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Ursolic acid and amine cyclodextrin clathrate compound

A technology of cyclodextrin and ursolic acid, which is applied in the field of pharmaceuticals, can solve the problems of low bioavailability and poor water solubility, and achieve the effects of overcoming poor water solubility, good stability and high safety

Inactive Publication Date: 2015-08-26
KUNMING UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Therefore, if the shortcomings of its poor water solubility and low bioavailability can be solved, it is expected to be used as a chemotherapeutic drug or chemotherapy combination drug in the prevention and treatment of tumors, and its application prospects are expected to be greatly improved.

Method used

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  • Ursolic acid and amine cyclodextrin clathrate compound
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  • Ursolic acid and amine cyclodextrin clathrate compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] Example 1: Preparation of inclusion compound of ursolic acid and mono-(6-ethylenediamino-6-deoxy)-β-cyclodextrin

[0027] (1) Preparation of single 6-OTs-β-CD

[0028] Take 210 g of β-cyclodextrin recrystallized with water, add it in batches to a three-necked bottle filled with 1300 mL of water, stir at room temperature, weigh 17.2 g of sodium hydroxide and dissolve it in 50 mL of water, and then slowly oxidize the hydroxide Sodium aqueous solution was added dropwise to the suspension of β-cyclodextrin until the reaction solution gradually became clear, and continued to stir for 1.5 h. After the cyclodextrin in the reaction solution was completely dissolved and became clear, acetonitrile containing 26.0 g of p-toluenesulfonyl chloride (80 mL) solution was slowly added dropwise to the reaction solution (dropped in about 30 minutes), continued to stir for 2 h, filtered off the insoluble matter, and the filtrate was adjusted to pH = 7.5 with 2 mol / L hydrochloric acid, at t...

Embodiment 2

[0034] Example 2: Preparation of inclusion compound of ursolic acid and mono-(6-diethylenetriamine-6-deoxy)-β-cyclodextrin

[0035] (1) The preparation method of single 6-OTs-β-CD is the same as step (1) of Example 1;

[0036] (2) Preparation of mono-(6-diethylenetriamine-6-deoxy)-β-cyclodextrin (DETA-β-CD)

[0037] Dissolve 3.0 g (2.3 mmol) of mono-6-OTs-β-CD in 20 mL of dry diethylenetriamine, stir at room temperature until completely dissolved, and react at 80°C for 10 h under nitrogen protection. After the reaction is completed, Slowly drop the reaction solution into 400 mL of acetone, stir at room temperature for 30 min, remove the filtrate by suction filtration, collect the white precipitate, dissolve the precipitate in a small amount of water, drop it into 300 mL of acetone again, stir for 0.5 h, and then suction filter The white precipitate was collected and dried in a vacuum oven. The resulting solid powder was ground and added to 200 mL of ethanol. After ultras...

Embodiment 3

[0041] Example 3: Preparation of inclusion compound of ursolic acid and mono-(6-amino-6-deoxy)-β-cyclodextrin

[0042] (1) The preparation method of single 6-OTs-β-CD is the same as step (1) of Example 1;

[0043] (2) Single-6-N 3 -β - Preparation of CDs

[0044] Accurately weigh 10 g (8 mmol) of mono-6-OTs-β - CD was dissolved in 35 mL DMF, followed by the addition of 1.5 g NaN 3 Stir well, heat the reaction at 75°C for 12 h, and check whether the raw material is completely reacted by TLC. After the reaction was complete, the reaction solution was slowly added dropwise to 400 mL of acetone, stirred at room temperature, and suction filtered to obtain a white solid. The obtained white crude product was dried for 24 hours and then uniformly placed in 400 mL of acetone, followed by ultrasonication for 10 min and suction filtration to obtain Pure mono-6-N 3 -β - CD, 90% yield. The product is characterized as follows: 1 H NMR (500 MHz, D 2 O, δ ppm): 5.77(s, 14H, 2, 3-OH...

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Abstract

The invention discloses a ursolic acid and amine cyclodextrin clathrate compound. The amine cyclodextrin is an amino-substituted beta-cyclodextrin, and can generate clathration with ursolic acid; and the amino on the amine cyclodextrin and the carboxyl on ursolic acid can produce ionic interaction, thus greatly improving the water solubility of ursolic acid, and facilitating the formation of a liquid ursolic acid preparation. The clathrate compound prepared by the method provided by the invention has good water-solubility, good stability, and good anti-tumor activity in vitro. Meanwhile, the preparation method is simple, mild in conditions and easy to operate, can be used to develop novel ursolic acid preparation and has important practical value.

Description

technical field [0001] The invention belongs to the technical field of pharmacy and relates to an inclusion compound of ursolic acid and amine cyclodextrin. Background technique [0002] Ursolic acid (as shown in formula Ⅱ) is called Ursolic acid in English, referred to as UA, also known as ursolic acid and ursolic acid. It is a natural pentacyclic triterpenoid compound, which is widely derived from a variety of plants, such as Leaves of privet of Oleaceae, whole plant of Prunella vulgaris of Labiatae, leaves and fruits of bearberry of Rhododendron, leaves of loquat of Rosaceae, etc.; [0003] [0004] Modern pharmacological studies have shown that ursolic acid has a variety of important biological activities, such as sedative, anti-inflammatory, antibacterial, anti-diabetic, anti-ulcer, liver protection, blood lipid lowering and antioxidant functions. At the same time, ursolic acid has also attracted much attention in its anti-tumor effect. Scholars at home and abro...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A61K31/56A61K47/48A61P35/00A61P35/02
Inventor 廖霞俐高凯牛绕梅杨铜泽杨波杨健
Owner KUNMING UNIV OF SCI & TECH
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