Cationic lipoid plastid and preparation method thereof

A cationic lipid, cationic technology, applied in the field of polymer preparation, can solve the problem of limited selection of hydrophobic parts

Active Publication Date: 2013-02-20
CHANGZHOU INST OF ENERGY STORAGE MATERIALS &DEVICES
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, due to method limitations, the selection of hydrophobic moieties is also very limited.

Method used

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  • Cationic lipoid plastid and preparation method thereof
  • Cationic lipoid plastid and preparation method thereof
  • Cationic lipoid plastid and preparation method thereof

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preparation example Construction

[0055] In order to obtain the cationic liposome, the present invention also provides a preparation method of the compound shown in the formula I, comprising:

[0056] a) Provide isopropylidene-2,2-dimethoxypropionic anhydride, mix it with propynyl alcohol in an organic solvent, and undergo a condensation reaction under the action of a catalyst to obtain 2,2-dimethylolpropionic anhydride Acid propynyl alcohol ester;

[0057] b) Mix the propynyl 2,2-dimethylol propionate obtained in step a) with a small molecule hydrophobic compound in an organic solvent, and under the action of a catalyst and a condensing agent, a condensation reaction occurs to obtain 2,2 -Small molecule hydrophobic compound modified by propynyl dimethylol propionate; the small molecule hydrophobic compound is selected from C6~C40 carboxylic acid, C6~C40 substituted carboxylic acid, carboxylated cholesterol or cholic acid.

[0058] c) Provide azide PAMAMG1~G3, mix with the small molecular hydrophobic compound...

Embodiment 1

[0098] Synthesis of isopropylidene-2,2-dimethoxypropionic acid:

[0099] Weigh 50.000g of 2,2-dimethylolpropionic acid, 3.550g of 4-toluenesulfonic acid monohydrate, and 69.0mL of 2,2-dimethoxypropane. 250.0 mL of acetone was added. Stir at room temperature for 2 hours. Then add about 5 mL of ammonia / ethanol (50:50) mixed solution into the reaction flask. The solvent was spin-dried at room temperature. Then it was dissolved with 250.0 mL of dichloromethane, and extracted twice with 20 mL of water once. The resulting organic phase was obtained using anhydrous MgSO 4 After drying, filter with a G4 sand core funnel and spin dry, vacuumize the oil pump for 8 hours to obtain white crystals of isopropylidene-2,2-dimethoxypropionic acid. The yield was 95%.

Embodiment 2

[0101] Synthesis of isopropylidene-2,2-dimethoxypropionic anhydride:

[0102] Weigh 30.000 g of isopropylidene-2,2-dimethoxypropionic acid, dissolve it in 150.0 mL of dichloromethane, then add 17.800 g of DCC, and stir at room temperature for 24 hours. After stopping the reaction, use a G4 sand core funnel to remove the insoluble matter by filtration. After rotary evaporation, use an oil pump to vacuum for 8 hours to obtain a yellow oily product, isopropylidene-2,2-dimethoxypropionic anhydride. The yield was 91%.

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Abstract

The invention provides a cationic lipoid plastid presented as formula I, wherein R is a substituent presented as formula II, III, IV and V, R' is C6-C40 of alkyl, C6-C40 of substituted alkyl, a cholesterol group or a cholic acid group. The novel cationic lipoid plastid takes PAMAM as a hydrophilic head and takes two hydrophobic chain sections as a hydrophobic tail, is good in biocompatibility and degradable, and provided with excellent properties of the PAMAM and lipoid plastid simultaneously. The invention further provides a preparation method of the cationic lipoid plastid presented as formula I. The method is high in generality, a plurality of compounds in similar structures can be obtained through the method, and a methodology platform is provided for studying the structure property relations of the compounds.

Description

technical field [0001] The invention relates to the field of polymer preparation, in particular to a cationic liposome and a preparation method thereof. Background technique [0002] Liposomes, also known as vesicles, are self-assembled bodies of lipid molecules in aqueous phase. It contains one or more lipid bilayer membranes, in each bilayer membrane structure, the hydrophobic parts of the lipid molecules are bound together by hydrophobic interactions, and the polar hydrophilic parts are directed towards the aqueous phase in the environment. [0003] Lipid molecules used in the preparation of liposomes include natural lipids and synthetic lipids. Most of their molecular structures have a common feature, that is, they are composed of two hydrophobic tail chains and a hydrophilic polar head. Liposomes are widely used in the medical field due to their special structure. It can be used as a substitute for human blood by encapsulating hemoglobin, as a vaccine adjuvant, as a ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G69/48
Inventor 肖春生张羽丁建勋贺超良庄秀丽陈学思
Owner CHANGZHOU INST OF ENERGY STORAGE MATERIALS &DEVICES
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