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Safe and efficient degradable lipid nanoparticles as well as preparation method and application thereof

A technology selected from and compounds, applied in the field of degradable lipid nanoparticles and its preparation, can solve the problems of the effective delivery of nucleic acids with physical and chemical stability

Pending Publication Date: 2022-07-29
SUZHOU TIANLAN BIOMATERIAL TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] In addition, the raw materials and components of LNP will affect the physicochemical stability of nucleic acid-LNP and the efficient delivery of nucleic acid

Method used

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  • Safe and efficient degradable lipid nanoparticles as well as preparation method and application thereof
  • Safe and efficient degradable lipid nanoparticles as well as preparation method and application thereof
  • Safe and efficient degradable lipid nanoparticles as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

preparation example Construction

[0068] The reaction formula of the preparation of degradable lipid nanoparticles of the present invention is as follows:

[0069]

[0070] It should be noted that the above reaction formula is just a Michael addition reaction between a typical double bond chemical (II) and an NH-containing structure (B-AH). When A or B additionally contains NH or B is H, the reaction occurs and follows the reaction mechanism here.

Embodiment 1

[0073] The synthesis of Lipidoid 53 includes the following steps:

[0074]

[0075] 6-Hydroxyhexyl acrylate (17.2 g, 0.1 mol), octanoic acid (17.3 g, 0.12 mol), EDC HCl (21.5 g, 0.12 mol), 4-dimethylaminopyridine (DMAP, 1.46 mol) were added to a round-bottomed flask. g, 0.012 mol) 300 mL of dichloromethane, and the reaction was stirred at room temperature for 12 hours. After the reaction, washed with dilute hydrochloric acid solution (1 wt %, 300 mL×2), water (300 mL×2) and saturated sodium bicarbonate solution (300 mL×2) successively. The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure to obtain a crude product. The crude product was purified by column chromatography (SiO 2 , n-hexane:dichloromethane=1:0 to 0:1) and purified to give compound 2 (20.8 g, 70%) as a yellow oil.

[0076] A (17.9 g, 0.06 mol) and diethylenetriamine (1.03 g, 0.01 mol) were sequentially added to a round-bottomed flask, and the reaction was stirred a...

Embodiment 2

[0078] The synthesis of Lipidoid 41 includes the following steps:

[0079]

[0080] 4-Hydroxybutylacrylamide (14.3g, 0.1mol), nonanoic acid (19g, 0.12mol), EDC HCl (21.5g, 0.12mol), 4-dimethylaminopyridine (DMAP, 1.46 g, 0.012 mol) 300 mL of dichloromethane, and the reaction was stirred at room temperature for 12 hours. After the reaction, washed with dilute hydrochloric acid solution (1 wt %, 300 mL×2), water (300 mL×2) and saturated sodium bicarbonate solution (300 mL×2) successively. The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure to obtain a crude product. The crude product was purified by column chromatography (SiO 2 , dichloromethane:methanol=1:0 to 5:1) was purified to give compound 2 (20.2 g, 71%) as a yellow oil. Then, A (13.7 g, 0.048 mol) and amino-tripolyethylene glycol (1.48 g, 0.01 mol) were sequentially added to the round-bottomed flask, and the reaction was stirred at 80°C for 48 hours. After the reaction...

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Abstract

The invention relates to safe and efficient degradable lipid nanoparticles, ionizable lipidosome containing the same, a preparation method of the safe and efficient degradable lipid nanoparticles and application of the safe and efficient degradable lipid nanoparticles in drug delivery.

Description

Technical field [0001] The present invention relates to the fields of biomedicine and biotechnology, and specifically to a safe and efficient degradable lipid nanoparticle and its preparation method and application. Background technique [0002] It is difficult for exogenous biomolecules and some drug molecules to penetrate the cell membrane and reach the cytoplasm to achieve therapeutic effects. Nucleic acid molecules (such as DNA and RNA) are a type of highly negatively charged biomolecules that must overcome the barrier of the cell membrane before they can be translated into the body and perform their intended functions and effects. Therefore, the therapeutic applications of this type of biomolecules are highly effective in the body. Delivery is an important challenge. [0003] Nucleic acids are essentially DNA or RNA molecules formed by the arrangement and combination of A, G, C, and T (U). RNA molecules can regulate protein expression properties in the body, making th...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C237/08C07C229/16C07D211/32C07D295/13C07D295/15C07C227/08C07C231/12A61K48/00A61K9/51A61K47/18A61K47/22
CPCC07C237/08C07C229/16C07D211/32C07D295/13C07D295/15A61K48/0033A61K48/005A61K9/5123
Inventor 熊必凤
Owner SUZHOU TIANLAN BIOMATERIAL TECH CO LTD
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