CN102964610A - Preparation method of polydopamine modified alginic acid microspheres - Google Patents
Preparation method of polydopamine modified alginic acid microspheres Download PDFInfo
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- CN102964610A CN102964610A CN2012104621986A CN201210462198A CN102964610A CN 102964610 A CN102964610 A CN 102964610A CN 2012104621986 A CN2012104621986 A CN 2012104621986A CN 201210462198 A CN201210462198 A CN 201210462198A CN 102964610 A CN102964610 A CN 102964610A
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Abstract
The invention discloses a preparation method of polydopamine modified alginic acid microspheres, which comprises the following steps of: under the protection of nitrogen, grafting dopamine to alginic acid by use of N-hydroxysuccinimide and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride; polymerizing the synthesized dopamine modified alginic acid under the slight alkaline condition to obtain a polydopamine modified alginic acid solution; dropwise adding the polydopamine modified alginic acid solution into a CaCl2 solution by a syringe; and aging to obtain polydopamine modified alginic acid microspheres. The method disclosed by the invention is simple in process, and the prepared modified alginic acid microspheres have higher swelling resistance and good mechanical properties.
Description
Technical field
The present invention relates to a kind of preparation method of poly-Dopamine HCL Alginate microparticles, belong to the original position covalent cross-linking and prepare Microspheres Technique.
Background technology
Lalgine is a kind of natural polysaccharide, is made of two kinds of structural units of guluronic acid (G section) and mannuronic acid (M section), can form gel with the polyvalent cation effect.Because Lalgine has good biocompatibility, gentle sol-gel process is widely used in pharmacy and biological technical field, as the carrier of medicine, viable cell and protein.
Because the Lalgine gel swelling is serious, the aperture is larger, molecular mass is leaked from gel easily less than the biomolecules of 300kDa and is waited the utilization that has limited the Lalgine gel ball.A lot of methods that are used for optimizing its embeddability properties and control its swelling have been reported at present.For example, after the biomacromolecule blend such as Lalgine and chitosan, form gel ball with cation sites again, the biomacromolecule of sneaking into can reduce the gel wetting ability, thereby controls its swelling.As in Lalgine, directly mixing inorganic particulate SiO
2, carbon nanotube and CaCO
3Deng, and then will mix Lalgine and the cation sites formation gel ball that inorganic particulate is arranged, and the adding of inorganic particulate has reduced the gel aperture, and network structure is also finer and close.As be coated with on the Lalgine gel ball surface for preparing one deck crosslinked biomolecules, to avoid the leakage of molecule.The research of present in-situ cross-linked method control Lalgine gel ball swelling yet there are no report.
Summary of the invention
The object of the present invention is to provide a kind of preparation method of poly-Dopamine HCL modification Alginate microparticles.It is simple that the method has process, and prepared modification Alginate microparticles has higher swelling resistance and good mechanical property.
The present invention is realized that by the following technical programs a kind of preparation method of poly-Dopamine HCL modification Alginate microparticles is characterized in that comprising following process;
(1) phosphate buffer soln that sodium alginate is added pH=5.5 dissolves, at N
2Protection and stirring are lower, add N-hydroxy-succinamide (NHS) and 1-ethyl-3-(3-dimethylaminopropyl with Lalgine monomer equimolar amount) carbodiimide hydrochloride (EDC), add again the Dopamine HCL that is equivalent to 0.5 ~ 3 times of molar weight of Lalgine monomer after 30 ~ 60min, use alcohol chromatography behind the reaction 8-14h, remove unreacted Dopamine HCL, N-hydroxy-succinamide and 1-ethyl-3-(3-dimethylaminopropyl) carbodiimide hydrochloride, obtain Dopamine HCL modification Lalgine (Alg-DA), freeze-drying is for subsequent use;
(2) it is that compound concentration is the solution of 10 ~ 25mg/ml in 7.5 ~ 8.5 Tris-HCl buffered soln that the Dopamine HCL modification Lalgine that step (1) is synthesized is dissolved in pH, stirs polymerization under the room temperature and obtains poly-Dopamine HCL modification Lalgine solution (Alg-PDA);
(3) drawing poly-Dopamine HCL modification Lalgine solution with syringe, is the CaCl of 0.2M to concentration
2Drip poly-Dopamine HCL modification Lalgine solution in the solution, after 30-60min is aging, filter out microballoon, remove Ca free in the microballoon with deionized water wash again
2+, obtain poly-Dopamine HCL modification Alginate microparticles.
The preparation method's that the present invention proposes advantage is: preparation condition is gentle, and raw material is cheap and easy to get, and preparation is simple.Microspherulite diameter 3 ± the 0.2mm for preparing because the rigidity network structure that the autohemagglutination of Dopamine HCL forms, the mechanical property of microballoon and swelling resistance be improved significantly.
Description of drawings
The Lalgine infrared spectrum (FTIR) of Fig. 1: embodiment one prepared Dopamine HCL modification Lalgine and non-modified.
The optical microscope photograph of Fig. 2: embodiment one prepared microballoon.
The optical microscope photograph of Fig. 3: embodiment two prepared microballoons.
The optical microscope photograph of Fig. 4: embodiment three prepared microballoons.
The optical microscope photograph of Fig. 5: embodiment four prepared microballoons.
Fig. 6: the optical microscope photograph of Comparative Examples one prepared Alginate microparticles.
Fig. 2-Fig. 5 is the poly-Dopamine HCL modification Alginate microparticles that the present invention prepares, and color is black, and Fig. 6 is unmodified Alginate microparticles, and color is white.The blackening of Alginate microparticles color is that Dopamine HCL generation autohemagglutination has formed poly-Dopamine HCL network on the Lalgine side chain because be grafted on after the modification.
Embodiment
Embodiment one
Be that the 5.05mmol Lalgine is dissolved in the phosphate buffer soln of 100ml pH=5.5, at N with the monomer molar number
2Under protection and the mechanical stirring; the N-hydroxy-succinamide (NHS) and the 5.05mmol 1-ethyl-3-(3-dimethylaminopropyl that add 5.05mmol) carbodiimide hydrochloride (EDC); the Dopamine HCL that adds 15.15 mmol after the 30-60min; use alcohol chromatography 3 times behind the reaction 12h; remove unreacted Dopamine HCL and NHS/EDC; obtain Alg-DA, freeze-drying is for subsequent use.
50mg Alg-DA is dissolved in 5ml pH=7.5 Tris-HCl obtains the solution that concentration is 10mg/ml in the buffered soln, autohemagglutination obtained Alg-PDA after magneton stirred 24h under the room temperature.
Draw Alg-PDA solution with internal diameter 0.4mm syringe, to 0.2M 25ml CaCl
2Drip in the solution, rate of addition is 1/s, uses the filtered through gauze microballoon after 30min is aging, uses the deionized water wash microballoon 3 times again, removes free Ca
2+, obtain at last poly-Dopamine HCL modification Alginate microparticles.
Embodiment two
Be that the 5.05mmol Lalgine is dissolved in the phosphate buffer soln of 100ml pH=5.5, at N with the monomer molar number
2Under protection and the mechanical stirring; the N-hydroxy-succinamide (NHS) and the 5.05mmol 1-ethyl-3-(3-dimethylaminopropyl that add 5.05mmol) carbodiimide hydrochloride (EDC); the Dopamine HCL that adds 10.1 mmol after the 30-60min; use alcohol chromatography 3 times behind the reaction 12h; remove unreacted Dopamine HCL and NHS/EDC; obtain Alg-DA, freeze-drying is for subsequent use.
50mg Alg-DA is dissolved in 5ml pH=7.5 Tris-HCl obtains the solution that concentration is 15mg/ml in the buffered soln, autohemagglutination obtained Alg-PDA after magneton stirred 24h under the room temperature.
Draw Alg-PDA solution with internal diameter 0.4mm syringe, to 0.2M 25ml CaCl
2Drip in the solution, rate of addition is 1/s, uses the filtered through gauze microballoon after 30min is aging, uses the deionized water wash microballoon 3 times again, removes free Ca
2+, obtain at last poly-Dopamine HCL modification Alginate microparticles.
Embodiment three
Be that the 5.05mmol Lalgine is dissolved in the phosphate buffer soln of 100ml pH=5.5, at N with the monomer molar number
2Under protection and the mechanical stirring; the N-hydroxy-succinamide (NHS) and the 5.05mmol 1-ethyl-3-(3-dimethylaminopropyl that add 5.05mmol) carbodiimide hydrochloride (EDC); the Dopamine HCL that adds 5.05 mmol after the 30-60min; use alcohol chromatography 3 times behind the reaction 12h; remove unreacted Dopamine HCL and NHS/EDC; obtain Alg-DA, freeze-drying is for subsequent use.
50mg Alg-DA is dissolved in 5ml pH=7.5 Tris-HCl obtains the solution that concentration is 20mg/ml in the buffered soln, autohemagglutination obtained Alg-PDA after magneton stirred 24h under the room temperature.
Draw Alg-PDA solution with internal diameter 0.4mm syringe, to 0.2M 25ml CaCl
2Drip in the solution, rate of addition is 1/s, uses the filtered through gauze microballoon after 30min is aging, uses the deionized water wash microballoon 3 times again, removes free Ca
2+, obtain at last poly-Dopamine HCL modification Alginate microparticles.
Embodiment four
Be that the 5.05mmol Lalgine is dissolved in the phosphate buffer soln of 100ml pH=5.5, at N with the monomer molar number
2Under protection and the mechanical stirring; the N-hydroxy-succinamide (NHS) and the 5.05mmol 1-ethyl-3-(3-dimethylaminopropyl that add 5.05mmol) carbodiimide hydrochloride (EDC); the Dopamine HCL that adds 2.53mmol after the 30-60min; use alcohol chromatography 3 times behind the reaction 12h; remove unreacted Dopamine HCL and NHS/EDC; obtain Alg-DA, freeze-drying is for subsequent use.
50mg Alg-DA is dissolved in 5ml pH=7.5 Tris-HCl obtains the solution that concentration is 25mg/ml in the buffered soln, autohemagglutination obtained Alg-PDA after magneton stirred 24h under the room temperature.
Draw Alg-PDA solution with internal diameter 0.4mm syringe, to 0.2M 25ml CaCl
2Drip in the solution, rate of addition is 1/s, uses the filtered through gauze microballoon after 30min is aging, uses the deionized water wash microballoon 3 times again, removes free Ca
2+, obtain at last poly-Dopamine HCL modification Alginate microparticles.
Comparative Examples one
The 75mg Lalgine is dissolved in the 5ml pH 7.5 Tris-HCl buffered soln obtains the solution that concentration is 15mg/ml, is that the 0.41mm syringe is drawn Lalgine solution with internal diameter, to 0.2M 25ml CaCl afterwards
2Drip in the solution, rate of addition is 1/s, uses the filtered through gauze microballoon after the aging 30min, uses the washed with de-ionized water microballoon 3 times again, washes free Ca off
2+, obtain at last Alginate microparticles.
Claims (1)
1. the preparation method of a poly-Dopamine HCL modification Alginate microparticles is characterized in that comprising following process;
(1) phosphate buffer soln that sodium alginate is added pH=5.5 dissolves, at N
2Protection and stirring are lower, add N-hydroxy-succinamide and 1-ethyl-3-(3-dimethylaminopropyl with Lalgine monomer equimolar amount) carbodiimide hydrochloride, after 30 ~ 60min, add again the Dopamine HCL that is equivalent to 0.5 ~ 3 times of molar weight of Lalgine monomer, use alcohol chromatography behind the reaction 8-14h, remove unreacted Dopamine HCL, N-hydroxy-succinamide and 1-ethyl-3-(3-dimethylaminopropyl) carbodiimide hydrochloride, obtain Dopamine HCL modification Lalgine, freeze-drying is for subsequent use;
(2) it is that compound concentration is the solution of 10 ~ 25mg/ml in 7.5 ~ 8.5 Tris-HCl buffered soln that the Dopamine HCL modification Lalgine that step (1) is synthesized is dissolved in pH, stirs polymerization under the room temperature and obtains poly-Dopamine HCL modification Lalgine solution;
(3) drawing poly-Dopamine HCL modification Lalgine solution with syringe, is the CaCl of 0.2M to concentration
2Drip poly-Dopamine HCL modification Lalgine solution in the solution, after 30-60min is aging, filter out microballoon, remove Ca free in the microballoon with deionized water wash again
2+, obtain poly-Dopamine HCL modification Alginate microparticles.
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