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Cholesterol pyrophosphate, and preparation method and use thereof

A pyrophosphorylated cholesterol and chemical structural formula technology, which is applied in the field of medicine, can solve problems affecting human health, achieve the effect of improving treatment effect and improving research progress

Active Publication Date: 2018-02-02
SOUTHWEST MEDICAL UNIVERISTY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Studies have found that an appropriate amount of cholesterol is of great significance to maintaining the normal physiological functions of the human body, but excessive accumulation of cholesterol in the body will also affect the health of the human body itself

Method used

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  • Cholesterol pyrophosphate, and preparation method and use thereof
  • Cholesterol pyrophosphate, and preparation method and use thereof
  • Cholesterol pyrophosphate, and preparation method and use thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0039] 1. At 0°C, dissolve cholesterol (1.933g, 5mmol) in 40mL of anhydrous dichloromethane, then slowly add triethylamine (1.125mL, 7.5mmol), DMAP (60mg, 0.5mmol), and finally slowly add Tosyl chloride (1.43g, 7.5mmol), stirred overnight at room temperature. Wash twice with 1mol / L hydrochloric acid, 40mL each time, and wash twice with saturated NaCl solution, 40mL each time. An appropriate amount of anhydrous Na was added to the organic layer 2 SO 4 dry. The organic solvent was evaporated by vacuum rotation. Pass through a silica gel column (petroleum ether: ethyl acetate 4:1).

[0040] 2. Product 2, (2.16g, 4mmol) was dissolved in 30mL of dry dioxane, and (15mL, 111mmol) triethylene glycol was added. (TLC identification of reaction endpoints). The organic solvent was evaporated, the reactant was dissolved in 50mL chloroform, saturated NaHCO 3 The solution was extracted twice, 50mL each time, and washed twice with saturated NaCl solution, 50mL each time. Appropriate a...

Embodiment 2

[0050] (1), 2,2-bis-(bromomethyl)propane-1,3-diol and an appropriate amount of sodium azide were dissolved in dimethylformamide, stirred overnight at 120°C, filtered, and the organic solvent was removed, the residue The standard ether / NaCl aqueous solution was extracted, the crude product was passed through a silica gel column, and eluted with chloroform:methanol=20:1, and further purified with bromoacetic acid (1:1.3, mol / mol) by adding an appropriate amount of anhydrous di in methyl chloride. Add 1.1 equivalents of dicyclohexylcarbodiimide (DCC) and 0.1 equivalents of 4-dimethylaminopyridine (DMAP) to the above solution at zero temperature, stir at room temperature for 4 hours, filter, evaporate to dryness under reduced pressure, and pass through a silica gel column (cyclohexane: Ethyl acetate 3:1) to obtain product 1.

[0051] (2), 1 equivalent of potassium tri(tetrabutylammonium) hydrogen pyrophosphate and 10.5 equivalents of the crude product were dissolved in an appropr...

Embodiment 3

[0059] The synthetic route is as follows:

[0060]

[0061] Synthesis of Bis-L-Phosphoserine Polypropylene Glycol Ethylene Oxide Polymer (a) and Pyrophosphate Polypropylene Glycol Ethylene Oxide Polymer (b)

[0062] Targeting HA kinetics in vitro:

[0063] Targeting kinetics of tooth-targeting polymeric micelles on HA with Figure 4 It can be seen that the targeting ability of tooth-targeting polymeric micelles (DPS-TBM) prepared with bis-L-phosphoserine polypropylene glycol ethylene oxide addition polymer is not as good as that of pyrophosphate polypropylene glycol ethylene oxide addition polymer. Teeth-targeting polymeric micelles (PPi-TBM) prepared from

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Abstract

The invention discloses a cholesterol pyrophosphate, and a preparation method and a use thereof. Cholesterol and pyrophosphate are connected through click chemistry, and the targeting auxiliary material cholesterol pyrophosphate (PPi-Chol) having strong affinity to bones is prepared through combining the wide application of the cholesterol in a medicinal preparation with the bone targeting property of the pyrophosphate, so the studying process of the bone targeting dosage form is greatly improved, and the therapy effect of bone related diseases is improved.

Description

technical field [0001] The invention relates to the technical field of medicine, in particular to pyrophosphorylated cholesterol and its preparation method and application. Background technique [0002] Click chemistry refers to a group of reactions with fast reaction, simple operation, easy purification, flexible reaction, good alignment and high product yield. Such as azidation 1,3-dipolar cycloaddition reaction, terminal alkyne dipolar cycloaddition reaction, etc. It is widely used in materials science, polymer chemistry, and medical science, such as bioconjugation, surface modification of nanoparticles, and polymer chemistry related to pharmaceuticals. [0003] Since it was first proposed by Dr. Barry Sharpless's team at the 217th Annual Meeting of the American Chemical Society in 1999, click chemistry has become a very hot topic, and the corresponding publications have grown almost exponentially. Statistics by SciFinder on December 31, 2007 A literature search perfo...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07J51/00A61P19/08C08G65/327C08G65/335C08G73/06
CPCC07J51/00C08G65/327C08G65/3356C08G73/0605C08G2650/04C08G2650/50
Inventor 钟志容刘中兵李春红郝娜林燕周美玲王述蓉王丽孙小端
Owner SOUTHWEST MEDICAL UNIVERISTY
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