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Novel cation lipoid, preparation and use thereof

A cationic lipid and solid lipid technology, applied in the chemical field, can solve the problems of high toxicity, affecting cell resistance to gene transfection, etc., and achieve the effects of small particle size, improved gene therapy effect, and strong binding ability

Inactive Publication Date: 2009-07-08
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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  • Novel cation lipoid, preparation and use thereof
  • Novel cation lipoid, preparation and use thereof
  • Novel cation lipoid, preparation and use thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0052] Embodiment 1. the 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 to dryness under reduced pressure to obtain lysine (Boc-Lys) protected by di-tert-butyl dicarbonate. Weigh 35 g (about 0.1 mol) of lysine (Boc-Lys) protected by di-tert-butyl dicarbonate and mix with 11.8 g (0.1 mol) 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 ...

Embodiment 2

[0056] Embodiment 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 to dryness under reduced pressure to obtain lysine (Boc-Lys) protected by di-tert-butyl dicarbonate. Weigh 35 g (about 0.1 mol) of lysine (Boc-Lys) protected by di-tert-butyl dicarbonate and mix with 11.8 g (0.1 mol) 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...

Embodiment 3

[0060] Embodiment 3. Synthesis of hexadecanoic acid 8-(2,6-diamino-hexanoyloxy) octyl ester

[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 dissolved in tetrahydrofuran under ice bath (Boc), control pH value 8-9, stir 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 (Boc). Weigh 35g (Boc-Lys) of lysine (Boc-Lys) protected by di-tert-butyl dicarbonate and mix with 14.6g (0.1mol) 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. Then add 25.6 g (0.1 ...

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Abstract

The invention relates to a method for designing and synthesizing novel single-chain cationic lipids and application of the novel single-chain cationic lipids in preparing a nuclear gene nano-carrier by adoption of the novel single-chain cationic lipids as a surfactant. The method belongs to the technical field of chemistry, and is characterized in that the single-chain cationic lipids with easy dissolution, high efficiency and low toxicity are prepared by a chemical synthesis method; the synthesis method is simple; and the yield of products is high. Moreover, the novel single-chain cationic lipids are taken as the surfactant and applied in various carrier materials, and the nuclear gene nano-carrier which has uniform particle diameter, high drug loading amount and good stability, and is easy in surface modification is prepared by various methods. When acted on various tumor cells, the prepared nuclear gene nano-carrier shows lowcytotoxicity and high transfection efficiency. The lipids have good stability, high surface activity and good biodegradability, and can be used for preparing various nuclear gene nano-carriers.

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