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Amphipathic chitosan with chemical crosslinking characteristic and preparation method thereof

A chemical cross-linking and chitosan technology, applied in the field of polymer chemistry, can solve problems such as insufficient consideration, achieve good biocompatibility, improve research and application value, and produce pure effects

Inactive Publication Date: 2012-05-30
GUANGZHOU CHEM CO LTD CHINESE ACADEMY OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

As a potential drug carrier, the modified group in the amphiphilic chitosan structure, especially the hydrophilic group in the outer layer of the microcapsule after crosslinking, has good biocompatibility and non-toxicity; and, The formation of stable microcapsules mainly depends on the chemical cross-linking of some active amino groups; therefore, the retention and effective protection of some active amino groups is very necessary during the modification process, but the current research on amphiphilic chitosan has little effect on these The problem is not considered enough

Method used

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  • Amphipathic chitosan with chemical crosslinking characteristic and preparation method thereof
  • Amphipathic chitosan with chemical crosslinking characteristic and preparation method thereof
  • Amphipathic chitosan with chemical crosslinking characteristic and preparation method thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0024] Embodiment 1: the preparation of N-octyl chitosan

[0025] Set the molecular weight to 5 x 10 4 Unmodified chitosan (5.0g, 31mmol) was mixed with 50ml methanol, mechanically stirred to disperse and 5.0ml octanal (32mmol) was added dropwise, and reacted at room temperature for 24h. Weigh 1.8g solid KBH 4 And after dissolving with 15ml of distilled water, slowly drop into the reaction solution, octanal and KBH 4 The molar ratio is 1:1, and the reaction is continued at room temperature for 24h; then neutralized with dilute hydrochloric acid solution, washed with methanol several times after standing and suction filtration, and vacuum-dried at 50°C to obtain 7.0g N-octyl chitosan . The degree of substitution (DS) of the octyl group on the 2-amino group was 54.3% by elemental analysis (see Table 1).

[0026] figure 1 -a is the infrared spectrum of unmodified chitosan; figure 2 It is the 1H NMR spectrum of unmodified chitosan.

Embodiment 2

[0027] Embodiment 2: the preparation of N-phthaloyl-N-octyl chitosan (NOOPC)

[0028] Take N-octyl chitosan (3.0g, containing 6.2mmol of amino groups) and phthalic anhydride (2.8g, 18.6mmol) respectively and mix them in 40ml of anhydrous DMF. 2 Reaction under protection for 6h. Then the reaction solution was poured into ice water, and the precipitate was precipitated. The precipitate was extracted with ethanol Soxhlet for 48 hours, and the purified precipitate was vacuum-dried at 50°C to obtain 3.6 g of N-phthaloyl-N-octyl shell polysaccharides.

[0029] figure 1 Middle b is the infrared spectrum of N-phthaloyl-N-octyl chitosan, obtained by figure 1 -b Visible, the position of the peak and its attribution are as follows: IR: 3556cm -1 (-OH,-NH 2 ); 2927, 2958, 1464cm -1 (octyl groups); 721, 1776, 1716cm -1 (phthalimide groups)).

Embodiment 3

[0030] Embodiment 3: the preparation of N-octyl-O-polyethylene glycol chitosan (NOOMC (I))

[0031] Take 1.5 g of N-phthaloyl-N-octyl chitosan (NOOPC), 10.2 g of iodopolyethylene glycol monomethyl ether (MPEGI) prepared in advance, freshly prepared Ag 2 O 1.2g, the molar ratio of the three is n(POCTS):n(MPEGI):n(Ag 2 (0) = 1:1:1, the reactants were mixed in 60ml DMF, stirred with magnetic force at 60°C for 16h, then added 80ml water and 50ml hydrazine hydrate (80%), the temperature rose to 90°C and continued to react for 15h; filtered to remove Insoluble matter in the solution, the obtained filtrate was evaporated to a viscous state, then added an appropriate amount of deionized water to dissolve, and then dialyzed with deionized water for 72 hours to remove DMF and excess iodopolyethylene glycol monomethyl ether, and the dialyzed solution It is an aqueous solution of N-octyl-O-polyethylene glycol chitosan, and the aqueous solution is distilled and concentrated to obtain yell...

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Abstract

The invention discloses amphipathic chitosan with a chemical crosslinking characteristic and a preparation method thereof. The method comprises the following steps of: reacting chitosan with long-chain aliphatic aldehyde to obtain N-long-chain alkyl chitosan; reacting the N-long-chain alkyl chitosan with phthalic anhydride; reacting an obtained product with iodo-polyethylene glycol monomethyl ether; and performing a deprotection reaction on an amino group by using hydrazine hydrate to obtain N-long-chain alkyl-O-polyglycol chitosan. In a preparation process, the method effectively protects the amino group in a chitosan molecule, avoids introducing a polyglycol group on the amino group, and remains part amino group in the amphipathic chitosan by removing the amino group protection; the product can serve as a precursor for preparing amphipathic chitosan hollow microcapsules; and polyethylene glycol with high biocompatibility, low toxicity and easy degradation is introduced on a hydroxylgroup of the chitosan to serve as a hydrophilic group, so that the research and application values of the derivative on a medicament carrier are improved.

Description

technical field [0001] The invention relates to the field of polymer chemistry, in particular to an amphiphilic chitosan with chemical crosslinking properties and a preparation method thereof. Background technique [0002] Amphiphilic block or graft copolymers are widely used in the fields of polymer science and medicine. The micelles or microcapsules with a cavity structure prepared by amphiphilic polymers can serve as a container for hydrophobic drugs, solubilize the drugs in the core, and reduce toxic and side effects; the outer shell can protect the drugs and improve drug stability and achieve sustained and controlled release; at the same time, the hydrated shell can prevent the mutual aggregation of hydrophobic cores between micelles and exist stably, and the purpose of targeted drug delivery can be achieved by modifying the surface of micelles, so the amphiphile Sexual copolymers have unique advantages in the delivery of poorly soluble drugs, macromolecular drugs and ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08G81/00C08B37/08C08G65/48
Inventor 赵旭升刘光华刘峰刘乃章
Owner GUANGZHOU CHEM CO LTD CHINESE ACADEMY OF SCI
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