CN103239729A - 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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- CN103239729A CN103239729A CN2013101528829A CN201310152882A CN103239729A CN 103239729 A CN103239729 A CN 103239729A CN 2013101528829 A CN2013101528829 A CN 2013101528829A CN 201310152882 A CN201310152882 A CN 201310152882A CN 103239729 A CN103239729 A CN 103239729A
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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 the nanosecond medical science field, particularly relate to a kind of nano-carrier that contains dissaving polymer and phospholipid and its preparation method and application.
Background technology
Traditional working out multiple nano-carrier that can carrying medicaments, wherein, is that two class main flow nano-carriers of representative can wrap up and transmit medicine, gene etc. with polymer nano granules and nanometer liposome, has become various countries scientist's research focus.
Be that two class main flow nano-carriers of representative have lot of advantages with polymer nano granules and nanometer liposome, solved a lot of difficult problems, as the solubility problem of insoluble drug, the problem of medicament slow release etc.But still there are problems such as relatively poor and half-life of biocompatibility is short in traditional polymer nanocomposite carrier or nanometer liposome carrier.
Summary of the invention
Based on this, be necessary to provide the nano-carrier that contains dissaving polymer and phospholipid that a kind of biocompatibility is better and the half-life is long.
A kind of nano-carrier that contains dissaving polymer and phospholipid comprises hyper-branched polyester H40, polycaprolactone, phospholipid and DSPE-Polyethylene Glycol-carboxyl linear polymer; Described polycaprolactone grafts on described hyper-branched polyester H40 and goes up the formation kernel, described phospholipid is surrounded on the described polycaprolactone outside and forms the intermediate layer, the DSPE of described DSPE-Polyethylene Glycol-carboxyl linear polymer is interspersed in the described intermediate layer, and Polyethylene Glycol and the carboxyl of described DSPE-Polyethylene Glycol-carboxyl linear polymer form skin.
Among embodiment, the mass ratio that is grafted with hyper-branched polyester H40, phospholipid and the DSPE-Polyethylene Glycol-carboxyl linear polymer of polycaprolactone is 1～5:0.24:0.06 therein.
Among embodiment, described intermediate layer is single layer structure therein.
Among embodiment, described phospholipid is soybean lecithin therein.
Among embodiment, the described particle diameter that contains the nano-carrier of 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 be initiator with hyper-branched polyester H40, at single hyper-branched polyester H40 surface grafting polycaprolactone (PCL), the H40-PCL that formation has the multi-arm structure and has monodispersity, thus be the high-efficient carrier that kernel is realized hydrophobic drug with hydrophobic H40-PCL, can control hydrophobic drug simultaneously and slowly discharge in vivo.And phospholipid is surrounded on formation midparent water layer on the polycaprolactone, makes the nano-carrier that contains dissaving polymer and phospholipid can avoid immune identification, thereby strengthens the half-life that it circulates in vivo.DSPE-Polyethylene Glycol-carboxyl (DSPE-PEG-COOH) linear polymer is interspersed in DSPE (DSPE) and forms skin in the phospholipid intermediate layer, Polyethylene Glycol shell and carboxyl are provided, thereby make the nano-carrier that contains dissaving polymer and phospholipid possess characteristics such as spatial stability, electrostatic stabilization and long circulation, carboxyl is easy to 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 excellent biological compatibility, and superior biodegradable can absorb or excrete by normal physiological pathway.The above-mentioned nano-carrier that contains dissaving polymer and phospholipid combines the advantage of polymer nano granules and nanometer liposome, has the characteristics of medicine carrying capacity height, good biocompatibility, long half time and monodispersity, and is difficult for reuniting, and has stronger stability.
The present invention also provides the above-mentioned nano-carrier that contains dissaving polymer and phospholipid to use at preparation pharmaceutical carrier preparation.
A kind of 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 vacuum environment, and at 135 ℃ of following stirring reactions, obtain polycaprolactone after the separation and purification and graft on intermediate product on the hyper-branched polyester H40, and described intermediate product is dissolved in the second cyanogen, preparation concentration is the second cyanogen solution of the intermediate product of 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 handled through silanization in advance;
Be that the ratio of 4:1 is dissolved in the ethanol water with phospholipid and DSPE-Polyethylene Glycol-carboxyl linear polymer according to mass ratio, and stir down in 65 ℃ that obtain mixed solution, wherein the mass fraction of ethanol is 4% in the ethanol water;
The ratio that according to volume is 1:1.5～6 dropwise is added to the second cyanogen solution of described intermediate product in the described mixed solution, and stirs down in 65 ℃, obtains the described nano-carrier that contains dissaving polymer and phospholipid.
Among embodiment, the step of described separation and purification is specially therein:
Post reaction mixture is dissolved in the chloroform, and the cold methanol that adds capacity then rapidly precipitates, and filters, and is fixed material;
With described solid matter drying at room temperature two days under vacuum condition, the polycaprolactone that obtains purification grafts on the intermediate product on the hyper-branched polyester H40.
Among embodiment, the described particle diameter that contains the nano-carrier of dissaving polymer and phospholipid is 20～40nm therein.
Among embodiment, described phospholipid is soybean lecithin therein.
The above-mentioned preparation method that contains the nano-carrier of dissaving polymer and phospholipid at first utilizes hyper-branched polyester H40 as initiator, and caprolactone is raw material, and stannous octoate is catalyst, the synthetic H40-PCL that has the multi-arm structure and have monodispersity; Then H40-PCL, phospholipid and DSPE-PEG-COOH are mixed, obtain containing the nano-carrier of dissaving polymer and phospholipid by step nanometer precipitation self assembly.Above-mentioned preparation method is simple and easy to do, and is easy and simple to handle, easy to utilize.
Description of drawings
Fig. 1 is the structural representation of the nano-carrier that contains dissaving polymer and phospholipid of an embodiment;
Fig. 2 is the flow chart of preparation method of the nano-carrier that contains dissaving polymer and phospholipid of an embodiment;
Fig. 3 is the grain-size graph of the nano-carrier that contains dissaving polymer and phospholipid of embodiment 1 preparation.
The specific embodiment
Below in conjunction with drawings and the specific embodiments nano-carrier of containing dissaving polymer and phospholipid and its preparation method and application is further detailed.
As shown in Figure 1, the nano-carrier that contains dissaving polymer and phospholipid of an embodiment comprises hyper-branched polyester H40, polycaprolactone, phospholipid and DSPE-Polyethylene Glycol-carboxyl linear polymer.
Wherein, polycaprolactone grafts on hyper-branched polyester H40 and goes up the formation kernel, phospholipid is surrounded on the polycaprolactone outside and forms the intermediate layer, and DSPE-Polyethylene Glycol-carboxyl linear polymer is interspersed in DSPE outer be used for providing Polyethylene Glycol shell and carboxyl are provided in the intermediate layer.
In the present embodiment, be grafted with the hyper-branched polyester H40(H40-PCL of polycaprolactone), the mass ratio of phospholipid and DSPE-Polyethylene Glycol-carboxyl linear polymer is 1～5:0.24:0.06.This mass-energy density guarantees that polycaprolactone reasonably grafts on the hyper-branched polyester H40, makes grafting density relatively suitable.Grafting density is too for a short time to be unfavorable for obtaining higher drug loading, and grafting density is not only wasted the particle diameter that raw material also can influence amphipathic supermolecule polymer too greatly.And DSPE-Polyethylene Glycol-carboxyl linear polymer is interspersed in formation skin in the phospholipid intermediate layer with DSPE, therefore, being surrounded on the consumption that forms the phospholipid in intermediate layer on the polycaprolactone can not be too big, the consumption of phospholipid is too big, will be unfavorable for that self assembly forms skin; Certainly, the consumption of phospholipid can not be too little, is unfavorable for forming the intermediate layer that strengthens the half-life that the nano-carrier that contains dissaving polymer and phospholipid circulates in vivo too for a short time.
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 be initiator with hyper-branched polyester H40, at single hyper-branched polyester H40 surface grafting polycaprolactone (PCL), the H40-PCL that formation has the multi-arm structure and has monodispersity, thus be the high-efficient carrier that kernel is realized hydrophobic drug with hydrophobic H40-PCL, can control hydrophobic drug simultaneously and slowly discharge in vivo.And contain the nano-carrier of dissaving polymer and phospholipid owing to have highly branched kernel, and can micelle solution assembling phenomenon not take place because carrier concn reduces, greatly promoted the stability of carrier.Wherein, polycaprolactone has excellent biological compatibility, and therefore superior biodegradable receives much concern, and obtains the approval of U.S. FDA.
And phospholipid has the biofilm structure of bilayer, have 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 characteristics such as surface-functionalized, and application prospect is very wide.In the present embodiment, phospholipid is surrounded on and forms the midparent water layer on the polycaprolactone, makes the nano-carrier that contains dissaving polymer and phospholipid can avoid immune identification, thereby strengthens the half-life that it circulates in vivo.The phospholipid intermediate layer is single layer structure, and phospholipid is soybean lecithin.
And DSPE-Polyethylene Glycol-carboxyl (DSPE-PEG-COOH) linear polymer is interspersed in the phospholipid intermediate layer with DSPE (DSPE) and form skin with Polyethylene Glycol and carboxyl, and being used for provides Polyethylene Glycol shell and carboxyl to nano-carrier.Thereby make the nano-carrier that contains dissaving polymer and phospholipid possess characteristics such as spatial stability, electrostatic stabilization and long circulation, carboxyl is easy to 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 excellent biological compatibility, and superior biodegradable can absorb or excrete by normal physiological pathway.
The nano-carrier that contains dissaving polymer and phospholipid has monodispersity and its adjustable grain control.In the present embodiment, the nano-carrier size that contains dissaving polymer and phospholipid is 20～40nm.
Can graft on the chain length of the polycaprolactone on the hyper-branched polyester H40 by the mole control recently of regulating hyper-branched polyester H40 and caprolactone, and then control contains the particle diameter of the nano-carrier of dissaving polymer and phospholipid.Wherein, smaller particle size can help pharmaceutical carrier to enter cell.
The above-mentioned nano-carrier that contains dissaving polymer and phospholipid combines the advantage of polymer nano granules and nanometer liposome, has medicine carrying capacity height, good biocompatibility, long half time and monodispersed characteristics, and is difficult for reuniting, and has stronger stability.Therefore, the above-mentioned nano-carrier that contains dissaving polymer and phospholipid can be used at preparation pharmaceutical carrier preparation.
In addition, present embodiment also provides a kind of preparation method that contains the nano-carrier of 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 vacuum environment, and at 135 ℃ of following stirring reactions, obtain polycaprolactone after the separation and purification and graft on intermediate product on the hyper-branched polyester H40, and intermediate product is dissolved in the second cyanogen, preparation concentration is the second cyanogen solution of the intermediate product of 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 handled through silanization in advance.
In the present embodiment, the step of separation and purification is specially:
Post reaction mixture is dissolved in the chloroform, and the cold methanol that adds capacity then rapidly precipitates, and filters, and is fixed material; With solid matter drying at room temperature two days under vacuum condition, the polycaprolactone that obtains purification grafts on the intermediate product on the hyper-branched polyester H40.
Because there is silanol groups (Si-OH) in glass surface, can produce absorption to samples such as protein, cause sample loss.Such group available silicon alkylation method carries out sealing treatment, reacts by silylating reagent dimethyldichlorosilane or hmds and carrier surface, to reduce it to the influence of subsequent polymerisation reaction.
Step 220, be that the ratio of 4:1 is dissolved in the ethanol water with phospholipid and DSPE-Polyethylene Glycol-carboxyl linear polymer according to mass ratio, and stir down in 65 ℃, obtain mixed solution, wherein, the mass fraction of ethanol is 4% in the ethanol water.
Step 230 is that the ratio of 1:1.5～6 dropwise is added to the second cyanogen solution of intermediate product in the mixed solution according to volume, and stirs down in 65 ℃, obtains containing the nano-carrier of dissaving polymer and phospholipid.
In the present embodiment, the particle diameter that contains the nano-carrier of dissaving polymer and phospholipid is 20～40nm.Phospholipid is soybean lecithin.
The above-mentioned preparation method that contains the nano-carrier of dissaving polymer and phospholipid at first utilizes hyper-branched polyester H40 as initiator, and caprolactone is raw material, and stannous octoate is catalyst, the synthetic H40-PCL that has the multi-arm structure and have monodispersity; Then H40-PCL, phospholipid and DSPE-PEG-COOH are mixed, obtain containing the nano-carrier of dissaving polymer and phospholipid by step nanometer precipitation self assembly.Above-mentioned preparation method is simple and easy to do, and is easy and simple to handle, easy to utilize.
Below be the specific embodiment part:
At first prepare two kinds of caprolactones and graft on intermediate product on the hyper-branched polyester H40, two kinds of intermediate products are respectively P1 and P2.
(1) preparation P1
200mg Boltorn H40,1000mg caprolactone and 1mg stannous octoate are joined in the polymerization pipe, and in vacuum state lower seal polymerization pipe, the polymerization pipe with good seal placed 135 ℃ of oil bath stirring reactions 8 hours then.Wherein, polymerization pipe is handled through silanization in advance, and is placed on the stirring rod that has magnetic of a bone dry in advance at polymerization pipe, before the use, gets rid of the air in the polymerization pipe earlier, and then with nitrogen purge polymerization pipe three times.Reaction is dissolved in post reaction mixture in the chloroform after finishing, and the cold methanol that adds capacity then fast precipitates, and filters, and is fixed material; With solid matter drying at room temperature two days under vacuum condition, obtain caprolactone and graft on intermediate product P1 on the hyper-branched polyester H40.
(2) preparation P2
400mg Boltorn H40,1500mg caprolactone and 1.5mg stannous octoate are joined in the polymerization pipe, and in vacuum state lower seal polymerization pipe, the polymerization pipe with good seal placed 135 ℃ of oil bath stirring reactions 8 hours then.Wherein, polymerization pipe is handled through silanization in advance, and is placed on the stirring rod that has magnetic of a bone dry in advance at polymerization pipe, before the use, gets rid of the air in the polymerization pipe earlier, and then with nitrogen purge polymerization pipe three times.Reaction is dissolved in post reaction mixture in the chloroform after finishing, and the cold methanol that adds capacity then fast precipitates, and filters, and is fixed material; With solid matter drying at room temperature two days under vacuum condition, obtain caprolactone and graft on intermediate product P2 on the hyper-branched polyester H40.
It is in 4% the ethanol water that 0.06mg DSPE-PEG-COOH and 0.24mg soybean lecithin are added to the 3mL mass fraction, and stirs down in 65 ℃, obtains mixed solution; Then under continuous stirring condition, in above-mentioned mixed solution, dropwise drip the second cyanogen solution that 1mL concentration is the P1 of 2mg/mL, and stirred 2 hours down in 65 ℃, during allow solvent evaporates, namely getting mean diameter is the nano-carrier that contains dissaving polymer and phospholipid of 22.9nm.
The grain-size graph of the nano-carrier that contains dissaving polymer and phospholipid that Fig. 3 prepares for present embodiment.
Embodiment 2
It is in 4% the ethanol water that 0.06mg DSPE-PEG-COOH and 0.24mg soybean lecithin are added to the 1.5mL mass fraction, and stirs down in 65 ℃, obtains mixed solution; Then under continuous stirring condition, in above-mentioned mixed solution, dropwise drip the second cyanogen solution that 1mL concentration is the P1 of 2mg/mL, and stirred 2 hours down in 65 ℃, during allow solvent evaporates, namely get particle size range at the nano-carrier that contains dissaving polymer and phospholipid of 20～40nm.
Embodiment 3
It is in 4% the ethanol water that 0.06mg DSPE-PEG-COOH and 0.24mg soybean lecithin are added to the 6mL mass fraction, and stirs down in 65 ℃, obtains mixed solution; Then under continuous stirring condition, in above-mentioned mixed solution, dropwise drip the second cyanogen solution that 1mL concentration is the P1 of 2mg/mL, and stirred 2 hours down in 65 ℃, during allow solvent evaporates, namely get particle size range at the nano-carrier that contains dissaving polymer and phospholipid of 20～40nm.
Embodiment 4
It is in 4% the ethanol water that 0.06mg DSPE-PEG-COOH and 0.24mg soybean lecithin are added to the 3mL mass fraction, and stirs down in 65 ℃, obtains mixed solution; Then under continuous stirring condition, in above-mentioned mixed solution, dropwise drip the second cyanogen solution that 1mL concentration is the P2 of 1mg/mL, and stirred 2 hours down in 65 ℃, during allow solvent evaporates, namely get particle size range at the nano-carrier that contains dissaving polymer and phospholipid of 20～40nm.
Embodiment 5
It is in 4% the ethanol water that 0.06mg DSPE-PEG-COOH and 0.24mg soybean lecithin are added to the 3mL mass fraction, and stirs down in 65 ℃, obtains mixed solution; Then under continuous stirring condition, in above-mentioned mixed solution, dropwise drip the second cyanogen solution that 1mL concentration is the P2 of 5mg/mL, and stirred 2 hours down in 65 ℃, during allow solvent evaporates, namely get particle size range at the nano-carrier that contains 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 claim of the present invention.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 (10)
1. a nano-carrier that contains dissaving polymer and phospholipid is characterized in that, comprises hyper-branched polyester H40, polycaprolactone, phospholipid and DSPE-Polyethylene Glycol-carboxyl linear polymer; Described polycaprolactone grafts on described hyper-branched polyester H40 and goes up the formation kernel, described phospholipid is surrounded on the described polycaprolactone outside and forms the intermediate layer, the DSPE of described DSPE-Polyethylene Glycol-carboxyl linear polymer is interspersed in the described intermediate layer, and Polyethylene Glycol and the carboxyl of described DSPE-Polyethylene Glycol-carboxyl linear polymer form skin.
2. the nano-carrier that contains dissaving polymer and phospholipid as claimed in claim 1, it is characterized in that the mass ratio that is grafted with hyper-branched polyester H40, phospholipid and the DSPE-Polyethylene Glycol-carboxyl linear polymer of polycaprolactone is 1～5:0.24:0.06.
3. the nano-carrier that contains dissaving polymer and phospholipid as claimed in claim 1 is characterized in that, described intermediate layer is single layer structure.
4. the nano-carrier that contains dissaving polymer and phospholipid as claimed in claim 1 is characterized in that, described phospholipid is soybean lecithin.
5. the nano-carrier that contains dissaving polymer and phospholipid as claimed in claim 1 is characterized in that, the described particle diameter that contains the nano-carrier of dissaving polymer and phospholipid is 20～40nm.
6. a preparation method that contains the nano-carrier of dissaving polymer and phospholipid is characterized in that, comprises the steps:
Hyper-branched polyester H40, caprolactone and stannous octoate are placed vacuum environment, and at 135 ℃ of following stirring reactions, obtain polycaprolactone after the separation and purification and graft on intermediate product on the hyper-branched polyester H40, and described intermediate product is dissolved in the second cyanogen, preparation concentration is the second cyanogen solution of the intermediate product of 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 handled through silanization in advance;
Be that the ratio of 4:1 is dissolved in the ethanol water with phospholipid and DSPE-Polyethylene Glycol-carboxyl linear polymer according to mass ratio, and stir down in 65 ℃ that obtain mixed solution, wherein the mass fraction of ethanol is 4% in the ethanol water;
The ratio that according to volume is 1:1.5～6 dropwise is added to the second cyanogen solution of described intermediate product in the described mixed solution, and stirs down in 65 ℃, obtains the described nano-carrier that contains dissaving polymer and phospholipid.
7. the preparation method that contains the nano-carrier of dissaving polymer and phospholipid as claimed in claim 6 is characterized in that, the step of described separation and purification is specially:
Post reaction mixture is dissolved in the chloroform, and the cold methanol that adds capacity then rapidly precipitates, and filters, and is fixed material;
With described solid matter drying at room temperature two days under vacuum condition, the polycaprolactone that obtains purification grafts on the intermediate product on the hyper-branched polyester H40.
8. the preparation method that contains the nano-carrier of dissaving polymer and phospholipid as claimed in claim 6 is characterized in that, the described particle diameter that contains the nano-carrier of dissaving polymer and phospholipid is 20～40nm.
9. the preparation method that contains the nano-carrier of dissaving polymer and phospholipid as claimed in claim 6 is characterized in that, described phospholipid is soybean lecithin.
10. as each described nano-carrier application on preparation pharmaceutical carrier preparation that contains dissaving polymer and phospholipid in the claim 1～5.
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN104587467A (en) * | 2014-12-26 | 2015-05-06 | 深圳先进技术研究院 | ICG-encapsulated polymer-phospholipid nano-particles and preparation method thereof |
| 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 |
| CN107660220A (en) * | 2015-04-02 | 2018-02-02 | 密歇根大学董事会 | Dissaving polymer and polycomplex and DNA or RNA delivery system comprising it |
| CN109116625A (en) * | 2018-09-03 | 2019-01-01 | 深圳市华星光电技术有限公司 | Backlight module and its optical diaphragm |
| CN110182798A (en) * | 2019-05-31 | 2019-08-30 | 上海应用技术大学 | A kind of Nitrogen-rich porous carbon material and its preparation method and application |
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| CN102276817A (en) * | 2011-04-22 | 2011-12-14 | 武汉大学 | Arborescent graft polycaprolactone |
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Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104587467A (en) * | 2014-12-26 | 2015-05-06 | 深圳先进技术研究院 | ICG-encapsulated polymer-phospholipid nano-particles and preparation method thereof |
| CN104587467B (en) * | 2014-12-26 | 2018-02-27 | 深圳先进技术研究院 | ICG-encapsulated polymer-phospholipid nano-particles and preparation method thereof |
| CN107660220A (en) * | 2015-04-02 | 2018-02-02 | 密歇根大学董事会 | Dissaving polymer and polycomplex and DNA or RNA delivery system comprising it |
| 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 |
| CN109116625A (en) * | 2018-09-03 | 2019-01-01 | 深圳市华星光电技术有限公司 | Backlight module and its optical diaphragm |
| CN110182798A (en) * | 2019-05-31 | 2019-08-30 | 上海应用技术大学 | A kind of Nitrogen-rich porous carbon material and its preparation method and application |
| 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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| CN103239729B (en) | 2014-10-29 |
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