CN104479150A - Preparation method of multiple cross-linked polysaccharide injectable hydrogel - Google Patents
Preparation method of multiple cross-linked polysaccharide injectable hydrogel Download PDFInfo
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Abstract
The invention discloses a preparation method of multiple cross-linked polysaccharide injectable hydrogel. Modified water-soluble chitosan with carboxyl or hydroxyl groups as a first component and a hydroformylation-modified polysaccharide polymer or polysaccharide polymer mixer as a second component produce electrostatic action with each other and undergo a Schiff-base reaction to produce the hydrogel with a multiple cross-linked net structure. The multiple cross-linked polysaccharide injectable hydrogel has gelling time of 5-200s and has good mechanical properties. Through change of a chitosan and polysaccharide modification rate, a mole ratio of two components and solid content of hydrogel, gelling time, mechanical strength, microscopic morphology and water content are adjusted and controlled. The gel network contains a large amount of amino, carboxyl and aldehyde groups as active groups, the active groups can be bonded to drugs and proteins by covalent bonds, the multiple cross-linked polysaccharide injectable hydrogel as a novel medical material with excellent biocompatibility has a good application prospect in the fields of regeneration medical science, tissue engineering and drug controlled release.
Description
Technical field
The present invention relates to a kind of hydrogel preparation method, particularly injectable hydrogel preparation method, be applied to the technical fields such as regenerative medicine, organizational project, medicine controlled releasing.
Background technology
Hydrogel is hydrophilic polymer network, and it can absorb a large amount of moisture, but can not be dissolved in the water due to the physical crosslinking between polymer chain and chemically crosslinked effect, can only swelling and keep certain shape.Hydrogel has good biocompatibility, water permeate, can be obtained the hydrogel material of diverse microcosmic stuctures and properties by synthetic, and these character make hydrogel obtain a wide range of applications at biomedical sector.In regenerative medicine field, the research of injection aquagel is especially noticeable.Injection aquagel can be used for bioactive molecules controlled release, cell embedding and be used as the aspect such as tissue stent material.Hydrogel in vivo original position is formed, and the height in surgical procedures so just can be avoided traumatic, healing acceleration, minimizing patient misery, reduction medical expense.Especially when being used for repairing the organizing of complicated shape, injection aquagel has adaptivity, and can solidify by body temperature, this is that general hydrogel is incomparable.Can say, injection aquagel is one of important directions of future biological medical material application development.
Injection aquagel can be divided into physical cross-linking hydrogel and chemically crosslinked aquagel by formation mechenism.The molecular chain of physical cross-linking hydrogel is connected by non covalent bond, as some time valency power effects such as model ylid bloom action, ionization, hydrogen bond action and hydrophobic interaction the cross-linked structure that formed, and these hydrogels generally can by phase co-conversion between sol-gel state.But physical crosslinking reactive force is more weak, easily destroyed when the ambient conditions such as pH value, ionic strength changes, mechanical property is poor, therefore is subject to certain restrictions in practical application.Chemically crosslinked aquagel then makes molecular chain form three-dimensional cross-linked network structure by covalent linkage effect by linking agent, performance comparatively physical cross-linking hydrogel is stablized, there is higher cross-linking density and good mechanical property, and can by degree of crosslinking and the swelling capacity regulating the consumption of linking agent to control gel.But chemically crosslinked aquagel uses the low molecule linking agent or the properties-correcting agent that there are certain toxic side effect, inevitably brings biocompatibility issues.
The material source of injection aquagel is mainly divided into synthesis and natural polymer.The latter comprises protein and polysaccharide, and have the similar biochemical structure of extracellular matrix and composition, good biocompatibility, cheap, material source is extensive.Chitosan is a kind of natural aminoglucose glycopolymers, and positively charged, its structure is similar to polysaccharide in the base of extracellular, and degraded product is in vivo glucosamine monomer, can absorb by human body.In addition, chitosan also has good biocompatibility, has no adverse reaction to tissue, and wide material sources, low price, is widely used in organizational project.Due in its molecule, intermolecular hydrogen bond action, make it be crystalline structure closely, so water insoluble and most of organic solvent.The poorly soluble principal element becoming the application of restriction chitosan.
Summary of the invention
In order to solve prior art problem, the object of the invention is to the deficiency overcoming prior art existence, a kind of multiple cross-linked polysaccharide injectable hydrogel preparation method is provided, take chitosan as main ingredient, using polyose polymer or polyose macromolecule mixture as second component, modification is carried out to two components, obtains good mechanical property, biocompatibility by schiff base reaction and electrostatic interaction good and can the multiple cross-linked hydrogel of injectable chitosan of rapid shaping.The present invention carries out water-soluble modified to chitosan, can be applied to the injection aquagel system of low cost and safety.
Create object for reaching foregoing invention, the present invention adopts following technical proposals:
A kind of multiple cross-linked polysaccharide injectable hydrogel preparation method, there is the water-soluble chitosan of carboxylic group or oh group after chemical modification as the first component, using the polyose polymer carrying out aldehyde radical chemical modification or carry out aldehyde radical chemical modification polyose macromolecule mixture as second component, by the electrostatic interaction between the component of two kinds of modifications and schiff base reaction, obtain the hydrogel with multiple cross-linked network structure.
As the preferred technical scheme of the present invention, the aldehyde grouping modified polysaccharide solution of preparation quality concentration to be the modified chitosan aqueous solution of 0.5 ~ 3wt% and mass concentration be 0.5 ~ 3wt% respectively, respectively as the first component and second component, by two components with volume ratio 9:1 ~ 1:9 mixing, by the electrostatic interaction between the component of two kinds of modifications and schiff base reaction, obtain the hydrogel with multiple cross-linked network structure.
As the technical scheme that the present invention is more preferably, with hydroxyl acids properties-correcting agent or anhydrides properties-correcting agent, chemical modification is carried out to chitosan, obtain the water-soluble chitosan with carboxylic group or oh group, hydroxyl acids properties-correcting agent adopts oxyacetic acid, lactic acid or lactobionic acid, and anhydrides properties-correcting agent adopts Succinic anhydried, Pyroglutaric acid or adipic anhydride.
As the first preferred version of technique scheme, preparation mass percent concentration is the chitosan aqueous solution of 0.1 ~ 1wt%, by properties-correcting agent and chitosan repeating unit mol ratio 0.5:1 ~ 6:1, add hydroxyl acids properties-correcting agent in chitosan aqueous solution after, be that being added in above-mentioned solution of 0.5:1 ~ 3:1 is dissolved by N-hydroxy-succinamide or I-hydroxybenzotriazole and chitosan repeating unit mol ratio, regulator solution pH is 4 ~ 7, add activator 1-ethyl-3-(3-dimethylamino-propyl) carbodiimide hydrochloride, be 0.5:1 ~ 5:1 according to 1-ethyl-3-(3-dimethylamino-propyl) carbodiimide hydrochloride and N-hydroxy-succinamide mol ratio, activator is added chitosan aqueous solution system.Make chitosan aqueous solution system react carry out 1 ~ 48h after, the pH value of chitosan aqueous solution system is adjusted to 7, then product dialysis freeze-drying, namely obtain through the acrylic modified water-soluble chitosan with oh group of hydroxyl.N-hydroxy-succinamide or I-hydroxybenzotriazole are not hydroxyl acids properties-correcting agent, are a kind of secondary activation agents, are used as supplementing of activator 1-ethyl-3-(3-dimethylamino-propyl) carbodiimide hydrochloride, play a part to improve activation efficiency.
As the second preferred version of technique scheme, preparation mass percent concentration is the chitosan aqueous solution of 0.1 ~ 1wt%, by properties-correcting agent and chitosan repeating unit mol ratio 0.5:1 ~ 6:1, anhydrides properties-correcting agent is added in chitosan aqueous solution, make chitosan aqueous solution system react carry out 10 ~ 48h after product acetone precipitation, the pH value of chitosan aqueous solution system is adjusted to 7, and freeze-drying of then being dialysed by product, namely obtains the water-soluble chitosan with oh group through anhydrides modification.
As the preferred version of technique scheme, adopt oxygenant, polysaccharide repeating unit being contained to adjacent hydroxyl or adjacent hydroxyl groups/amino carries out oxidation modification, obtains aldehyde grouping modified polysaccharide derivates.
Scheme is more preferably as technique scheme, preparation mass percent concentration is the polyose water-soluble polymers of 0.1 ~ 1wt%, add oxygenant, oxygenant and polysaccharide polymer repeating unit mol ratio are 0.1:1 ~ 1:1, react 1 ~ 5h under lucifuge condition after, then add ethylene glycol in polyose water-soluble polymers system, ethylene glycol and oxygenant mol ratio are 1:1 ~ 2:1, then modified product to be dialysed freeze-drying, namely obtain aldehyde grouping modified polysaccharide derivates.
Above-mentioned oxygenant preferably adopts sodium periodate, potassium bichromate, hydrogen peroxide or S-WAT.
Above-mentioned polyose polymer preferably adopts cm-chitosan, hyaluronic acid, carboxymethyl cellulose or sodium alginate.
The present invention compared with prior art, has following apparent outstanding substantive distinguishing features and remarkable advantage:
1. the present invention is directed to the defect of chemically crosslinked aquagel and physical cross-linking hydrogel, prepare the injection aquagel based on electrostatic interaction and schiff bases chemically crosslinked, chemical modification is carried out to chitosan, introduce carboxyl, the groups such as hydroxyl, prepare the water-soluble chitosan dissolved in neutral conditions, metal carboxylate polysaccharide is carried out partial oxidation process, obtain aldehyde radical polysaccharide derivates, by the electrostatic interaction in the schiff base reaction between the aldehyde radical on the amino on modified chitosan and aldehyde radical polysaccharide derivates and amino and polysaccharide between carboxyl, successfully prepare chitosan injection aquagel,
2. the hydrogel that prepared by the present invention effectively can avoid the use of small molecules linking agent, improves the biocompatibility of hydrogel, can strengthen stability and the physical strength of single effect hydrogel simultaneously;
3. the injection aquagel gelation time prepared of the present invention is between 5 ~ 200s, adopt multiple cross-linked one-tenth adhesive process, make this hydrogel have good mechanical property, can be regulated and controled gelation time, mechanical strength, microscopic appearance, water content by the solid content changing chitosan and the degree of modification of polysaccharide, the mol ratio of two components and hydrogel;
4. a large amount of amino, carboxyl, the aldehyde radical isoreactivity group that contain of the gel network inside of the hydrogel prepared of the present invention, can by covalent linkage and medicine and protein binding;
5. the hydrogel prepared of the present invention is as the excellent new medical material of a kind of novel biocompatibility, has good application prospect in fields such as organizational project, medicine controlled releasing, regenerative medicines.
Embodiment
Details are as follows for the preferred embodiments of the present invention:
embodiment one:
In the present embodiment, a kind of multiple cross-linked polysaccharide injectable hydrogel preparation method, its preparation process is as follows:
Take 0.3g chitosan, be dissolved in 100ml water, add 0.264mL lactic acid, after complete stirring and dissolving, add
n-N-Hydroxysuccinimide 0.424g, regulates pH to 4.8,1-ethyl-(3-dimethylaminopropyl) phosphinylidyne diimmonium salt hydrochlorate 1.411g, and reaction 36h, is transferred to 7.0 by pH.Product dialysis freeze-drying; Taking Lalgine 2.5g joins in the water of 50mL, stirring and dissolving in a water bath, until completely dissolved, adds sodium periodate 1.08g, under lucifuge condition, reacts 3h, adds 600 μ L ethylene glycol termination reactions.Product dialysis freeze-drying.Respectively modified chitosan and Lalgine are mixed with the aqueous solution of 0.5wt%, equal-volume mixes, and obtain hydrogel after 156s, storage modulus is 132 pa.
The present embodiment has the hydrogel of multiple cross-linked structure by electrostatic interaction and schiff bases chemically crosslinked preparation, and gives its good mechanical property.Can be regulated and controled gelation time, mechanical strength, microscopic appearance, water content by the solid content changing chitosan and the degree of modification of another fraction polysaccharide, the mol ratio of two components and hydrogel.Gel network a large amount of amino of containing of inside and aldehyde radical isoreactivity group can by covalent linkage and medicine and protein binding.
embodiment two:
The present embodiment is substantially identical with embodiment one, and special feature is:
In the present embodiment, take 0.3g chitosan, be dissolved in 100mL water, add 0.132mL oxyacetic acid, progressively drip after a certain amount of hydrochloric acid to chitosan dissolves completely, add
n-N-Hydroxysuccinimide 0.424g, regulates pH to 4.7,1-ethyl-(3-dimethylaminopropyl) phosphinylidyne diimmonium salt hydrochlorate 1.411g, after reaction 48h, pH is transferred to 7.0.Product dialysis freeze-drying; Taking hyaluronate sodium 2.5g joins in the water of 50mL, stirring and dissolving in a water bath, until completely dissolved, adds sodium periodate 1.08g, under lucifuge condition, reacts 4h, adds 600 μ L ethylene glycol termination reactions.Product dialysis freeze-drying.Respectively modified chitosan and hyaluronate sodium are mixed with the aqueous solution of 1wt%, equal-volume mixes, and obtain hydrogel after 70s, storage modulus is 257 pa.
embodiment three:
The present embodiment and previous embodiment are substantially identical, and special feature is:
In the present embodiment, take 0.3g chitosan, be dissolved in 100mL water, add 0.132mL lactic acid, progressively drip after a certain amount of hydrochloric acid to chitosan dissolves completely, add
n-N-Hydroxysuccinimide 0.636g, regulates pH to 4.7,1-ethyl-(3-dimethylaminopropyl) phosphinylidyne diimmonium salt hydrochlorate 2.116g, after reaction 48h, pH is transferred to 7.0.Product dialysis freeze-drying; Taking cm-chitosan 2.5g joins in the water of 50mL, stirring and dissolving in a water bath, until completely dissolved, adds sodium periodate 1.08g, under lucifuge condition, reacts 3h, adds 600 μ L ethylene glycol termination reactions.Product filters, acetone sedimentation, then dissolves dialysis freeze-drying.Respectively two kinds of modified chitosan are made the aqueous solution of 1wt%, equal-volume mixes, and obtain hydrogel after 113s, storage modulus is 195 pa.
embodiment four:
The present embodiment and previous embodiment are substantially identical, and special feature is:
In the present embodiment, take 0.3g chitosan, be dissolved in 100mL aqueous acetic acid, the mass concentration 1wt% of aqueous acetic acid, add 0.6738mL Succinic anhydried, reaction 24h, then pH is transferred to 7.0.Product filters, dialysis freeze-drying; Taking carboxymethyl cellulose 2.5g joins in the water of 50mL, stirring and dissolving in a water bath, until completely dissolved, adds sodium periodate 1.62g, under lucifuge condition, reacts 1h, adds 800 μ L ethylene glycol termination reactions.Product dialysis freeze-drying.Respectively modified chitosan and carboxymethyl cellulose are mixed with the aqueous solution of 3wt%, equal-volume mixes, and obtain hydrogel after 18s, storage modulus is 1528 pa.
embodiment five:
The present embodiment and previous embodiment are substantially identical, and special feature is:
In the present embodiment, take 0.3g chitosan, be dissolved in 100mL water, add 0.132mL lactic acid, progressively drip after a certain amount of hydrochloric acid to chitosan dissolves completely, add
n-N-Hydroxysuccinimide 0.636g, regulates pH to 4.7,1-ethyl-(3-dimethylaminopropyl) phosphinylidyne diimmonium salt hydrochlorate 2.116g, reaction 48h, then pH is transferred to 7.0.Product filters, dialysis freeze-drying; Taking sodium alginate 2.5g joins in the water of 50mL, stirring and dissolving in a water bath, until completely dissolved, adds sodium periodate 1.08g, under lucifuge condition, reacts 1h, adds 600 μ L ethylene glycol termination reactions.Product dialysis freeze-drying.Respectively modified chitosan and sodium alginate are mixed with the aqueous solution of 2.5wt%, mix, obtain hydrogel after 65s with volume 2:8, storage modulus is 912 pa.
The invention is not restricted to above-described embodiment; multiple change can also be made according to the object of innovation and creation of the present invention; change, the modification made under all spirit according to technical solution of the present invention and principle, substitute, combination, to simplify; all should be the substitute mode of equivalence; as long as goal of the invention according to the invention; only otherwise deviate from know-why and the inventive concept of the present invention's multiple cross-linked polysaccharide injectable hydrogel preparation method, all protection scope of the present invention is belonged to.
Claims (9)
1. a multiple cross-linked polysaccharide injectable hydrogel preparation method, it is characterized in that: there is the water-soluble chitosan of carboxylic group or oh group after chemical modification as the first component, using the polyose polymer carrying out aldehyde radical chemical modification or carry out aldehyde radical chemical modification polyose macromolecule mixture as second component, by the electrostatic interaction between the component of two kinds of modifications and schiff base reaction, obtain the hydrogel with multiple cross-linked network structure.
2. multiple cross-linked polysaccharide injectable hydrogel preparation method according to claim 1, it is characterized in that: the aldehyde grouping modified polysaccharide solution of preparation quality concentration to be the modified chitosan aqueous solution of 0.5 ~ 3wt% and mass concentration be 0.5 ~ 3wt% respectively, respectively as the first component and second component, by two components with volume ratio 9:1 ~ 1:9 mixing, by the electrostatic interaction between the component of two kinds of modifications and schiff base reaction, obtain the hydrogel with multiple cross-linked network structure.
3. multiple cross-linked polysaccharide injectable hydrogel preparation method according to claim 2, it is characterized in that: with hydroxyl acids properties-correcting agent or anhydrides properties-correcting agent, chemical modification is carried out to chitosan, obtain the water-soluble chitosan with carboxylic group or oh group, hydroxyl acids properties-correcting agent adopts oxyacetic acid, lactic acid or lactobionic acid, and anhydrides properties-correcting agent adopts Succinic anhydried, Pyroglutaric acid or adipic anhydride.
4. multiple cross-linked polysaccharide injectable hydrogel preparation method according to claim 3, it is characterized in that: preparation mass percent concentration is the chitosan aqueous solution of 0.1 ~ 1wt%, by properties-correcting agent and chitosan repeating unit mol ratio 0.5:1 ~ 6:1, add hydroxyl acids properties-correcting agent in chitosan aqueous solution after, be that being added in above-mentioned solution of 0.5:1 ~ 3:1 is dissolved by N-hydroxy-succinamide or I-hydroxybenzotriazole and chitosan repeating unit mol ratio, regulator solution pH is 4 ~ 7, add activator 1-ethyl-3-(3-dimethylamino-propyl) carbodiimide hydrochloride, be 0.5:1 ~ 5:1 according to 1-ethyl-3-(3-dimethylamino-propyl) carbodiimide hydrochloride and N-hydroxy-succinamide mol ratio, activator is added chitosan aqueous solution system, make chitosan aqueous solution system react carry out 1 ~ 48h after, the pH value of chitosan aqueous solution system is adjusted to 7, then product dialysis freeze-drying, namely obtain through the acrylic modified water-soluble chitosan with oh group of hydroxyl.
5. multiple cross-linked polysaccharide injectable hydrogel preparation method according to claim 3, it is characterized in that: preparation mass percent concentration is the chitosan aqueous solution of 0.1 ~ 1wt%, by properties-correcting agent and chitosan repeating unit mol ratio 0.5:1 ~ 6:1, anhydrides properties-correcting agent is added in chitosan aqueous solution, make chitosan aqueous solution system react carry out 10 ~ 48h after product acetone precipitation, the pH value of chitosan aqueous solution system is adjusted to 7, then product to be dialysed freeze-drying, namely obtain the water-soluble chitosan with oh group through anhydrides modification.
6. according to multiple cross-linked polysaccharide injectable hydrogel preparation method described in any one in claim 1 ~ 5, it is characterized in that: adopt oxygenant, polysaccharide repeating unit being contained to adjacent hydroxyl or adjacent hydroxyl groups/amino carries out oxidation modification, obtains aldehyde grouping modified polysaccharide derivates.
7. multiple cross-linked polysaccharide injectable hydrogel preparation method according to claim 6, it is characterized in that: preparation mass percent concentration is the polyose water-soluble polymers of 0.1 ~ 1wt%, add oxygenant, oxygenant and polysaccharide polymer repeating unit mol ratio are 0.1:1 ~ 1:1, react 1 ~ 5h under lucifuge condition after, ethylene glycol is added again in polyose water-soluble polymers system, ethylene glycol and oxygenant mol ratio are 1:1 ~ 2:1, then modified product to be dialysed freeze-drying, namely obtain aldehyde grouping modified polysaccharide derivates.
8. multiple cross-linked polysaccharide injectable hydrogel preparation method according to claim 6, is characterized in that: described oxygenant adopts sodium periodate, potassium bichromate, hydrogen peroxide or S-WAT.
9., according to multiple cross-linked polysaccharide injectable hydrogel preparation method described in any one in claim 1 ~ 8, it is characterized in that: described polyose polymer is cm-chitosan, hyaluronic acid, carboxymethyl cellulose or sodium alginate.
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