Amphipathic chitosan derivative and preparation method and application thereof

A chitosan derivative, chitosan technology, applied in the direction of drug combination, pharmaceutical formula, organic active ingredients, etc., can solve few problems such as natural polymer modification research, achieve potential application value, mild preparation reaction conditions , source-rich effects

Inactive Publication Date: 2011-11-16
SUN YAT SEN UNIV
View PDF3 Cites 27 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, this gene and drug co-delivery system has shown great potential in tumor therapy, but the relevant researches are mainly focused on synthetic polymer carriers, and little research is involved in the modification of natural polymers.

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Amphipathic chitosan derivative and preparation method and application thereof
  • Amphipathic chitosan derivative and preparation method and application thereof
  • Amphipathic chitosan derivative and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0044] Example 1 Preparation of PAMAM-Cs-DCA

[0045] (1) Synthesis of 6-azido-N-amino-chitosan-g-deoxycholic acid graft polymer:

[0046] a Under the protection of nitrogen, 3.0g chitosan (weight average molecular weight is 10000, deacetylation degree is 70%) is dissolved in 60mLN, in the mixed solvent of N-dimethylformamide and water (95:5, v / v ), add 9.0g phthalic anhydride, stir and react at 120°C for 8 hours, after the reaction, cool to 25°C, precipitate with ice water, filter, wash the resulting product three times with methanol, and dry it in vacuum to obtain N- Phthalamido-chitosan, yield: 80%.

[0047] bUnder the protection of nitrogen, dissolve 1.0g N-phthalamido-chitosan in 100mL N-methyl-pyrrolidone, stir to dissolve, and add 6.05g N-bromosuccinimide in an ice-water bath and 10.3g triphenylphosphine, heated up to 70°C and reacted with magnetic stirring under nitrogen protection for 6 hours (rotating speed was 600 rpm). After the reaction, the product was centrifu...

Embodiment 2

[0056] Example 2 Preparation of PAMAM-Cs-DCA

[0057] (1) Synthesis of 6-azido-N-amino-chitosan-g-deoxycholic acid graft polymer:

[0058] a Under nitrogen protection, 3.0g chitosan (weight average molecular weight is 14000, deacetylation degree is 90%) is dissolved in 50mL N, in the mixed solvent of N-dimethylformamide and water (90:10, v / v), add 10g of phthalic anhydride, stir and react at 100°C for 10 hours, after the reaction, cool to room temperature at 25°C, precipitate with ice water, filter, wash the resulting product with methanol three times, and dry it under vacuum to obtain N - Phthalamido-chitosan, yield: 85%.

[0059] bUnder the protection of nitrogen, dissolve 1.0g N-phthalamido-chitosan in 50mL N-methyl-pyrrolidone, stir to dissolve, and add 7.26g N-bromosuccinimide in an ice-water bath And 12.4g triphenylphosphine, be warming up to 80 ℃ and under nitrogen protection magnetic stirring reaction 4 hours (rotating speed is 1200 rev / min), after reaction finishes...

Embodiment 3

[0068] Example 3 Preparation of PAMAM-Cs-DCA

[0069] (1) Synthesis of 6-azido-N-amino-chitosan-g-deoxycholic acid graft polymer:

[0070] a Under nitrogen protection, 3.2g chitosan (weight average molecular weight is 12000, deacetylation degree is 80%) is dissolved in 60mL N, in the mixed solvent of N-dimethylformamide and water (14:1, v / v), add 10g of phthalic anhydride, stir and react at 110°C for 9 hours, after the reaction is over, cool to 30°C, precipitate with ice water, filter, wash the resulting product with methanol three times, and obtain N- Phthalamido-chitosan, yield: 83%.

[0071] bUnder the protection of nitrogen, dissolve 1.0g N-phthalamido-chitosan in 75mL N-methyl-pyrrolidone, stir to dissolve, and add 6.50g N-bromosuccinimide in an ice-water bath And 11.0g triphenylphosphine, be warming up to 75 ℃ and under nitrogen protection magnetic stirring reaction 5 hours (rotating speed is 900 rev / min), after reaction finishes, the product is centrifuged, filtered,...

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to view more

PUM

PropertyMeasurementUnit
particle sizeaaaaaaaaaa
particle diameteraaaaaaaaaa
degree of graftingaaaaaaaaaa
Login to view more

Abstract

The invention discloses an amphipathic chitosan derivative PAMAM-Cs-DCA (Poly(amido amine)-chitosan-deoxycholic acid). The PAMAM-Cs-DCA is prepared by sequentially grafting a PAMAM unit and a deoxycholic acid unit on a main chain of chitosan by click chemical reaction and amidation reaction. The preparation method has mild reaction conditions, high efficiency and selectivity. The invention also discloses an application of the amphipathic chitosan derivative in preparing an anticancer drug carrier: the amphipathic chitosan derivative forms nanomicelle which takes the PAMAM unit and chitosan asa hydrophilic shell and takes the DCA unit as a hydrophobic core by self assembly in a water solution, wherein hydrophobic anticancer drugs can be coated in the core, and the shell can be compounded with pDNA (plasmid deoxyribonucleic acid) to realize co-transmission of the drugs and genes. Due to the unique molecular structure, the amphipathic chitosan derivative has potential application valuesin the fields of gene therapy, controlled release of drugs, tissue engineering and the like.

Description

technical field [0001] The invention belongs to the field of functional polymer materials, and in particular relates to an amphiphilic chitosan derivative and a preparation method and application thereof. Background technique [0002] At present, treating cancer patients with anticancer drugs is one of the hotspots in clinical research, but the large side effects and multi-drug resistance of anticancer drugs limit their clinical application, and the use of gene therapy can avoid the above shortcomings (Heike, Y. ; Kasono, K.; Kunisaki, C., et al. Int. J. Cancer, 2001, 92: 115.). Due to the rapid spread of tumor cells, it is difficult to achieve long-term effective suppression with a single gene therapy method, so combining gene and drug therapy to inhibit tumor cells has become a new research direction. Bae et al. (Qiu, L.Y.; Bae, Y.H. Biomaterials, 2007, 28: 4132.) grafted polycaprolactone (PCL) onto polyethyleneimine (PEI) to synthesize a series of amphiphilic cationic mi...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to view more

Application Information

Patent Timeline
no application Login to view more
Patent Type & Authority Applications(China)
IPC IPC(8): C08B37/08A61K47/36A61K31/704A61K48/00A61P35/00
Inventor 邓俊杰张黎明
Owner SUN YAT SEN UNIV
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Try Eureka
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap