CN109134760A - A kind of preparation and application of hydrophobically modified Sodium Alginate Hydrogel Films - Google Patents
A kind of preparation and application of hydrophobically modified Sodium Alginate Hydrogel Films Download PDFInfo
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- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
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- C08J2351/00—Characterised by the use of graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Derivatives of such polymers
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Abstract
The present invention is the preparation and application of a kind of hydrophobically modified Sodium Alginate Hydrogel Films, first sodium alginate is controlled and is degraded, increase dissolution and reactivity worth, then in the blending agent of tetrahydrofuran and water, using ammonium ceric nitrate as initiator, graft copolymerization is carried out to sodium alginate with methacrylate-based monomer, the graft copolymer using sodium alginate as main chain, polyacrylate for branch has been obtained, so that sodium alginate is obtained hydrophobically modified by graft copolymerization.Sodium alginate after hydrophobically modified is crosslinked, hydrogel is prepared, hydrogel is used for the load and release of 5 FU 5 fluorouracil.The result shows that: the hydrogel stability enhancing after grafting has slow release effect for 5 FU 5 fluorouracil.
Description
Technical field
The present invention relates to the preparations and application of a kind of hydrophobically modified Sodium Alginate Hydrogel Films, belong to bio-medical material technology
Field.
Background technique
5 FU 5 fluorouracil clinic is mainly used for treating colon and rectum carcinoma and oophoroma etc., but directly oral to stomach
Stimulation is serious, and injection can cause phlebitis or endarteritis.
Sodium alginate, which is used as pharmaceutical carrier, huge superiority, but sodium alginate gel mechanical strength is bad, holds
Easily burst release, therefore the application as pharmaceutical carrier is limited to.Sodium alginate is a kind of Natural linear extracted from brown alga
Polysaccharide is made of the beta-D-mannuronic acid (M unit) and guluronic acid (G unit) of 1-4 bonding, and molecular formula is
(C6H7O6Na)n.Sodium alginate is widely used in cosmetics, food and pharmaceutical preparation, without toxicity and irritation, therefore can be used for mouth
Clothes and external application.
Sodium alginate is usually and Ca2+Bond together to form hydrogel, unique physicochemical property and good biocompatibility, quilt
It is widely used in the fields such as pharmaceutical preparation, organizational project, clinical treatment, cell culture, food processing as medical material, but
Ca2+The sodium alginate gel structural stability of crosslinking is bad, and mechanical strength is poor.
Summary of the invention
In order to solve sodium alginate gel bad mechanical strength in the prior art, it is easy the problems such as being released as pharmaceutical carrier,
The present invention provides the methods for first passing through free radical grafting copolymerization, and methacrylate monomers to be made to be graft-polymerized to sodium alginate master
On chain, to realize the hydrophobically modified to sodium alginate, then modified sodium alginate is subjected to covalent cross-linking and prepares hydrogel
Method improves sustained release of the sodium alginate as pharmaceutical carrier to improve the mechanical strength and stability of Sodium Alginate Hydrogel Films
Performance.
To achieve the goals above, The technical solution adopted by the invention is as follows:
A kind of preparation method of hydrophobically modified Sodium Alginate Hydrogel Films, preparation step contain following 4 step:
1) sodium alginate is made into aqueous solution, appropriate hydrochloric acid solution is added, is stirred to react 5~7 at a temperature of 75~85 DEG C
Hour, it is cooled to room temperature, inclines and fall supernatant liquor, sodium hydroxide solution, which is added dropwise, dissolves product, repeats above-mentioned plus hydrochloric acid precipitation-and adds
It dilute solution of sodium hydroxide dissolving step 1~3 time, is dissolved for the last time with sodium hydroxide solution, it is product ethanol precipitation, static,
Incline and fall supernatant liquor, solid product is collected in product centrifuge separation, and freeze-drying obtains sodium alginate catabolite；
2) sodium alginate catabolite obtained by step 1) is made into aqueous solution, is in addition configured to methacrylate monomers
Above-mentioned sodium alginate soln and methacrylic acid ester solution are mixed and stirred for uniformly, by sodium alginate weight by tetrahydrofuran solution
3.3~5.8wt% addition ammonium ceric nitrate of amount is initiator, stirs evenly, is passed through N2, it is placed in 60~70 DEG C of thermostat water baths
In, it is stirred to react 4~6 hours, obtains graft copolymer crude product, be freeze-dried, obtain after crude product is washed with dehydrated alcohol
To graft copolymer；
3) graft copolymer obtained by step 2) is made into the solution of 4~6wt% in distilled water, by crosslinking agent in advance with suitable
Amount tetrahydrofuran is made into 8~12wt% solution, is added in the solution of graft copolymer, then add 1- (3- dimethylamino third
Base) -3- ethyl-carbodiimide hydrochloride, n-hydroxysuccinimide stirs evenly, and 45~55 DEG C of temperature control reactions 20~24 are small
When, obtain hydrogel；
4) by hydrogel obtained by step 3) with excessive distilled water immersion 20~24 hours, incline leachate, replaces fresh steaming
Distilled water washing by soaking, repetition 1~3 time again, finally filters, is freeze-dried, obtain hydrophobically modified Sodium Alginate Hydrogel Films.
Selected crosslinking agent includes lysine, and the weight ratio of lysine and graft copolymer is 8.0~8.3%%, is selected altogether
Valence crosslinking method is the stability in order to increase hydrogel.
Sodium alginate is degraded, the molecular weight of sodium alginate is reduced, is conducive to the solubility property grafting for increasing sodium alginate
The efficiency of polymerization, and the contact of reactant is unfolded, is conducive to the sodium alginate segment after degradation, and reactivity worth improves.
During preparing hydrophobically modified Sodium Alginate Hydrogel Films, specific methacrylate-based monomer used is optional
It selects one of following: methyl methacrylate, ethyl methacrylate, n propyl methacrylate or the positive fourth of methacrylic acid
Ester.
Further, in step 2), sodium alginate is made into the aqueous solution of 4~8wt%, and methacrylate monomers are configured to
Concentration is the tetrahydrofuran solution of 4~8wt%, and 1.25:1~2:1 is added two solution by volume.
The present invention also provides application of the hydrophobically modified Sodium Alginate Hydrogel Films in terms of 5 FU 5 fluorouracil sustained release.
Any one hydrogel sample is prepared according to the method, is put into the 5 FU 5 fluorouracil solution that pH value is 7.4,
It is taken out after sufficiently impregnating.Then at room temperature, release experiment is carried out in the buffer solution that pH value is 7.4.
Beneficial effects of the present invention: be based on the above technical method, the present invention mainly have it is following the utility model has the advantages that
1. sodium alginate biocompatibility and biodegradability are good, as primary raw material, medical material can satisfy
It is required that；
2. the contact of reactant is unfolded, is conducive to the sodium alginate segment after degradation, reactivity worth is improved, grafting efficiency
It is good；
3. the hydrogel that modified sodium alginate copolymer is formed, hydrophobicity increases, stability enhancing, mechanical strength
It is high, convenient to use；
4. the copolymer of the grafted sodium alginate obtained with the present invention is prepared into hydrogel, the alginic acid after hydrophobically modified
Sodium hydrogel greatly improves the adsorption capacity of drug, and slow release effect also becomes due to enhancing with the active force of drug molecule
It is more obvious.5 FU 5 fluorouracil is loaded and discharged as pharmaceutical carrier, the results showed that slow release effect enhancing.
5. the Sodium Alginate Hydrogel Films for using lysine to be prepared as crosslinking agent, Product Safety is good, and toxicity is low.
Detailed description of the invention
Fig. 1 copolymer infrared spectrogram；(A) sodium alginate before modified；(B) sodium alginate after graft modification.
Cumulative release percentage (cumulative release%) of Fig. 2 hydrogel to 5 FU 5 fluorouracil: (B) grafting changes
Property Sodium Alginate Hydrogel Films；(C) pure sodium alginate hydrogel.
Specific embodiment
Embodiment 1
Step 1: weighing powdered sodium alginate 7.5g, is added to stirring and dissolving in the distilled water of 350ml, and 2M hydrochloric acid is added
Solution 30ml is stirred to react 6 hours at a temperature of 80 DEG C, is cooled to room temperature, inclines and fall supernatant liquor, and 2M sodium hydroxide solution is added dropwise
Product is dissolved, then is precipitated with 2M hydrochloric acid solution, repeatedly for three times by dissolution-precipitating, after being dissolved for the last time with sodium hydroxide,
It is 95% ethanol precipitation of product, static, it is poured off supernatant liquor, solid product is collected in product centrifuge separation, and freeze-drying obtains
Sodium alginate catabolite；By measuring intrinsic viscosity and the calculating of solution, before the number-average molecular weight of sodium alginate is by degrading
227000 drop to 23200 after degradation；
Step 2: the sodium alginate after weighing 6 grams of degradations is added to the 250 milliliter of three neck burning for filling 100 milliliters of distilled water
In bottle, stirring covers rubber stopper to its dissolution.The inside is emptied as nitrogen is passed through 30 minutes by rubber stopper insertion needle
Air；Compound concentration is the tetrahydrofuran solution 50mL of the methyl methacrylate of 8wt%, adds 0.2 gram of ammonium ceric nitrate, is placed in
In 65 DEG C of thermostat water baths, it is stirred to react 5 hours, obtains graft copolymer crude product, reactant cooled to room temperature adds
Entering appropriate dehydrated alcohol is precipitated out polymer, then is freeze-dried after product is washed 3 times with dehydrated alcohol, obtains grafting altogether
Polymers.
Graft copolymer obtained by step 2: being made into the solution of 5wt% by step 3 in distilled water, and 0.48 gram of lysine is pre-
It is first made into the solution of 10wt% with appropriate tetrahydrofuran, is added in graft copolymer solution, then adds 0.9 gram of 1- (3- diformazan
Aminopropyl) -3- ethyl-carbodiimide hydrochloride, 0.6 gram of n-hydroxysuccinimide catalyst, it stirs evenly, temperature control 45~
55 DEG C are reacted 24 hours, and hydrogel is obtained；
Step 4: by hydrogel obtained by step 3 with excessive distilled water immersion 20~24 hours, then incline leachate, replacement
Water recently distilled washing by soaking again, is repeated 3 times, and finally filters, is freeze-dried, obtains drying regime hydrophobically modified sodium alginate
Hydrogel.
The dosage for changing methyl methacrylate is respectively 60mL, 70mL or 80mL, and the dosage of corresponding ammonium ceric nitrate changes
Respectively 0.25g, 0.30g or 0.35g, it is respectively 0.46g, 0.49g, 0.50g that the dosage of lysine, which changes, and other conditions are constant
Carry out synthetic reaction.
Embodiment 2
Such as embodiment 1, but methyl methacrylate being changed to ethyl methacrylate, solvent is still tetrahydrofuran,
Concentration and volume do not change.
Embodiment 3
Such as embodiment 1, but methyl methacrylate is changed to n propyl methacrylate, solvent is still tetrahydro furan
It mutters, concentration and volume do not change.
Embodiment 4
Such as embodiment 1, but methyl methacrylate is changed to n-BMA, solvent is still tetrahydro furan
It mutters, concentration and volume do not change.
Embodiment 5
The test of swelling behavior rate: water bath with thermostatic control set temperature is 25 DEG C, and the xerogel weighed in advance is put into deionization
In water, it is sufficiently dipped to swelling equilibrium, wipes the hydrogel being sufficiently swollen away surface moisture content, is weighed, swelling ratio is calculated.
Swelling behavior rate calculation formula:
Swelling ratio G=(W2- W1)/W1× 100%
W in formula2For the weight for sufficiently impregnating the hydrogel after reaching swelling equilibrium in deionized water；W1For xerogel
Weight.
The synthesis of 1 hydrophobically modified Sodium Alginate Hydrogel Films of table and swelling ratio
A): sodium alginate is made into the aqueous solution of 6wt%；B): A, B, C, D respectively represent methyl methacrylate, methyl-prop
Olefin(e) acid ethyl ester, propyl methacrylate, butyl methacrylate are respectively made into the tetrahydrofuran solution that concentration is 8wt%；C):
Swelling ratio in deionized water.
Embodiment 6
Hydrogel, which disintegrates, to be tested: being prepared comparative sample first, pure sodium alginate is made into the aqueous solution of 6wt%, by medical
Injection needle is added dropwise in the calcium chloride solution that concentration is 5wt%, after curing 4h, with pure water three times, is separated by filtration, and is dried
It does to constant weight.
Respectively by hydrophobically modified Sodium Alginate Hydrogel Films prepared by the present invention and with the calcium cross-linked pure sodium alginate water of chlorination
Gel is placed in the PBS buffer solution of pH=7.4, observes hydrogel disintegration situation.The result shows that: use the calcium cross-linked pure sea of chlorination
Mosanom hydrogel microsphere starts to disintegrate after 2 hours, and gel gradually ruptures, and disintegrates completely after 8 hours and enters in aqueous solution.
And gel-like structure is still maintained after hydrophobically modified Sodium Alginate Hydrogel Films 24 hours, illustrate with better stability.This is because
In the hydrogel of ionomer, phosphate anion is complexed in calcium ion and buffer solution, so that calcium ion is detached from gel structure,
So that gel is gradually disintegrated, ruptures.And in hydrophobically modified Sodium Alginate Hydrogel Films, one side sodium alginate is able to hydrophobic change
Property, another aspect covalent cross-linking Sodium Alginate Hydrogel Films, covalent bond structure is stablized.
Embodiment 7
Using KBr pressed disc method sample preparation, 1 gained hydrophobically modified sodium alginate graft copolymer of embodiment and KBr are pressed into quality
Mixing more uniform than 1:100 is simultaneously fully ground in the agate mortar, and tabletting after drying under infrared lamp carries out examination of infrared spectrum,
It can be seen that in 2960cm-1The absorption peak that place occurs is by-the CH in the sodium alginate molecule after being grafted3The flexible vibration of C-H
Caused by dynamic.In 2875cm-1Place is the-CH in sodium alginate molecule2C-H stretching band.In 1713cm-1Place
Bands of a spectrum, caused by being the C=O stretching vibration after being grafted in sodium alginate in methyl methacrylate, and carboxylic in pure sodium alginate
The C=O stretching vibration of base is in 1611cm-1Place.In 1466cm-1Place is the-CH in sodium alginate molecule2C-H bending vibration
Bands of a spectrum.In 1449cm-1The absorption peak that place occurs is by-the CH in the sodium alginate molecule after being grafted3C-H bending vibration draw
It rises.Infrared signature absorption peak illustrates that graft reaction is successful.
Embodiment 8
Weighing and being put into concentration by 1 gained xerogel of embodiment is in 0.5mg/mL 5 FU 5 fluorouracil solution, after impregnating one day
It takes out, is transferred in the buffer solution that 500 ml of ph are 7.4, carries out release experiment, take 3 milliliters of samples every certain time,
Its absorbance is tested at 265nm, to observe release conditions, calculates cumulative release percentage.
As shown in Fig. 2, graft modification Sodium Alginate Hydrogel Films enhance 5 FU 5 fluorouracil slow release effect, add up to release in 30h
Percentage 79% is put, and pure sodium alginate hydrogel is under the same conditions, adds up release percentage 80% in 10h.
Claims (7)
1. a kind of preparation method of hydrophobically modified Sodium Alginate Hydrogel Films, it is characterised in that: preparation step contains following 4 step:
1) sodium alginate is made into aqueous solution, appropriate hydrochloric acid solution is added, is stirred to react at a temperature of 75 ~ 85 DEG C 5 ~ 7 hours, it is cold
But to room temperature, incline and fall supernatant liquor, sodium hydroxide solution, which is added dropwise, dissolves product, repeats above-mentioned plus hydrochloric acid precipitation-plus hydroxide
Sodium weak solution dissolving step 1 ~ 3 time, is dissolved with sodium hydroxide solution for the last time, product ethanol precipitation, static, is inclined and is fallen upper layer
Solid product is collected in clear liquid, product centrifuge separation, and freeze-drying obtains sodium alginate catabolite；
2) sodium alginate catabolite obtained by step 1) is made into aqueous solution, methacrylate monomers is in addition configured to tetrahydro
Above-mentioned sodium alginate soln and methacrylic acid ester solution are mixed and stirred for uniformly, by sodium alginate weight by tetrahydrofuran solution
It is initiator that 3.3 ~ 5.8wt%, which adds ammonium ceric nitrate, stirs evenly, is passed through N2, it is placed in 60 ~ 70 DEG C of thermostat water baths, stirring is anti-
It answers 4 ~ 6 hours, obtains graft copolymer crude product, be freeze-dried after crude product is washed with dehydrated alcohol, obtain graft copolymerization
Object；
3) graft copolymer obtained by step 2 is made into the solution of 4 ~ 6wt% in distilled water, crosslinking agent is used to appropriate tetrahydro in advance
Furans is made into 8 ~ 12wt% solution, is added in the solution of graft copolymer, then adds 1- (3- dimethylamino-propyl) -3- ethyl
Carbodiimide hydrochloride, n-hydroxysuccinimide stir evenly, and 45 ~ 55 DEG C of temperature control are reacted 20 ~ 24 hours, obtain hydrogel；
4) by hydrogel obtained by step 3) with excessive distilled water immersion 20 ~ 24 hours, incline leachate, and replacement water recently distilled is again
Secondary washing by soaking repeats 1 ~ 3 time, finally filters, is freeze-dried, obtains hydrophobically modified Sodium Alginate Hydrogel Films.
2. the preparation method of hydrophobically modified Sodium Alginate Hydrogel Films according to claim 1, it is characterised in that: step 3)
In, crosslinking agent includes lysine.
3. the preparation method of hydrophobically modified Sodium Alginate Hydrogel Films according to claim 2, it is characterized in that being: step 2
Middle methacrylate-based monomer are as follows: methyl methacrylate, ethyl methacrylate, n propyl methacrylate or methyl-prop
Olefin(e) acid N-butyl.
4. the preparation method of hydrophobically modified Sodium Alginate Hydrogel Films according to claim 2, it is characterised in that: step 2
In, sodium alginate is made into the aqueous solution of 4 ~ 8wt%, and it is molten that methacrylate monomers are configured to the tetrahydrofuran that concentration is 4 ~ 8wt%
Liquid, 1.25:1 ~ 2:1 is added two solution by volume.
5. the preparation method of hydrophobically modified Sodium Alginate Hydrogel Films according to claim 2, it is characterised in that: the crosslinking
The weight ratio of agent and graft copolymer is 8.0 ~ 8.3%.
6. a kind of preparation method of hydrophobically modified Sodium Alginate Hydrogel Films described in any claim according to claim 1 ~ 5 obtains
The hydrophobically modified Sodium Alginate Hydrogel Films arrived.
7. a kind of application of hydrophobically modified Sodium Alginate Hydrogel Films according to claim 6 in terms of medicament slow release, special
Sign is: the hydrophobically modified Sodium Alginate Hydrogel Films are used for the sustained release of 5 FU 5 fluorouracil.
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Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS57106611A (en) * | 1980-12-22 | 1982-07-02 | Sanwa Kagaku Kenkyusho:Kk | Coating remedy |
| CN102485759A (en) * | 2010-12-03 | 2012-06-06 | 江南大学 | Preparation and application of butyl methacrylate grafted sodium alginate hydrogel |
| CN103130912A (en) * | 2011-12-02 | 2013-06-05 | 江南大学 | One-step method of preparing covalence crosslinked and hydrophobic modified sodium alga acid hydrogel |
| CN104873467A (en) * | 2014-02-28 | 2015-09-02 | 江南大学 | Preparation method of biodegradable interpenetrating network polymer microspheres |
| CN105694030A (en) * | 2016-04-05 | 2016-06-22 | 中国科学院化学研究所 | Oligo-polyamino acid and sodium alginate combined hybrid antibacterial hydrogel |
-
2018
- 2018-08-10 CN CN201810910117.1A patent/CN109134760B/en active Active
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS57106611A (en) * | 1980-12-22 | 1982-07-02 | Sanwa Kagaku Kenkyusho:Kk | Coating remedy |
| CN102485759A (en) * | 2010-12-03 | 2012-06-06 | 江南大学 | Preparation and application of butyl methacrylate grafted sodium alginate hydrogel |
| CN103130912A (en) * | 2011-12-02 | 2013-06-05 | 江南大学 | One-step method of preparing covalence crosslinked and hydrophobic modified sodium alga acid hydrogel |
| CN104873467A (en) * | 2014-02-28 | 2015-09-02 | 江南大学 | Preparation method of biodegradable interpenetrating network polymer microspheres |
| CN105694030A (en) * | 2016-04-05 | 2016-06-22 | 中国科学院化学研究所 | Oligo-polyamino acid and sodium alginate combined hybrid antibacterial hydrogel |
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