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Cationic amino lipid as well as synthesis method and application thereof

An amino lipid and cation technology, applied in the field of cell transfection, can solve the problems of limiting the application range of liposome transfection reagents, high production and R&D costs, ineffective transfection, etc., so as to reduce production costs and improve production. rate, the effect of reducing the difficulty of the reaction

Active Publication Date: 2020-05-01
SOUTHEAST UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Many cell lines, especially primary cells such as stem cells, cannot be effectively transfected with most existing liposome reagents
[0006] 2. The synthesis is complex and expensive
Due to the current mainstream liposome transfection reagents often have extremely complex structures, their production and research and development costs are high, resulting in high prices of liposome transfection reagents, which greatly limits the use of liposome transfection reagents. Application range

Method used

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  • Cationic amino lipid as well as synthesis method and application thereof
  • Cationic amino lipid as well as synthesis method and application thereof
  • Cationic amino lipid as well as synthesis method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] A cationic amino lipid, the structural formula of the cationic amino lipid is as shown in formula (I),

[0028]

[0029] The synthetic method of above-mentioned cationic amino lipid comprises the following steps:

[0030] Step 1. propargylamine and lauryl mercaptan are added in the tetrahydrofuran solution with the mol ratio of 1:1.5, and the solution concentration of final reactant total amount is 30mg / mL, then add free radical photoinitiator, described free radical The photoinitiator is benzoin dimethyl ether, and the addition amount of the free radical photoinitiator is 1% of the total mass of the reactants. After purging nitrogen to remove oxygen, it is placed under ultraviolet light for 1h. The wavelength of ultraviolet light is 250nm, and the intensity is 3mW / cm. Obtain compound (II)

[0031] Step 2. Add dimethylaminoethyl acrylate to the solution that has been reacted in step 1. The mol ratio of dimethylaminoethyl acrylate and propargylamine is 1:1, and the...

Embodiment 2

[0033] A cationic amino lipid, the structural formula of the cationic amino lipid is as shown in formula (I),

[0034]

[0035] The synthetic method of above-mentioned cationic amino lipid comprises the following steps:

[0036] Step 1. Propargylamine and dodecyl mercaptan are added in the dichloromethane (DCM) solution with the molar ratio of 1:2, and the solution concentration of final reactant total amount is 500mg / mL, then add free radical photoinitiator , the free radical photoinitiator is benzoin dimethyl ether, and the addition amount of the free radical photoinitiator is 5% of the total mass of the reactants. After nitrogen deoxygenation, it is placed under ultraviolet light for 3h. The wavelength of ultraviolet light is 365nm, and the intensity Be 0.5mW / cm, obtain compound (II)

[0037] Step 2. Add dimethylaminoethyl acrylate to the solution that has been reacted in step 1. The molar ratio of dimethylaminoethyl acrylate and propargylamine is 2:1, and then add an...

Embodiment 3

[0039] A cationic amino lipid, the structural formula of the cationic amino lipid is as shown in formula (I),

[0040]

[0041] The synthetic method step of above-mentioned cationic amino lipid is as follows:

[0042] Step 1. Synthetic 2,3-bis(dodecyl sulfide)-propylamine (compound (II) ), 0.5mmol propargylamine and 1mmol dodecyl mercaptan were dissolved in 3mL THF (tetrahydrofuran), and then 5mg free radical photoinitiator benzoin dimethyl ether (DMPA) was added, and transferred to a 20mL glass vial, and nitrogen gas was removed After oxygenation for 5 minutes, place the glass bottle under 365nm UV light for 1 hour, and the reaction formula is as follows:

[0043]

[0044] Step 2. Add 1mmol dimethylaminoethyl acrylate to the glass vial after the reaction in step 1, stir evenly, add 0.1mmol alkaline substance 1,8-diazabicycloundec-7-ene, and stir overnight . Then the solution is poured into a 25mL single-necked flask, and THF (tetrahydrofuran) is evaporated to obtain...

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Abstract

The invention discloses cationic amino lipid as well as a synthesis method and application thereof, and belongs to the field of cell transfection. The structure of the cationic amino lipid is shown inthe specification. The synthesis reaction conditions are mild, the solvent selectivity is high, the reaction difficulty is greatly reduced, the yield is improved, the raw materials are simple and cheap, and the production cost is greatly reduced. The cationic amino lipid molecule provided by the invention has the characteristics of high efficiency and low toxicity, can achieve a good effect in serum, and greatly simplifies the operation steps of transfection.

Description

technical field [0001] The invention belongs to the field of cell transfection, and specifically relates to a cationic amino lipid and its synthesis method and application. Background technique [0002] Among all types of non-viral transfection reagents, liposome-based transfection reagents are recognized as the most effective. This is because liposome transfection reagents are easy to use and often highly efficient. Liposomes are artificially prepared spherical vesicles with a bilayer structure, which can fuse with other bilayers, such as cell membranes, to transport the molecules it wraps from the outside of the cell membrane to the inside of the cell. Due to their unique properties, liposomes are widely used for drug delivery. Liposomes can carry both hydrophilic molecules and hydrophobic molecules, which can be well combined with biologically active molecules, such as various drugs, nucleic acids, polypeptides, etc., and can deliver these substances into cells to regul...

Claims

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Application Information

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IPC IPC(8): C07C319/20C07C323/25C12N15/88
CPCC07C319/18C07C319/20C07C323/25C12N15/88
Inventor 杜鑫郭一君郭昊
Owner SOUTHEAST UNIV
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