CN101139443A - Method for preparing hydroxypropyl chitose nano particle - Google Patents
Method for preparing hydroxypropyl chitose nano particle Download PDFInfo
- Publication number
- CN101139443A CN101139443A CNA2007100535054A CN200710053505A CN101139443A CN 101139443 A CN101139443 A CN 101139443A CN A2007100535054 A CNA2007100535054 A CN A2007100535054A CN 200710053505 A CN200710053505 A CN 200710053505A CN 101139443 A CN101139443 A CN 101139443A
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- Prior art keywords
- hydroxypropyl chitosan
- hydroxypropyl
- chitosan
- solution
- preparation
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- 239000002105 nanoparticle Substances 0.000 title claims description 12
- -1 hydroxypropyl chitose Chemical compound 0.000 title claims description 5
- 238000000034 method Methods 0.000 title abstract description 7
- LKAPTZKZHMOIRE-UHFFFAOYSA-N chitose Natural products OCC1OC(C=O)C(O)C1O LKAPTZKZHMOIRE-UHFFFAOYSA-N 0.000 title 1
- 229940054190 hydroxypropyl chitosan Drugs 0.000 claims abstract description 22
- 238000002360 preparation method Methods 0.000 claims abstract description 9
- 229910052708 sodium Inorganic materials 0.000 claims abstract description 6
- 239000011734 sodium Substances 0.000 claims abstract description 6
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims abstract description 5
- 230000010494 opalescence Effects 0.000 claims abstract description 5
- 235000019830 sodium polyphosphate Nutrition 0.000 claims abstract description 3
- 239000007864 aqueous solution Substances 0.000 claims description 6
- 239000000243 solution Substances 0.000 claims description 6
- 238000013019 agitation Methods 0.000 claims description 4
- 229920000137 polyphosphoric acid Polymers 0.000 claims description 4
- 238000001914 filtration Methods 0.000 claims description 2
- 239000007788 liquid Substances 0.000 claims description 2
- 230000004044 response Effects 0.000 claims description 2
- 239000002245 particle Substances 0.000 abstract description 16
- 229920001661 Chitosan Polymers 0.000 abstract description 9
- 239000003814 drug Substances 0.000 abstract description 6
- 229940079593 drug Drugs 0.000 abstract description 5
- 231100000252 nontoxic Toxicity 0.000 abstract description 4
- 230000003000 nontoxic effect Effects 0.000 abstract description 4
- 238000006243 chemical reaction Methods 0.000 abstract description 3
- 108090000623 proteins and genes Proteins 0.000 abstract description 3
- 102000004169 proteins and genes Human genes 0.000 abstract description 3
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 abstract description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 abstract 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 abstract 2
- 238000003756 stirring Methods 0.000 abstract 2
- 239000000969 carrier Substances 0.000 abstract 1
- 239000007795 chemical reaction product Substances 0.000 abstract 1
- 150000002500 ions Chemical class 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 230000007935 neutral effect Effects 0.000 abstract 1
- 239000000047 product Substances 0.000 abstract 1
- 230000005540 biological transmission Effects 0.000 description 4
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- MSWZFWKMSRAUBD-IVMDWMLBSA-N 2-amino-2-deoxy-D-glucopyranose Chemical compound N[C@H]1C(O)O[C@H](CO)[C@@H](O)[C@@H]1O MSWZFWKMSRAUBD-IVMDWMLBSA-N 0.000 description 2
- MSWZFWKMSRAUBD-UHFFFAOYSA-N beta-D-galactosamine Natural products NC1C(O)OC(CO)C(O)C1O MSWZFWKMSRAUBD-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 229960002442 glucosamine Drugs 0.000 description 2
- 150000004676 glycans Chemical class 0.000 description 2
- 230000002045 lasting effect Effects 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 229920001282 polysaccharide Polymers 0.000 description 2
- 239000005017 polysaccharide Substances 0.000 description 2
- 235000019832 sodium triphosphate Nutrition 0.000 description 2
- 229920002101 Chitin Polymers 0.000 description 1
- 229920002307 Dextran Polymers 0.000 description 1
- SXRSQZLOMIGNAQ-UHFFFAOYSA-N Glutaraldehyde Chemical compound O=CCCCC=O SXRSQZLOMIGNAQ-UHFFFAOYSA-N 0.000 description 1
- DUKURNFHYQXCJG-UHFFFAOYSA-N Lewis A pentasaccharide Natural products OC1C(O)C(O)C(C)OC1OC1C(OC2C(C(O)C(O)C(CO)O2)O)C(NC(C)=O)C(OC2C(C(OC3C(OC(O)C(O)C3O)CO)OC(CO)C2O)O)OC1CO DUKURNFHYQXCJG-UHFFFAOYSA-N 0.000 description 1
- OVRNDRQMDRJTHS-FMDGEEDCSA-N N-acetyl-beta-D-glucosamine Chemical compound CC(=O)N[C@H]1[C@H](O)O[C@H](CO)[C@@H](O)[C@@H]1O OVRNDRQMDRJTHS-FMDGEEDCSA-N 0.000 description 1
- 101710194948 Protein phosphatase PhpP Proteins 0.000 description 1
- 206010070834 Sensitisation Diseases 0.000 description 1
- NWGKJDSIEKMTRX-AAZCQSIUSA-N Sorbitan monooleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O NWGKJDSIEKMTRX-AAZCQSIUSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000001154 acute effect Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000013270 controlled release Methods 0.000 description 1
- 230000006196 deacetylation Effects 0.000 description 1
- 238000003381 deacetylation reaction Methods 0.000 description 1
- 230000002939 deleterious effect Effects 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 238000012377 drug delivery Methods 0.000 description 1
- 230000009881 electrostatic interaction Effects 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000004005 microsphere Substances 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 238000002703 mutagenesis Methods 0.000 description 1
- 231100000350 mutagenesis Toxicity 0.000 description 1
- 229950006780 n-acetylglucosamine Drugs 0.000 description 1
- HWGNBUXHKFFFIH-UHFFFAOYSA-I pentasodium;[oxido(phosphonatooxy)phosphoryl] phosphate Chemical compound [Na+].[Na+].[Na+].[Na+].[Na+].[O-]P([O-])(=O)OP([O-])(=O)OP([O-])([O-])=O HWGNBUXHKFFFIH-UHFFFAOYSA-I 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000008313 sensitization Effects 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- UNXRWKVEANCORM-UHFFFAOYSA-I triphosphate(5-) Chemical compound [O-]P([O-])(=O)OP([O-])(=O)OP([O-])([O-])=O UNXRWKVEANCORM-UHFFFAOYSA-I 0.000 description 1
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- Medicinal Preparation (AREA)
Abstract
The present invention relates to a hydroxypropyl chitosan nanometer particle and the preparation method for the hydroxypropyl chitosan nanometer particle. The nanometer particle is obtained through ion gel method, including: chitosan, sodium hydroxidand and isopropyl alcohol are mixed for stirring at room temperature; excessive propylene oxide is added in to the mixture for sufficient reaction at 60 DEG C; After the reaction, the Ph value is adjusted to be neutral; the reaction product is deposited by acetone and is cleaned for several times; then the product is dried in vacuum to get hydroxypropyl chitosan; with constant magnetic-force stirring, the water solution of hydroxypropyl chitosan is slowly added with sodium polyphosphate solution; when the solution is of opalescence, hydroxypropyl chitosan nanometer particles are obtained. The diameter of the hydroxypropyl chitosan nanometer particles obtained by the present invention can be controlled. The hydroxypropyl chitosan nanometer particles can be biologically degraded with in a non-toxic and harmless way. The preparation method is moderate. The hydroxypropyl chitosan nanometer particles can be used as the carriers of protein drugs.
Description
Technical field
The present invention relates to that a kind of particle diameter is controlled, stability better, the preparation method of the hydroxypropyl chitosan nano particles of useful as drug carrier.
Background technology
Chitosan, chemistry β by name-(1,4)-2-acetylaminohydroxyphenylarsonic acid 2-deoxidation-D-dextran is the product of de-acetyl chitin, the straight-chain polysaccharide of being made up of glucosamine and acetylglucosamine structural unit.Chitosan is as a kind of positively charged natural polysaccharide, itself has character such as nontoxic, nonirritant, no sensitization, no mutagenesis, and degraded product is low molecule oligochitosan and glucosamine to have excellent biological compatibility and biological degradability.Preparation of Chitosan after the modification is become Nano microsphere or particulate, as useful for drug delivery and controlled release carrier, advantage such as have the entrapment efficiency height, stability is strong and drug release time is long, can effectively avoid problems such as side effect that the acute variation of drug level causes and result of treatment be undesirable, be a big focus of present chitosan applied research.Medicine is by dissolving and be coated in the particle, or is attached to particle surface by adsorption, slowly discharges after being transported to patient part by carrier again.
At present, the method that is used to prepare chitosan particle is more, but great majority all need to use emulsifying agents such as linking agents such as glutaraldehyde, formaldehyde and Span-80, and these materials can not normally be degraded in human body, are deleterious to human body.And the ionic gel method is to utilize mutual oppositely charged between chitosan and the tripoly phosphate sodium STPP, forms nanoparticle by electrostatic interaction, is a kind of nontoxic method.
Summary of the invention
The preparation method who the purpose of this invention is to provide a kind of hydroxypropyl chitosan nano particles, hydroxypropyl chitosan nano particles can be used as the carrier that wraps up protein medicaments.
The present invention is achieved like this, and it is characterized in that: hydroxypropyl chitosan is mixed with concentration is respectively 0.8,1.0,1.5, the aqueous solution of 2.0mg/ml, with 0.22 μ m filter paper filtering, regulates pH between 5-6.Sodium polyphosphate is mixed with concentration is respectively 0.4,0.8, the aqueous solution of 1.0mg/ml, continuing under the magnetic agitation, slowly drip the polyphosphoric acid sodium solution in the hydroxypropyl sugar aqueous solution, question response liquid presents till the tangible opalescence.
Technique effect of the present invention is: the reaction conditions gentleness, and production technique is simple, is easy to suitability for industrialized production, and the hydroxypropyl chitosan nano particles particle diameter that obtains is controlled, biodegradable, nontoxic, can be used for the carrier as protein drug.
Description of drawings
Fig. 1 is the transmission electron microscope picture of the hydroxypropyl chitosan nano particles of embodiment 1 preparation;
Fig. 2 is the transmission electron microscope picture of the hydroxypropyl chitosan nano particles of embodiment 2 preparations.
Embodiment
Embodiment 1
The present invention is raw material with deacetylation greater than 90% chitosan, and itself and excessive propylene oxide are reacted, and generates water miscible hydroxypropyl chitosan.The hydroxypropyl sugar soln of measuring 5ml 1.0mg/ml under lasting magnetic agitation condition, slowly drips the polyphosphoric acid sodium solution of 0.8mg/ml in there-necked flask, rate of addition is that 20-40 drips/min, treats to stop to drip after solution presents tangible opalescence.
By the transmission electron microscope photo of Fig. 1 as can be seen, this hydroxypropyl chitosan nano particles shape presents the sphere of rule, and particle diameter is about 240nm.
Embodiment 2
The hydroxypropyl sugar soln of measuring 5ml2.0mg/ml under lasting magnetic agitation condition, slowly drips the polyphosphoric acid sodium solution of 0.8mg/ml in there-necked flask, rate of addition is that 20-40 drips/min, treats to stop to drip after solution presents tangible opalescence.
By the transmission electron microscope photo of Fig. 2 as can be seen, this hydroxypropyl chitosan nano particles presents the sphere of rule, and particle diameter is about 360nm.Diameter of particle increases to some extent than the particle diameter among the embodiment 1 among the embodiment 2, and this mainly causes owing to reactant hydroxypropyl chitosan concentration increases.
Claims (1)
1. the preparation method of a hydroxypropyl chitosan nano particles, it is characterized in that: hydroxypropyl chitosan is mixed with concentration is respectively 0.8,1.0,1.5, the aqueous solution of 2.0mg/ml, with 0.22 μ m filter paper filtering, regulate pH between 5-6, sodium polyphosphate is mixed with concentration is respectively 0.4,0.8, the aqueous solution of 1.0mg/ml, continuing under the magnetic agitation, slowly drip the polyphosphoric acid sodium solution in the hydroxypropyl sugar aqueous solution, question response liquid presents till the tangible opalescence.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNB2007100535054A CN100569835C (en) | 2007-10-06 | 2007-10-06 | A kind of preparation method of hydroxypropyl chitosan nano particles |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNB2007100535054A CN100569835C (en) | 2007-10-06 | 2007-10-06 | A kind of preparation method of hydroxypropyl chitosan nano particles |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN101139443A true CN101139443A (en) | 2008-03-12 |
| CN100569835C CN100569835C (en) | 2009-12-16 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CNB2007100535054A Expired - Fee Related CN100569835C (en) | 2007-10-06 | 2007-10-06 | A kind of preparation method of hydroxypropyl chitosan nano particles |
Country Status (1)
| Country | Link |
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| CN (1) | CN100569835C (en) |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101806766A (en) * | 2010-04-09 | 2010-08-18 | 济南大学 | Hydroxypropyl /carbon nanotube decoration electrochemical sensor and preparation method and application thereof |
| CN101844059A (en) * | 2010-04-22 | 2010-09-29 | 上海理工大学 | Preparation method of chitosan/sodium polyphosphate porous microcarrier |
| CN107840900A (en) * | 2017-12-21 | 2018-03-27 | 陕西科技大学 | A kind of O hydroxypropyl chitosans and preparation method thereof |
| CN111134119A (en) * | 2020-02-19 | 2020-05-12 | 湖南省植物保护研究所 | Nano chitosan-thiamethoxam water agent and preparation method and application thereof |
| CN112029158A (en) * | 2020-07-31 | 2020-12-04 | 华南理工大学 | Chitosan-based composite response membrane with carbon dioxide response behavior and preparation method and application thereof |
| CN112826982A (en) * | 2021-01-21 | 2021-05-25 | 曲哲 | Dental implant with bioactive surface and preparation method thereof |
-
2007
- 2007-10-06 CN CNB2007100535054A patent/CN100569835C/en not_active Expired - Fee Related
Cited By (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101806766A (en) * | 2010-04-09 | 2010-08-18 | 济南大学 | Hydroxypropyl /carbon nanotube decoration electrochemical sensor and preparation method and application thereof |
| CN101806766B (en) * | 2010-04-09 | 2013-01-02 | 济南大学 | Hydroxypropyl /carbon nanotube decoration electrochemical sensor and preparation method and application thereof |
| CN101844059A (en) * | 2010-04-22 | 2010-09-29 | 上海理工大学 | Preparation method of chitosan/sodium polyphosphate porous microcarrier |
| CN101844059B (en) * | 2010-04-22 | 2012-07-25 | 上海理工大学 | Preparation method of chitosan/sodium polyphosphate porous microcarrier |
| CN107840900A (en) * | 2017-12-21 | 2018-03-27 | 陕西科技大学 | A kind of O hydroxypropyl chitosans and preparation method thereof |
| CN111134119A (en) * | 2020-02-19 | 2020-05-12 | 湖南省植物保护研究所 | Nano chitosan-thiamethoxam water agent and preparation method and application thereof |
| CN111134119B (en) * | 2020-02-19 | 2020-11-20 | 湖南省植物保护研究所 | Nano chitosan-thiamethoxam water agent and preparation method and application thereof |
| CN112029158A (en) * | 2020-07-31 | 2020-12-04 | 华南理工大学 | Chitosan-based composite response membrane with carbon dioxide response behavior and preparation method and application thereof |
| CN112029158B (en) * | 2020-07-31 | 2021-06-08 | 华南理工大学 | Chitosan-based composite response membrane with carbon dioxide response behavior and preparation method and application thereof |
| CN112826982A (en) * | 2021-01-21 | 2021-05-25 | 曲哲 | Dental implant with bioactive surface and preparation method thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| CN100569835C (en) | 2009-12-16 |
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Owner name: STATE ELECTRIC NET CROP. Free format text: FORMER OWNER: NANCHANG UNIV. OF AVIATION Effective date: 20130912 Owner name: JIANGXI ELECTRIC POWER SCIENCE ACADEMY NANCHANG UN Effective date: 20130912 |
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Free format text: CORRECT: ADDRESS; FROM: 330063 NANCHANG, JIANGXI PROVINCE TO: 100007 DONGCHENG, BEIJING |
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| TR01 | Transfer of patent right |
Effective date of registration: 20130912 Address after: 100007 No. 86 West Chang'an Avenue, Beijing Patentee after: State Grid Corporation of China Patentee after: Jiangxi Electric Power Science Academy Patentee after: Nanchang Univ. of Aviation Address before: 696 No. 330063 Jiangxi province Nanchang Honggutan Feng and South Avenue Patentee before: Nanchang Univ. of Aviation |
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Granted publication date: 20091216 Termination date: 20181006 |