CN106693039A - Preparation method of medical hydrogel with good biological adhesion - Google Patents
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- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
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- A61L24/04—Surgical adhesives or cements; Adhesives for colostomy devices containing macromolecular materials
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Abstract
The invention discloses a preparation method of medical hydrogel with good biological adhesion. The hydrogel is prepared from end-group-modified four-arm polyethylene glycol dopamine and four-arm polyethylene glycol phenylboronic acid, and the two components are physically mixed by a mixing tool and then covalently crosslinked. The preparation method comprises the following steps of: 1) preparation of the four-arm polyethylene glycol dopamine; 2) preparation of the four-arm polyethylene glycol phenylboronic acid; and 3) preparation of the medical hydrogel. The preparation method disclosed by the invention has the advantages that due to existence of dopamine groups, stronger biological adhesion is endowed for the hydrogel, and the hydrogel can be self-repaired; the preparation method of the medical hydrogel is simple; and compared with the traditional medical gel, the medical hydrogel has the advantages of repeated use and good biodegradability and good biocompatibility, and can be used for organism environments at different parts.
Description
Technical field
It is more particularly to a kind of with good biological adhesiveness the invention belongs to biodegradable polymer field
The preparation method of medical aquogel.
Background technology
Hydrogel has tridimensional network, for multiple fields, such as in bio-medical, can be used for organizational project and
Insoluble drug release etc..Hydrogel with self-reparing capability can extend its service life.Some are similar to the natural of hydrogel
Biological tissue inherently has superior self-reparing capability, such as cardiac valves.Usual dynamic non-covalent key can be prepared with certainly
Repair ability hydrogel, reuses it.Phenyl boric acid and vicinal diamines can form dynamic boric acid ester bond.Bioadhesive
Agent requirement has good bioadhesive, and describing property of biology is good, degradable.The invention comes from the adhesion of marine mussel secretion
Albumen, content dopamine higher (DOPA) has been the main component of adhesive attraction in this protein, and its resulting structure is just
It is 3,4- dihydroxy-phenylalanine.It can form covalent bond by with the functional group such as sulfydryl, amino, realize good life
Thing adhesive attraction.
The content of the invention
It is an object of the invention to being directed to above-mentioned technical Analysis and there is problem, there is provided it is a kind of it is reusable, have
The preparation method of the medical aquogel of good biological adhesiveness, the method is by four arm polyethylene glycol Succinimidyl glutarates
Four arm polyethylene glycol DOPA that are terminal-modified that four arm polyethylene glycol amino terminals are modified to phenyl boric acid into dopamine, will obtaining
Amine and four arm polyethylene glycol phenyl boric acid solution are mixed, and are formed in situ polyester resin.And due to the formation of dynamic boric acid ester bond,
So that the presence that hydrogel has self-reparing capability, DOPA amine groups also gives the good bioadhesive of hydrogel simultaneously.
Hydrogel precursor polymer in the present invention is four arm polyethylene glycol dopamines and four arm polyethylene glycol phenyl boric acids.The poly- second two of four arms
It with the dopamine hydrochloride of four arm polyethylene glycol Succinimidyl glutarates and small molecule is Material synthesis that alcohol dopamine is.
Four arm polyethylene glycol phenyl boric acids are being prepared to Carboxybenzeneboronic acid pinacol ester with four arm polyethylene glycol amino and small molecule.
Technical scheme：
A kind of preparation method of the medical aquogel with good biological adhesiveness, comprises the following steps：
1) preparation of four arm polyethylene glycol dopamines
Four arm polyethylene glycol Succinimidyl glutarates and dimethyl sulfoxide (DMSO) are mixed to get reaction solution a, the poly- second of four arms
Glycol Succinimidyl glutarate is 0.1mmol with the amount ratio of dimethyl sulfoxide (DMSO)：4mL；By dopamine hydrochloride and diformazan
Base sulfoxide is mixed to get reaction solution b, and dopamine hydrochloride is 0.6mmol with the amount ratio of dimethyl sulfoxide (DMSO)：1mL；By reaction solution a
Mix with reaction solution b, add triethylamine and be well mixed, reacted 3 days under normal temperature, precipitated with ether, suction filtration obtains white solid
Four arm polyethylene glycol dopamines, four arm polyethylene glycol Succinimidyl glutarates, dopamine hydrochloride and triethylamine mole
Than being 1：6：6；
2) preparation of four arm polyethylene glycol phenyl boric acids
Four arm polyethylene glycol amino and dichloromethane are mixed to get mixed liquor a, four arm polyethylene glycol amino and dichloromethane
The amount ratio of alkane is 0.1mmol：5mL；Mixed liquor b will be mixed to get to Carboxybenzeneboronic acid pinacol ester and dichloromethane, to carboxylic
Base phenyl boric acid pinacol ester is 0.8mmol with the amount ratio of dichloromethane：1mL；By DCC (N, N '-dicyclohexylcarbodiimide)
Be mixed to get mixed liquor c, DCC (N, N '-dicyclohexylcarbodiimide) with dichloromethane is with the amount ratio of dichloromethane
0.8mmol：2mL；Three kinds of mixed liquors a, b, c are mixed, four arm polyethylene glycol amino, to Carboxybenzeneboronic acid pinacol ester and DCC
The mol ratio of (N, N '-dicyclohexylcarbodiimide) is 0.1：0.8：0.8, stirring at normal temperature is reacted 1 day, is first filtered to remove precipitation,
Filtrate is precipitated with the ether of 70mL, and four arm polyethylene glycol amino are 0.1mmol with the amount ratio of ether：70mL, obtains after suction filtration
The arm polyethylene glycol phenyl boric acid of white solid four；
3) preparation of medical aquogel
Configured in the 0.01mol/L sodium borate decahydrate cushioning liquid that four arm polyethylene glycol dopamines are added pH=9
Into the solution a of 15wt%；The 0.01mol/L sodium borate decahydrates of pH=9 are added to buffer four arm polyethylene glycol phenyl boric acids molten
The solution b of 15wt% is configured in liquid；Solution a is mixed with solution b normal temperature, the volume ratio of solution a and solution b is 1:1, system
Obtain medical aquogel.
The molecular weight of the four arms polyethylene glycol Succinimidyl glutarate is 5000-50000, four arm polyethylene glycol ammonia
The molecular weight of base is 10000.
The preparation method of the medical aquogel is as follows：
(A)
(B)
A kind of detection method of the prepared medical aquogel with good biological adhesiveness, step is as follows：
1) one piece of integral gel is cut into two pieces, and by one of use methylene blue staining, afterwards by two blocks of hydrogels
Tangent plane put together, in 30s can significantly observe gel selfreparing；
2) pigskin is cut into 2.5cm × 3cm, 1h is soaked in 37 DEG C of PBS, use cyanoacrylate
Class adhesive adheres on a glass pigskin, solidifies 1h, and the hydrogel 0.6g for weighing preparation is coated in pigskin end, covers same
The glass plate of pigskin is adhered to, a complete model is formed, overlapping area is recorded with digital display calliper, then with 100g counterweight pressures
30min, with tensilon (thinking carefully Science and Technology Co., Ltd. in length and breadth in Shenzhen) with the speed tensile of 5mm/min, record is maximum
Power, detects adhesion property.
It is an advantage of the invention that：The method prepare medical aquogel have good biological adhesiveness, can selfreparing,
Medical domain can play a significant role, and have a extensive future.
Brief description of the drawings
Fig. 1 is the self-healing properties detection of the Medical Adhesive hydrogel for preparing.
Fig. 2 is the adhesion property detection of the Medical Adhesive hydrogel for preparing.
Specific embodiment
With reference to specific embodiment, technical scheme is expanded on further.These embodiments are only used for this explanation
Rather than the scope of limitation invention.In addition, it is to be understood that after present disclosure has been read, those skilled in the art can be with
The present invention is made various changes or modifications, these equivalent form of values equally fall into the protection domain that the present invention is limited.In embodiment
The experimental technique of unreceipted actual conditions, generally according to the condition described in normal condition and handbook, or according to manufacturer
Proposed condition；Material, reagent used etc., unless otherwise specified, can be obtained by commercial sources.
Embodiment：
A kind of preparation method of the medical aquogel with good biological adhesiveness, comprises the following steps：
1) preparation of four arm polyethylene glycol dopamines
The four arm polyethylene glycol Succinimidyl glutarates that 1g, molecular weight are 10000 are weighed, the dimethyl of 4mL is added
Sulfoxide is allowed to dissolve；Dopamine hydrochloride 0.1g is weighed, adds 1mL dimethyl sulfoxide (DMSO)s to be allowed to dissolve；Two reaction solutions are mixed, then
The μ L of 83 μ L triethylamines 83, react 3 days under normal temperature, are precipitated with ether, and suction filtration obtains four arm polyethylene glycol dopamine white solids
0.9g, yield 90%, gained solid vacuum is saved backup.
2) preparation of four arm polyethylene glycol phenyl boric acids
The four arm polyethylene glycol amino that 1g, molecular weight are 10000 are weighed, adds the dichloromethane of 5mL to be allowed to dissolve；Weigh
To Carboxybenzeneboronic acid pinacol ester 0.2g, the dichloromethane of 1mL is added to be allowed to dissolve；Weigh DCC (N, N '-dicyclohexyl carbon two
Imines) 0.2g, it is allowed to dissolve with the dichloromethane of 2mL；Three kinds of mixed liquors are mixed, stirring at normal temperature is reacted 1 day, is first filtered to remove
Precipitation, filtrate is precipitated with the ether of 70mL, and suction filtration is obtained) four arm polyethylene glycol phenyl boric acid white solid 0.85g, yield 85%,
The white solid for obtaining is placed in standby in drier.
3) preparation of medical aquogel
Weigh step 1) in the four arm polyethylene glycol dopamine white solids that obtain add the water of 0.01mol/L ten of pH=9
The four arm polyethylene glycol dopamine solution a of 15wt% are configured in conjunction sodium tetraborate cushioning liquid；Weigh step 2) in obtain
Four arm polyethylene glycol phenyl boric acid white solids, are configured in the 0.01mol/L sodium borate decahydrate cushioning liquid for adding pH=9
The four arm polyethylene glycol phenyl boric acid solution b of 15wt%；By solution a with mixing under solution b normal temperature is obtained medical aquogel.
The detection of the medical aquogel of preparation：
1) the self-healing properties detection of medical aquogel
One piece of integral gel is cut into two pieces, and by one of use methylene blue staining, afterwards by two blocks of hydrogels
Tangent plane is put together, and the selfreparing of gel can be significantly observed in 30s.Testing result referring to Fig. 1, in figure：A is to be cut into two
The gel of block, it is one of to use methylene blue staining；B is that the tangent plane of two blocks of hydrogels is put together, places 30s；C is to use tweezer
Sub-folder plays the selfreparing situation that its section is observed in hydrogel one end.As can be seen from the results, the hydrogel has selfreparing work(
Energy.
2) the adhesion property detection of medical aquogel
Pigskin is cut into 2.5cm × 3cm, 1h is soaked in 37 DEG C of PBS.With cyano-acrylate binder by pigskin
Adhesion on a glass, solidifies 1h, weighs obtained medical aquogel 0.6g and is coated in pigskin end, covers same adhesion pigskin
Glass plate, forms a complete model, and overlapping area is recorded with digital display calliper.Afterwards 30min is pressed with 100g counterweights.With omnipotent
Puller system (thinking carefully Science and Technology Co., Ltd. in length and breadth in Shenzhen) records maximum, force with the speed tensile of 5mm/min.Each sample is surveyed
Average for 5 times.Testing result referring to Fig. 2, in figure：A is the schematic diagram of hydrogel adhesion property detection sample, and b is with pig
Skin and glass plate are the primary and secondary adhesive strength figure of substrate surface.As can be seen from the results, the hydrogel is to pigskin
The secondary adhesion that adhesion can reach after 5kPa, and selfreparing does not have substantially decrease.
Claims (3)
1. a kind of preparation method of the medical aquogel with good biological adhesiveness, it is characterised in that step is as follows：
1) preparation of four arm polyethylene glycol dopamines
Four arm polyethylene glycol Succinimidyl glutarates and dimethyl sulfoxide (DMSO) are mixed to get reaction solution a, four arm polyethylene glycol
Succinimidyl glutarate is 0.1mmol with the amount ratio of dimethyl sulfoxide (DMSO)：4mL；Dopamine hydrochloride and dimethyl is sub-
Sulfone is mixed to get reaction solution b, and dopamine hydrochloride is 0.6mmol with the amount ratio of dimethyl sulfoxide (DMSO)：1mL；By reaction solution a with it is anti-
Answer liquid b to mix, add triethylamine and be well mixed, reacted 3 days under normal temperature, precipitated with ether, suction filtration obtains the arm of white solid four
Polyethylene glycol dopamine, the mol ratio of four arm polyethylene glycol Succinimidyl glutarates, dopamine hydrochloride and triethylamine is
1：6：6；
2) preparation of four arm polyethylene glycol phenyl boric acids
Four arm polyethylene glycol amino and dichloromethane are mixed to get mixed liquor a, four arm polyethylene glycol amino and dichloromethane
Amount ratio is 0.1mmol：5mL；Mixed liquor b will be mixed to get to Carboxybenzeneboronic acid pinacol ester and dichloromethane, to carboxyl benzene
Pinacol borate is 0.8mmol with the amount ratio of dichloromethane：1mL；By DCC (N, N '-dicyclohexylcarbodiimide) and two
It is 0.8mmol that chloromethanes is mixed to get mixed liquor c, DCC (N, N '-dicyclohexylcarbodiimide) with the amount ratio of dichloromethane：
2mL；Three kinds of mixed liquors a, b, c are mixed, four arm polyethylene glycol amino, to Carboxybenzeneboronic acid pinacol ester and DCC (N, N '-two
Carbodicyclo hexylimide) mol ratio be 0.1：0.8：0.8, stirring at normal temperature is reacted 1 day, is first filtered to remove precipitation, and filtrate is used
The ether precipitation of 70mL, four arm polyethylene glycol amino are 0.1mmol with the amount ratio of ether：70mL, obtains white solid after suction filtration
The arm polyethylene glycol phenyl boric acid of body four；
3) preparation of medical aquogel
It is configured in the 0.01mol/L sodium borate decahydrate cushioning liquid that four arm polyethylene glycol dopamines are added pH=9
The solution a of 15wt%；Four arm polyethylene glycol phenyl boric acids are added the 0.01mol/L sodium borate decahydrate cushioning liquid of pH=9
In be configured to the solution b of 15wt%；Solution a is mixed with solution b normal temperature, the volume ratio of solution a and solution b is 1:1, it is obtained
Medical aquogel.
2. there is the preparation method of the medical aquogel of good biological adhesiveness according to claim 1, it is characterised in that：Institute
The molecular weight of four arm polyethylene glycol Succinimidyl glutarates is stated for 5000-50000, the molecular weight of four arm polyethylene glycol amino
It is 10000.
3. a kind of detection method of the medical aquogel with good biological adhesiveness prepared by claim 1, its feature exists
It is as follows in step：
1) one piece of integral gel is cut into two pieces, and by one of use methylene blue staining, afterwards cutting two blocks of hydrogels
Face is put together, and the selfreparing of gel can be significantly observed in 30s；
2) pigskin is cut into 2.5cm × 3cm, 1h is soaked in 37 DEG C of PBS, it is viscous with cyanoacrylate
Mixture adheres on a glass pigskin, solidifies 1h, and the hydrogel 0.6g for weighing preparation is coated in pigskin end, covers same adhesion
The glass plate of pigskin, forms a complete model, and overlapping area is recorded with digital display calliper, then presses 30min with 100g counterweights,
With tensilon (thinking carefully Science and Technology Co., Ltd. in length and breadth in Shenzhen) with the speed tensile of 5mm/min, maximum, force, detection are recorded
Adhesion property.
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| CN107233629A (en) * | 2017-06-21 | 2017-10-10 | 深圳市第二人民医院 | Injection aquagel and its preparation and application |
| CN108014365A (en) * | 2017-12-14 | 2018-05-11 | 沈伟 | A kind of sealer hydrogel and its kit and preparation method |
| CN108676127A (en) * | 2018-07-02 | 2018-10-19 | 南开大学 | It is a kind of with high intensity, high resiliency, electric conductivity and the reversible adhesion of temperature control Nanometer composite hydrogel preparation method |
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| CN110484184A (en) * | 2019-08-26 | 2019-11-22 | 中国科学院长春应用化学研究所 | A kind of hydrogel adhesive and the preparation method and application thereof |
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