CN103642165A - Preparation method of divinyl glucose sebacate/isopropyl acrylamide copolymer nanoparticles - Google Patents
Preparation method of divinyl glucose sebacate/isopropyl acrylamide copolymer nanoparticles Download PDFInfo
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Abstract
The invention relates to a preparation method of divinyl glucose sebacate/isopropyl acrylamide copolymer nanoparticles, which comprises the following steps: dissolving divinyl sebacate and glucose in anhydrous pyridine, adding alkaline proteinase, separating and purifying to obtain vinyl glucose sebacate; adding N-isopropylacrylamide, an initiator and a solvent into the vinyl glucose sebacate, and stirring to perform polymerization reaction in a nitrogen protective atmosphere, thereby obtaining a vinyl glucose sebacate/isopropyl acrylamide copolymer; and adding the copolymer and PLCL into a solvent to obtain an electronic injection solution, carrying out electronic injection, and drying. The method is simple to operate, and has the advantages of manageable product, high economy and environmental protection; and the obtained nanoparticles contain abundant reactive hydrophilic active functional groups, have the phase-change temperature which is approximate to the body temperature, enhance the specific adsorption of the material surface, improve the biocompatibility of the material surface, and have wide application prospects.
Description
Technical field
The invention belongs to the preparation field of organic nanometer granule, particularly a kind of preparation method of glucose sebacic acid divinyl fat/N-isopropylacrylamide copolymer nano particle.
Background technology
Sugar and protein, lipid is the same with nucleic acid, is the important component that forms organism.The carbohydrate of surface of cell membrane has participated in the target of albumen, cell recognition, the important physiological process such as antibody-AI.Glycosylation material has high wetting ability and anti-non-specific protein absorption and the high characteristics such as biocompatibility, therefore be widely used in very much protein separation, the specificity of bacterium catches, the aspects such as cultivation of bio-medical material and cell, can also prepare surface-functionalized separatory membrane.Carbohydrate can directly carry out specific identification with protein, completes the transmission of bioinformation.Therefore, preparation has the glycosylation material of protein specific identification, has application prospect very widely.
NIPA is owing to having hydrophilic amide group and hydrophobic sec.-propyl in molecule, its homogeneous polymer has the good characteristics such as lower Kraft point (LCST).Because its polymkeric substance has at 32 ℃, be above this special dissolution characteristics of water-insoluble, developing the raw material for the manufacture of some temperature sensibility polymer gel.Easily polymerization separately of common radical polymerization initiator for NIPA, also easily copolymerization.Therefore, it becomes the focus of current thermoresponsive investigation of materials.
Nanotechnology, computer technology, genetic engineering technique are listed in large front line science technology of 21 century 3.Nanotechnology this by the extensive good front line science of common people, its maximum value be can and different subject or field intersection, thereby produce new industry or subject.Nano microsphere often claims microballoon, comprise nanometer ball and micron ball, be one of current of paramount importance nanotechnology product, can be widely used in the various fields such as bio-pharmaceuticals, medical diagnosis on disease, environmental monitoring, purifying treatment, liquid crystal display, makeup, paint.
Utilize sugary nano particle prepared by static electric jet technology to there are the potentiality of specific adsorption mechanism between follow-up study protein.
Summary of the invention
Technical problem to be solved by this invention is to provide a kind of preparation method of glucose sebacic acid divinyl fat/N-isopropylacrylamide copolymer nano particle, the method is simple to operate, product is easily processed and economic environmental protection, this nano particle contain abundant can reactive hydrophilic activated functional groups and there is the transformation temperature close to body temperature, when having improved the specific adsorption of material surface and having improved the biocompatibility of material surface, on the basis of phase-change characteristic, can there be a lot of potential application.
The preparation method of a kind of glucose sebacic acid divinyl fat/N-isopropylacrylamide copolymer nano particle of the present invention, comprising:
(1) the sebacic acid divinyl fat that is 1-4:1 by mol ratio and glucose are dissolved in anhydrous pyridine, add Sumizyme MP, under 40-60 ℃ of condition, react 3-5 days, and separating-purifying obtains glucose ethene fat; Wherein the amount ratio of Sumizyme MP and anhydrous pyridine is 0.5-1.5g:50-100ml;
(2) in above-mentioned glucose ethene fat, add NIPA, initiator and solvent, then stirring reaction 3-8h under 55-60 ℃ of nitrogen protection, obtains glucose ethene fat/N-isopropylacrylamide multipolymer after polyreaction finishes; Wherein the mol ratio of NIPA and glucose ethene fat is 1-50:1, and initiator accounts for the 0.2-2% of glucose ethene fat and NIPA quality sum;
(3) above-mentioned glucose ethene fat/N-isopropylacrylamide multipolymer and PLCL are added in solvent, stir to obtain glucose ethene fat/N-isopropylacrylamide multipolymer EFI liquid, then carry out static EFI, be drying to obtain glucose ethene fat/N-isopropylacrylamide copolymer nano particle, wherein to account for the massfraction of EFI liquid be 3-30% for glucose ethene fat/N-isopropylacrylamide multipolymer and PLCL sum, and the mol ratio of glucose ethene fat/N-isopropylacrylamide multipolymer and PLCL is 1:1.
In described step (1), reaction is carried out in constant-temperature shaking incubator, and rotating speed is 200rpm.
In described step (1), separating-purifying is: use silica gel column chromatography separating-purifying, eluent is ethyl acetate, and developping agent is that volume ratio is the ethyl acetate of 17:3:1, the mixed solution of first alcohol and water, uses I
2colour developing.
In described step (2), initiator is Diisopropyl azodicarboxylate AIBN, and solvent is dehydrated alcohol, and glucose ethene fat and the NIPA concentration sum in ethanol solution is 2-3mol/L.
After polyreaction finishes in described step (2), product is removed to the no glucose ethene fat of reaction through 3500D dialysis membrane.
Solvent in described step (3) is dehydrated alcohol.
In described step (3), in glucose ethene fat/N-isopropylacrylamide multipolymer, the mol ratio of glucose ethene fat and N-isopropylacrylamide is 1:5-1:25.
In described step (3), EFI processing parameter is: specification of syringe is 5mL, and syringe needle internal diameter is 0.4-0.7mm, ejection flow velocity 0.8-2mL/h, static voltage 10-18kV, receiving screen adopts the reception of aluminium foil ground connection, and accepting distance is 10-20cm, adopts orthogonal method to regulate EFI parameter to carry out EFI.
In described step (3), dry temperature is 30-60 ℃, and be 24-48h time of drying.
Glucose ethene fat/N-isopropylacrylamide copolymer nano particle of described step (3) gained is applied to separation and purification, research carbohydrate and the protein specific adsorption mechanism of protein.
In the present invention, the preparation method of sebacic acid divinyl fat used is as follows:
By the sebacic acid of certain molar weight, vinyl acetate (1:1～1:10mol/mol), 1g～5g mercuric acetate, acetate in minute copper is mixed in 250mL flask, after stirring at room 1～15min, add the 0.1-0.5mL vitriol oil, constant temperature stirring reaction 8h at 50 ℃～70 ℃.React the complete blue settled solution that obtains.After reaction solution is cooling, add 0.1～1.5g sodium acetate, anhydrous, fully concussion is to remove sulfuric acid wherein, and after standing filtration, rotary evaporation is removed excessive vinyl acetate.Surplus solution, through silica gel column chromatography (300～400 order) separating-purifying, obtains sebacic acid divinyl fat.
Sugar is a kind of in biomolecules, is extensively present in organism, and be polyhydroxyl compound, there is extremely strong wetting ability, therefore, sugar is introduced to the surface of material, will effectively improve the biocompatibility of material surface.And can there is identification mutually with specific lectin in carbohydrate, will be conducive to prepare albumen sepn medium, cell cultures microcarrier, pharmaceutical carrier (sustained-release micro-spheres), non-viral gene transfection carrier etc.
The present invention carries out EFI by NIPA and the copolymerization of glucose ethene fat, obtains at nano level glucose ethene fat/N-isopropylacrylamide copolymer nano particle.This mould material contain abundant can reactive hydrophilic activated functional groups, improve the non-specific adsorption of material surface and improved the biocompatibility of material surface, it does the potentiality that follow-up related experiment is analyzed to have application, and can interact with specific lectin, there is the potential quality of preparation albumen sepn medium.Because glucose ethene fat/N-isopropylacrylamide copolymer nano particle has controlled LCST value, there is the target release that realizes medicine, as application potentials such as pharmaceutical carriers.
Beneficial effect:
(1) the present invention adopts aqueous phase precipitation polymerization process to prepare glucose ethene resin copolymer, and preparation method is simple to operate, product is easily processed and economic environmental protection;
(2) in the present invention, NIPA copolymer nano particle is a class specific surface, the solid support material of high porosity;
(3) in the present invention, glycosylation nanofiber is for the specific recognition of protein, efficient, fast, is conducive to study the mechanism of specific recognition between carbohydrate and protein, and can be repeatedly used, and is easy to suitability for industrialized production.
Accompanying drawing explanation
Fig. 1 is that the Thermo-sensitive of embodiment 1 gained is containing the Infrared Characterization of sugar copolymer;
Fig. 2 is that the Thermo-sensitive of embodiment 1 gained is containing the nuclear-magnetism sign of sugar copolymer;
Fig. 3 is that the Thermo-sensitive of embodiment 1-3 gained is containing the LCST value of sugar copolymer;
Fig. 4 is the stereoscan photograph (EFI voltage is 10kV, and receiving range is 15cm, and injection flow velocity is 1.0ml/h) of the sugary copolymer nano particle of Thermo-sensitive of embodiment 1-3 gained.
Embodiment
Below in conjunction with specific embodiment, further set forth the present invention.Should be understood that these embodiment are only not used in and limit the scope of the invention for the present invention is described.In addition should be understood that those skilled in the art can make various changes or modifications the present invention after having read the content of the present invention's instruction, these equivalent form of values fall within the application's appended claims limited range equally.
(1) by sebacic acid divinyl fat and glucose according to a certain percentage (4:1, mol ratio) be dissolved in anhydrous pyridine, utilize enzymatic synthetic technology synthesis of glucose ethene fat.After reaction finishes, crude product silica gel column chromatography separating-purifying, eluent is ethyl acetate, developping agent is ethyl acetate, first alcohol and water (17:3:1, v/v/v), uses I
2colour developing.Above-mentioned glycolipid is put in micro-polymerizing pipe, add a certain amount of NIPA (with the mol ratio of glucose ethene fat be 7:1), with Diisopropyl azodicarboxylate (AIBN) (massfraction that accounts for glucose ethene fat and NIPA total mass is 2.0) as initiator, add dehydrated alcohol to make solvent (monomer concentration is 2.5mol/L dehydrated alcohol), sealing, with oil pump, vacuumize rear logical nitrogen, repeated multiple times.System is placed in to stirring reaction 6h under 50-60 ℃ of nitrogen protection.
(2) by the Thermo-sensitive glucose ethene resin copolymer of certain mass and PLCL, according to mol ratio, be that 1:1 adds in dehydrated alcohol, in multipolymer, the mol ratio of glucose lipid and NIPAM is 1:10, stirred for several hour is extremely dissolved completely, standing a few hours make bubble completely dissolve in EFI liquid, stir and form homogeneous EFI liquid.
(3) with syringe, extract Thermo-sensitive containing sugar copolymer, be fixed on electric injection device, control ejection flow velocity 1.0ml/h, static voltage 10kV, receiving screen adopts the reception of aluminium foil ground connection, and the distance of syringe needle and receiving screen is 10-20cm, adopts orthogonal method (to change a certain parameter, fix other parameter) regulate different EFI parameters to carry out EFI, obtain the sugary copolymer nano particle of Thermo-sensitive; Put into vacuum drying oven 30-60 ℃ of freeze-day with constant temperature 36h, make regeneration nano composite membrane, its electromicroscopic photograph as shown in Figure 4 (A).
(1) by sebacic acid divinyl fat and glucose according to a certain percentage (4:1, mol ratio) be dissolved in anhydrous pyridine, utilize enzymatic synthetic technology synthesis of glucose ethene fat.After reaction finishes, crude product silica gel column chromatography separating-purifying, eluent is ethyl acetate, developping agent is ethyl acetate, first alcohol and water (17:3:1, v/v/v), uses I
2colour developing.Add a certain amount of NIPA (with the mol ratio of glucose ethene fat be 7:1), with Diisopropyl azodicarboxylate (AIBN) (massfraction that accounts for glucose ethene fat and NIPA total mass is 2.0) as initiator, add dehydrated alcohol to make solvent (monomer concentration is 2.5mol/L dehydrated alcohol), sealing, with oil pump, vacuumize rear logical nitrogen, repeated multiple times.System is placed in to stirring reaction 6h under 55-60 ℃ of nitrogen protection.
(2) by the Thermo-sensitive glucose ethene resin copolymer of certain mass and PLCL, according to mol ratio, be that 1:1 adds in dehydrated alcohol, in multipolymer, the mol ratio of glucose lipid and NIPAM is 1:15, stirred for several hour is extremely dissolved completely, standing a few hours make bubble completely dissolve in EFI liquid, stir and form homogeneous EFI liquid.
(3) with syringe, extract Thermo-sensitive containing sugar copolymer, be fixed on electric injection device, control ejection flow velocity 1.0ml/h, static voltage 10kV, receiving screen adopts the reception of aluminium foil ground connection, and the distance of syringe needle and receiving screen is 10-20cm, adopts orthogonal method (to change a certain parameter, fix other parameter) regulate different EFI parameters to carry out EFI, obtain the sugary copolymer nano particle of Thermo-sensitive; Put into vacuum drying oven 60-80 ℃ of freeze-day with constant temperature 24h, make regeneration nano composite membrane, its electromicroscopic photograph is as shown in Fig. 4 (B).
(1) by sebacic acid divinyl fat and glucose according to a certain percentage (4:1, mol ratio) be dissolved in anhydrous pyridine, utilize enzymatic synthetic technology synthesis of glucose ethene fat.After reaction finishes, crude product silica gel column chromatography separating-purifying, eluent is ethyl acetate, developping agent is ethyl acetate, first alcohol and water (17:3:1, v/v/v), uses I
2colour developing.Above-mentioned glycolipid is put in micro-polymerizing pipe, add a certain amount of NIPA (with the mol ratio of glucose ethene fat be 7:1), with Diisopropyl azodicarboxylate (AIBN) (massfraction that accounts for glucose ethene fat and NIPA total mass is 2.0) as initiator, add dehydrated alcohol to make solvent (monomer concentration is 2.5mol/L dehydrated alcohol), sealing, with oil pump, vacuumize rear logical nitrogen, repeated multiple times.System is placed in to stirring reaction 6h under 50-60 ℃ of nitrogen protection.
(2) by the Thermo-sensitive glucose ethene resin copolymer of certain mass and PLCL, according to mol ratio, be that 1:1 adds in dehydrated alcohol, in multipolymer, the mol ratio of glucose lipid and NIPAM is 1:20, stirred for several hour is extremely dissolved completely, standing a few hours make bubble completely dissolve in EFI liquid, stir and form homogeneous EFI liquid.
(3) with syringe, extract Thermo-sensitive containing sugar copolymer, be fixed on electric injection device, control ejection flow velocity 1.0ml/h, static voltage 10kV, receiving screen adopts the reception of aluminium foil ground connection, and the distance of syringe needle and receiving screen is 10-20cm, adopts orthogonal method (to change a certain parameter, fix other parameter) regulate different EFI parameters to carry out EFI, obtain the sugary copolymer nano particle of Thermo-sensitive; Put into vacuum drying oven 60-80 ℃ of freeze-day with constant temperature 24h, make regeneration nano composite membrane, its electromicroscopic photograph is as shown in Fig. 4 (C).
Claims (10)
1. a preparation method for glucose sebacic acid divinyl fat/N-isopropylacrylamide copolymer nano particle, comprising:
(1) the sebacic acid divinyl fat that is 1-4:1 by mol ratio and glucose are dissolved in anhydrous pyridine, add Sumizyme MP, under 40-60 ℃ of condition, react 3-5 days, and separating-purifying obtains glucose ethene fat; Wherein the amount ratio of Sumizyme MP and anhydrous pyridine is 0.5-1.5g:50-100ml;
(2) in above-mentioned glucose ethene fat, add NIPA, initiator and solvent, then stirring reaction 3-8h under 55-60 ℃ of nitrogen protection, obtains glucose ethene fat/N-isopropylacrylamide multipolymer after polyreaction finishes; Wherein the mol ratio of NIPA and glucose ethene fat is 1-50:1, and initiator accounts for the 0.2-2% of glucose ethene fat and NIPA quality sum;
(3) above-mentioned glucose ethene fat/N-isopropylacrylamide multipolymer and PLCL are added in solvent, stir to obtain glucose ethene fat/N-isopropylacrylamide multipolymer EFI liquid, then carry out EFI, be drying to obtain glucose ethene fat/N-isopropylacrylamide copolymer nano particle, wherein to account for the massfraction of EFI liquid be 3-30% for glucose ethene fat/N-isopropylacrylamide multipolymer and PLCL sum, and the mol ratio of glucose ethene fat/N-isopropylacrylamide multipolymer and PLCL is 1:1.
2. the preparation method of a kind of glucose sebacic acid divinyl fat/N-isopropylacrylamide copolymer nano particle according to claim 1, is characterized in that: in described step (1), reaction is carried out in constant-temperature shaking incubator, and rotating speed is 200rpm.
3. the preparation method of a kind of glucose sebacic acid divinyl fat/N-isopropylacrylamide copolymer nano particle according to claim 1, it is characterized in that: in described step (1), separating-purifying is: use silica gel column chromatography separating-purifying, eluent is ethyl acetate, developping agent is that volume ratio is the ethyl acetate of 17:3:1, the mixed solution of first alcohol and water, uses I
2colour developing.
4. the preparation method of a kind of glucose sebacic acid divinyl fat/N-isopropylacrylamide copolymer nano particle according to claim 1, it is characterized in that: in described step (2), initiator is Diisopropyl azodicarboxylate AIBN, solvent is dehydrated alcohol, and glucose ethene fat and the NIPA concentration sum in ethanol solution is 2-3mol/L.
5. the preparation method of a kind of glucose sebacic acid divinyl fat/N-isopropylacrylamide copolymer nano particle according to claim 1, it is characterized in that: after polyreaction finishes in described step (2), product is removed to the no glucose ethene fat of reaction through 3500D dialysis membrane.
6. the preparation method of a kind of glucose sebacic acid divinyl fat/N-isopropylacrylamide copolymer nano particle according to claim 1, is characterized in that: the solvent in described step (3) is dehydrated alcohol.
7. the preparation method of a kind of glucose sebacic acid divinyl fat/N-isopropylacrylamide copolymer nano particle according to claim 1, it is characterized in that: in described step (3), in glucose ethene fat/N-isopropylacrylamide multipolymer, the mol ratio of glucose ethene fat and N-isopropylacrylamide is 1:5-1:25.
8. the preparation method of a kind of glucose sebacic acid divinyl fat/N-isopropylacrylamide copolymer nano particle according to claim 1, it is characterized in that: in described step (3), EFI processing parameter is: specification of syringe is 5mL, syringe needle internal diameter is 0.4-0.7mm, ejection flow velocity 0.8-2mL/h, static voltage 10-18kV, receiving screen adopts the reception of aluminium foil ground connection, and accepting distance is 10-20cm, adopts orthogonal method to regulate EFI parameter to carry out EFI.
9. the preparation method of a kind of glucose sebacic acid divinyl fat/N-isopropylacrylamide copolymer nano particle according to claim 1, is characterized in that: in described step (3), dry temperature is 30-60 ℃, and be 24-48h time of drying.
10. the preparation method of a kind of glucose sebacic acid divinyl fat/N-isopropylacrylamide copolymer nano particle according to claim 1, is characterized in that: glucose ethene fat/N-isopropylacrylamide copolymer nano particle of described step (3) gained is applied to the separation and purification of protein.
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Application publication date: 20140319 |