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Stearyl 11-deoxyglycyrrhetinate, derivative, cantharidin liposome, preparation method and application

A technology of cantharidin lipid and stearyl ester, applied in the field of preparation, 11-deoxyglycyrrhetinic acid stearyl ester, derivatives, cantharidin liposome field, can solve problems such as restricting wide application, pseudoaldosteronism, etc. , achieve the effects of inducing apoptosis, inhibiting tumor cell proliferation, and facilitating storage

Active Publication Date: 2022-01-04
HUNAN UNIV OF CHINESE MEDICINE
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

For example, Wu Chao and others disclosed the use of glycyrrhetinic acid stearyl ester-3-O-galactoside to modify the cantharidin liposome Cantharidin liposomes, but stearyl glycyrrhetinate-3-O-galactoside is often accompanied by pseudoaldosteronism (manifested as edema, eczema, hypokalemia, etc. after long-term medication), limiting Its wide application in clinical

Method used

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  • Stearyl 11-deoxyglycyrrhetinate, derivative, cantharidin liposome, preparation method and application
  • Stearyl 11-deoxyglycyrrhetinate, derivative, cantharidin liposome, preparation method and application
  • Stearyl 11-deoxyglycyrrhetinate, derivative, cantharidin liposome, preparation method and application

Examples

Experimental program
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Effect test

Embodiment 1

[0057] Synthesis of stearyl 11-deoxyglycyrrhetinate: take 0.45g HgCl 2 , add 15mL of hydrochloric acid solution with a concentration of 1.2mol / L, fully shake to dissolve, then add 4.5g of uniformly ground zinc powder, shake fully for 5min, remove the water phase, and wash twice with 5mL of dioxane to obtain , set aside; take 0.45g of the prepared zinc amalgam in a 50mL round bottom flask, add 0.72g of stearyl glycyrrhetinate and 13.5mL of dioxane to fully dissolve it, and use an ice-water bath to control the temperature at about 10°C. Add 1.5mL of hydrochloric acid with a concentration of 12mol / L within 30min, keep stirring at 10°C to continue the reaction for 5h after the addition is complete, TLC indicates the end point, pour the reaction solution into about 100mL of distilled water to precipitate a white precipitate, filter it with suction, dry it, and purify it. have to.

Embodiment 2

[0059] Synthesis of 11-stearyl deoxyglycyrrhetinate: take by weighing 0.70 g of stearyl deoxyglycyrrhetinate obtained in Example 1, 2.1 g of succinic anhydride and 0.01 g of DMAP (4-dimethylaminopyridine) in a circle Add 20mL of anhydrous double-distilled pyridine to the bottom flask, heat to reflux at 106°C, and check the reaction process by TLC. After the reaction, pour the reaction solution into 200mL of distilled water to form a brown precipitate, filter it, dry and purify it.

Embodiment 3

[0061] Synthesis of 11-stearyl deoxyglycyrrhetinate-3-O-galactoside: Weigh 4 g of stearyl deoxyglycyrrhetinate obtained in Example 1, 3.3 g of bromoacetyl galactoside, and 3.8 g of silver oxide , 8.7g of dried gypsum, 0.4g of iodine, and 20ml of chloroform were placed in a 50ml round-bottomed flask, mixed thoroughly, and magnetically stirred at 15°C for 5h. During the reaction period, the reaction process was detected by TLC every 1 h (developing agent: ethyl acetate-petroleum ether=1:5; thin-layer plate: silica gel G plate; chromogenic agent: iodine) until the end of the reaction. Filter the reaction solution, rinse the filter residue twice with 20ml of chloroform, collect the filtrate and evaporate to dryness on a water bath at 60°C, and purify to obtain 11-deoxyglycyrrhetinic acid stearyl-3-O-bromoacetylgalactoside ; Take 0.5 g of pure stearyl 11-deoxyglycyrrhetinate-3-O-galactoside, add 60 ml of 5 mg / ml methanol-sodium methoxide solution, and stir magnetically at 30°C for ...

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Abstract

The invention discloses a 11-deoxyglycyrrhetinic acid stearyl ester, a derivative, a cantharidin liposome, a preparation method and an application, wherein the 11-deoxyglycyrrhetinic acid stearyl ester is directly synthesized glycyrrhetinic acid stearyl Adding zinc amalgam to the alcohol ester for deoxidation treatment, that is, first esterification and then deoxygenation treatment, 11-deoxy stearyl glycyrrhetinate is acylated with succinic anhydride to obtain 11-deoxy stearyl glycyrrhetinate, Reaction with bromoacetylgalactoside, etc. to obtain 11‑deoxyglycyrrhetinic acid stearyl ester‑3‑O‑galactoside; 3‑O‑galactoside-modified cantharidin liposome has good liver targeting, can reduce its adverse reactions, inhibit tumor cell proliferation, induce its apoptosis, enhance drug efficacy, and have a high liposome encapsulation efficiency .

Description

technical field [0001] The invention belongs to the technical field of drug carriers, and in particular relates to stearyl 11-deoxyglycyrrhetinate, derivatives, cantharidin liposomes, preparation methods and applications. Background technique [0002] Liposome, as a main carrier for drug passive targeting, is mainly phagocytized and further eliminated by non-parenchymal cells of the liver after intravenous administration, and rarely reaches hepatic parenchymal cells. In fact, most diseases related to the liver, such as liver cancer, hepatitis, and cirrhosis, mostly occur in parenchymal cells, which are important cells of the liver and most of the metabolic sites of the liver. Therefore, only by improving the targeting of liposomes in hepatic parenchymal cells can anticancer drugs play a better role. [0003] Cantharidin is an anti-cancer active ingredient contained in the insect Cantharidin of the Coleoptera Turnipaceae. It is an anti-tumor drug developed in my country. It ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07J63/00A61K31/56A61K47/54A61K47/69A61P35/00
CPCC07J63/008A61K31/56A61K47/554A61K47/6911A61P35/00
Inventor 夏新华杜可杨晶颜红周莉莉周容钟思雨袁礼彭颖唐颖楠邹蔓姝朱坤乔勇
Owner HUNAN UNIV OF CHINESE MEDICINE
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