CN104740646A - Self-crosslinked nano-capsule - Google Patents
Self-crosslinked nano-capsule Download PDFInfo
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- CN104740646A CN104740646A CN201510147902.2A CN201510147902A CN104740646A CN 104740646 A CN104740646 A CN 104740646A CN 201510147902 A CN201510147902 A CN 201510147902A CN 104740646 A CN104740646 A CN 104740646A
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- 239000002088 nanocapsule Substances 0.000 title claims abstract description 67
- 229920000642 polymer Polymers 0.000 claims abstract description 48
- 239000002202 Polyethylene glycol Substances 0.000 claims abstract description 17
- 229920001223 polyethylene glycol Polymers 0.000 claims abstract description 17
- 238000000034 method Methods 0.000 claims abstract description 9
- 102000004169 proteins and genes Human genes 0.000 claims description 28
- 108090000623 proteins and genes Proteins 0.000 claims description 28
- 238000004132 cross linking Methods 0.000 claims description 12
- 230000000694 effects Effects 0.000 claims description 10
- 230000006320 pegylation Effects 0.000 claims description 10
- 229920000724 poly(L-arginine) polymer Polymers 0.000 claims description 10
- 108010011110 polyarginine Proteins 0.000 claims description 10
- 229920001661 Chitosan Polymers 0.000 claims description 7
- 229920002518 Polyallylamine hydrochloride Polymers 0.000 claims description 7
- 108010039918 Polylysine Proteins 0.000 claims description 7
- 238000006243 chemical reaction Methods 0.000 claims description 7
- 230000003993 interaction Effects 0.000 claims description 7
- 230000016507 interphase Effects 0.000 claims description 7
- 229920000656 polylysine Polymers 0.000 claims description 7
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 6
- 239000003153 chemical reaction reagent Substances 0.000 claims description 6
- 238000004140 cleaning Methods 0.000 claims description 6
- 230000004048 modification Effects 0.000 claims description 6
- 238000012986 modification Methods 0.000 claims description 6
- 108020004707 nucleic acids Proteins 0.000 claims description 6
- 102000039446 nucleic acids Human genes 0.000 claims description 6
- 150000007523 nucleic acids Chemical class 0.000 claims description 6
- 229910052760 oxygen Inorganic materials 0.000 claims description 6
- 239000001301 oxygen Substances 0.000 claims description 6
- 108090000790 Enzymes Proteins 0.000 claims description 5
- 102000004190 Enzymes Human genes 0.000 claims description 5
- 230000015572 biosynthetic process Effects 0.000 claims description 4
- -1 succinimide ester Chemical class 0.000 claims description 3
- KZNICNPSHKQLFF-UHFFFAOYSA-N dihydromaleimide Natural products O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 claims description 2
- 239000000463 material Substances 0.000 claims description 2
- 229960002317 succinimide Drugs 0.000 claims description 2
- 230000008569 process Effects 0.000 abstract description 4
- 239000010410 layer Substances 0.000 abstract 5
- 239000012792 core layer Substances 0.000 abstract 4
- 239000011258 core-shell material Substances 0.000 abstract 1
- 239000003814 drug Substances 0.000 description 10
- 230000005540 biological transmission Effects 0.000 description 5
- 238000001727 in vivo Methods 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- RFVNOJDQRGSOEL-UHFFFAOYSA-N 2-hydroxyethyl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCCO RFVNOJDQRGSOEL-UHFFFAOYSA-N 0.000 description 4
- 108010025188 Alcohol oxidase Proteins 0.000 description 4
- 108010015776 Glucose oxidase Proteins 0.000 description 4
- 239000004366 Glucose oxidase Substances 0.000 description 4
- 239000002775 capsule Substances 0.000 description 4
- 229940079593 drug Drugs 0.000 description 4
- 238000002296 dynamic light scattering Methods 0.000 description 4
- 229940088598 enzyme Drugs 0.000 description 4
- 229940116332 glucose oxidase Drugs 0.000 description 4
- 235000019420 glucose oxidase Nutrition 0.000 description 4
- 229940100242 glycol stearate Drugs 0.000 description 4
- 108091003079 Bovine Serum Albumin Proteins 0.000 description 3
- 229940098773 bovine serum albumin Drugs 0.000 description 3
- 230000001804 emulsifying effect Effects 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 238000011160 research Methods 0.000 description 3
- IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 description 2
- 108010051109 Cell-Penetrating Peptides Proteins 0.000 description 2
- 102000020313 Cell-Penetrating Peptides Human genes 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 230000004071 biological effect Effects 0.000 description 2
- 239000003995 emulsifying agent Substances 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 229940067606 lecithin Drugs 0.000 description 2
- 239000000787 lecithin Substances 0.000 description 2
- 235000010445 lecithin Nutrition 0.000 description 2
- 239000002502 liposome Substances 0.000 description 2
- 210000003712 lysosome Anatomy 0.000 description 2
- 230000001868 lysosomic effect Effects 0.000 description 2
- 239000003094 microcapsule Substances 0.000 description 2
- 239000002195 soluble material Substances 0.000 description 2
- 238000013097 stability assessment Methods 0.000 description 2
- 206010068516 Encapsulation reaction Diseases 0.000 description 1
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 1
- 108091005804 Peptidases Proteins 0.000 description 1
- 239000004365 Protease Substances 0.000 description 1
- 102100037486 Reverse transcriptase/ribonuclease H Human genes 0.000 description 1
- 102000004142 Trypsin Human genes 0.000 description 1
- 108090000631 Trypsin Proteins 0.000 description 1
- 108010092464 Urate Oxidase Proteins 0.000 description 1
- 125000000539 amino acid group Chemical group 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 238000003745 diagnosis Methods 0.000 description 1
- 230000005847 immunogenicity Effects 0.000 description 1
- 230000003834 intracellular effect Effects 0.000 description 1
- 229920002521 macromolecule Polymers 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 230000004952 protein activity Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000004083 survival effect Effects 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000008685 targeting Effects 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 239000012588 trypsin Substances 0.000 description 1
- 229940005267 urate oxidase Drugs 0.000 description 1
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- Cosmetics (AREA)
- Medicinal Preparation (AREA)
Abstract
The invention discloses a self-crosslinked nano-capsule and belongs to the field of biomedicines. The self-crosslinked nano-capsule disclosed by the invention comprises a core layer and a shell layer, wherein the shell layer is a macromolecular polymer modified by sulfydryl and polyethylene glycol with positive charges, the core layer is a loading molecule with negative charges, the shell layer and the core layer are automatically crosslinked by virtue of the action of the positive and negative charges, the shell layer wraps the core layer to form the nano-capsule, and disulfide bonds are formed among sulfydryl on the shell layer to fasten the nano-capsule. The self-crosslinked nano-capsule disclosed by the invention is simple in synthetic step, the whole process just takes about 5 minutes, and the formed nano-capsule is uniform in grain size. As a result of the special core-shell structure, the self-crosslinked nano-capsule in an internal environment is high in stability and long in circulating time.
Description
Technical field
The present invention relates to degradable and the target administration Nano capsule field of medicine field, be specifically related to have the Nano capsule of self-crosslinking of core, shell structure.
Background technology
As everyone knows, along with the development of modern biology, the latent effect of increasing protein in biological diagnosis treatment is slowly found.Compare with traditional medicine, pharmaceutical grade protein has high specific and high efficiency, but simultaneously they are as equally very responsive in temperature, pH etc. for the environment in the external world, extraneous factor very easily affects amino acid residue and secondary protein structure thus causes the change of protein conformation and the loss of activity or forfeiture.Protease simultaneously in body is also grave danger of these pharmaceutical grade proteins.
In order to overcome the problems referred to above, many protein carriers are devised one after another, wherein common are liposome and high molecular polymer.But, liposome destroys as the lysosome identification in the easy body of protein carrier, high molecular polymer Nano capsule is easily affected as its stability in vivo during carrier, particularly under the existence of various enzyme, very easily lose protein active, meanwhile, the building-up process of macromolecule carrier also very time and effort consuming.
The research of Nano medication is a very vital new direction in drug research, and medicine is loaded in Nano medication mainly through methods such as encapsulating and absorption.Research Nano medication to have carried out for many years abroad, it has small particle size range and can enter easily in the various histoorgans of human body and carry out Co ntrolled release, reduces survival dose, alleviates or eliminate toxic and side effects, improve medicine stability, the advantages such as the targeting absorption of profit and medicine.Present Nano capsule preparation method is generally nucleocapsid double-decker, stratum nucleare is the medicine of required load, and shell is the high molecular polymer etc. of parcel, and stratum nucleare and shell form the structure of nucleocapsid by the effect such as organic solvent, emulsifying agent emulsifying, prepare consuming time, complicated operation.In stability, generally all use CCP (cell penetrating peptide) now and be linked on high molecular polymer, really improve polymer in intracellular transmission efficiency, but its stability aspect existing problems.The microcapsule of the patent No. a kind of year oil soluble material that be the disclosure of the invention of CN101953817A, take polymer as shell, oil soluble material is core, and hydrophilic and oleophilic substance emulsifying on two-phase interface forms microcapsule structure, this invention reaction condition is strict, makes consumes resources larger.The patent No. is that the patent of invention of CN102802616A discloses a kind of poly arginine Nano capsule, this invention is shell with positively charged poly arginine, with electronegative lecithin for core, the coated process of nucleocapsid structure is completed by the effect of positive and negative charge, this invention also applies emulsifying agent to act on hydrophilic poly arginine and the lecithin of oleophylic simultaneously, although the simplicity that this invention has used positive and negative charge to combine, but still apply emulsifying to make up the not strong feature of its binding ability, can find and a kind ofly self strengthen this positive and negative charge binding ability and make its method being unlikely to scatter very necessary.
Summary of the invention
The object of the invention is for the deficiencies in the prior art, a kind of Nano capsule of self-crosslinking is provided.
Object of the present invention realizes by following technical scheme:
A kind of Nano capsule of self-crosslinking, comprise stratum nucleare and shell structurre, shell parcel stratum nucleare forms Nano capsule, it is characterized in that described shell is sulfydryl and polyethyleneglycol modified positively charged high molecular polymer, stratum nucleare is electronegative supporting molecular, shell and stratum nucleare are by the automatically cross-linked formation Nano capsule of positive and negative charge effect, and the sulfydryl on shell forms the fastening Nano capsule of disulfide bond.
Described high molecular polymer is selected from the polymer such as polyallylamine hydrochlorides, chitosan, polylysine, poly arginine.
Described high molecular polymer is rich in positive charge group, positive charge wherein come from amino, guanidine radicals and and the similar positively charged group of structural property; Described sulfydryl and Polyethylene Glycol are connected on polymer by positive charge group on modified high molecular polymer.
Described supporting molecular comprises protein, nucleic acid and other elements with negative charge, and described protein comprises the protein matter such as enzyme, antibody, and described nucleic acid comprises the nucleic acid materials such as DNA, RNA.
Described Nano capsule stratum nucleare diameter is 10-20nm, and described shell thickness is 3-5nm.
Prepare a method for the Nano capsule of self-crosslinking, comprise the following steps:
1) being rich in the high molecular polymer of positive charge group and succinimide ester modifies after Polyethylene Glycol mixes a period of time with certain proportion, and cleaning is separated, and can obtain part positive charge group by the high molecular polymer of Pegylation;
2) in above-mentioned polymer, add a certain amount of Te Laote reagent again, after reaction a period of time, the high molecular polymer of sulfydryl, Polyethylene Glycol and positive charge base group modification must be contained;
3) above-mentioned high molecular polymer and electronegative load albumen are mixed in certain proportion, positive and negative charge attracts the Nano capsule forming polymer wrapped load albumen, pass into oxygen wherein again, after a period of time, the interphase interaction of polymer surfaces sulfydryl forms disulfide bond, fasten Nano capsule, be formed in the Nano capsule that I is cross-linked.
Beneficial effect
Patent of the present invention forms the Nano capsule of shell parcel stratum nucleare by attracting each other of positive and negative charge between the supporting molecular of stratum nucleare negative charge and the high molecular polymer of shell positive charge, then makes the sulfydryl interphase interaction on polymer form the fastening Nano capsule of disulfide bond by Oxidation.Positive and negative charge attracts and the formation of disulfide bond makes synthesis step of the present invention simple, whole process only about 5 minutes consuming time; The protein nano capsule grain diameter of self-crosslinking is homogeneous, and because protein is not modified, its activity is protected, the high molecular polymer shell protected protein matter outside stratum nucleare is not by the effect of enzyme, protect its too early release in vivo simultaneously, extend its circulation time in vivo; The polyethylene group modified can strengthen the immunogenicity that Nano capsule stability in vivo and dissolubility can also control Nano capsule simultaneously, avoids the disorganization such as the lysosome in body.
Accompanying drawing explanation
Fig. 1 technology path method figure of the present invention.
Fig. 2 stability assessment figure of the present invention.
Detailed description of the invention
The preparation of embodiment 1 polyallylamine hydrochloride and glucoseoxidase Nano capsule
1) be rich in after the polyallylamine hydrochloride of positive charge group and Polyethylene Glycol stearate mix a period of time with the ratio of mol ratio 1: 6, cleaning is separated, and can obtain part positive charge group by the polyallylamine hydrochloride of Pegylation;
2) in above-mentioned Pegylation polyallylamine hydrochloride, add Te Laote reagent with the mol ratio of 1: 5 again, after reaction a period of time, the polyallylamine hydrochloride of sulfydryl, Polyethylene Glycol and positive charge base group modification must be contained;
3) above-mentioned high molecular polymer and electronegative glucoseoxidase are mixed in certain proportion, positive and negative charge attracts the Nano capsule forming polymer wrapped glucoseoxidase, pass into oxygen wherein again, after a period of time, the interphase interaction of polymer surfaces sulfydryl forms disulfide bond, fasten Nano capsule, form the Nano capsule of self-crosslinking.
Used by the Nano capsule of above-mentioned gained transmission electron microscope (TEM) and dynamic light scattering (DSL) to measure respectively, it is very homogeneous that result shows above-mentioned capsule grain diameter, and the diameter of stratum nucleare is between 10-18nm, and shell thickness is 4nm.
The preparation of embodiment 2 chitosan and enhanced green fluorescence protein Nano capsule
1) chitosan and Polyethylene Glycol stearate that are rich in positive charge group are mixed with the ratio of mol ratio 1: 6, after a period of time, cleaning is separated, and can obtain part positive charge group by the chitosan of Pegylation;
2) in above-mentioned Pegylation chitosan, add Te Laote reagent with the mol ratio of 1: 5 again, after reaction a period of time, the chitosan of sulfydryl, Polyethylene Glycol and positive charge base group modification must be contained;
3) above-mentioned high molecular polymer and electronegative enhanced green fluorescence protein are mixed in certain proportion, positive and negative charge attracts the Nano capsule forming polymer wrapped enhanced green fluorescence protein, pass into oxygen wherein again, after a period of time, the interphase interaction of polymer surfaces sulfydryl forms disulfide bond, fasten Nano capsule, form the Nano capsule of self-crosslinking.
Used by the Nano capsule of above-mentioned gained transmission electron microscope (TEM) and dynamic light scattering (DSL) to measure respectively, it is very homogeneous that result shows above-mentioned capsule grain diameter, and the diameter of stratum nucleare is between 10-20nm, and shell thickness is 5nm.
The preparation of embodiment 3 polylysine and bovine serum albumin Nano capsule
1) be rich in after the polylysine of positive charge group and Polyethylene Glycol stearate mix a period of time with the ratio of mol ratio 1: 6, cleaning is separated, and can obtain part positive charge group by the polylysine of Pegylation;
2) in above-mentioned Pegylation polylysine, add Te Laote reagent with the mol ratio of 1: 5 again, after reaction a period of time, the polylysine of sulfydryl, Polyethylene Glycol and positive charge base group modification must be contained;
3) above-mentioned high molecular polymer and electronegative bovine serum albumin are mixed in certain proportion, positive and negative charge attracts the Nano capsule forming polymer wrapped bovine serum albumin, pass into oxygen wherein again, after a period of time, the interphase interaction of polymer surfaces sulfydryl forms disulfide bond, fasten Nano capsule, form the Nano capsule of self-crosslinking.
Used by the Nano capsule of above-mentioned gained transmission electron microscope (TEM) and dynamic light scattering (DSL) to measure respectively, it is very homogeneous that result shows above-mentioned capsule grain diameter, and the diameter of stratum nucleare is between 12-19nm, and shell thickness is 3nm.
The preparation of embodiment 4 poly arginine and alcohol oxidase Nano capsule
1) be rich in after the poly arginine of positive charge group and Polyethylene Glycol stearate mix a period of time with the ratio of mol ratio 1: 6, cleaning is separated, and can obtain part positive charge group by the poly arginine of Pegylation;
2) in above-mentioned Pegylation poly arginine, add Te Laote reagent with the mol ratio of 1: 5 again, after reaction a period of time, the poly arginine of sulfydryl, Polyethylene Glycol and positive charge base group modification must be contained;
3) above-mentioned high molecular polymer and electronegative alcohol oxidase are mixed in certain proportion, positive and negative charge attracts the Nano capsule forming polymer wrapped alcohol oxidase, pass into oxygen wherein again, after a period of time, the interphase interaction of polymer surfaces sulfydryl forms disulfide bond, fasten Nano capsule, form the Nano capsule of self-crosslinking.
Used by the Nano capsule of above-mentioned gained transmission electron microscope (TEM) and dynamic light scattering (DSL) to measure respectively, it is very homogeneous that result shows above-mentioned capsule grain diameter, and the diameter of stratum nucleare is between 11-18nm, and shell thickness is 5nm.
Embodiment 5 Nano capsule stability assessment
By several Nano capsule simulated in vivo environment obtained above through circulation after a while, then its nucleocapsid structure is untied, each protein active now and the original protein activity before not generating Nano capsule are compared test, result as shown in Figure 2, as can be seen from figure bis-(a), glucoseoxidase, Radix Cochleariae officinalis hydroperoxide enzyme, enhanced green fluorescence protein still can reach more than 95% of former protein active through encapsulation reaction unpacking its biological activity of being honored as a queen, urate oxidase and its activity of alcohol oxidase also can reach more than 80% of original protein, as can be seen from figure bis-(b), same a kind of protein, under trypsin acting, the Nano capsule having polymer wrapped can keep its protein active not lose in long-time, under similarity condition, do not have the protein wrapped up can lose its biological activity very soon, Nano capsule is very effective for the protection of protein active as can be seen here.
Claims (6)
1. the Nano capsule of a self-crosslinking, comprise stratum nucleare and shell structurre, shell parcel stratum nucleare forms Nano capsule, it is characterized in that shell is sulfydryl and polyethyleneglycol modified positively charged high molecular polymer, stratum nucleare is electronegative supporting molecular, shell and stratum nucleare are by the automatically cross-linked formation Nano capsule of positive and negative charge effect, and the sulfydryl on shell forms the fastening Nano capsule of disulfide bond.
2. Nano capsule according to claim 1, is characterized in that described high molecular polymer comprises polyallylamine hydrochlorides, chitosan, polylysine, poly arginine etc.
3. Nano capsule according to claim 1, it is characterized in that the positive charge in described high molecular polymer comes from the similar positively charged group of amino, guanidine radicals and structural property, described sulfydryl and Polyethylene Glycol are connected on polymer by the positive charge group on part modified high molecular polymer.
4. Nano capsule according to claim 1, it is characterized in that described supporting molecular is protein, other elements with negative charge of nucleic acid, described protein comprises the protein matter such as enzyme, antibody, and described nucleic acid comprises the nucleic acid materials such as DNA, RNA.
5. Nano capsule according to claim 1, it is characterized in that described Nano capsule stratum nucleare diameter is 10-20nm, described shell thickness is 3-5nm.
6. prepare a method for the Nano capsule of self-crosslinking, comprise the following steps:
1) being rich in the high molecular polymer of positive charge group and succinimide ester modifies after Polyethylene Glycol mixes a period of time with certain proportion, and cleaning is separated, and can obtain part positive charge group by the high molecular polymer of Pegylation;
2) in above-mentioned polymer, add a certain amount of Te Laote reagent again, after reaction a period of time, the high molecular polymer of sulfydryl, Polyethylene Glycol and positive charge base group modification must be contained;
3) above-mentioned high molecular polymer and electronegative load albumen are mixed in certain proportion, positive and negative charge attracts the Nano capsule forming polymer wrapped load albumen, pass into oxygen wherein again, after a period of time, the interphase interaction of polymer surfaces sulfydryl forms disulfide bond, fasten Nano capsule, be formed in the Nano capsule that I is cross-linked.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN108424904A (en) * | 2017-12-12 | 2018-08-21 | 南京迪格诺斯生物技术有限公司 | A method of improving library construction reagent stability |
| WO2020172972A1 (en) * | 2019-02-28 | 2020-09-03 | 中国科学院大连化学物理研究所 | Glucose oxidase-based nanocapsule sensor and preparation and application thereof |
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| CN101955708A (en) * | 2010-09-01 | 2011-01-26 | 广东德美精细化工股份有限公司 | Method for preparing nano microcapsule water-based color paste |
| US7879313B1 (en) * | 2005-01-04 | 2011-02-01 | Gp Medical, Inc. | Nanoparticles for protein drug delivery |
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2015
- 2015-03-27 CN CN201510147902.2A patent/CN104740646A/en active Pending
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| Publication number | Priority date | Publication date | Assignee | Title |
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| US7879313B1 (en) * | 2005-01-04 | 2011-02-01 | Gp Medical, Inc. | Nanoparticles for protein drug delivery |
| CN101955708A (en) * | 2010-09-01 | 2011-01-26 | 广东德美精细化工股份有限公司 | Method for preparing nano microcapsule water-based color paste |
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108424904A (en) * | 2017-12-12 | 2018-08-21 | 南京迪格诺斯生物技术有限公司 | A method of improving library construction reagent stability |
| WO2020172972A1 (en) * | 2019-02-28 | 2020-09-03 | 中国科学院大连化学物理研究所 | Glucose oxidase-based nanocapsule sensor and preparation and application thereof |
| CN111624244A (en) * | 2019-02-28 | 2020-09-04 | 中国科学院大连化学物理研究所 | Glucose oxidase nano capsule sensor and preparation and application thereof |
| CN111624244B (en) * | 2019-02-28 | 2021-12-21 | 中国科学院大连化学物理研究所 | A kind of glucose oxidase nanocapsule sensor and its preparation and application |
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