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Ceramide compound as well as cationic liposome, preparation method and application thereof

A technology of cationic liposomes and ceramides, applied in the field of biomedicine, can solve problems that have not been reported before, and achieve the effects of good passage, strong targeting, and strong fat solubility

Active Publication Date: 2021-07-16
ZHEJIANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Past studies have proposed using short- and medium-chain fatty acids as materials to prepare liposomes, but using this new type of ceramide as the main membrane material to construct cationic liposomes as delivery carriers for nucleic acid drugs has rarely or hardly been used so far. reported

Method used

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  • Ceramide compound as well as cationic liposome, preparation method and application thereof
  • Ceramide compound as well as cationic liposome, preparation method and application thereof
  • Ceramide compound as well as cationic liposome, preparation method and application thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0064] The preparation of embodiment 1 ceramide

[0065] 0.15 g of 10-hydroxyoctadecanoic acid (0.5 mmol) was dissolved in 5 mL of dichloromethane, 0.848 g of Dess-Martin oxidant (DMP, 2 mmol) and 0.84 g of sodium bicarbonate (10 mmol) were added. The mixed solution was stirred overnight at room temperature (25±5°C). Add 20 mL of saturated sodium thiosulfate to the mixed solution and continue to stir for 2 hours, then extract with ethyl acetate, dry the organic phase over anhydrous magnesium sulfate, concentrate under reduced pressure, and separate and purify the crude product by flash column chromatography to obtain 10-carbonyl octadecanoic acid ;

[0066] Collect 0.15 g of 10-carbonyl octadecanoic acid (0.5 mmol), dissolve it in 5 mL of methanol, then add 0.616 g of ammonium acetate (8 mmol), and react at room temperature for 1.5 hours. Add 0.24g sodium cyanoborohydride (5mmol) to the mixed solution, stir for 2 days, then extract with ethyl acetate, dry the organic phase o...

Embodiment 2

[0071] The preparation of embodiment 2 ceramide

[0072] 0.15 g of 10-hydroxyoctadecanoic acid (0.5 mmol) was dissolved in 5 mL of chloroform, 0.424 g of Dess-Martin oxidizer (DMP, 1 mmol) and 1.68 g of sodium bicarbonate (20 mmol) were added. The mixed solution was stirred overnight at room temperature. Add 5.772 mL of saturated sodium thiosulfate to the mixed solution and continue to stir for 3 hours, then extract with ethyl acetate, dry the organic phase over anhydrous magnesium sulfate, concentrate under reduced pressure, and separate and purify the crude product by flash column chromatography to obtain 10-carbonyl octadecadeca Carbonic acid;

[0073] Collect 0.15 g of 10-carbonyl octadecanoic acid (0.5 mmol), dissolve it in 5 mL of isopropanol, then add 0.385 g of ammonium acetate (5 mmol), and react at room temperature for 1.5 hours. Add 0.288g sodium cyanoborohydride (6mmol) to the mixed solution, stir for 2 days, then extract with ethyl acetate, dry the organic phase...

Embodiment 3

[0078] The structure identification of embodiment 3 ceramide

[0079] Utilize nuclear magnetic resonance spectrum to measure the ceramide structure that embodiment 1 prepares, obtain corresponding proton nuclear magnetic resonance spectrum figure and carbon nuclear magnetic resonance spectrum figure, as figure 1 and 2 As shown, the ceramide has a structural formula shown in Formula I from the spectrogram results. The nuclear magnetic resonance spectroscopy determination method is a conventional technical means in the art, and will not be repeated here.

[0080] 1 H NMR (600MHz, CDCl 3 ): δ6.50(d, J=7.1Hz, 1H), 5.78(dt, J=15.1, 6.9Hz, 1H, H-5), 5.53(dd, J=15.1, 5.5Hz, 1H, H-4 ),5.31-5.38(m,2H),5.18(d,J=9.3Hz,1H),4.30-4.31(m,1H),3.90-3.97(m,3H),3.68-3.70(m,2H), 3.48(b,1H),2.23(t,J=7.5Hz,2H),2.15(q,2H),2.05(q,2H),2.01(q,4H),1.61-1.65(m,4H),1.42 -1.47(m,2H),1.26-1.36(m,64H),0.87-0.89(m,9H).

[0081] 13 C NMR (150MHz, CDCl 3 ): δ173.8, 173.0, 133.6, 130.0, 129.7, 129.1, 74...

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Abstract

The invention discloses a ceramide compound as well as a cationic liposome, a preparation method and application thereof. The invention provides a ceramide compound with a structure as shown in a formula I. The ceramide compound has the advantages of higher stability and fat solubility and capability of better passing through a skin cuticle. The cationic liposome based on the compound has the advantages of good homogeneity, stable and reliable quality, simple and convenient preparation process, capability of efficiently carrying and delivering nucleic acid, excellent transdermal performance and the like. Compared with a commercialized gene transfection reagent liposome 2000, the cationic liposome based on the ceramide compound has obviously low cytotoxicity and obviously improved gene transfection efficiency, and compared with a traditional liposome, the cationic liposome based on the ceramide compound can improve the endocytosis efficiency of a drug, has more excellent transdermal efficiency, and can be used as a novel lipid gene carrier functional reagent in transfection of nucleic acid drugs.

Description

technical field [0001] The invention belongs to the technical field of biomedicine, and specifically relates to a ceramide compound and cationic liposome, a preparation method and application thereof. Background technique [0002] With the development of molecular biology and the completion of the Human Genome Project, gene therapy has gradually become a treatment method for major diseases that seriously threaten human health, such as genetic diseases, malignant tumors, AIDS, and cardiovascular and cerebrovascular diseases. This method is to introduce normal genes or genes with therapeutic effects into target cells in a specific way to correct gene defects and finally achieve the purpose of treating diseases. Compared with traditional treatment methods, gene therapy can specifically treat target cells and has long-term efficacy. However, since exogenous genes are easily degraded in whole or in part by nucleases after entering cells, the expression efficiency of exogenous ge...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C237/22C07C231/14C07C231/02C07C231/12C07C233/49C07C227/04C07C227/18C07C229/08C07C51/373C07C59/185A61K9/127A61K47/18A61K47/28
CPCC07C237/22C07C231/14C07C231/02C07C231/12C07C227/04C07C227/18C07C51/373A61K9/127A61K47/28A61K47/186A61K47/18C07C59/185C07C229/08C07C233/49
Inventor 彭丽华王毛泽黄奕谕
Owner ZHEJIANG UNIV
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