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A kind of novel cationic lipid and its preparation method and application

A technology of cationic lipids and solid lipids, applied in the chemical field, can solve the problems of high toxicity, affecting cell resistance to gene transfection, etc., achieve the effect of small particle size, improve the effect of gene therapy, and improve the stability

Inactive Publication Date: 2012-02-15
SHANDONG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, it has been reported that single-chain cationic lipids are more toxic than double-chain ones, affecting cell tolerance and gene transfection

Method used

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  • A kind of novel cationic lipid and its preparation method and application
  • A kind of novel cationic lipid and its preparation method and application
  • A kind of novel cationic lipid and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0052] Example 1. Synthesis of 6-(2,6-diamino-hexanoyloxy)hexyl dodecanoate (LHLN)

[0053] Weigh 15 g (about 0.1 mol) of lysine (Lys), add 200 mL (0.2 mol) of 1 mol / L sodium hydroxide to dissolve, add dropwise the amino protecting agent di-tert-butyl dicarbonate (Boc) dissolved in tetrahydrofuran under ice bath , control the pH value to 8-9, and stir the reaction at room temperature for 24 hours. After extraction, the water was evaporated under reduced pressure to obtain lysine (Boc-Lys) protected by di-tert-butyl dicarbonate. Weigh 35g (about 0.1mol) of lysine (Boc-Lys) protected by di-tert-butyl dicarbonate (Boc-Lys) and mix with 11.8g (0.1mol) of hexanediol, dissolve in anhydrous dichloromethane, add catalyst 4-dichloromethane under ice bath 2.44 g (0.02 mol) of methylaminopyridine (DMAP) and 22.66 g (0.11 mol) of dehydrating agent N, N'-dicyclohexylcarbodiimide (DCC), were stirred and reacted at room temperature for 24 hours. After extraction, the water was evaporated t...

Embodiment 2

[0056] Example 2. Synthesis of 6-(2,6-diamino-hexanoyloxy)hexyl myristate

[0057] Weigh 15 g (about 0.1 mol) of lysine (Lys), add 200 mL (0.2 mol) of 1 mol / L sodium hydroxide to dissolve, add dropwise the amino protecting agent di-tert-butyl dicarbonate (Boc) dissolved in tetrahydrofuran under ice bath , control the pH value to 8-9, and stir the reaction at room temperature for 24 hours. After extraction, the water was evaporated under reduced pressure to obtain lysine (Boc-Lys) protected by di-tert-butyl dicarbonate. Weigh 35g (about 0.1mol) of lysine (Boc-Lys) protected by di-tert-butyl dicarbonate (Boc-Lys) and mix with 11.8g (0.1mol) of hexanediol, dissolve in anhydrous dichloromethane, add catalyst 4-dichloromethane under ice bath 2.44 g (0.02 mol) of methylaminopyridine (DMAP) and 22.66 g (0.11 mol) of dehydrating agent N, N'-dicyclohexylcarbodiimide (DCC), were stirred and reacted at room temperature for 24 hours. After extraction, the water was evaporated to dryness...

Embodiment 3

[0060] Example 3. Synthesis of 8-(2,6-diamino-hexanoyloxy)octyl hexadecanoate

[0061] Weigh 15 g (about 0.1 mol) of lysine (Lys), add 200 mL (0.2 mol) of 1 mol / L sodium hydroxide to dissolve, add dropwise the amino protecting agent di-tert-butyl dicarbonate (Boc) dissolved in tetrahydrofuran under ice bath , control the pH value to 8-9, and stir the reaction at room temperature for 24 hours. After extraction, the water was evaporated to dryness under reduced pressure to obtain lysine (Boc-Lys) protected by di-tert-butyl dicarbonate (Boc). Weigh 35 g (about 0.1 mol) of lysine (Boc-Lys) protected by di-tert-butyl dicarbonate and mix with 14.6 g (0.1 mol) of octanediol, dissolve in anhydrous dichloromethane, add catalyst 4- Dimethylaminopyridine (DMAP) 2.44g (0.02mol) and dehydrating agent N,N'-dicyclohexylcarbodiimide (DCC) 22.66g (0.11mol) were stirred and reacted at room temperature for 24 hours. After extraction, the water was evaporated to dryness under reduced pressure. ...

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Abstract

The invention designs and synthesizes a novel single-chain cationic lipid, and uses it as a surfactant in the preparation of gene-loaded nanocarriers. It belongs to the field of chemical technology. The characteristic is that the single-chain cationic lipid with easy solubility, high efficiency and low toxicity is prepared by chemical synthesis method, the synthesis method is simple, and the product yield is high. And as a surfactant, it is applied to various carrier materials, and gene-loaded nanocarriers with uniform particle size, high drug loading, good stability and easy surface modification are prepared by various methods. The prepared gene-loaded nanocarrier acts on a variety of tumor cells, and all exhibit low cytotoxicity and high transfection efficiency. The lipid has good stability, high surface activity and good biodegradability, and can be used to prepare various gene-loaded cationic nanocarriers.

Description

technical field [0001] The invention relates to a novel single-chain cationic lipid, its preparation method and its application in gene-charged nano-carriers, and belongs to the field of chemical technology. Background technique [0002] Gene therapy is a hot spot in modern cancer treatment, and it is gradually becoming a reality. The main goal of gene therapy is the successful delivery of genetic material to target tissues, organs or cells. However, naked therapeutic genes are easily degraded by nucleases, showing poor cellular uptake efficiency. Therefore, the preparation of safe and efficient gene carriers has become a necessary condition for successful gene therapy. [0003] Viral vectors can effectively transfect genetic material into host cells, but they have many disadvantages, such as easy carcinogenesis, mutagenicity, and the possibility of inducing immune responses to make transgene expression disappear. Therefore, more and more people have turned their attentio...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C229/26C07C227/18C07C227/14A61K47/18A61K48/00A61P35/00
Inventor 张娜余汪洋徐文方
Owner SHANDONG UNIV