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Sulfhydrylated amphipathic chitosan polymer carrier as well as preparation method and application thereof

A chitosan derivative, amphiphilic technology, applied in the field of pharmaceutical preparations, can solve problems such as poor solubility and oral administration restrictions

Inactive Publication Date: 2013-06-12
CHINA PHARM UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] Polymeric micelles are thermodynamically stable systems spontaneously formed by amphiphilic polymers, which have a good solubilization effect on poorly soluble drugs. Many drugs with good activity are limited in oral administration due to their poor solubility.

Method used

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  • Sulfhydrylated amphipathic chitosan polymer carrier as well as preparation method and application thereof
  • Sulfhydrylated amphipathic chitosan polymer carrier as well as preparation method and application thereof
  • Sulfhydrylated amphipathic chitosan polymer carrier as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0087] Embodiment 1: Preparation of 6-O-carboxymethyl-2-N-octyl-2-N-mercaptoacetyl chitosan

[0088] 1. Preparation of 6-O-carboxymethyl-2-N-octyl chitosan

[0089] 1.1 Preparation of 16-O-carboxymethyl chitosan

[0090] Dissolve 1g of chitosan in acetic acid aqueous solution, stir to dissolve, then add an equal volume of isopropanol, add NaOH in batches, alkalinize in a water bath at 40°C, dissolve 6g of chloroacetic acid in isopropanol, add dropwise to the reaction solution, and react at 40°C After a certain period of time, pour off the supernatant and add 40mL of water to make it a clear and transparent yellow solution. Adjust the pH of the solution to neutral with HAC, disperse in methanol, filter, wash the filter cake with methanol / water (90:10, v:v) several times, dissolve the filter cake in 20 mL of water, filter, and lyophilize to obtain 6-O - Carboxymethyl chitosan.

[0091] 1.2 Preparation of 6-O-carboxymethyl-2-N-octyl chitosan

[0092] 6-O-carboxymethyl chitosan ...

Embodiment 2

[0096] Embodiment 2: Preparation of 6-O-hydroxyethyl-2-N-deoxycholic acid-2-N-(N-acetyl-L-cysteine) chitosan

[0097] 1. Preparation of 6-O-hydroxyethyl-2-N-deoxycholic acid chitosan

[0098] 1.1 Preparation of 16-O-hydroxyethyl chitosan

[0099] Chitosan 1g, suspended in 15ml 2% HAC, dropwise added 50% NaOH 10ml, alkalized in water bath at 40°C for 12h, added dropwise ethylene oxide in ice bath, stirred in ice bath for 2-6h, condensed and refluxed, heated to 30-50°C Continue to react at ℃, pour off the supernatant, add a certain amount of water, adjust to neutral with 5M HCl, transfer to a dialysis bag (MWCO=12000-14000), dialyze with distilled water overnight, and freeze-dry the dialyzate to obtain 6-O - Hydroxyethyl chitosan.

[0100] 1. Preparation of 26-O-hydroxyethyl-2-N-deoxycholic acid chitosan

[0101] 0.5 g of 6-O-hydroxyethyl chitosan was dissolved in distilled water, after an appropriate amount of deoxycholic acid, 1.5 times the molar ratio (compared with deoxyc...

Embodiment 3

[0105] Embodiment 3: Preparation of 6-O-carboxymethyl-2-N-cholic acid-2-N-glutathione chitosan

[0106] 1. Preparation of 6-O-carboxymethyl-2-N-cholic acid chitosan

[0107] 1.1 Preparation of 16-O-carboxymethyl chitosan

[0108] Method is the same as 1.1 in Example 1.

[0109] 1. Preparation of 26-O-carboxymethyl-2-N-cholic acid chitosan

[0110] Dissolve 0.5 g of 6-O-carboxymethyl chitosan in distilled water, dissolve an appropriate amount of cholic acid, 1.5 times the molar ratio (compared to cholic acid) of EDC and NHS in methanol, add it to the reaction solution, and stir to react After 24 hours, evaporate at 40° C., adjust the pH to 7 with 5% NaOH, dialyze and freeze-dry to obtain 6-O-carboxymethyl-2-N-cholic acid chitosan.

[0111] 1.3 The reaction sequence of the above two steps can be reversed, that is, cholic acid is first introduced into the chitosan skeleton, and then carboxymethyl is introduced.

[0112] 2. Preparation of 6-O-carboxymethyl-2-N-cholic acid-2-N-...

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Abstract

The invention relates to a sulfhydrylated amphipathic chitosan derivative carrier with biological adhesiveness. The derivatives are structured by respectively introducing hydrophilic groups, hydrophobic groups and groups containing sulfydryl. The derivative in an aqueous medium can be self-assembled to nano-micelle so as to load pharmaceutically active or pharmacologically active molecules. After the carrier reaches the mucosa of a living body, the sulfydryl groups can be bonded with surface protein of the mucosa through covalent bonds: disulfide bonds, so that the detaining and acting time of micelle on the surface of the mucosa is prolonged. In addition, the chitosan derivative further has the function of mutual effect in compact connection with cells and opening compact connection with cells of the mucosa. The auxiliary material can be used as the carrier of the pharmaceutically active or pharmacologically active molecules to be used for administration via oral administration, ocular administration, nasal mucosa administration and the like, so that medicine absorption is remarkably improved, and the bioavailability is improved. The carrier provided by the invention is simple in preparation method and manure in process, so that the carrier is suitable for large-scale continuous production.

Description

technical field [0001] The invention belongs to the field of pharmaceutical preparations, and relates to the synthesis and preparation of a bioadhesive mercaptolated amphiphilic chitosan derivative carrier and its use as a carrier of pharmaceutically active or pharmacologically active molecules for oral administration, eye or nasal mucosa, etc. Application of route of administration. Background technique [0002] With the development of pharmacy and pharmacokinetics, people have realized that the absorption of drugs largely depends on the migration behavior of drugs at the absorption site. While the traditional oral preparation releases the drug in the gastrointestinal tract, it also migrates with the emptying of the stomach and intestinal peristalsis; the traditional ophthalmic preparations have the washing of the drug by tears and the removal of the nasal mucosa and cilia during administration of the nasal mucosa Effects such as affecting the absorption of drugs. If the ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A61K47/36A61K9/19C08B37/08A61K31/337A61K38/13A61K31/7052
Inventor 周建平霍美蓉姚玲玲于艳芳
Owner CHINA PHARM UNIV
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