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Galactose modified sulfhydryl chitosan quaternary ammonium salt nanoparticle, as well as preparation method and application thereof

A technology of thiolated chitosan and chitosan quaternary ammonium salt, which is applied in the field of medicine, can solve the problems of inability to guarantee stable and rapid drug release, easy drug resistance, and lack of drug resistance, and achieve good cell adhesion and mucosal adhesion, Protection from degradation, good stability

Inactive Publication Date: 2013-05-08
FUDAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The above-mentioned drug delivery system also lacks an effective way to control the binding force between the drug and the carrier, and cannot guarantee the stability of the drug contained in the physiological environment and the rapid release of the therapeutic target.
In addition, the galactose-modified carriers in the existing literature only carry one drug, and single-target therapy is prone to drug resistance. Reports on combined administration of targets and synergistic treatment of diseases

Method used

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  • Galactose modified sulfhydryl chitosan quaternary ammonium salt nanoparticle, as well as preparation method and application thereof
  • Galactose modified sulfhydryl chitosan quaternary ammonium salt nanoparticle, as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0055] The preparation of the thiolated chitosan quaternary ammonium salt of embodiment 1 galactose modification

[0056] According to the method reported in the literature (Eur J Pharm Biopharm 2004,57:77-83), TMC was synthesized in methylpyrrolidone solvent. The molecular weight of chitosan was 30 kDa, and the reaction time was 45 min, 120 min and 180 min, respectively. The degrees of ammonification were 15%, 30% and 60%, respectively. Cl - Type Anion Exchange Resin Removal I - , lyophilized; Weigh 50 mg of lacturonic acid (LA) and dissolve it in 3 mL of tetramethylethylenediamine (TEMED) / HCl buffer (pH 4.7), add 1-ethyl-3 -(3-Dimethylaminopropyl)-carbodiimide hydrochloride (EDC) and N - Hydroxysuccinimide (NHS), stir to dissolve; weigh 100 mg TMC and dissolve in 12 mL TEMED / HCl buffer (pH 4.7); mix LA and TMC solution, add 1 mol / L NaOH to adjust pH to 3.0, room temperature Stir for 24 h, purify by ultrafiltration (MWCO 10 kDa) at 4 °C, and freeze-dry to obtain GT; weigh...

Embodiment 2

[0057] The preparation of the thiolated chitosan quaternary ammonium salt of embodiment 2 galactose modification

[0058] According to the method reported in the literature (Eur J Pharm Biopharm 2004,57:77-83), TMC was synthesized in methylpyrrolidone solvent, the molecular weight of chitosan was 100 kDa, and the reaction time was 45 min, 120 min and 180 min, respectively. The degrees of ammonification were 15%, 30% and 60%, respectively. Cl - Type Anion Exchange Resin Removal I - , lyophilized; Weigh 150 mg of lacturonic acid (LA) and dissolve in 3 mL of tetramethylethylenediamine (TEMED) / HCl buffer (pH 4.7), add 1-ethyl-3 -(3-Dimethylaminopropyl)-carbodiimide hydrochloride (EDC) and N - Hydroxysuccinimide (NHS), stir to dissolve; weigh 100 mg TMC and dissolve in 12 mL TEMED / HCl buffer (pH 4.7); mix LA and TMC solution, add 1 mol / L NaOH to adjust pH to 4.0, room temperature Stir for 24 h, purify by ultrafiltration (MWCO 10 kDa) at 4 °C, and freeze-dry to obtain GT; weigh ...

Embodiment 3

[0059] The preparation of the thiolated chitosan quaternary ammonium salt of embodiment 3 galactose modification

[0060] According to the method reported in the literature (Eur J Pharm Biopharm 2004,57:77-83), TMC was synthesized in methylpyrrolidone solvent, the molecular weight of chitosan was 200 kDa, and the reaction time was 45 min, 120 min and 180 min, respectively. The degrees of ammonification were 15%, 30% and 60%, respectively. Cl - Type Anion Exchange Resin Removal I - , lyophilized; Weigh 120 mg of lacturonic acid (LA) and dissolve in 3 mL of tetramethylethylenediamine (TEMED) / HCl buffer (pH 4.7), add 1-ethyl-3 -(3-Dimethylaminopropyl)-carbodiimide hydrochloride (EDC) andN - Hydroxysuccinimide (NHS), stir to dissolve; weigh 100 mg TMC and dissolve in 12 mL TEMED / HCl buffer (pH 4.7); mix LA and TMC solution, add 1 mol / L NaOH to adjust pH to 5.0, room temperature Stir for 72 h, purify by ultrafiltration (MWCO 10 kDa) at 4 °C, and freeze-dry to obtain GT; weigh 10...

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Abstract

The invention belongs to the technical field of medicines and specifically provides a galactose modified sulfhydryl chitosan quaternary ammonium salt nanoparticle, as well as a preparation method and an application of the nanoparticle. The nanoparticle provided by the invention is generated by positively charged galactose modified sulfhydryl chitosan quaternary ammonium salt and an ionic cross linking agent under an ionic cross linking action, and meanwhile is entrapped with protein polypeptide medicine or nucleic acid medicine, wherein the galactose modified sulfhydryl chitosan quaternary ammonium salt is formed by sequentially enabling amino of chitosan to be subjected to quaternization, galactose modification and sulfhydryl modification. The preparation process of the nanoparticle is simple, the organic solvent is not required, and the activity of the protein polypeptide medicine or the nucleic acid medicine can be protected. The nanoparticle is stable in structure, can actively target inflammation macrophage and liver cancer cell, effectively improves small intestine absorption of oral-taken medicine and improves the transfection efficiency of nucleic medicine, has anti-inflammation and anti-tumor effects which are better than those of the existing chitosan nanoparticles, and can be used for preparing an oral-taken medicating system, united medicating system, and the like.

Description

technical field [0001] The invention belongs to the technical field of medicine, and in particular relates to a galactose-modified thiol chitosan quaternary ammonium salt nanoparticle and a preparation method and application thereof. Background technique [0002] Nanoparticles are a new type of drug delivery system, which can carry various drugs such as chemotherapy drugs and gene drugs. Nanoparticles can change the distribution of drugs in vivo, and have the functions of targeted drug delivery, sustained release of drugs, reduction of drug side effects, solubilization of insoluble drugs, improvement of drug stability, promotion of biofilm transport and absorption, and improvement of bioavailability of biomacromolecular drugs Degree and other advantages (Adv Drug Deliv Rev 2008,60:1638-1649), especially widely used in biomacromolecule drug delivery systems. The preparation methods of nanoparticles mainly include covalent cross-linking method, ionic cross-linking method, com...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A61K9/00A61K47/36A61K45/00A61K48/00
Inventor 唐翠印春华韩路张婧
Owner FUDAN UNIV
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