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Water-soluble coenzyme Q 10 compound and preparation method thereof

A complex, water-soluble technology, applied in the field of water-soluble coenzyme Q10 complex and its preparation, to achieve the effect of improving solubility

Inactive Publication Date: 2012-10-10
YUNNAN NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

But so far, there has been no report on the inclusion of coenzyme Q10 molecules with polyamine-modified cyclodextrins to obtain solid-state complexes

Method used

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  • Water-soluble coenzyme Q 10 compound and preparation method thereof
  • Water-soluble coenzyme Q 10 compound and preparation method thereof
  • Water-soluble coenzyme Q 10 compound and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] Example 1. The complex of mono-[6-(diethylenetriamine)-6-deoxy]-β-cyclodextrin and coenzyme Q10 involved in the present invention is prepared as follows:

[0026] 1) For the synthetic route of mono-[6-(diethylenetriamine)-6-deoxy]-β-cyclodextrin, see Figure 5 . (Synthesized according to literature, I.Tabushi, N.Shimizu, T.Sugimoto, M.Shiozuka, K.Yamamura, J.Am.Chem.Soc.1977,99,7100; I.Tabushi, N.Shimizu, Jpn.Kodai Tokkyo Koho 78 102 985, 1978 [Chem. Abstr., 1979, 90, 39196b])

[0027]Into a 100mL dry round-bottomed flask, add 40mL of diethylenetriamine purified by distillation, add 5.0g of mono-(6-oxo-6-p-toluenesulfonyl)-β-cyclodextrin while stirring, protect with nitrogen, and dissolve Raise the temperature to about 76°C and react for 7 hours, then distill off most of the diethylenetriamine under reduced pressure, add the remaining liquid to acetone, collect the precipitate by suction filtration, repeat the operation once, and replace the acetone with absolute eth...

Embodiment 2

[0043] Example 2. The preparation method of water-soluble coenzyme Q10 complex is:

[0044] 1) Dissolve coenzyme Q10 in tetrahydrofuran, and then add the obtained solution to mono-[6-(diethylenetriamine)-6-deoxy]-β-cyclodextrin aqueous solution, and the input coenzyme Q10 and the input mono- The molar ratio of [6-(diethylenetriamine)-6-deoxy]-β-cyclodextrin is 1:1.

[0045] The solution was sealed and stirred at 20°C for 4 days to react;

[0046] 2) Remove tetrahydrofuran by evaporation, remove coenzyme Q10 that does not participate in inclusion by suction filtration, and evaporate the resulting filtrate to dryness to obtain brownish-red crystals, which are dried in vacuo to obtain mono-[6-(diethylenetriamine)-6-deoxy] - Complex of β-cyclodextrin and coenzyme Q10. The weight ratio of coenzyme Q10 to mono-[6-(diethylenetriamine)-6-deoxy]-β-cyclodextrin in the obtained complex is 1:1.4.

[0047] All the other are with embodiment 1.

Embodiment 3

[0048] Embodiment 3: The preparation method of water-soluble coenzyme Q10 complex is: dissolving coenzyme Q10 in tetrahydrofuran, then adding mono-[6-(diethylenetriamine)-6-deoxy]-β-cyclodextrose to the resulting solution In the refined aqueous solution, the molar ratio of the input coenzyme Q10 to the input mono-[6-(diethylenetriamine)-6-deoxy]-β-cyclodextrin is 1:3. Stir at 38°C for 2 days for the reaction ; All the other are with embodiment 2.

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Abstract

The invention relates to a water-soluble coenzyme Q10 compound and a preparation method thereof, belonging to the technical field of fine chemical industry. The product is a compound of mono-[6-dithylenetriamine]-6-deoxizing]-beta-cyclodextrin and coenzyme Q10. The preparation method comprises the following steps of: (1) dissolving the coenzyme Q10 in tetrahydrofuran, adding the obtained solutionto a mono-[6-dithylenetriamine]-6-deoxizing]-beta-cyclodextrin water solution, and stirring for 2-4 days at 20-40 DEG C for reacting, wherein the molar ratio of the poured coenzyme Q10 to the poured mono-[6-dithylenetriamine]-6-deoxizing]-beta-cyclodextrin is 1: 1-1: 3; and (2) evaporating to remove the tetrahydrofuran, filtering to remove the coenzyme Q10 which does not participate in inclusion,evaporating the obtained filtrate to dryness to obtain crystals and drying in vacuum. In the invention, a solid compound obtained through preparing by adopting a supermolecular method and separating can rapidly dissolve in water so that the water solubility of the coenzyme Q10 is improved to 1.52mg / mL from the original 8.0*10-5mg / mL, with 19,000 times of solubilization. The compound prepared by adopting the preparation method disclosed by the invention can be used as a substitute of the coenzyme Q10 to be applied to clinic, and a new water-soluble controlled-release compound is provided for clinical trial of the coenzyme Q10.

Description

technical field [0001] The invention relates to a water-soluble coenzyme Q10 complex and a preparation method thereof, belonging to the technical field of fine chemicals, and in particular to the preparation of coenzymes by using mono-[6-(diethylenetriamine)-6-deoxy]-β-cyclodextrin functional molecules Water-soluble complex of Q10. The water-soluble coenzyme Q10 complex can solubilize and slow-release coenzyme Q10, thereby enhancing and prolonging the drug effect. Background technique [0002] The structure of coenzyme Q10(1) is shown below, and its chemical name is 2,3-dimethoxy-5-methyl-6-decisopentenylbenzoquinone (2,3-Dimethoxy-5-methyl-6- decaprenyl-1,4-benzoquinone), is a quinone ring compound. In 1940, Moore et al. discovered that coenzyme Q10 is a kind of fat-soluble quinone compound with common characteristics with vitamins. It widely exists in the mitochondria of cells such as animals, plants, and microorganisms, and can transport electrons in various biological ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08B37/16A61K31/122A61K47/48A61P9/04A61P9/10A61P31/12A61P11/00A61P11/06A61P39/06A61P35/00A61K47/61
Inventor 赵焱朱洪友顾娟赵勇迟绍明李琮刘剑虹
Owner YUNNAN NORMAL UNIV
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