CN103239729B - Nano-carrier containing hyperbranched polymer and phospholipids as well as preparation method and application for same - Google Patents
Nano-carrier containing hyperbranched polymer and phospholipids as well as preparation method and application for same Download PDFInfo
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Abstract
The invention relates to a nano-carrier containing a hyperbranched polymer and phospholipids. The nano-carrier comprises hyperbranched polyester H40, polycaprolactone, phospholipids and a distearoyl phosphatidylethanolamine-polyethylene glycol-carboxyl linear polymer, wherein polycaprolactone is grafted on hyperbranched polyester H40 to form an inner core, the phospholipids are wound on polycaprolactone to form a middle layer, and distearoyl phosphatidylethanolamine in the distearoyl phosphatidylethanolamine-polyethylene glycol-carboxyl linear polymer penetrates in the middle layer, and polyethylene glycol and carboxyl group in the distearoyl phosphatidylethanolamine-polyethylene glycol-carboxyl linear polymer form an outer layer. The nano-carrier containing the hyperbranched polymer and the phospholipids aforementioned integrates the advantages of polymer nano-particles and nano-liposomes, has the characteristics of being high in medicine-loading capacity, good in biocompatibility, long in half-life period and monodisperse, as well as is not easy to agglomerate and strong in stability. Additionally, the invention further relates to a preparation method and application for the nano-carrier containing the hyperbranched polymer and the phospholipids.
Description
Technical field
The present invention relates to nanosecond medical science field, particularly relate to a kind of nano-carrier containing dissaving polymer and phospholipid and its preparation method and application.
Background technology
Traditional work out multiple nano-carrier that can carrying medicaments, wherein, the two class main flow nano-carriers that polymer nano granules and nanometer liposome be representative of take can wrap up and transmit medicine, gene etc., have become various countries scientist's study hotspot.
The two class main flow nano-carriers that polymer nano granules and nanometer liposome be representative of take have lot of advantages, have solved a lot of difficult problems, as problem of the solubility problem of insoluble drug, medicament slow release etc.But still there is the problems such as poor and half-life of biocompatibility is shorter in traditional polymer nanoparticle drug carriers or nanometer liposome carrier.
Summary of the invention
Based on this, be necessary the nano-carrier containing dissaving polymer and phospholipid that provides a kind of biocompatibility better and the half-life is long.
A nano-carrier containing dissaving polymer and phospholipid, comprises hyper-branched polyester H40, polycaprolactone, phospholipid and DSPE-PEG-COOH linear polymer; Described polycaprolactone grafts on the upper kernel that forms of described hyper-branched polyester H40, described phospholipid is surrounded on described polycaprolactone outside and forms intermediate layer, the DSPE of described DSPE-PEG-COOH linear polymer is interspersed in described intermediate layer, and Polyethylene Glycol and the carboxyl of described DSPE-PEG-COOH linear polymer form skin.
In an embodiment, the mass ratio that is grafted with hyper-branched polyester H40, phospholipid and the DSPE-PEG-COOH linear polymer of polycaprolactone is 1～5:0.24:0.06 therein.
In an embodiment, described intermediate layer is single layer structure therein.
In an embodiment, described phospholipid is soybean lecithin therein.
In an embodiment, the particle diameter of the described nano-carrier containing dissaving polymer and phospholipid is 20～40nm therein.
Because hyper-branched polyester H40 has highly branched construction features, and a large amount of reactive terminal hydroxyl of its surface enrichment, therefore, can take hyper-branched polyester H40 as initiator, at single hyper-branched polyester H40 surface grafting polycaprolactone (PCL), formation has multi-arm structure and has the H40-PCL of monodispersity, thereby take hydrophobic H40-PCL realizes the high-efficient carrier of hydrophobic drug as kernel, can control hydrophobic drug simultaneously and slowly discharge in vivo.And phospholipid is surrounded on polycaprolactone and forms midparent water layer, make can avoid immune identification containing the nano-carrier of dissaving polymer and phospholipid, thereby strengthen the half-life that it circulates in vivo.DSPE-PEG-COOH (DSPE-PEG-COOH) linear polymer is interspersed in formation skin in phospholipid intermediate layer with DSPE (DSPE), Polyethylene Glycol shell and carboxyl are provided, thereby make to possess the features such as spatial stability, electrostatic stabilization and long circulation containing the nano-carrier of dissaving polymer and phospholipid, carboxyl is easy to the parts such as cross-linking antibody, peptide, probe simultaneously, thereby can have targeting so that contain the nano-carrier of dissaving polymer and phospholipid.And H40-PCL, soybean lecithin and DSPE-PEG-COOH have good biocompatibility, superior biodegradable, can be absorbed or be excreted by normal physiological pathway.The above-mentioned nano-carrier containing dissaving polymer and phospholipid combines the advantage of polymer nano granules and nanometer liposome, has that medicine carrying capacity is high, a feature of good biocompatibility, long half time and monodispersity, and is difficult for reunion, has stronger stability.
The present invention also provides the above-mentioned nano-carrier containing dissaving polymer and phospholipid to apply preparing on pharmaceutical carrier preparation.
A preparation method that contains the nano-carrier of dissaving polymer and phospholipid, comprises the steps:
Hyper-branched polyester H40, caprolactone and stannous octoate are placed in to vacuum environment, and at 135 ℃ stirring reaction, after separation and purification, obtain polycaprolactone and graft on the intermediate product on hyper-branched polyester H40, and described intermediate product is dissolved in second cyanogen, the second cyanogen solution of the intermediate product that preparation concentration is 1～5mg/mL, wherein, the terminal hydroxyl of described hyper-branched polyester H40 and the mol ratio of described caprolactone are 1:20～1:50, the quality of described stannous octoate is 1 ‰ of described caprolactone, and described vacuum environment is processed through silanization in advance;
The ratio that is 4:1 according to mass ratio by phospholipid and DSPE-PEG-COOH linear polymer is dissolved in ethanol water, and stirs at 65 ℃, obtains mixed solution, and wherein in ethanol water, the mass fraction of ethanol is 4%;
The ratio that is 1:1.5～6 according to volume is dropwise added to the second cyanogen solution of described intermediate product in described mixed solution, and stirs at 65 ℃, obtains the described nano-carrier containing dissaving polymer and phospholipid.
In an embodiment, the step of described separation and purification is specially therein:
Reacted mixture is dissolved in chloroform, then adds rapidly enough cold methanols to precipitate, filter, be fixed material;
By described solid matter drying at room temperature two days under vacuum condition, the polycaprolactone that obtains purification grafts on the intermediate product on hyper-branched polyester H40.
In an embodiment, the particle diameter of the described nano-carrier containing dissaving polymer and phospholipid is 20～40nm therein.
In an embodiment, described phospholipid is soybean lecithin therein.
The preparation method of the above-mentioned nano-carrier containing dissaving polymer and phospholipid, first utilizes hyper-branched polyester H40 as initiator, and caprolactone is raw material, and stannous octoate is catalyst, the synthetic H40-PCL that has multi-arm structure and have monodispersity; Then H40-PCL, phospholipid and DSPE-PEG-COOH are mixed, by a step nanometer precipitation self assembly, obtain the nano-carrier containing dissaving polymer and phospholipid.Above-mentioned preparation method is simple and easy to do, easy and simple to handle, easy to utilize.
Accompanying drawing explanation
Fig. 1 is the structural representation of the nano-carrier containing dissaving polymer and phospholipid of an embodiment;
Fig. 2 is the flow chart of preparation method of the nano-carrier containing dissaving polymer and phospholipid of an embodiment;
Fig. 3 is the grain-size graph of the nano-carrier containing dissaving polymer and phospholipid of embodiment 1 preparation.
The specific embodiment
Below in conjunction with drawings and the specific embodiments, nano-carrier containing dissaving polymer and phospholipid and its preparation method and application is further detailed.
As shown in Figure 1, the nano-carrier containing dissaving polymer and phospholipid of an embodiment comprises hyper-branched polyester H40, polycaprolactone, phospholipid and DSPE-PEG-COOH linear polymer.
Wherein, polycaprolactone grafts on the upper kernel that forms of hyper-branched polyester H40, phospholipid is surrounded on polycaprolactone outside and forms intermediate layer, and DSPE-PEG-COOH linear polymer is interspersed in intermediate layer and forms skin for Polyethylene Glycol shell and carboxyl are provided with DSPE.
In the present embodiment, be grafted with the hyper-branched polyester H40(H40-PCL of polycaprolactone), the mass ratio of phospholipid and DSPE-PEG-COOH linear polymer is 1～5:0.24:0.06.This mass-energy density guarantees that polycaprolactone reasonably grafts on hyper-branched polyester H40 above, makes grafting density relatively suitable.The too little drug loading that is unfavorable for that acquisition is higher of grafting density, not only waste raw material also can affect the particle diameter of amphipathic supermolecule polymer to grafting density too greatly.And DSPE-PEG-COOH linear polymer is interspersed in formation skin in phospholipid intermediate layer with DSPE, therefore, the consumption that is surrounded on the phospholipid that forms intermediate layer on polycaprolactone can not be too large, the consumption of phospholipid is too large, will be unfavorable for that self assembly forms skin; Certainly, the consumption of phospholipid can not be too little, the intermediate layer of the half-life that the too little nano-carrier that is unfavorable for form strengthening containing dissaving polymer and phospholipid circulates in vivo.
In the present embodiment, hyper-branched polyester H40, is commercial Boltorn H40.Hyper-branched polyester H40 has highly branched construction features, and a large amount of reactive terminal hydroxyl of its surface enrichment, therefore, can take hyper-branched polyester H40 as initiator, at single hyper-branched polyester H40 surface grafting polycaprolactone (PCL), formation has multi-arm structure and has the H40-PCL of monodispersity, thereby take hydrophobic H40-PCL realizes the high-efficient carrier of hydrophobic drug as kernel, can control hydrophobic drug simultaneously and slowly discharge in vivo.And the nano-carrier that contains dissaving polymer and phospholipid is owing to having highly branched kernel, can micelle de-assembly phenomenon not occur because carrier concn reduces, and greatly promote the stability of carrier.Wherein, polycaprolactone has good biocompatibility, and therefore superior biodegradable receives much concern, and obtain the approval of U.S. FDA.
And phospholipid has the biofilm structure of bilayer, there is the characteristics such as fabulous hydrophilic, lipotropy and natural targeting, long-lasting, pardon, and nontoxic, non-immunogenicity, infiltration rate is fast, bioavailability is high, be easy to the features such as surface-functionalized, application prospect is very wide.In the present embodiment, phospholipid is surrounded on polycaprolactone and forms midparent water layer, makes can avoid immune identification containing the nano-carrier of dissaving polymer and phospholipid, thereby strengthens the half-life that it circulates in vivo.Phospholipid intermediate layer is single layer structure, and phospholipid is soybean lecithin.
And DSPE-PEG-COOH (DSPE-PEG-COOH) linear polymer is interspersed in phospholipid intermediate layer and with Polyethylene Glycol and carboxyl with DSPE (DSPE) and forms skin, for Polyethylene Glycol shell and carboxyl are provided to nano-carrier.Thereby make to possess the features such as spatial stability, electrostatic stabilization and long circulation containing the nano-carrier of dissaving polymer and phospholipid, carboxyl is easy to the parts such as cross-linking antibody, peptide, probe simultaneously, thereby can have targeting so that contain the nano-carrier of dissaving polymer and phospholipid.And H40-PCL, soybean lecithin and DSPE-PEG-COOH have good biocompatibility, superior biodegradable, can be absorbed or be excreted by normal physiological pathway.
Containing the nano-carrier of dissaving polymer and phospholipid, there is monodispersity and its particle diameter can regulate and control.In the present embodiment, the nano-carrier size containing dissaving polymer and phospholipid is 20～40nm.
Can graft on the chain length of the polycaprolactone on hyper-branched polyester H40 by mole recently control of adjusting hyper-branched polyester H40 and caprolactone, and then control the particle diameter containing the nano-carrier of dissaving polymer and phospholipid.Wherein, less particle diameter can contribute to pharmaceutical carrier to enter cell.
The above-mentioned nano-carrier containing dissaving polymer and phospholipid combines the advantage of polymer nano granules and nanometer liposome, has that medicine carrying capacity is high, good biocompatibility, long half time and a monodispersed feature, and is difficult for reunion, has stronger stability.Therefore, the above-mentioned nano-carrier containing dissaving polymer and phospholipid can be applied preparing on pharmaceutical carrier preparation.
In addition, present embodiment also provides a kind of preparation method of the nano-carrier containing dissaving polymer and phospholipid, as shown in Figure 2, specifically comprises the steps:
Step 210, hyper-branched polyester H40, caprolactone and stannous octoate are placed in to vacuum environment, and at 135 ℃ stirring reaction, after separation and purification, obtain polycaprolactone and graft on the intermediate product on hyper-branched polyester H40, and intermediate product is dissolved in second cyanogen, the second cyanogen solution of the intermediate product that preparation concentration is 1～5mg/mL, wherein, the terminal hydroxyl of hyper-branched polyester H40 and the mol ratio of caprolactone are 1:20～1:50, the quality of stannous octoate is 1 ‰ of caprolactone, and vacuum environment is processed through silanization in advance.
In the present embodiment, the step of separation and purification is specially:
Reacted mixture is dissolved in chloroform, then adds rapidly enough cold methanols to precipitate, filter, be fixed material; By solid matter drying at room temperature two days under vacuum condition, the polycaprolactone that obtains purification grafts on the intermediate product on hyper-branched polyester H40.
Because glass surface exists silanol groups (Si-OH), can produce absorption to samples such as protein, cause sample loss.Such group can carry out sealing treatment with silanization method, reacts, to reduce its impact on subsequent polymerisation reaction by silylating reagent dimethyldichlorosilane or hmds with carrier surface.
Step 220, the ratio that is 4:1 according to mass ratio by phospholipid and DSPE-PEG-COOH linear polymer is dissolved in ethanol water, and stirs at 65 ℃, obtains mixed solution, wherein, in ethanol water, the mass fraction of ethanol is 4%.
Step 230, the ratio that is 1:1.5～6 according to volume is dropwise added to the second cyanogen solution of intermediate product in mixed solution, and stirs at 65 ℃, obtains the nano-carrier containing dissaving polymer and phospholipid.
In the present embodiment, the particle diameter containing the nano-carrier of dissaving polymer and phospholipid is 20～40nm.Phospholipid is soybean lecithin.
The preparation method of the above-mentioned nano-carrier containing dissaving polymer and phospholipid, first utilizes hyper-branched polyester H40 as initiator, and caprolactone is raw material, and stannous octoate is catalyst, the synthetic H40-PCL that has multi-arm structure and have monodispersity; Then H40-PCL, phospholipid and DSPE-PEG-COOH are mixed, by a step nanometer precipitation self assembly, obtain the nano-carrier containing dissaving polymer and phospholipid.Above-mentioned preparation method is simple and easy to do, easy and simple to handle, easy to utilize.
Be below specific embodiment part:
First prepare two kinds of caprolactones and graft on the intermediate product on hyper-branched polyester H40, two kinds of intermediate products are respectively P1 and P2.
(1) prepare P1
200mg Boltorn H40,1000mg caprolactone and 1mg stannous octoate are joined in polymerization pipe, and in vacuum state lower seal polymerization pipe, then the polymerization pipe of good seal is placed in to 135 ℃ of oil bath stirring reactions 8 hours.Wherein, polymerization pipe is processed through silanization in advance, and is placed in advance the magnetic stirring rod of being with of a bone dry at polymerization pipe, before use, first gets rid of the air in polymerization pipe, and then with nitrogen purge polymerization pipe three times.After reaction finishes, reacted mixture is dissolved in chloroform, then adds fast enough cold methanols to precipitate, filter, be fixed material; By solid matter drying at room temperature two days under vacuum condition, obtain caprolactone and graft on the intermediate product P1 on hyper-branched polyester H40.
(2) prepare P2
400mg Boltorn H40,1500mg caprolactone and 1.5mg stannous octoate are joined in polymerization pipe, and in vacuum state lower seal polymerization pipe, then the polymerization pipe of good seal is placed in to 135 ℃ of oil bath stirring reactions 8 hours.Wherein, polymerization pipe is processed through silanization in advance, and is placed in advance the magnetic stirring rod of being with of a bone dry at polymerization pipe, before use, first gets rid of the air in polymerization pipe, and then with nitrogen purge polymerization pipe three times.After reaction finishes, reacted mixture is dissolved in chloroform, then adds fast enough cold methanols to precipitate, filter, be fixed material; By solid matter drying at room temperature two days under vacuum condition, obtain caprolactone and graft on the intermediate product P2 on hyper-branched polyester H40.
Embodiment 1
It is in 4% ethanol water that 0.06mg DSPE-PEG-COOH and 0.24mg soybean lecithin are added to 3mL mass fraction, and stirs at 65 ℃, obtains mixed solution; Then under the condition constantly stirring, in above-mentioned mixed solution, dropwise drip the second cyanogen solution that 1mL concentration is the P1 of 2mg/mL, and at 65 ℃, stir 2 hours, during allow solvent evaporates, obtain mean diameter and be the nano-carrier containing dissaving polymer and phospholipid of 22.9nm.
Fig. 3 is the grain-size graph of the nano-carrier containing dissaving polymer and phospholipid for preparing of the present embodiment.
Embodiment 2
It is in 4% ethanol water that 0.06mg DSPE-PEG-COOH and 0.24mg soybean lecithin are added to 1.5mL mass fraction, and stirs at 65 ℃, obtains mixed solution; Then under the condition constantly stirring, in above-mentioned mixed solution, dropwise drip the second cyanogen solution that 1mL concentration is the P1 of 2mg/mL, and at 65 ℃, stir 2 hours, during allow solvent evaporates, obtain particle size range at the nano-carrier containing dissaving polymer and phospholipid of 20～40nm.
Embodiment 3
It is in 4% ethanol water that 0.06mg DSPE-PEG-COOH and 0.24mg soybean lecithin are added to 6mL mass fraction, and stirs at 65 ℃, obtains mixed solution; Then under the condition constantly stirring, in above-mentioned mixed solution, dropwise drip the second cyanogen solution that 1mL concentration is the P1 of 2mg/mL, and at 65 ℃, stir 2 hours, during allow solvent evaporates, obtain particle size range at the nano-carrier containing dissaving polymer and phospholipid of 20～40nm.
Embodiment 4
It is in 4% ethanol water that 0.06mg DSPE-PEG-COOH and 0.24mg soybean lecithin are added to 3mL mass fraction, and stirs at 65 ℃, obtains mixed solution; Then under the condition constantly stirring, in above-mentioned mixed solution, dropwise drip the second cyanogen solution that 1mL concentration is the P2 of 1mg/mL, and at 65 ℃, stir 2 hours, during allow solvent evaporates, obtain particle size range at the nano-carrier containing dissaving polymer and phospholipid of 20～40nm.
Embodiment 5
It is in 4% ethanol water that 0.06mg DSPE-PEG-COOH and 0.24mg soybean lecithin are added to 3mL mass fraction, and stirs at 65 ℃, obtains mixed solution; Then under the condition constantly stirring, in above-mentioned mixed solution, dropwise drip the second cyanogen solution that 1mL concentration is the P2 of 5mg/mL, and at 65 ℃, stir 2 hours, during allow solvent evaporates, obtain particle size range at the nano-carrier containing dissaving polymer and phospholipid of 20～40nm.
The above embodiment has only expressed several embodiment of the present invention, and it describes comparatively concrete and detailed, but can not therefore be interpreted as the restriction to the scope of the claims of the present invention.It should be pointed out that for the person of ordinary skill of the art, without departing from the inventive concept of the premise, can also make some distortion and improvement, these all belong to protection scope of the present invention.Therefore, the protection domain of patent of the present invention should be as the criterion with claims.
Claims (9)
1. containing a nano-carrier for dissaving polymer and phospholipid, it is characterized in that, comprise hyper-branched polyester H40, polycaprolactone, phospholipid and DSPE-PEG-COOH linear polymer; Described polycaprolactone grafts on the upper kernel that forms of described hyper-branched polyester H40, described phospholipid is surrounded on described polycaprolactone outside and forms intermediate layer, the DSPE of described DSPE-PEG-COOH linear polymer is interspersed in described intermediate layer, and Polyethylene Glycol and the carboxyl of described DSPE-PEG-COOH linear polymer form skin;
The mass ratio that is grafted with hyper-branched polyester H40, phospholipid and the DSPE-PEG-COOH linear polymer of polycaprolactone is 1～5:0.24:0.06.
2. the nano-carrier containing dissaving polymer and phospholipid as claimed in claim 1, is characterized in that, described intermediate layer is single layer structure.
3. the nano-carrier containing dissaving polymer and phospholipid as claimed in claim 1, is characterized in that, described phospholipid is soybean lecithin.
4. the nano-carrier containing dissaving polymer and phospholipid as claimed in claim 1, is characterized in that, the particle diameter of the described nano-carrier containing dissaving polymer and phospholipid is 20～40nm.
5. a preparation method for the nano-carrier containing dissaving polymer and phospholipid as claimed in claim 1, is characterized in that, comprises the steps:
Hyper-branched polyester H40, caprolactone and stannous octoate are placed in to vacuum environment, and at 135 ℃ stirring reaction, after separation and purification, obtain polycaprolactone and graft on the intermediate product on hyper-branched polyester H40, and described intermediate product is dissolved in second cyanogen, the second cyanogen solution of the intermediate product that preparation concentration is 1～5mg/mL, wherein, the terminal hydroxyl of described hyper-branched polyester H40 and the mol ratio of described caprolactone are 1:20～1:50, the quality of described stannous octoate is 1 ‰ of described caprolactone, and described vacuum environment is processed through silanization in advance;
The ratio that is 4:1 according to mass ratio by phospholipid and DSPE-PEG-COOH linear polymer is dissolved in ethanol water, and stirs at 65 ℃, obtains mixed solution, and wherein in ethanol water, the mass fraction of ethanol is 4%;
The ratio that is 1:1.5～6 according to volume is dropwise added to the second cyanogen solution of described intermediate product in described mixed solution, and stirs at 65 ℃, obtains the described nano-carrier containing dissaving polymer and phospholipid.
6. the preparation method of the nano-carrier containing dissaving polymer and phospholipid as claimed in claim 5, is characterized in that, the step of described separation and purification is specially:
Reacted mixture is dissolved in chloroform, then adds rapidly enough cold methanols to precipitate, filter, be fixed material;
By described solid matter drying at room temperature two days under vacuum condition, the polycaprolactone that obtains purification grafts on the intermediate product on hyper-branched polyester H40.
7. the preparation method of the nano-carrier containing dissaving polymer and phospholipid as claimed in claim 5, is characterized in that, the particle diameter of the described nano-carrier containing dissaving polymer and phospholipid is 20～40nm.
8. the preparation method of the nano-carrier containing dissaving polymer and phospholipid as claimed in claim 5, is characterized in that, described phospholipid is soybean lecithin.
9. the nano-carrier containing dissaving polymer and phospholipid as described in any one in claim 1～4 is in the application of preparing on pharmaceutical carrier preparation.
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| EP3277743B1 (en) * | 2015-04-02 | 2022-12-28 | The Regents of The University of Michigan | Hyperbranched polymers and polyplexes and dna or rna delivery systems including the same |
| CN107156617A (en) * | 2017-05-03 | 2017-09-15 | 安徽倮倮米业有限公司 | A kind of sea sedge brown rice egg roll |
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| CN110182798B (en) * | 2019-05-31 | 2022-08-23 | 上海应用技术大学 | Nitrogen-rich porous carbon material and preparation method and application thereof |
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| 《Biodegradable and biocompatible multi-arm star amphiphilic block copolymer as a carrier for hydrophobic drug delivery》;Santosh Aryal et al.;《International Journal of Biological Macromolecules》;20090213;第44卷;全文 * |
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