CN105348548B - A kind of hydrogel microsphere based on glucan and preparation method thereof - Google Patents
A kind of hydrogel microsphere based on glucan and preparation method thereof Download PDFInfo
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- CN105348548B CN105348548B CN201510704378.4A CN201510704378A CN105348548B CN 105348548 B CN105348548 B CN 105348548B CN 201510704378 A CN201510704378 A CN 201510704378A CN 105348548 B CN105348548 B CN 105348548B
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Abstract
The present invention relates to a kind of hydrogel microsphere based on glucan and preparation method thereof, belong to biological medical polymer material technical field.Glucan is dissolved in water at room temperature first, sodium metaperiodate is added and obtains mixed liquor, is dialysed after stirring, freeze-drying obtains part aldehyde radical glucan solid;Obtained part aldehyde radical glucan is dissolved in deionized water and added and has dissolved the cyclohexane solution of emulsifying agent, amine cross-linking agent stirring is added, finally by sediment is collected by centrifugation, chemical crosslinking type dextran hydrogel microballoon is obtained after cleaning;Sodium borohydride is added into the chemical crosslinking type dextran hydrogel microballoon for obtaining being scattered in deionized water, 24h is stirred at room temperature, finally by sediment is collected by centrifugation, the dextran hydrogel microballoon after being reduced after deionized water is cleaned.The present invention proposes that using " Water-In-Oil " Reverse Microemulsion System as reaction medium preparation particle size is controllable and has the glucan based aquagel microballoon of good stability.
Description
Technical field
The present invention relates to a kind of hydrogel microsphere based on glucan and preparation method thereof, belong to biological medical polymer material
Expect technical field.
Background technology
Hydrogel be a kind of polymer by the three-dimensional net structure being physically or chemically cross-linked to form, in aqueous can
It is swelled and keeps large quantity of moisture and can not dissolve, hydrophilic small molecule can spreads in hydrogel.Hydrogel microsphere is simultaneously
Possess hydrogel and the ambilateral characteristic of micro-/ nano particle.Because it has less size, larger specific surface area etc.,
Dimensional stability also with hydrogel and high solution-absorbency energy simultaneously, therefore, hydrogel micro-/ nano particle are cured as biology
There is huge application potential and wide application prospect in fields such as organizational project, drug deliveries with material(The
development of microgels/nanogels for drug delivery applications, Progress in
Polymer Science, 2008. 33: 448-477; Microgels in Drug Delivery, in Microgel
Suspensions, 2011, Wiley-VCH Verlag GmbH & Co. KGaA. 375-405).
Hydrogel based on natural macromolecular material has excellent biological safety, is received much concern as biomaterial.
Polysaccharide is a kind of natural polymer with good biocompatibility, is had with the hydrogel that natural polysaccharide high polymer material is built
Good biocompatibility and biological degradability, it is widely used in organizational project as biological medical polymer material, gene carries
Body and pharmaceutical carrier, the at present research on polysaccharide gel microballoon are carried out mainly around chitosan and alginic acid.Glucan
(dextran), also known as dextran, it is the bacterial polysaccharide that a large amount of free hydroxyl groups are carried on a kind of molecular structure, has good
Water solubility and biological safety.Since 1840s, glucan is wide as a kind of provisional plasma substitute
It is general to be applied to clinic, therefore before there is extensive clinical practice as drug carrier material based on the hydrogel microsphere of glucan
Scape.
At present, the preparation method using polymer as the hydrogel microsphere of material foundation is generally divided into four major classes(Nanogels
as Pharmaceutical Carriers: Finite Networks of Infinite Capabilities.Angewandte Chemie International Edition, 2009. 48: 5418-5429):(1)Using between macromolecule
Hydrogen bond, close and distant waterpower, the physical force " self assembly " such as electrostatic force form hydrogel microsphere;(2)By triggering micro emulsion
Monomer polymerization in liquid system prepares gel micro-ball, and polymerization process can be carried out in homogeneous system, can also be with nanometer
Carried out in the out-phase environment of size;(3)By chemical crosslinking, gel micro-ball is formed with covalent key connection between macromolecule;(4)Utilize
The nano material such as " imprint lithography " or " microfluid " processing method prepares hydrogel microsphere.Wherein, microemulsion polymerization method leads to
It is often to be added to polymerized monomer containing emulsifying agent and the aqueous phase of no initiator(Oil phase)In, add to oil phase(Aqueous phase)In acutely stir
Mix to form droplet, add initiator or by high-energy radiation in aqueous phase(Oil phase)Middle initiation monomer polymerize to form nanoparticle
Son.And the reverse micro emulsion method of " Water-In-Oil " has that reaction condition is gentle, gel is micro- in terms of hydrogel nanoparticles are prepared
The advantages that spherolite footpath is easily controlled, therefore be a kind of common method for preparing micro-/ nano particulate material(The Generation
of Nanoparticles in Miniemulsions. Advanced Materials, 2001. 13: 765-768;
Miniemulsion Polymerization and the Structure of Polymer and Hybrid
Nanoparticles. Angewandte Chemie International Edition, 2009. 48: 4488-4507),
But at present on this method be used for prepare glucan based aquagel document report it is less, not yet propose applicable reaction condition and
Surfactant system.
The content of the invention
For the above-mentioned problems of the prior art and deficiency, the present invention provides a kind of hydrogel microsphere based on glucan
And preparation method thereof.The present invention is proposed using " Water-In-Oil " Reverse Microemulsion System as reaction medium, anti-phase micro- by adjusting composition
The factors such as kinds of surfactants, content, surfactant compound ratio and the emulsification method of emulsion, preparing particle size can
Control and the glucan based aquagel microballoon with good stability, the present invention are achieved through the following technical solutions.
A kind of hydrogel microsphere based on glucan, its structural formula can represent as follows:
。
A kind of preparation method of the above-mentioned hydrogel microsphere based on glucan, its specific steps include as follows:
(1)The preparation of aldehyde radical glucan
It is at room temperature 10 according to solid-to-liquid ratio by glucan:100g/ml is dissolved in water, be subsequently placed in ice-water bath according to
Sugar unit/IO4 -Mol ratio is 2:1~1:1, which adds sodium metaperiodate, obtains mixed liquor, and mixed liquor is stirred under the conditions of room temperature, lucifuge
2 ~ 6h is reacted, the solution of acquisition is dialysed 2 ~ 3 days in deionized water with regenerated cellulose bag filter, and every 3 ~ 5h is changed in dialysis procedure
Deionized water, it is freeze-dried after the completion of dialysis and obtains the part aldehyde radical glucan solid that aldehyde radical degree is 40 ~ 60%
(There are 40 ~ 60 to be oxidized in i.e. every 100 sugar units, specific aldehyde radical degree is measured by hydroxylamine hydrochloride titration);
(2)The preparation of dextran hydrogel microballoon
By step(1)Obtained part aldehyde radical glucan solid is dissolved in deionized water that to obtain concentration be 100 ~ 200mg/
ML aldehyde radical glucan aqueous solution, at room temperature, aldehyde radical glucan aqueous solution is added to the hexamethylene for having dissolved emulsifying agent
In solution, emulsification forms reverse micro emulsion, then adds amine cross-linking agent and stirs 10 ~ 12h, is precipitated finally by being collected by centrifugation
Thing, sediment obtain chemical crosslinking type dextran hydrogel microballoon after ethanol cleans, are scattered in deionized water and preserve;
(3)The reduction of dextran hydrogel microballoon
To step(2)Obtain being scattered in the chemical crosslinking type dextran hydrogel microballoon in deionized water and add hydroboration
Sodium, 24h is stirred at room temperature, finally by sediment is collected by centrifugation, after sediment is reduced after deionized water is cleaned
Dextran hydrogel microballoon, is scattered in deionized water and preserves.
The step(1)In glucan be molecular weight 10000g/mol ~ 100000g/mol glucan in any
Kind.
The step(2)Middle aldehyde radical glucan aqueous solution is 1 with hexamethylene volume ratio:5~1:10.
The step(2)In emulsifying agent be polyoxyethylenes (5) nonylplenyl ether(CO-520), anhydrous sorbitol oleic acid
Ester(Span80)Or Span80/ sorbitan monooleate APEOs(Tween80)Built agent(In the built agent
Tween80 is the 5% ~ 20% of Span80 mass)Any of, the addition of emulsifying agent is the 10 ~ 50% of hexamethylene quality.
The step(2)Middle emulsification is mechanical agitation emulsification or ultrasonic emulsification.
The step(2)In amine cross-linking agent be ethylenediamine, lysine, any of arginine carry two amino
Compound, it according to the mol ratio of amino in aldehyde radical in the aldehyde radical glucan of part and amine cross-linking agent is 1 that addition, which is,:1~2:
1 adds.
The step(2)In amine cross-linking agent be dendroid polyethyleneimine that molecular weight is 600g/mol ~ 1800g/mol
Amine(PEI)Any of carry two or more amino compound, addition be according to aldehyde radical in the aldehyde radical glucan of part
Mol ratio with amino in amine cross-linking agent is 2:1~1:5 add.
The step(3)Middle sodium borohydride and the mol ratio of C=N double bonds in chemical crosslinking type dextran hydrogel microballoon are
2:1~10:1。
The preparation process schematic process of hydrogel microsphere of the invention based on glucan(Using ethylenediamine as crosslinking agent as
Example)It is as follows:
The beneficial effects of the invention are as follows:
1st, glucan based aquagel microballoon produced by the present invention is a kind of hydrogel microsphere based on natural macromolecular material,
With good biological safety, stability and potential applicability in clinical practice.
2nd, glucan based aquagel microballoon of the present invention is obtained by reverse micro emulsion cross-linking method, anti-phase by regulating and controlling
Kinds of surfactants, composition and the emulsification method of microemulsion can regulate and control to its pattern, particle diameter.
Brief description of the drawings
Fig. 1 is that the embodiment of the present invention 1 reduces front and rear infrared spectrogram, and wherein a is gel micro-ball infrared spectrum before reduction
Figure, b are the infrared spectrogram of dextran hydrogel microballoon after reduction;
Fig. 2 is gel micro-ball stereoscan photograph before the embodiment of the present invention 1 reduces;
Fig. 3 is gel micro-ball stereoscan photograph before the embodiment of the present invention 2 reduces;
Fig. 4 is gel micro-ball stereoscan photograph before the embodiment of the present invention 4 reduces;
Fig. 5 is gel micro-ball stereoscan photograph before the embodiment of the present invention 7 reduces.
Embodiment
With reference to the accompanying drawings and detailed description, the invention will be further described.
Embodiment 1
The hydrogel microsphere based on glucan, its structural formula can represent as follows:
。
The preparation method of the above-mentioned hydrogel microsphere based on glucan, its specific steps include as follows:
(1)The preparation of aldehyde radical glucan
By 5.0g glucans(Glucan T10, molecular weight 10000g/mol)It is at room temperature 10 according to solid-to-liquid ratio:
100g/ml is dissolved in water, and is subsequently placed in ice-water bath according to sugar unit/IO4 -Mol ratio is 1:1 addition sodium metaperiodate is mixed
Close liquid, by mixed liquor under the conditions of room temperature, lucifuge stirring reaction 4h, the solution regenerated cellulose bag filter of acquisition(Retention point
Son amount is 5kD)Dialyse 2 ~ 3 days in deionized water, every 3 ~ 5h changes a deionized water in dialysis procedure, is freezed after the completion of dialysis
It is dried to obtain the part aldehyde radical glucan solid that aldehyde radical degree is 60%(There are 60 to be oxidized in i.e. every 100 sugar units);
(2)The preparation of dextran hydrogel microballoon
By step(1)Obtained 0.15g parts aldehyde radical glucan solid, which is dissolved in, to be obtained concentration in 1.0mL deionized waters and is
150mg/mL aldehyde radical glucan aqueous solution, at room temperature, aldehyde radical glucan aqueous solution is added and has dissolved emulsifying agent
In cyclohexane solution, it is stirred vigorously 15min and emulsifies to form reverse micro emulsion, then adds amine cross-linking agent stirring 12h, finally lead to
Cross centrifugation(1500rpm, 5min)Sediment is collected, sediment obtains chemical crosslinking type glucan water after ethanol cleans 5 ~ 6 times
Gel micro-ball, it is scattered in 2.0mL deionized waters and preserves, the chemical crosslinking type dextran hydrogel microballoon is obtained by vacuum drying
Obtain faint yellow solid powder, its infrared spectrum such as Fig. 1(a)It is shown;Using SEM to the gel micro-ball of acquisition
Pattern is observed, as a result as shown in Figure 2:The sephadex microsphere obtained under the conditions of this has regular spherical structure,
Microsphere features smooth surface, particle diameter distribution is between 30 ~ 90 μm;Its cyclohexane dosage is 8.0mL, aldehyde radical glucan aqueous solution with
Hexamethylene volume ratio is 1:8, emulsifying agent Span80, addition 2.0g(The addition of emulsifying agent is cyclohexane solution quality
32%), stir as mechanical agitation;Wherein amine cross-linking agent is ethylenediamine, and addition is according to aldehyde in the aldehyde radical glucan of part
The mol ratio of base and amino in amine cross-linking agent is 2:1 adds(About 18 μ L);
(3)The reduction of dextran hydrogel microballoon
To step(2)Obtain being scattered in addition 50mg boron in the chemical crosslinking type dextran hydrogel microballoon in deionized water
Sodium hydride(Sodium borohydride and the mol ratio of C=N double bonds in dextran hydrogel microballoon are about 2.5:1), 24h is stirred at room temperature,
Finally by centrifugation(1500rpm, 5min)Sediment is collected, after sediment is reduced after deionized water is cleaned 5 ~ 6 times
Dextran hydrogel microballoon, it is scattered in 2.0mL deionized waters and preserves.Dextran hydrogel microballoon after reduction is done by vacuum
White solid powder, its infrared spectrum such as Fig. 1 are obtained after dry(b)It is shown.
Embodiment 2
The hydrogel microsphere based on glucan, its structural formula can represent as follows:
。
The preparation method of the above-mentioned hydrogel microsphere based on glucan, its specific steps include as follows:
(1)The preparation of aldehyde radical glucan
By 5.0g glucans(Dextran T 40, molecular weight 40000g/mol)It is at room temperature 10 according to solid-to-liquid ratio:
100g/ml is dissolved in water, and is subsequently placed in ice-water bath according to sugar unit/IO4 -Mol ratio is 1:1 addition sodium metaperiodate is mixed
Close liquid, by mixed liquor under the conditions of room temperature, lucifuge stirring reaction 4h, the solution regenerated cellulose bag filter of acquisition(Retention point
Son amount is 7kD)Dialyse 2 ~ 3 days in deionized water, every 3 ~ 5h changes a deionized water in dialysis procedure, is freezed after the completion of dialysis
It is dried to obtain the part aldehyde radical glucan solid that aldehyde radical degree is 60%(There are 60 to be oxidized in i.e. every 100 sugar units);
(2)The preparation of dextran hydrogel microballoon
By step(1)Obtained 0.15g parts aldehyde radical glucan solid, which is dissolved in, to be obtained concentration in 1.0mL deionized waters and is
150mg/mL aldehyde radical glucan aqueous solution, at room temperature, aldehyde radical glucan aqueous solution is added and has dissolved emulsifying agent
In cyclohexane solution, it is stirred vigorously 15min and emulsifies to form reverse micro emulsion, then adds amine cross-linking agent stirring 12h, finally lead to
Cross centrifugation(3000rpm, 5min)Sediment is collected, sediment obtains chemical crosslinking type glucan water after ethanol cleans 5 ~ 6 times
Gel micro-ball, it is scattered in 2.0ml deionized waters and preserves, the pattern of the gel micro-ball of acquisition is entered using SEM
Observation is gone, as a result as shown in Figure 3:The sephadex microsphere obtained under the conditions of this has regular spherical structure, microballoon table
Face is smooth, and particle diameter distribution is between 10 ~ 50 μm;Its cyclohexane dosage is 8.0mL, aldehyde radical glucan aqueous solution and hexamethylene
Volume ratio is 1:8, emulsifying agent is Span80/Tween80 built agent, and addition Span80 is 2.0g, Tween80 0.2g
(The addition of emulsifying agent is the 35% of hexamethylene quality), stir as mechanical agitation;Wherein amine cross-linking agent is ethylenediamine, is added
Measure to be 2 according to the mol ratio of amino in aldehyde radical in the aldehyde radical glucan of part and amine cross-linking agent:1 adds(About 18 μ L);
(3)The reduction of dextran hydrogel microballoon
To step(2)Obtain being scattered in addition 50mg boron in the chemical crosslinking type dextran hydrogel microballoon in deionized water
Sodium hydride(The mol ratio of sodium borohydride and C=N double bonds in chemical crosslinking type dextran hydrogel microballoon is 2.5:1), at room temperature
24h is stirred, finally by centrifugation(3000rpm, 5min)Sediment is collected, sediment obtains after deionized water is cleaned 5 ~ 6 times
Dextran hydrogel microballoon after reduction, is scattered in 2.0mL deionized waters and preserves.Dextran hydrogel microballoon point after reduction
Dissipate in disodium hydrogen phosphate-citrate buffer solution of different pH a series of, its stability is observed, as a result such as the institute of table 1
Show:Under the environmental conditions of pH > 4.0, sephadex microsphere has good stability in aqueous, as pH value of solution < 4.0
When, sephadex microsphere is destructurized, less stable.
Table 1
Embodiment 3
The hydrogel microsphere based on glucan, its structural formula can represent as follows:
。
The preparation method of the above-mentioned hydrogel microsphere based on glucan, its specific steps include as follows:
(1)The preparation of aldehyde radical glucan
By 5.0g glucans(Dextran T 70, molecular weight 70000g/mol)It is at room temperature 10 according to solid-to-liquid ratio:
100g/ml is dissolved in water, and is subsequently placed in ice-water bath according to sugar unit/IO4 -Mol ratio is 1:1 addition sodium metaperiodate is mixed
Close liquid, by mixed liquor under the conditions of room temperature, lucifuge stirring reaction 4h, by the regenerated cellulose bag filter of the solution after stirring(Cut
It is 7kD to stay molecular weight)Dialyse 2 ~ 3 days in deionized water, every 3 ~ 5h changes a deionized water in dialysis procedure, after the completion of dialysis
Freeze-drying obtains the part aldehyde radical glucan solid that aldehyde radical degree is 60%(There are 60 by oxygen in i.e. every 100 sugar units
Change);
(2)The preparation of dextran hydrogel microballoon
By step(1)Obtained 0.1g parts aldehyde radical glucan solid, which is dissolved in, to be obtained concentration in 1.0mL deionized waters and is
100mg/mL aldehyde radical glucan aqueous solution, at room temperature, aldehyde radical glucan aqueous solution is added and has dissolved emulsifying agent
In cyclohexane solution, it is stirred vigorously 15min and emulsifies to form reverse micro emulsion, then adds amine cross-linking agent stirring 12h, finally lead to
Cross centrifugation(3000rpm, 5min)Sediment is collected, sediment obtains chemical crosslinking type glucan water after ethanol cleans 5 ~ 6 times
Gel micro-ball, it is scattered in 2.0ml deionized waters and preserves;Its cyclohexane dosage is 8.0mL, aldehyde radical glucan aqueous solution with
Hexamethylene volume ratio is 1:8, emulsifying agent is Span80/Tween80 built agent, and addition Span80 is 2.0g, and Tween80 is
0.4g(The addition of emulsifying agent is the 38% of cyclohexane solution quality), stir as mechanical agitation;Wherein amine cross-linking agent is second two
Amine, it according to the mol ratio of amino in aldehyde radical in the aldehyde radical glucan of part and amine cross-linking agent is 2 that addition, which is,:1 adds(About 12
μL);
(3)The reduction of dextran hydrogel microballoon
To step(2)Obtain being scattered in addition 50mg boron in the chemical crosslinking type dextran hydrogel microballoon in deionized water
Sodium hydride(Sodium borohydride and the mol ratio of C=N double bonds in chemical crosslinking type dextran hydrogel microballoon are about 4:1), at room temperature
24h is stirred, finally by centrifugation(3000rpm, 5min)Sediment is collected, sediment obtains after deionized water is cleaned 5 ~ 6 times
Dextran hydrogel microballoon after reduction, is scattered in 2.0mL deionized waters and preserves.
Embodiment 4
The hydrogel microsphere based on glucan, its structural formula can represent as follows:
。
The preparation method of the above-mentioned hydrogel microsphere based on glucan, its specific steps include as follows:
(1)The preparation of aldehyde radical glucan
By 5.0g glucans(Dextran T 40, molecular weight 40000g/mol)It is at room temperature 10 according to solid-to-liquid ratio:
100g/ml is dissolved in water, and is subsequently placed in ice-water bath according to sugar unit/IO4 -Mol ratio is 1:1 addition sodium metaperiodate is mixed
Close liquid, by mixed liquor under the conditions of room temperature, lucifuge stirring reaction 4h, the solution regenerated cellulose bag filter of acquisition(Retention point
Son amount is 7kD)Dialyse 2 ~ 3 days in deionized water, every 3 ~ 5h changes a deionized water in dialysis procedure, is freezed after the completion of dialysis
It is dried to obtain the part aldehyde radical glucan solid that aldehyde radical degree is 60%(There are 60 to be oxidized in i.e. every 100 sugar units);
(2)The preparation of dextran hydrogel microballoon
By step(1)Obtained 0.1g parts aldehyde radical glucan solid, which is dissolved in, to be obtained concentration in 1.0mL deionized waters and is
100mg/mL aldehyde radical glucan aqueous solution, at room temperature, aldehyde radical glucan aqueous solution is added and has dissolved emulsifying agent
In cyclohexane solution, it is stirred vigorously 30min and emulsifies to form reverse micro emulsion, then adds amine cross-linking agent stirring 12h, finally lead to
Cross centrifugation(4000rpm, 5min)Sediment is collected, sediment obtains chemical crosslinking type glucan water after ethanol cleans 5 ~ 6 times
Gel micro-ball, it is scattered in 2.0ml deionized waters and preserves, the pattern of the gel micro-ball of acquisition is entered using SEM
Observation is gone, as a result as shown in Figure 4:The sephadex microsphere obtained under the conditions of this has regular spherical structure, microballoon table
Face is smooth, and particle diameter distribution is between 2 ~ 6 μm;Its cyclohexane dosage is 8.0mL, aldehyde radical glucan aqueous solution and hexamethylene body
Product is than being 1:8, emulsifying agent CO-520, addition 3.0g(The addition of emulsifying agent is the 48% of hexamethylene quality), stir and be
Mechanical agitation;Wherein amine cross-linking agent is ethylenediamine, and addition is to be crosslinked according to aldehyde radical in the aldehyde radical glucan of part and amine
The mol ratio of amino is 2 in agent:1 adds(About 12 μ L);
(3)The reduction of dextran hydrogel microballoon
To step(2)Obtain being scattered in addition 40mg boron in the chemical crosslinking type dextran hydrogel microballoon in deionized water
Sodium hydride(Sodium borohydride and the mol ratio of C=N double bonds in chemical crosslinking type dextran hydrogel microballoon are about 3:1), at room temperature
24h is stirred, finally by centrifugation(4000rpm, 5min)Sediment is collected, sediment obtains after deionized water is cleaned 5 ~ 6 times
Dextran hydrogel microballoon after reduction, is scattered in 2.0mL deionized waters and preserves.
Embodiment 5
The hydrogel microsphere based on glucan, its structural formula can represent as follows:
。
The preparation method of the above-mentioned hydrogel microsphere based on glucan, its specific steps include as follows:
(1)The preparation of aldehyde radical glucan
By 5.0g glucans(Dextran T 40, molecular weight 40000g/mol)It is at room temperature 10 according to solid-to-liquid ratio:
100g/ml is dissolved in water, and is subsequently placed in ice-water bath according to sugar unit/IO4 -Mol ratio is 2:1 addition sodium metaperiodate is mixed
Close liquid, by mixed liquor under the conditions of room temperature, lucifuge stirring reaction 6h, the solution regenerated cellulose bag filter of acquisition(Retention point
Son amount is 7kD)Dialyse 2 ~ 3 days in deionized water, every 3 ~ 5h changes a deionized water in dialysis procedure, is freezed after the completion of dialysis
It is dried to obtain the part aldehyde radical glucan solid that aldehyde radical degree is 40%(There are 40 to be oxidized in i.e. every 100 sugar units);
(2)The preparation of dextran hydrogel microballoon
By step(1)Obtained 0.1g parts aldehyde radical glucan solid, which is dissolved in, to be obtained concentration in 1.0mL deionized waters and is
100mg/mL aldehyde radical glucan aqueous solution, at room temperature, aldehyde radical glucan aqueous solution is added and has dissolved emulsifying agent
In cyclohexane solution, it is stirred vigorously 30min and emulsifies to form reverse micro emulsion, then adds amine cross-linking agent stirring 12h, finally lead to
Cross centrifugation(3000rpm, 5min)Sediment is collected, sediment obtains chemical crosslinking type glucan water after ethanol cleans 5 ~ 6 times
Gel micro-ball, it is scattered in 2.0ml deionized waters and preserves;Its cyclohexane dosage is 8.0mL, aldehyde radical glucan aqueous solution with
The volume ratio of hexamethylene is 1:8, emulsifying agent is Span80/Tween80 built agents, and addition is that Span80 is 2.0g, Tween80
For 0.2g(The addition of emulsifying agent is the 35% of hexamethylene quality), stir as mechanical agitation;Wherein amine cross-linking agent is PEI
(PEI molecular weight is 600g/mol, and its solution concentration is 0.25g/mL), addition is according to aldehyde radical in the aldehyde radical glucan of part
Mol ratio with amino in amine cross-linking agent is 1:1 adds(0.2mL);
(3)The reduction of chemical crosslinking type dextran hydrogel microballoon
To step(2)Obtain being scattered in addition 40mg boron in the chemical crosslinking type dextran hydrogel microballoon in deionized water
Sodium hydride(The mol ratio of sodium borohydride and C=N double bonds in chemical crosslinking type dextran hydrogel microballoon is 2:1), stir at room temperature
24h is mixed, finally by centrifugation(3000rpm, 5min)Sediment is collected, sediment is gone back after deionized water is cleaned 5 ~ 6 times
Dextran hydrogel microballoon after original, is scattered in 2.0mL deionized waters and preserves.
Embodiment 6
The hydrogel microsphere based on glucan, its structural formula can represent as follows:
。
The preparation method of the above-mentioned hydrogel microsphere based on glucan, its specific steps include as follows:
(1)The preparation of aldehyde radical glucan
By 5.0g glucans(Dextran T 70, molecular weight 70000g/mol)It is at room temperature 10 according to solid-to-liquid ratio:
100g/ml is dissolved in water, and is subsequently placed in ice-water bath according to sugar unit/IO4 -Mol ratio is 2:1 addition sodium metaperiodate is mixed
Close liquid, by mixed liquor under the conditions of room temperature, lucifuge stirring reaction 6h, the solution regenerated cellulose bag filter of acquisition(Retention point
Son amount is 7kD)Dialyse 2 ~ 3 days in deionized water, every 3 ~ 5h changes a deionized water in dialysis procedure, is freezed after the completion of dialysis
It is dried to obtain the part aldehyde radical glucan solid that aldehyde radical degree is about 40%(There are 40 by oxygen in i.e. every 100 sugar units
Change);
(2)The preparation of dextran hydrogel microballoon
By step(1)Obtained 0.2g parts aldehyde radical glucan solid, which is dissolved in, to be obtained concentration in 1.0mL deionized waters and is
200mg/mL aldehyde radical glucan aqueous solution, at room temperature, aldehyde radical glucan aqueous solution is added and has dissolved emulsifying agent
In cyclohexane solution, it is stirred vigorously 30min and emulsifies to form reverse micro emulsion, then adds amine cross-linking agent stirring 10h, finally lead to
Cross centrifugation(1500rpm, 5min)Sediment is collected, sediment obtains chemical crosslinking type glucan water after ethanol cleans 5 ~ 6 times
Gel micro-ball, it is scattered in 2.0ml deionized waters and preserves;Its cyclohexane dosage is 10.0mL, aldehyde radical glucan aqueous solution
It is 1 with hexamethylene volume ratio:10, emulsifying agent Span80, the addition of emulsifying agent are the 10% of hexamethylene quality, are stirred as machine
Tool stirs;Wherein amine cross-linking agent is PEI(PEI molecular weight is 1800g/mol, and its solution concentration is 0.5g/mL), addition is
Mol ratio according to amino in aldehyde radical in the aldehyde radical glucan of part and amine cross-linking agent is 2:1 adds(0.2mL);
(3)The reduction of dextran hydrogel microballoon
To step(2)Obtain being scattered in the chemical crosslinking type dextran hydrogel microballoon in deionized water and add hydroboration
Sodium(The mol ratio of sodium borohydride and chemical crosslinking type dextran hydrogel microballoon C=N double bonds is 2:1), 24h is stirred at room temperature,
Finally by centrifugation(1500rpm, 5min)Sediment is collected, after sediment is reduced after deionized water is cleaned 5 ~ 6 times
Dextran hydrogel microballoon, it is scattered in 2.0mL deionized waters and preserves.
Embodiment 7
The hydrogel microsphere based on glucan, its structural formula can represent as follows:
。
The preparation method of the above-mentioned hydrogel microsphere based on glucan, its specific steps include as follows:
(1)The preparation of aldehyde radical glucan
By 5.0g glucans(Dextran T 40, molecular weight 40000g/mol)It is at room temperature 10 according to solid-to-liquid ratio:
100g/ml is dissolved in water, and is subsequently placed in ice-water bath according to sugar unit/IO4 -Mol ratio is 1:1 addition sodium metaperiodate is mixed
Close liquid, by mixed liquor under the conditions of room temperature, lucifuge stirring reaction 4h, the solution regenerated cellulose bag filter of acquisition(Retention point
Son amount is 7kD)Dialyse 2 ~ 3 days in deionized water, every 3 ~ 5h changes a deionized water in dialysis procedure, is freezed after the completion of dialysis
It is dried to obtain the part aldehyde radical glucan solid that aldehyde radical degree is 60%(There are 60 to be oxidized in i.e. every 100 sugar units);
(2)The preparation of dextran hydrogel microballoon
By step(1)Obtained 0.1g parts aldehyde radical glucan solid, which is dissolved in, to be obtained concentration in 1.0mL deionized waters and is
100mg/mL aldehyde radical glucan aqueous solution, at room temperature, aldehyde radical glucan aqueous solution is added and has dissolved emulsifying agent
In cyclohexane solution, ultrasonic emulsification forms reverse micro emulsion, amine cross-linking agent stirring 12h is then added, finally by centrifugation
(5000rpm, 5min)Sediment is collected, it is micro- that sediment obtains chemical crosslinking type dextran hydrogel after ethanol cleans 5 ~ 6 times
Ball, it is scattered in 2.0ml deionized waters and preserves;The pattern of the gel micro-ball of acquisition is seen using SEM
Examine, as a result as shown in Figure 5:The sephadex microsphere obtained under the conditions of this has regular spherical structure, and particle diameter distribution is 200
Between ~ 500nm;Its cyclohexane dosage is 8.0mL, and aldehyde radical glucan aqueous solution is 1 with hexamethylene volume ratio:8, emulsifying agent
For Span80/Tween80 built agents, addition is that Span80 is 2.0g, Tween80 0.2g(The addition of emulsifying agent is ring
The 35% of hexane solution quality), ultrasonic emulsification condition is:Power 130W, amplitude 75%;Amine cross-linking agent is ethylenediamine, addition
To be 2 according to the mol ratio of amino in aldehyde radical in the aldehyde radical glucan of part and amine cross-linking agent:1 adds(About 12 μ L);
(3)The reduction of dextran hydrogel microballoon
To step(2)Obtain being scattered in addition 50mg boron in the chemical crosslinking type dextran hydrogel microballoon in deionized water
Sodium hydride(Sodium borohydride and the mol ratio of C=N double bonds in chemical crosslinking type dextran hydrogel microballoon are about 4:1), at room temperature
24h is stirred, finally by centrifugation(5000rpm, 5min)Sediment is collected, sediment obtains after deionized water is cleaned 5 ~ 6 times
Dextran hydrogel microballoon after reduction, is scattered in 2.0mL deionized waters and preserves.
Embodiment 8
The hydrogel microsphere based on glucan, its structural formula can represent as follows:
。
The preparation method of the above-mentioned hydrogel microsphere based on glucan, its specific steps include as follows:
(1)The preparation of aldehyde radical glucan
By 5.0g glucans(Dextran T 40, molecular weight 40000g/mol)It is at room temperature 10 according to solid-to-liquid ratio:
100g/ml is dissolved in water, and is subsequently placed in ice-water bath according to sugar unit/IO4 -Mol ratio is 1:1 addition sodium metaperiodate is mixed
Close liquid, by mixed liquor under the conditions of room temperature, lucifuge stirring reaction 4h, the solution regenerated cellulose bag filter of acquisition(Retention point
Son amount is 7kD)Dialyse 2 ~ 3 days in deionized water, every 3 ~ 5h changes a deionized water in dialysis procedure, is freezed after the completion of dialysis
It is dried to obtain the part aldehyde radical glucan solid that aldehyde radical degree is 60%(There are 60 to be oxidized in i.e. every 100 sugar units);
(2)The preparation of dextran hydrogel microballoon
By step(1)Obtained 0.1g parts aldehyde radical glucan solid, which is dissolved in, to be obtained concentration in 1.0mL deionized waters and is
100mg/mL aldehyde radical glucan aqueous solution, at room temperature, aldehyde radical glucan aqueous solution is added and has dissolved emulsifying agent
In cyclohexane solution, ultrasonic emulsification forms reverse micro emulsion, amine cross-linking agent stirring 12h is then added, finally by centrifugation
(5000rpm, 5min)Sediment is collected, it is micro- that sediment obtains chemical crosslinking type dextran hydrogel after ethanol cleans 5 ~ 6 times
Ball, it is scattered in 2.0ml deionized waters and preserves;The pattern of the gel micro-ball of acquisition is seen using SEM
Examine, as a result as shown in Figure 5:The sephadex microsphere obtained under the conditions of this has regular spherical structure, and particle diameter distribution is 200
Between ~ 500nm;Its cyclohexane dosage is 8.0mL, and aldehyde radical glucan aqueous solution is 1 with hexamethylene volume ratio:8, emulsifying agent
For Span80/Tween80 built agents, addition is that Span80 is 2.0g, Tween80 0.2g(The addition of emulsifying agent is ring
The 35% of hexane solution quality), ultrasonic emulsification condition is:Power 130W, amplitude 75%;Wherein amine cross-linking agent is PEI(PEI points
Son amount is 600g/mol, and its solution concentration is 0.5g/mL), addition is according to aldehyde radical and amine in the aldehyde radical glucan of part
The mol ratio of amino is 1 in crosslinking agent:5 add;
(3)The reduction of dextran hydrogel microballoon
To step(2)Obtain being scattered in addition 50mg boron in the chemical crosslinking type dextran hydrogel microballoon in deionized water
Sodium hydride(Sodium borohydride and the mol ratio of C=N double bonds in chemical crosslinking type dextran hydrogel microballoon are about 10:1), in room temperature
Lower stirring 24h, finally by centrifugation(5000rpm, 5min)Sediment is collected, sediment obtains after deionized water is cleaned 5 ~ 6 times
Dextran hydrogel microballoon after to reduction, is scattered in 2.0mL deionized waters and preserves.
Above in association with accompanying drawing to the present invention embodiment be explained in detail, but the present invention be not limited to it is above-mentioned
Embodiment, can also be before present inventive concept not be departed from those of ordinary skill in the art's possessed knowledge
Put that various changes can be made.
Claims (7)
1. a kind of preparation method of the hydrogel microsphere based on glucan, it is somebody's turn to do the hydrogel microsphere based on glucan, structure Shi Kebiao
Show as follows:
, it is characterised in that specific steps include as follows:
(1)The preparation of aldehyde radical glucan
It is at room temperature 10 according to solid-to-liquid ratio by glucan:100g/ml is dissolved in water, and is subsequently placed in ice-water bath according to sugared single
Member/IO4 -Mol ratio is 2:1~1:1 add sodium metaperiodate obtain mixed liquor, by mixed liquor under the conditions of room temperature, lucifuge stirring reaction
2 ~ 6h, the solution of acquisition are dialysed 2 ~ 3 days in deionized water with regenerated cellulose bag filter, and every 3 ~ 5h is changed once in dialysis procedure
Deionized water, it is freeze-dried after the completion of dialysis and obtains the part aldehyde radical glucan solid that aldehyde radical degree is 40 ~ 60%;
(2)The preparation of dextran hydrogel microballoon
By step(1)Obtained part aldehyde radical glucan solid, which is dissolved in, obtains concentration as 100 ~ 200mg/mL's in deionized water
Aldehyde radical glucan aqueous solution, at room temperature, aldehyde radical glucan aqueous solution is added to the cyclohexane solution for having dissolved emulsifying agent
In, emulsification forms reverse micro emulsion, then adds amine cross-linking agent and stirs 10 ~ 12h, finally by sediment is collected by centrifugation, sinks
Starch obtains chemical crosslinking type dextran hydrogel microballoon after ethanol cleans, and is scattered in deionized water and preserves;
(3)The reduction of dextran hydrogel microballoon
To step(2)Obtain being scattered in the chemical crosslinking type dextran hydrogel microballoon in deionized water and add sodium borohydride,
24h is stirred at room temperature, finally by sediment is collected by centrifugation, the Portugal after sediment is reduced after deionized water is cleaned gathers
Syrup gel micro-ball, is scattered in deionized water and preserves;
The step(2)In amine cross-linking agent be ethylenediamine, the change of lysine, any of arginine with two amino
Compound, it according to the mol ratio of amino in aldehyde radical in the aldehyde radical glucan solid of part and amine cross-linking agent is 1 that addition, which is,:1~2:
1 adds.
2. the preparation method of the hydrogel microsphere according to claim 1 based on glucan, it is characterised in that:The step
(1)In glucan be molecular weight 10000g/mol ~ 100000g/mol any of glucan.
3. the preparation method of the hydrogel microsphere according to claim 1 based on glucan, it is characterised in that:The step
(2)The volume ratio of middle aldehyde radical glucan aqueous solution and hexamethylene is 1:5~1:10.
4. the preparation method of the hydrogel microsphere according to claim 1 based on glucan, it is characterised in that:The step
(2)In emulsifying agent for the nonylplenyl ether of polyoxyethylenes five, sorbitan monooleate or Span80/ anhydrous sorbitols list oil
Any of built agent of acid ester polyoxyethylene ether, the addition of emulsifying agent are the 10 ~ 50% of hexamethylene quality.
5. the preparation method of the hydrogel microsphere according to claim 1 based on glucan, it is characterised in that:The step
(2)Middle emulsification is mechanical agitation emulsification or ultrasonic emulsification.
6. the preparation method of the hydrogel microsphere according to claim 1 based on glucan, it is characterised in that:The step
(2)In amine cross-linking agent be that any of dendroid polyethyleneimine that molecular weight is 600g/mol ~ 1800g/mol carries
The compound of two or more amino, addition are according to amino in aldehyde radical in the aldehyde radical glucan solid of part and amine cross-linking agent
Mol ratio be 2:1~1:5 add.
7. the preparation method of the hydrogel microsphere according to claim 1 based on glucan, it is characterised in that:The step
(3)The mol ratio of middle sodium borohydride and C=N double bonds in chemical crosslinking type dextran hydrogel microballoon is 2:1~10:1.
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CN106729772B (en) * | 2017-01-05 | 2021-06-18 | 昆明理工大学 | Magnetic resonance contrast agent based on magnetic glucan hydrogel microspheres and preparation method thereof |
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