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Solanesol derivative and preparation method and application thereof

A technology of solanesol derivatives, applied in the field of preparation of solanesol derivatives, can solve problems such as poor permeability of gastrointestinal mucosa, unstable chemical properties, and limited pharmacological activity, and achieve improved physical and chemical stability and good dilution Stability, effect of improving water solubility

Active Publication Date: 2017-07-18
HENAN UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Due to CoQ 10 Large molecular weight (863Da), strong fat solubility, poor water solubility (0.7ng / mL, 37°C) and other reasons lead to poor permeability of the gastrointestinal mucosa and poor absorption
And because of its unstable chemical properties to light, heat and oxides, CoQ 10 The low bioavailability in clinical application seriously limits the display of its pharmacological activity, and it is difficult to achieve the desired drug effect.

Method used

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  • Solanesol derivative and preparation method and application thereof
  • Solanesol derivative and preparation method and application thereof
  • Solanesol derivative and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] A solanesol derivative, the derivative structure is as follows:

[0033]

[0034] The synthetic route of above-mentioned solanesol derivative is as follows:

[0035]

[0036] Concrete synthetic steps are as follows:

[0037] (1) Weigh 4.0g SOL (solanesol) and 0.4g DMAP (4-dimethylaminopyridine) and dissolve them in about 25mL anhydrous CH 2 Cl 2 Medium, N 2 Under protection, drop 1.0 g of succinic anhydride and 1.0 mL of triethylamine in 15 mL of DMF into the aforementioned CH 2 Cl 2 Solution, react at room temperature for 48h, after the reaction, the reaction solution is transferred to the funnel, add 30mL distilled water to wash, let it stand, take CH 2 Cl 2 Layers were repeated twice, and the solvent was removed by rotary evaporation. Use petroleum ether:ethyl acetate=1:1 (v / v) as the mobile phase to pass through the silica gel column, TLC monitors the outflow of the product, spins the mobile phase to dryness, and vacuum-dries to obtain the light yellow ta...

Embodiment 2

[0040] A solanesol derivative, the derivative structure is as follows:

[0041]

[0042] The synthetic route of above-mentioned solanesol derivative is as follows:

[0043]

[0044] Concrete synthetic steps are as follows:

[0045] (1) Weigh 4.0g SOL (solanesol) and 0.4g DMAP (4-dimethylaminopyridine) and dissolve them in about 25mL anhydrous CH 2 Cl 2 Medium, N 2 Under protection, drop 1.0 g of succinic anhydride and 1.0 mL of triethylamine in 15 mL of DMF into the aforementioned CH 2 Cl 2 Solution, react at room temperature for 48h, after the reaction, the reaction solution is transferred to the funnel, add 30mL distilled water to wash, let it stand, take CH 2 Cl 2 Layers were repeated twice, and the solvent was removed by rotary evaporation. Use petroleum ether:ethyl acetate=1:1 (v / v) as the mobile phase to pass through the silica gel column, TLC monitors the outflow of the product, spins the mobile phase to dryness, and vacuum-dries to obtain the light yellow ...

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Abstract

The invention discloses a solanesol derivative and a preparation method and application thereof. The structure of the solanesol derivative is as shown in the formula, wherein n is smaller than or equal to 114 and greater than or equal to 45 and n is an integer. Through an experiment, SPGS can be self-assembled in a water solution to form a stable nano-micelle structure and the drug loading capacity on CoQ10 can each over 39%. The light stability inspection result of CoQ10 in a preparation shows that the residual amount of CoQ10 in an ethanol solution and a water solution is 54.35% and 28.25% separately after 24h light treatment; the content of the CoQ10 in a CoQ10-SPGC preparation obtained through SPGC entrapment can still reach over 88% of the initial amount; and the stability on light can be obviously improved through SPGC entrapment on the CoQ10. Pharmacokinetic experiments in SD rats show that the bioavailability of the CoQ10 can be improved to over three times that of a CoQ10 naked drug by a CoQ10-SPGC micelle preparation.

Description

technical field [0001] The invention belongs to the fields of medicinal polymer materials and biomedicine, and specifically relates to a solanesol derivative, a preparation method and an application thereof. Background technique [0002] coenzyme Q 10 (Abbreviated as: CoQ 10 ) is a fat-soluble, vitamin-like endogenous substance widely present in cells in the body, known as ubiquinone or ubiquinone ketone, which is a yellow crystalline powder, insoluble in water and methanol, slightly soluble in ethanol; easily soluble in Acetone, n-hexane, ether and other less polar solvents; and more sensitive to light and humidity. CoQ 10 It mainly exists in the body tissues with active metabolism, such as heart, muscle and immune tissue cells, and it exerts many physiological and biochemical functions. [0003] Scientific studies have shown that CoQ 10 In the body, it can: participate in the transfer of electrons in the mitochondrial respiratory chain, inhibit lipid peroxidation; pro...

Claims

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Application Information

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IPC IPC(8): C08G65/332A61K47/69A61K47/59A61K31/122A61K31/045
CPCA61K31/045A61K31/122C08G65/3322A61K2300/00
Inventor 宋仕永秦本凯潘洋洋侯甜甜吴晓贺郁惠敏
Owner HENAN UNIVERSITY
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