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Galactose-artemisinin and method for preparing same

A technology of galactose and artemisinin, which is applied in pharmaceutical formulations, sugar derivatives, medical preparations containing active ingredients, etc., can solve the problems of increasing reaction steps, products or environmental pollution, reducing reaction efficiency, etc. Activity, solving poor treatment selectivity, reducing the effect of toxic and side effects

Inactive Publication Date: 2008-11-19
CHONGQING UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In this process, in order to introduce the sugar ring into artemisinin in a targeted manner, the sugar group must first be protected and reacted. After the reaction is settled, deprotection is required, which increases the reaction steps and reduces the reaction efficiency. The rate is generally between 20-30%
At the same time, the downstream separation and purification is complicated, time-consuming and labor-intensive, and some solvents used in the reaction process, such as: acetone, dichloromethane, etc., will also pollute the product or the environment

Method used

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  • Galactose-artemisinin and method for preparing same
  • Galactose-artemisinin and method for preparing same
  • Galactose-artemisinin and method for preparing same

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0068] Example 1. Synthesis of receptors—reduction of artemisinin

[0069] Add 2.81g (0.01mol) artemisinin, 0.454g (0.012mol) NaHB 4 And 10mL of anhydrous methanol stirred at room temperature for 24h. The filtrate was distilled under reduced pressure to recover methanol. The residue was dissolved in 250 mL of water, then extracted three times with 50 mL of ethyl acetate, the organic layer was washed with a small amount of water, and the water washings and the water layer were combined. It was extracted with ethyl acetate, and the organic layers were combined. Evaporation of solvent, drying to obtain product - dihydroartemisinin;

Embodiment 2

[0070] Example 2. Synthesis of Donor——Preparation of UDP-Galactose

[0071] Dissolve 2.0 g of galactose in a 500 mL double-distilled water flask, and stir at a constant speed on a magnetic stirrer for 2 h. On a high-speed centrifuge at 12000rpm, centrifuge for 20min, and take the supernatant. Add 450mL of 0.4% galactose solution obtained in the previous step to 450mL of absolute ethanol, and stir gently; take out the milky white flocculent precipitate and put it in a flask, squeeze out excess water, add 450mL of deionized water, and stir until completely dissolved.

[0072] Take 20 mL of the reconstituted galactose solution, add different volumes of UDP respectively, and treat with 20 MHz, 36% ultrasonic wave for 30 min. Remove the free UDP in the solution, take 10 1.5mL Ep tubes, and add 1mL of the solution after ultrasonic treatment to each tube; turn on the vacuum centrifuge, set the temperature at 30°C, 1400rpm, and a vacuum of <20hPa, and place them in turn for 120min to...

Embodiment 3

[0073] Example 3. Enzyme-catalyzed synthesis process - preparation of galactose-artemisinin

[0074] see figure 1 . Dissolve 1.4107g (equivalent to 5mmol) of dihydroartemisinin in 50mmol / L sodium azide, add 10mmol of UDP-galactose, and 5μmol of galactose glycosyltransferase, and finally add pH7.4 phosphate buffer solution diluted to 10 mL. The entire solution was incubated at a constant temperature of 37° C. for 3 days at a rotational speed of 200 r / min. Then, fully dialyze with a dialysis bag in 50 mmol / L sodium azide, pH 7.4 phosphate buffer to remove unbound galactose molecules to obtain galactose-artemisinin (or glycosylated artemisinin).

[0075] The chemical name of the galactose-artemisinin is (3R, 5aS, 6R, 8aS, 9R, 12S, 12aR)-octahydro-3,6,9-trimethyl-3,12-oxo-12H- Pyrano[4,3-j]-1,2-benzodisepin-10-O-galactosyl, molecular formula C 21 h 34 o 10 , the molecular weight is 446.51, and the structural formula is:

[0076]

[0077] All samples were frozen in a -70...

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PUM

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Abstract

The invention relates to a galactose-arteannuin and a preparation method for the same. The preparation method comprises the following: (1) a step of preparing dihydro-arteannuin; (2) a step of preparing UDP-galactose; (3) a step of preparing the galactose-arteannuin. The invention adopts glycosyltransferase to catalyze the glycosylation reaction of the arteannuin with gentle conditions during a synthetic process, convenient operation, high product purity and higher yield. An elementary cell experiment verifies that: the galactose-arteannuin has better performance of inhibiting the activity of a tumor cell Hela than the parent substance of the arteannuin without any toxic and side effect on normal cells. The galactose-arteannuin prepared through the method is easy to prepare with a good pharmaceutical prospect.

Description

technical field [0001] The invention belongs to the field of bioengineering pharmaceuticals, and in particular relates to a galactose-artemisinin and a preparation method thereof. Background technique [0002] Enzyme-catalyzed synthesis is an indispensable biocatalytic method in modern organic synthesis. It can convert unprotected high-functional substrates under mild conditions and in an environmentally friendly manner to obtain highly regioselective and stereoselective products. The method has the advantages of simplifying the synthesis route, uncomplicated reaction products, easy separation and purification, avoiding the use of toxic substances and solvents in the synthesis process, and the like. Recent studies have shown that enzyme-catalyzed synthesis of vitamin A and glucuronic acid-linked conjugates can increase cancer chemopreventive activity or reduce toxicity compared with the parent compound. [0003] Artemisinin molecules have many chains, making artemisinin and...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07H17/04C12P19/60A61K31/7048A61P35/00
Inventor 陈国平任彦荣胡宗利
Owner CHONGQING UNIV
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