CN105732965A - Preparing method and application of segmented copolymer based on nonlinearity - Google Patents
Preparing method and application of segmented copolymer based on nonlinearity Download PDFInfo
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
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- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
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Abstract
The invention relates to a synthesizing method of a segmented copolymer based on nonlinearity and a preparing method of micelle. Polymannose hydroxyl serves as an activator to induce lactide ring opening polymerization, the nonlinear polymannose-polyactic acid segmented copolymer is obtained, and the nanometer-scale micelle with high stability is prepared in an aqueous solution in a self-assembling mode. The dimension of particles can be controlled by regulating the molecular weight of polymannose and the molecular weight of polyactic acid. The segmented copolymer and the micelle can be applied to the fields of medicine loading, controlled release and targeted administration and have the effects of improving the water solubility of hydrophpbic medicine and the pharmacological function, reducing toxicity and the like.
Description
Technical field
The present invention relates to a kind of Preparation method and use based on non-linear poly-mannose polylactic-acid block copolymer.
Background technology
In recent years, Biodegradable high molecular has a wide range of applications in fields such as organizational project, drug controlled release and environmentally conscious materials engineerings, with polycaprolactone, polylactic acid and be representative with the block copolymer of Polyethylene Glycol aliphatic polyester show excellent biocompatibility, medicine permeability and biological degradability, obtain the favor of increasing researcher.
The amphipathic nature block polymer for controlled drug delivery systems of current most study is concentrated mainly on two blocks and triblock polymer.Constitute the mainly Polyethylene Glycol (PEG) of amphipathic nature block polymer hydrophilic block or be called polyoxyethylene (PEO), there is good hydrophilic, the interfacial free energy contacted with water is low, water has extended configuration, thus there is significantly high pliability, it is possible to provide certain spatial stability effect.The hydrophilic improving pharmaceutical carrier surface can reduce leakage and the blood vessel endothelium reticular system phagocytosis to medicine of medicine, had both improve the safety of medication, and had extended again the blood circulation time of medicine.Hydrophobic block then may often be such that and utilizes polylactic acid, polycaprolactone, polyoxypropylene, polystyrene, polyamino acid, and they constitute the amphipathic copolymer of various diblock or three blocks together with PEG-, can form various micelle.
Mannose (Mannose) is a kind of monosaccharide, is also a kind of hexose, currently the only for saccharic nutrient clinically, is distributed widely in body fluid and tissue, particularly in nerve, skin, testis, retina, liver and intestinal；There is bio-compatible and biodegradability.And gather mannose and be polymerized by mannose monomer, there is higher hydrophilic and biodegradable.
Summary of the invention
For above-mentioned prior art, first purpose of the present invention is to provide a kind of based on non-linear poly-mannose-polylactic-acid block copolymer.
Second purpose of the present invention is to provide a kind of nano-micelle material and preparation method thereof.
For achieving the above object, the present invention adopts the following technical scheme that
According to the first aspect of the invention, it is provided that a kind of based on non-linear poly-mannose-polylactic-acid block copolymer, in described block copolymer, the mass ratio of poly-mannose and polylactic acid is (1-4): (1-16)；The molecular weight of described poly-mannose is 2000-10000, and on the poly-mannose hydroxyl that described polylactic acid is connected to, the total molecular weight of polylactic acid is 2000-10000.
The preparation method that the present invention also provides for above-mentioned poly-mannose-polylactic-acid block copolymer, step is as follows:
1-4:1-16 in mass ratio, the poly-mannose weighing molecular weight 2000-10000 adds airtight there-necked flask, stirring.100 DEG C of stirring 0.5h it are warming up to after being evacuated to-0.1Mpa.Then it is cooled to 60 DEG C of logical nitrogen protections and adds lactide, stir.Suction-0.1Mpa, is filled with nitrogen after being warming up to 80 DEG C of stirring 0.5h, is then added dropwise to a small amount of stannous octoate.After dropwising, the lower 150 DEG C of reaction 4h that heat up of continuing nitrogen protection.Then 150 DEG C of evacuation 2h are kept.After pass into nitrogen and lower the temperature simultaneously.It is cooled to addition 25ml dichloromethane when temperature is 50 DEG C.After stirring, system is poured slowly in the 500ml absolute ether of-20 DEG C, quickly stirs.A large amount of solid is had to generate.Sucking filtration after stirring 10min, washes three times with absolute ether, then decompression drying, to obtain final product.
According to the second aspect of the invention, it is provided that a kind of nano-micelle particle, above-mentioned poly-mannose-polylactic-acid block copolymer prepared by the mode of self assembly.Micelle particle can in the form of a solution or lyophilized powder form preserve.
In the micelle particle of the present invention, poly-mannose is high-hydrophilic polymer, nontoxic and degradable, there is high biocompatibility, hydrophilic outer layer is provided for micelle particle, increase the water solublity of particle, the absorption of the biological active matter confrontation micelle particles such as other protein, enzyme, polypeptide can also be prevented in blood circulation process, the existence of poly-mannose effectively shields human body reticuloendothelial system (RES) to the phagocytosis of micelle particle and rejection, extends micelle particle circulation time in blood；To have the biodegradable polylactic acid kernel as micelle particle of high degree of biocompatibility.
The present invention also provides for above-mentioned nano-micelle particle preparation method, and step is as follows:
(1) poly-mannose-polylactic-acid block copolymer is dissolved in organic solvent, adopts the method for decompression distillation, lyophilization or spray drying to remove organic solvent, obtain film matrix；
(2) in film matrix, add the water for injection of preheating, by rocking, stirring, the mode of ultrasonic or vortex, poly-mannose-polylactic-acid block copolymer aquation is self-assembled into micelle.
In step (1), organic solvent can be any one in acetonitrile, methanol, ethanol, isopropanol, oxolane, dioxane, dichloromethane, chloroform.
The present invention also provides for above-mentioned poly-mannose-polylactic-acid block copolymer or nano-micelle particle as the application in pharmaceutical carrier.Preferably, described medicine is oil-soluble medicine molecule.Its concrete application process is as follows:
(1) poly-mannose-polylactic-acid block copolymer and medicine are completely dissolved in organic solvent, make material and medicine form uniform solution I；
(2) organic solvent in solution I is thoroughly removed by the mode adopting decompression distillation, direct lyophilization or spray drying, obtains uniform material-medicine transparent membrane substrate；
(3) adding the water for injection of preheating in above-mentioned substrate, by rocking, stirring, the mode such as ultrasonic, vortex, carrier material aquation is self-assembled into micelle, is wrapped in hydrophobic cores by pharmaceutical pack, is formed containing drug solns II；
(4) in drug micelles solution II, add freeze drying protectant, then cross 0.45 μm of coarse filtration respectively, degerming after 0.22 μm of fine straining；
(5) filtrate being placed in-40 DEG C of refrigerators, pre-freeze 2～6h, then the unwatering that progressively distils, namely lyophilizing obtains carrier micelle lyophilized powder；
Wherein,
In step (1), organic solvent can be any one in acetonitrile, methanol, ethanol, isopropanol, oxolane, dioxane, dichloromethane, chloroform；
In step (2), direct freeze drying process, its solvent can be ethanol: water, and volume ratio is 1:10～1:100；Or the tert-butyl alcohol: water, volume ratio is 1:10～1:100.The more preferably tert-butyl alcohol: water, volume ratio is 2:8～4:6.
The micelle particle adopting the present invention is used for wrapping up oil-soluble medicine molecule, and its micelle medicine carrying amount is mass percent 5%～30%, and entrapment efficiency is 80～99%.
Beneficial effect:
Micelle obtained by the present invention has higher stability, and its critical micelle concentration is 4.16 × 10-5～3.17 × 10-4G/L scope, is better than the spherical micelle that the polyethylene glycol-polylactic acid block copolymer of equimolecular quantity assembles；The micelle simultaneously having wrapped up oil-soluble medicine demonstrates the controllable release characteristic to drug molecule in the phosphoric acid normal saline buffer solution that acid-base value is 7.4.Micelle obtained by the present invention, in drug release, Targeting delivery and growth drug effect etc., all has potential application prospect.
Accompanying drawing illustrates:
Fig. 1: paclitaxel micelle freeze-drying powder and solution appearance after redissolving, is water, lyophilized powder and micelle redissolution solution from left to right successively；
Fig. 2: paclitaxel micelle grain size distribution；
Fig. 3: paclitaxel micelle particle transmission electron microscope picture.
Detailed description of the invention:
Embodiment 1: the poly-mannose-polylactic-acid block copolymer of synthesis
The 10g poly-mannose taking molecular weight 2000 is claimed to add airtight there-necked flask, stirring.100 DEG C of stirring 0.5h it are warming up to after being evacuated to-0.1Mpa.Then it is cooled to 60 DEG C of logical nitrogen protections and adds 10g lactide, stir.Suction-0.1Mpa, is filled with nitrogen after being warming up to 80 DEG C of stirring 0.5h, is then added dropwise to appropriate stannous octoate.After dropwising, the lower 150 DEG C of reaction 4h that heat up of continuing nitrogen protection.Then 150 DEG C of evacuation 2h are kept.After pass into nitrogen and lower the temperature simultaneously.It is cooled to addition 25ml dichloromethane when temperature is 50 DEG C.After stirring, system is poured slowly in the 500ml absolute ether of-20 DEG C, quickly stirs.A large amount of solid is had to generate.Sucking filtration after stirring 10min, washes three times with absolute ether, and then decompression drying obtains off-white powder is product.
The chemical constitution of copolymer and composition adopt infrared spectrum, NMR (Nuclear Magnetic Resonance) spectrum identify and calculate；The molecular weight and molecualr weight distribution of copolymer uses gel permeation chromatography device to measure；After measured, poly-mannose-polylactic acid average molecular weight that the present embodiment obtains is 4000.
Embodiment 2: the poly-mannose-polylactic-acid block copolymer of synthesis
The 10g poly-mannose taking molecular weight 2000 is claimed to add airtight there-necked flask, stirring.100 DEG C of stirring 0.5h it are warming up to after being evacuated to-0.1Mpa.Then it is cooled to 60 DEG C of logical nitrogen protections and adds 20g lactide, stir.Suction-0.1Mpa, is filled with nitrogen after being warming up to 80 DEG C of stirring 0.5h, is then added dropwise to a small amount of stannous octoate.After dropwising, the lower 150 DEG C of reaction 4h that heat up of continuing nitrogen protection.Then 150 DEG C of evacuation 2h are kept.After pass into nitrogen and lower the temperature simultaneously.It is cooled to addition 25ml dichloromethane when temperature is 50 DEG C.After stirring, system is poured slowly in the 500ml absolute ether of-20 DEG C, quickly stirs.A large amount of solid is had to generate.Sucking filtration after stirring 10min, washes three times with absolute ether, and then decompression drying obtains off-white powder is product, and its poly-mannose-polylactic acid average molecular weight obtained is 6000.
Embodiment 3: the poly-mannose-polylactic-acid block copolymer of synthesis
The 10g poly-mannose taking molecular weight 8000 is claimed to add airtight there-necked flask, stirring.100 DEG C of stirring 0.5h it are warming up to after being evacuated to-0.1Mpa.Then it is cooled to 60 DEG C of logical nitrogen protections and adds 5g lactide, stir.Suction-0.1Mpa, is filled with nitrogen after being warming up to 80 DEG C of stirring 0.5h, is then added dropwise to appropriate stannous octoate.After dropwising, the lower 150 DEG C of reaction 4h that heat up of continuing nitrogen protection.Then 150 DEG C of evacuation 2h are kept.After pass into nitrogen and lower the temperature simultaneously.It is cooled to addition 25ml dichloromethane when temperature is 50 DEG C.After stirring, system is poured slowly in the 500ml absolute ether of-20 DEG C, quickly stirs.A large amount of solid is had to generate.Sucking filtration after stirring 10min, washes three times with absolute ether, and then decompression drying obtains off-white powder is product, and its poly-mannose-polylactic acid average molecular weight obtained is 12000.
Embodiment 4: prepare the micelle of the poly-mannose-polylactic-acid block copolymer of paclitaxel
1) poly-mannose-polylactic-acid block copolymer embodiment 1 obtained and paclitaxel are completely dissolved in methanol, make material and medicine form uniform solution I；Wherein paclitaxel and poly-mannose-polylactic-acid block copolymer are by weight ratio: taxol drug 1 part, poly-mannose-polylactic-acid block copolymer 50 parts.
2) methanol in solution I is thoroughly removed by the distillation mode that reduces pressure, it is preferable that decompression distillation, obtain uniform material-medicine transparent membrane substrate；
3) adding the water for injection of preheating in above-mentioned substrate, by rocking, stirring, the mode such as ultrasonic, vortex, carrier material aquation is self-assembled into micelle, is wrapped in hydrophobic cores by paclitaxel, is formed containing drug solns II；
4) in paclitaxel micellar solution II, add lactose freeze drying protectant, then cross 0.45 μm of coarse filtration respectively, degerming after 0.22 μm of fine straining；
5) filtrate being placed in-40 DEG C of refrigerators, pre-freeze 2-6h, it is preferable that 2-3h, then the unwatering that progressively distils, namely lyophilizing obtains paclitaxel micelle freeze-drying powder.Solution appearance after paclitaxel micelle freeze-drying powder and redissolution is as it is shown in figure 1, be water, lyophilized powder and micelle redissolution solution from left to right successively.
In the present embodiment, the form of micelle particle adopts field emission scanning electron microscope and transmission electron microscope is observed and record；The critical micelle concentration of micelle uses fluorescence spectrophotometer detection and calculates.Paclitaxel micelle grain size distribution is as shown in Figure 2；Paclitaxel micelle particle transmission electron microscope picture is as shown in Figure 3.
Claims (10)
1. one kind based on non-linear poly-mannose-polylactic-acid block copolymer, it is characterised in that in described block copolymer, and the mass ratio of poly-mannose and polylactic acid is (1-4): (1-16)；The molecular weight of described poly-mannose is 2000-10000, and on the poly-mannose hydroxyl that described polylactic acid is connected to, the total molecular weight of polylactic acid is 2000-10000.
2. the preparation method based on non-linear poly-mannose-polylactic-acid block copolymer described in claim 1, it is characterised in that step is as follows: 1-4:1-16 in mass ratio, the poly-mannose weighing molecular weight 2000-10000 adds airtight there-necked flask, stirring；100 DEG C of stirring 0.5h it are warming up to after being evacuated to-0.1Mpa；Then it is cooled to 60 DEG C of logical nitrogen protections and adds lactide, stir；Suction-0.1Mpa, is filled with nitrogen after being warming up to 80 DEG C of stirring 0.5h, is then added dropwise to a small amount of stannous octoate；After dropwising, the lower 150 DEG C of reaction 4h that heat up of continuing nitrogen protection；Then 150 DEG C of evacuation 2h are kept；After pass into nitrogen and lower the temperature simultaneously；It is cooled to addition 25ml dichloromethane when temperature is 50 DEG C；After stirring, system is poured slowly in the 500ml absolute ether of-20 DEG C, quickly stirs, have a large amount of solid to generate；Sucking filtration after stirring 10min, washes three times with absolute ether, then decompression drying, to obtain final product.
3. a nano-micelle particle, it is characterised in that the poly-mannose-polylactic-acid block copolymer described in claim 1 is prepared by the mode of self assembly.
4. the preparation method of the nano-micelle particle described in claim 3, it is characterised in that step is as follows:
(1) poly-mannose-polylactic-acid block copolymer is dissolved in organic solvent, adopts the method for decompression distillation, lyophilization or spray drying to remove organic solvent, obtain film matrix；
(2) in film matrix, add the water for injection of preheating, by rocking, stirring, the mode of ultrasonic or vortex, poly-mannose-polylactic-acid block copolymer aquation is self-assembled into micelle.
Wherein, in step (1), described organic solvent is any one in acetonitrile, methanol, ethanol, isopropanol, oxolane, dioxane, dichloromethane, chloroform.
5. the poly-mannose-polylactic-acid block copolymer described in claim 1 or the nano-micelle particle described in claim 3 are as the application in pharmaceutical carrier.
6. apply as claimed in claim 5, it is characterised in that described medicine is fat-soluble medicine molecule.
7. apply as claimed in claim 5, it is characterised in that its application process is as follows:
(1) poly-mannose-polylactic-acid block copolymer and medicine are completely dissolved in organic solvent, make material and medicine form uniform solution I；
(2) organic solvent in solution I is thoroughly removed by the mode adopting decompression distillation, direct lyophilization or spray drying, obtains uniform material-medicine transparent membrane substrate；
(3) adding the water for injection of preheating in above-mentioned substrate, by rocking, stirring, the mode of ultrasonic or vortex, poly-mannose-polylactic-acid block copolymer aquation is self-assembled into micelle, is wrapped in hydrophobic cores by pharmaceutical pack, is formed containing drug solns II；
(4) in drug micelles solution II, add freeze drying protectant, then cross 0.45 μm of coarse filtration respectively, degerming after 0.22 μm of fine straining；
(5) filtrate being placed in-40 DEG C of refrigerators, pre-freeze 2～6h, then the unwatering that progressively distils, namely lyophilizing obtains carrier micelle lyophilized powder.
8. application according to claim 7, it is characterised in that in step (1), described organic solvent is any one in acetonitrile, methanol, ethanol, isopropanol, oxolane, dioxane, dichloromethane, chloroform.
9. application according to claim 7, it is characterised in that in step (2), direct freeze drying process, its solvent can be ethanol: water, and volume ratio is 1:10～1:100；Or the tert-butyl alcohol: water, volume ratio is 1:10～1:100.
10. application according to claim 9, it is characterised in that in step (2), direct freeze drying process, its solvent can be the tert-butyl alcohol: water, and volume ratio is 2:8～4:6.
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Cited By (1)
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| CN105982855A (en) * | 2016-03-07 | 2016-10-05 | 山东华铂凯盛生物科技有限公司 | Micelle lyophilized preparation of nonlinear mannan-polylactic acid segmented copolymer supported taxane medicines, as well as preparation method and application thereof |
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| CN101628947A (en) * | 2009-08-14 | 2010-01-20 | 暨南大学 | Chitosan-polylactic acid graft copolymer and preparation method and application thereof |
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| CN105982855A (en) * | 2016-03-07 | 2016-10-05 | 山东华铂凯盛生物科技有限公司 | Micelle lyophilized preparation of nonlinear mannan-polylactic acid segmented copolymer supported taxane medicines, as well as preparation method and application thereof |
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