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Propylene glycol amine derivate cationic liposome nano particles and preparation method thereof

A cationic liposome and nanoparticle technology, applied in the directions of liposome delivery, genetic material components, pharmaceutical formulations, etc., can solve the problems of low toxicity of non-viral vectors, easy to cause immune response, poor safety, etc., and achieve simple synthesis operation. , the preparation cost is low, the surface charge is moderate

Active Publication Date: 2012-07-04
湖南远泰生物技术有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] At present, there are two types of vectors used in gene therapy: viral vectors and non-viral vectors. Among them, viral vectors are highly efficient but easily cause immune reactions, and their safety is poor, while non-viral vectors have low toxicity and relatively low efficiency. Improving the efficiency of non-viral vectors has become the current research direction of gene therapy vectors

Method used

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  • Propylene glycol amine derivate cationic liposome nano particles and preparation method thereof
  • Propylene glycol amine derivate cationic liposome nano particles and preparation method thereof
  • Propylene glycol amine derivate cationic liposome nano particles and preparation method thereof

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Experimental program
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Embodiment 1

[0028] Embodiment 1. Preparation of propylene glycol amine derivative cationic liposome TMA-Apd-C12 nanoparticles:

[0029]Add epichlorohydrin (23.6 g, 260.0 mmol), p-toluenesulfonic acid monohydrate (0.10 g, 0.58 mmol) and water (20 mL) successively into a 100 mL round bottom flask, and reflux the reaction. TLC (petroleum ether: ethyl acetate = 1:1) detected that after 6 hours of reaction, there was no significant change in the reaction, the reaction was stopped, cooled to room temperature, the reaction solution turned bright yellow, and concentrated. After separation by column chromatography (eluent: petroleum ether: ethyl acetate = 2: 1), 3-chloro-1,2-propanediol was obtained as a colorless liquid

[0030]

[0031] To a 50 mL round bottom flask was added 3-chloro-1,2-propanediol (2.6 g, 24.0 mmol) and water (15 mL). The reaction mixture was cooled to 0°C with an ice-water bath, and sodium hydroxide (5.0 g, 120.0 mmol) was slowly added with stirring. After the addit...

Embodiment 2

[0038] Embodiment 2. Preparation of propylene glycol amine derivative cationic liposome HEDMA-Apd-C12 nanoparticles:

[0039] Add 2,3-di-n-dodecyloxy-1-( N , N -Dimethyl)propylamine (0.3 g, 0.7 mmol) and acetonitrile (20 mL), added bromoethanol (0.4 g, 3.5 mmol) dropwise with stirring, and refluxed for 12 h. TLC (ethyl acetate) detection showed that the reaction of raw materials was basically complete. Concentrate to obtain a yellow solid, which is dissolved in ethyl acetate, cooled to room temperature, and a white solid precipitates out, filtered to obtain a white solid bromide 2,3-di-n-dodecyloxy-1-( N , N -Dimethyl- N -(2-Hydroxyethyl))propylammonium

[0040]

[0041] Take bromide 2,3-di-n-dodecyloxy-1-( N , N -Dimethyl- N -(2-Hydroxyethyl))propylammonium (5.8 mg, 0.01 mmol) was dispersed with double-distilled water (10 mL) by ultrasonic waves to obtain cationic liposome HEDMA-Apd-C12 nanoparticles, measured by Zetasizer Nano ZS instrument Average particle size...

Embodiment 3

[0042] Embodiment 3. Preparation of propylene glycol amine derivative cationic liposome TMA-Apd-C8 nanoparticles:

[0043] Add to a 50 mL round bottom flask N , N -Dimethylamino-1,2-propanediol (2.3 g, 20.4 mmol ) and tetrahydrofuran (40 mL). The reaction mixture was cooled to 0°C with an ice-water bath, and sodium hydride (2.0 g, 81.6 mmol) was slowly added in batches while stirring. After the addition was complete, the temperature of the reaction mixture was raised to normal temperature, and the ice-water bath was removed. Slowly add n-octyl bromide (7.9 g, 40.8 mmol) dropwise, and reflux for 24 h. TLC (ethyl acetate) detection showed that the reaction of raw materials was basically complete. Concentrate, extract with water and ethyl acetate, dry the organic phase over anhydrous sodium sulfate, filter and concentrate. The residue was separated by column chromatography (eluent: petroleum ether: ethyl acetate=1:1) to obtain bright yellow liquid 2,3-di-n-octyloxy-1-( N , ...

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Abstract

The invention discloses propylene glycol amine derivate cationic liposome nano particles and a preparation method thereof. The nano particles are iodated 2,3-dialkoxy-1-(N,N,N-trimethyl)propanaminium or bromized 2,3-dialkoxy-1-(N,N-dimethyl-N-(2-hydroxyethyl))propanaminium, wherein the alkoxy includes n-octyloxy, n-dodecyloxy, n-myristyloxy, n-hexadecyloxy and n-octadecyloxy. The propylene glycol amine derivatecationic liposome nano particles have the advantages of good structural stability, moderate particle size, narrow particle size distribution, moderate surface charges, low preparation cost and the like, can meet the basic requirements of a DNA (deoxyribonucleic acid) transfer carrier, and have potential in combining and transferring gene medicines through electrostatic effect.

Description

technical field [0001] The invention relates to a propylene glycol amine derivative cationic liposome nanoparticle and a preparation method thereof. Background technique [0002] With the advancement of life science technology and the development of bioengineering, nucleic acid and nucleic acid derivatives are widely used in the treatment of some major diseases such as cancer, cardiovascular disease, leukemia, AIDS, etc. due to their unique pharmacological effects. The core of nucleic acid drug therapy is to introduce nucleic acid drugs into specific cells and maintain their functions stably. However, due to the barrier of cell membranes, it is difficult for nucleic acid drug molecules to be directly transferred into cells. Even if nucleic acid drugs are transferred into cells, there are many problems such as virus recombination, carcinogenesis, immunity, etc., and their safety cannot be guaranteed; at the same time, nucleic acid drugs such as antisense nucleic acid,...

Claims

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Application Information

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IPC IPC(8): A61K9/127A61K9/14A61K47/18A61K48/00
Inventor 向双林曾佑林张健赵春艳刘珊刘美艳苏胜培曾盈胡翔
Owner 湖南远泰生物技术有限公司
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