000 abstract description 3
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- KIUKXJAPPMFGSW-DNGZLQJQSA-N (2S,3S,4S,5R,6R)-6-[(2S,3R,4R,5S,6R)-3-Acetamido-2-[(2S,3S,4R,5R,6R)-6-[(2R,3R,4R,5S,6R)-3-acetamido-2,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-2-carboxy-4,5-dihydroxyoxan-3-yl]oxy-5-hydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-3,4,5-trihydroxyoxane-2-carboxylic acid Chemical compound CC(=O)N[C@H]1[C@H](O)O[C@H](CO)[C@@H](O)[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@H](O[C@H]2[C@@H]([C@@H](O[C@H]3[C@@H]([C@@H](O)[C@H](O)[C@H](O3)C(O)=O)O)[C@H](O)[C@@H](CO)O2)NC(C)=O)[C@@H](C(O)=O)O1 KIUKXJAPPMFGSW-DNGZLQJQSA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J3/00—Processes of treating or compounding macromolecular substances
- C08J3/02—Making solutions, dispersions, lattices or gels by other methods than by solution, emulsion or suspension polymerisation techniques
- C08J3/03—Making solutions, dispersions, lattices or gels by other methods than by solution, emulsion or suspension polymerisation techniques in aqueous media
- C08J3/075—Macromolecular gels
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F226/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen
- C08F226/06—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen by a heterocyclic ring containing nitrogen
- C08F226/10—N-Vinyl-pyrrolidone
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2339/00—Characterised by the use of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen; Derivatives of such polymers
- C08J2339/04—Homopolymers or copolymers of monomers containing heterocyclic rings having nitrogen as ring member
- C08J2339/06—Homopolymers or copolymers of N-vinyl-pyrrolidones
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2467/00—Characterised by the use of polyesters obtained by reactions forming a carboxylic ester link in the main chain; Derivatives of such polymers
- C08J2467/04—Polyesters derived from hydroxy carboxylic acids, e.g. lactones
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- Dispersion Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Polymerisation Methods In General (AREA)
Abstract
The invention relates to a biocompatible degradable interpenetrating network hydrogel and a preparation method thereof. The degradable hydrogel with biocompatibility is obtained by forming an interpenetrating network between a high molecular chain in a phase transition critical state and a degradable polymer. The preparation method comprises the following steps: dissolving active monomer, degradable polymer and initiator in a solvent according to a certain proportion to prepare uniform precursor solution; obtaining a polymer by initiating free radical polymerization; rinsing with deionized water to obtain the degradable interpenetrating network hydrogel. The method has the advantages of high speed, high efficiency, low cost, rapid molding, low reaction temperature and the like, and the prepared hydrogel has degradability, excellent mechanical property and good biocompatibility and can be used in the field of regenerative medicine.
Description
Technical Field
The invention belongs to the technical field of functional polymer material preparation, and particularly relates to a preparation method of biocompatible degradable interpenetrating network hydrogel.
Background
The interpenetrating network hydrogel is a novel polymer material, has excellent mechanical property and biocompatibility, and is widely applied to the field of tissue engineering. Tissue engineering is a technology which uses the intersection of multiple disciplines such as materials, cell biology, biomechanics and the like, and aims to promote the growth and differentiation of cells through the biocompatibility and biological characteristics of the materials so as to reconstruct or repair human tissues and organs. The interpenetrating network hydrogel has various applications as an excellent tissue engineering material: interpenetrating network hydrogels may be used for tissue repair, such as cartilage, nerves, muscles, and the like. Interpenetrating network hydrogels are generally composed of two or more high molecular polymers, and there are many limitations on the choice of polymers in order to achieve hydrogel preparation while ensuring biocompatibility and degradability. Shi et al (M.Shi, J.Kim, G.Nian, Z.Suo, highly entangled hydrogels with degradable cross-links. Extreme Mechanics Letters 59,101953 (2023).) synthesized polyacrylamide hydrogels with disulfide cross-links, entanglement slowed degradation when in aqueous cysteine. Wang et al (W.Wang et al, extracellular matrix mimicking dynamic interpenetrating network hydrogel for skin tissue engineering. Chemical Engineering Journal 457,141362 (2023).) prepared a dynamic interpenetrating polymer network hydrogel by photopolymerization and oxidation of methacryloyl gelatin and hyaluronic acid, and was used in tissue engineering. However, a method for realizing the biocompatible degradable interpenetrating network hydrogel by utilizing free radical polymerization by adjusting the mass ratio of active monomers has not been reported yet.
Disclosure of Invention
The invention aims to overcome the defects of the prior art and provide a biocompatible and degradable interpenetrating network hydrogel, and another aim of the invention is to provide a preparation method of the biocompatible and degradable interpenetrating network hydrogel. The method has the advantages of high speed, high efficiency, low cost, rapid molding, low reaction temperature and the like, and the prepared hydrogel has degradability, excellent mechanical property and good biocompatibility and can be used in the field of regenerative medicine.
The specific technical scheme of the invention is as follows: a biocompatible degradable interpenetrating network hydrogel, characterized by: the phase transition critical state polymer chain and the degradable polymer form an interpenetrating network to obtain the degradable hydrogel with biocompatibility, the hydrogel is hydrolyzed in PBS solution, and the cell survival rate is 150% -155%.
The invention also provides a method for preparing the biocompatible degradable interpenetrating network hydrogel, which comprises the following specific steps:
(1) Dissolving active monomer, degradable polymer and initiator in solvent, heating to accelerate dissolution, and preparing into uniform precursor solution;
(2) Obtaining a polymer by initiating free radical polymerization;
(3) Rinsing with deionized water to obtain the degradable interpenetrating network hydrogel.
Preferably, the active monomer accounts for 50-60% of the mass of the precursor solution; the mass percentage of the degradable polymer in the precursor solution is 2.5-15%; the initiator accounts for 0.05 to 0.1 percent of the mass of the precursor solution, and the balance is solvent except active monomer, degradable polymer and initiator.
Preferably, the reactive monomers in the step (1) are acrylate monomers containing hydroxyl groups and N-vinyl pyrrolidone, wherein the mass ratio of the acrylate monomers containing hydroxyl groups to the N-vinyl pyrrolidone is between 1:3.7 and 1:4.
Preferably, the acrylate monomer containing hydroxyl is hydroxyethyl acrylate, hydroxypropyl acrylate or hydroxyethyl methacrylate.
Preferably, the degradable polymer in step (1) is polycaprolactone or modified polycaprolactone.
Preferably, the initiator in step (1) is ammonium persulfate or potassium persulfate.
Preferably, the solvent in the step (1) is an aqueous solution of trifluoroethanol, wherein the mass concentration of trifluoroethanol is 50-70%.
Preferably, the temperature at which the free radical polymerization is initiated in step (2) is from 60 to 120 ℃.
The beneficial effects are that:
the invention develops a biocompatible degradable interpenetrating network hydrogel and a preparation method thereof, and the prepared hydrogel has degradability and good biocompatibility and can be used in the field of regenerative medicine.
Drawings
FIG. 1 is a graph of cytotoxicity of hydrogels against L929 fibroblasts.
FIG. 2 is a graph of mass loss of hydrogels as a function of in vitro degradation time.
FIG. 3 is a graph of saturation swelling of hydrogels as a function of in vitro degradation time.
Detailed Description
The present invention will be described with reference to the following specific examples, but the present invention is not limited to these examples.
Example 1
1.7g of hydroxypropyl acrylate, 6.3. 6.3g N-vinyl pyrrolidone and 2.4g of polycaprolactone are respectively weighed, mixed with 5.592g of 70wt% trifluoroethanol aqueous solution, placed on a stirring table, stirred under the condition of heating to 40 ℃ and dissolved rapidly, and a uniform transparent solution is obtained. Standing and cooling to room temperature, weighing 0.008g of ammonium persulfate to dissolve in a solvent, stirring and dissolving to prepare a precursor solution of gel, uniformly mixing, and ultrasonically removing bubbles in the solution. The precursor solution was transferred to a closed rectangular flat plate mold. The temperature of the electric iron was adjusted to 120 c, and the leftmost side of the plate was heated for 30s using the electric iron, and the heat source was removed. The solution forms a stable front end surface and travels at a constant speed until the front polymerization is completed. And taking out the obtained polymer, and rinsing with deionized water to obtain the degradable interpenetrating network hydrogel.
The biocompatibility of the gels of the invention was tested using the following method:
the biocompatibility experiments were performed on L929 fibroblasts using the MTT method. L929 fibroblasts were first digested, counted and 10 per well 4 Cell plating, filling the edge hole with PBS, culturing overnight, incubating the sample with the cells after sterilization, adding MTT solution for treatment after 24 hours, and measuring absorbance value at 490nm by a microplate reader to evaluate the cell survival rate. The results are shown in FIG. 1, and the cell survival rate is 155% as shown in the figure, indicating that the hydrogel is inThe growth of cells can be promoted while maintaining the physiological activity of normal cells.
The degradability of the gels of the invention was tested using the following method:
degradation of the hydrogel was verified by mass change and ESD change of the hydrogel before and after hydrolysis in PBS buffer. Briefly, the lyophilized hydrogel flakes were cut into small pieces and weighed. The hydrogels were immersed in PBS (ph=7.4) buffer solution and accelerated degradation experiments were performed at ambient temperature of 70±1 ℃. The infusion solution was changed daily. At defined time points (3, 6, 9 or 12 days) the samples were removed, wiped with absorbent paper for excess surface moisture and weighed. And freeze-drying and weighing again. The mass loss is calculated by the following formula:
wherein W is de To simulate the quality of the dried hydrogel after degradation treatment, W 0 Is the initial mass of the hydrogel in the dry state. The results are shown in fig. 2, and the mass loss is obviously reduced in 12 days, so that the hydrogel is proved to be degraded.
The saturation swelling is calculated by the following formula:
wherein W is t Is the quality of hydrogel after water absorption. The results are shown in FIG. 3, and the saturation swelling degree is greatly increased, so that the degradation of the hydrogel is also proved.
Example 2
1.7g of hydroxyethyl methacrylate, 6.3. 6.3g N-vinyl pyrrolidone and 0.8g of polycaprolactone are respectively weighed, mixed with 7.1840 g of 60wt% trifluoroethanol aqueous solution, placed on a stirring table, stirred under the condition of heating to 40 ℃ and dissolved rapidly, and a uniform transparent solution is obtained. Standing and cooling to room temperature, weighing 0.016g of ammonium persulfate to dissolve in a solvent, stirring and dissolving to prepare a precursor solution of gel, uniformly mixing, and ultrasonically removing bubbles in the solution. The precursor solution was transferred to a closed rectangular flat plate mold. The temperature of the electric iron was adjusted to 100 c, and the leftmost side of the plate was heated for 30s using the electric iron, and the heat source was removed. The solution forms a stable front end surface and travels at a constant speed until the front polymerization is completed. And taking out the obtained polymer, and rinsing with deionized water to obtain the degradable interpenetrating network hydrogel. The hydrogel was tested for biocompatibility and cell viability was 154%. The gel of this example was tested for degradability by the method of example 1, and the saturation swelling was greatly increased, again demonstrating the degradation of the hydrogel.
Example 3
1.92g of hydroxyethyl acrylate, 7.68. 7.68g N-vinylpyrrolidone and 0.4g of polycaprolactone-polylactic acid-polycaprolactone are respectively weighed and mixed with 5.992g of 50wt% trifluoroethanol aqueous solution, and the mixture is placed on a stirring table and stirred under the condition of heating to 40 ℃ to accelerate dissolution, thus obtaining uniform transparent solution. Standing and cooling to room temperature, weighing 0.008g of ammonium persulfate to dissolve in a solvent, stirring and dissolving to prepare a precursor solution of gel, uniformly mixing, and ultrasonically removing bubbles in the solution. The precursor solution was transferred to a closed rectangular flat plate mold. The temperature of the electric iron was adjusted to 60 c, and the leftmost side of the plate was heated for 30s using the electric iron, and the heat source was removed. The solution forms a stable front end surface and travels at a constant speed until the front polymerization is completed. And taking out the obtained polymer, and rinsing with deionized water to obtain the degradable interpenetrating network hydrogel. The hydrogels were tested for biocompatibility with 150% cell viability. The gel of this example was tested for degradability by the method of example 1, and the saturation swelling was greatly increased, again demonstrating the degradation of the hydrogel.
While the present invention has been described in detail through the foregoing description of the preferred embodiment, it should be understood that the foregoing description is not to be considered as limiting the invention. Many modifications and substitutions of the present invention will become apparent to those of ordinary skill in the art upon reading the foregoing. Accordingly, the scope of the invention should be limited only by the attached claims.
Claims (9)
1. A biocompatible degradable interpenetrating network hydrogel, characterized by: the phase transition critical state polymer chain and the degradable polymer form an interpenetrating network to obtain the degradable hydrogel with biocompatibility, the hydrogel is hydrolyzed in PBS solution, and the cell survival rate is 150% -155%.
2. A method of preparing the biocompatible degradable interpenetrating network hydrogel of claim 1 comprising the specific steps of:
(1) Dissolving active monomer, degradable polymer and initiator in solvent, heating and dissolving to prepare uniform precursor solution;
(2) Obtaining a polymer by initiating free radical polymerization;
(3) Rinsing with deionized water to obtain the degradable interpenetrating network hydrogel.
3. The method according to claim 2, characterized in that the reactive monomer accounts for 50-60% of the mass of the precursor solution; the mass percentage of the degradable polymer in the precursor solution is 2.5-15%;
the mass percentage of the initiator in the precursor solution is 0.05-0.1%.
4. The method according to claim 2, wherein the reactive monomers in step (1) are hydroxyl group-containing acrylate monomers and N-vinylpyrrolidone, wherein the mass ratio of hydroxyl group-containing acrylate monomers to N-vinylpyrrolidone is between 1:3.7 and 1:4.
5. A method according to claim 3, wherein the hydroxy group-containing acrylate monomer is hydroxyethyl acrylate, hydroxypropyl acrylate or hydroxyethyl methacrylate.
6. The method according to claim 2, characterized in that in step (1) the degradable polymer is polycaprolactone or modified polycaprolactone.
7. The method according to claim 2, wherein the initiator in step (1) is ammonium persulfate or potassium persulfate.
8. The method according to claim 2, wherein the solvent in the step (1) is an aqueous trifluoroethanol solution, and the mass concentration of trifluoroethanol is 50 to 70%.
9. The process according to claim 2, wherein the temperature at which the free radical polymerization is initiated in step (2) is 60 to 120 ℃.
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