PH-sensitive chitosan drug-carrying micelle with targeting and fluorescent characteristics and preparation method thereof

A technology of fluorescent properties and drug-loaded micelles, which is applied in the direction of pharmaceutical formulations, medical preparations containing active ingredients, and medical preparations containing active ingredients. To solve the problems of normal organ cell damage, etc., to achieve good pH-sensitive drug release performance and reduce toxic and side effects

Active Publication Date: 2017-02-22
TIANJIN CHENGJIAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, while anticancer drugs kill cancer cells, they also cause serious damage to some normal organ cells in the body, and also cause damage

Method used

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  • PH-sensitive chitosan drug-carrying micelle with targeting and fluorescent characteristics and preparation method thereof
  • PH-sensitive chitosan drug-carrying micelle with targeting and fluorescent characteristics and preparation method thereof
  • PH-sensitive chitosan drug-carrying micelle with targeting and fluorescent characteristics and preparation method thereof

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preparation example Construction

[0030]The construction idea of ​​the pH-sensitive chitosan drug-loaded micelles with both targeting and fluorescence of the present invention is to use pH-sensitive amphiphilic N-octyl-N'-(2-carboxycyclohexylcarbonyl ) Chitosan (OCCC) is a drug-loaded micelle, with polyethylene glycol as a connecting arm, and folic acid and fluorescent dye thiazole orange are grafted on both ends of it, so as to construct a targeted, pH-sensitive, Multifunctional chitosan drug-loaded micelles integrating stealth and fluorescent tracer. In the preparation process of the chitosan drug-loaded micelles, chitosan was firstly used as the main body, and hydrophobic octyl chains were grafted on it by reductive amination reaction, and the acid-sensitive β-carboxylic acid amide bond was used as the linking arm. Hydrophilic carboxyl cyclohexanoyl group, thereby constructing amphiphilic chitosan with pH-sensitive properties; then, in the amino-terminated polyethylene glycol (H 2 N-PEG-NH 2 ) were prepar...

Embodiment 1

[0043] Taking chitosan-based drug-loaded micelles FA-PEG-(OCCC-1)-PEG-TO prepared from OC-1 prepared with chitosan as the main body during the preparation of OC as an example

[0044] Weigh 4g of chitosan (CTS), place it in anhydrous methanol (MeOH), and swell at 30°C under mechanical stirring; then slowly add 10mL of octanal dropwise to the reaction solution, and keep the reaction for 5h After that, add sodium borohydride 2gNaBH in six batches 4 , continue to reduce at room temperature for 12h, adjust the pH value of the reaction solution to 6-8 after the reduction reaction is completed; Octyl chitosan (OC); Weigh 1g of the aforementioned N-octyl chitosan (OC) and place it in a reaction flask, and use anhydrous dimethyl sulfoxide (DMSO) to swell it. Add 1 g of hexahydrophthalic anhydride dropwise to the reaction bottle, raise the temperature to 80°C and react for 12 hours; after the reaction, pour the reaction solution into deionized water and place it in an ice-water bath, ...

Embodiment 2

[0049] Taking chitosan drug-loaded micelles FA-PEG-(OCCC-2)-PEG-TO as an example prepared by taking OC-2 prepared as chitosan as the main body during the preparation of OC with a holding time of 8h

[0050]Weigh 4g of chitosan (CTS), place it in anhydrous methanol (MeOH), and swell at 30°C under mechanical stirring; then slowly add 11.5mL of octanal dropwise to the reaction solution, and keep the reaction After 8h, add sodium borohydride 2gNaBH in six batches 4 , continue to reduce at room temperature for 20h, adjust the pH value of the reaction solution to 6-8 after the reduction reaction is completed; the reaction solution is suction filtered, and the filter cake is alternately washed with methanol and deionized water, and then the filter cake is vacuum-dried to obtain light yellow N- Octyl chitosan (OC); Weigh 1g of the aforementioned N-octyl chitosan (OC) and place it in a reaction flask, and use anhydrous dimethyl sulfoxide (DMSO) to swell it. Add 1.2g of hexahydrophthal...

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Abstract

The invention discloses PH-sensitive chitosan drug-carrying micelle with targeting and fluorescent characteristics and a preparation method thereof; the multifunctional chitosan drug-carrying micelle with targeting property, PH sensitivity, invisibility and fluorescent tracing combined in a whole is constructed by using PH-sensitive amphiphilic chitosan as drug-carrying micelle and polyethylene glycol as a link arm, and grafting folic acid and fluorescent dye thiazole orange to two ends of the micelle; the chitosan drug-carrying micelle of the invention has good fluorescent properties, and has good drug-carrying property for anticancer drug 5-fluorouracil, with drug-carrying efficiency up to 42.76%; under physiological environmental PH (PH=7.4), accumulative drug release within 8 h is only 2%, accumulative drug release within 26 h is less than 8%, and toxic and side effects of the chitosan drug-carrying micelle for normal tissue cells during transport of the anticancer drug 5-fluorouracil can be decreased; in addition, under tumor cell lysosome PH value (PH=4.5), good PH-sensitive drug release property is exhibited, and 5-fluorouracil release within 4 h is up to 95%.

Description

technical field [0001] The invention belongs to the interdisciplinary field of chemistry and biomedicine, and specifically relates to a pH-sensitive chitosan drug-loaded micelle with targeting and fluorescence properties and a preparation method thereof. Background technique [0002] Cancer is a serious disease that seriously endangers human health and has attracted extensive attention from researchers at home and abroad. In cancer treatment methods, chemotherapy with anticancer drugs is one of the most effective methods to completely kill cancer cells in the body of cancer patients after surgery. However, while anticancer drugs kill cancer cells, they also cause serious damage to some normal organ cells in the body, and also cause damage to certain tissues and organs such as liver, kidney, heart, lung, etc., seriously affecting cancer cells. Patient outcomes and quality of life. Based on this, how to improve the targeting of anticancer drug delivery system has always been...

Claims

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Application Information

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IPC IPC(8): A61K9/107A61K47/36A61K47/22A61K47/10A61K31/513A61P35/00C08G81/00
CPCA61K9/1075A61K31/513A61K47/10A61K47/22A61K47/36C08G81/00
Inventor 费学宁李书蓓曹凌云张宝莲于妙卓
Owner TIANJIN CHENGJIAN UNIV
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