Amphipathic phospholipid molecule with reducing response and application thereof in drug sustained release

An amphiphilic phospholipid, responsive technology, which can be used in medical preparations with non-active ingredients, phosphorus-organic compounds, organic chemistry, etc., and can solve the problems of limited use of reducing agents, difficulty in separation and purification, and cumbersome synthesis of reduction-responsive vesicles.

Active Publication Date: 2016-07-20
CHINA UNIV OF PETROLEUM (EAST CHINA)
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The synthesis of reduction-responsive vesicles reported so far is very cumbersome, and separation and purification are very difficult
In addition, limited by the synthesis methods, many research groups modify the reducing functional groups on the amphiphile head group or the hydrophilic-hydrophobic linking part, which objectively limits the use of different types of reducing agents.

Method used

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  • Amphipathic phospholipid molecule with reducing response and application thereof in drug sustained release
  • Amphipathic phospholipid molecule with reducing response and application thereof in drug sustained release
  • Amphipathic phospholipid molecule with reducing response and application thereof in drug sustained release

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specific Embodiment approach

[0034]

[0035] Synthetic route: a. 2,2'-dithiodipyridine, triethylamine, 0°C; b. Mercaptopropionic acid, triethylamine, dichloromethane, 25°C; c. 1-hexadecanoyl-glycerol - Phosphocholine, dicyclohexylcarbodiimide, dichloromethane, 25°C.

[0036] Step a: Dissolve 20 g of dodecylmercaptan and 10 g of triethylamine in 200 ml of dichloromethane, add a solution of 88 g of 2,2'-dithiobipyridine in 100 ml of dichloromethane with stirring in an ice bath , the reaction solution was stirred at 0° C. for 1 hour, then naturally rose to room temperature, and continued to stir for 24 hours. After the reaction was finished, the reaction solution was concentrated until a large amount of crystals appeared, and suction filtered. The filter cake was washed with 200 ml of n-hexane, and the combined filtrate was crystallized with 50 ml of glacial ether to obtain 25 g of compound 2 (light yellow solid), with a yield of 79%;

[0037] Step b: 15.5 grams of compound 2 and 5.3 grams of mercaptopro...

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Abstract

The invention relates to the field of drug carrier design, and particularly relates to an amphipathic phospholipid molecule with reducing response and application thereof in drug sustained release. According to the amphipathic phospholipid molecule, n-alkyl thiol serving as an initial raw material is firstly activated by 2,2'-dithiodipyridine, and further reacts with mercaptopropionic acid to obtain fatty acid containing a disulfide bond on delta 3 position; carboxylic acid performs an esterification reaction with 1-hexadecanoyl-sn-glycero-3-phosphocholine to obtain an amphipathic phospholipid molecule of glycerol 2-hydroxyl ester containing disulfide bond on the delta 3 position. The phospholipid molecule can be prepared by a simple organic unit reaction, and the phospholipid vesicle prepared from the phospholipid molecule has excellent drug encapsulating and controlled-release capabilities.

Description

technical field [0001] The invention relates to the field of drug carrier design, in particular to a reduction-responsive amphiphilic phospholipid molecule and its application in drug sustained release. Background technique [0002] Stimuli-responsive phospholipid molecules are one of the main directions in the design of new drug carriers in recent years. Introducing an environment-responsive unit into the amphiphilic phospholipid molecular structure can make the phospholipid vesicle undergo a structural phase transition, chemical structure isomerization or dissociation when subjected to specific physical, chemical or biological stimuli, and then lead to the release of the drug. By introducing different types of stimulus-responsive units into the structure of phospholipid molecules and adjusting the position of the response units in the phospholipids, the preparation of different types of stimuli-responsive vesicles can be achieved. [0003] Vesicles with reduction-respons...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F9/09A61K47/24A61K9/127
CPCA61K9/127A61K47/24C07F9/091
Inventor 孙亚伟姬燕云徐海曹美文王继乾王栋
Owner CHINA UNIV OF PETROLEUM (EAST CHINA)
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