Phospholipid compound and preparation method thereof

A phospholipid compound, separation and purification technology, applied in the directions of edible phospholipid compositions, chemical instruments and methods, compounds of elements of Group 5/15 of the periodic table, etc. And other issues

Inactive Publication Date: 2019-09-20
SOUTHEAST UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The degradation of ordinary phospholipids depends on the hydrolysis of ester bonds, and it is difficult to degrade quickly
Common phospholipids have no special functions, which limits its application range, especially the inability to construct functional nanoparticles

Method used

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  • Phospholipid compound and preparation method thereof
  • Phospholipid compound and preparation method thereof
  • Phospholipid compound and preparation method thereof

Examples

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preparation example Construction

[0037] Its preparation method comprises the following steps (partial bis-n-alkyl dithio-n-alkanoic acid glycerophosphorylcholine synthetic route such as figure 1 shown):

[0038] (1) The trityl-protected mercapto-n-alkanoic acid was dissolved in dimethyl sulfoxide, and a catalytic amount of N,N'-carbonyldiimidazole and 1,8-diazabicyclo[5.4.0]undecyl- 7-ene, add glycerophosphocholine, stir and react at room temperature to 60°C for 1 to 12 hours, after the reaction is completed, add distilled water to the reaction solution, then add dichloromethane for extraction, concentrate the extract and use column chromatography to separate and purify, to obtain The intermediate bis-trityl mercapto-n-alkanoic acid glycerophosphocholine;

[0039] (2) Dissolve bis-trityl mercapto n-alkanoic acid glycerophosphorylcholine in dichloromethane, add appropriate amount of trifluoroacetic acid and triethylsilane, stir and react at room temperature for 0.5 to 6 hours, and remove the protective group ...

Embodiment 1

[0049] Embodiment 1 bis-n-octyl dithiopropionate glycerophosphocholine

[0050] A kind of phospholipid compound, this compound is bis-n-octyl dithiopropionate glycerophosphocholine (in the formula, m gets 2, n gets 7), and its structure is:

[0051]

[0052] Its preparation steps are as follows:

[0053] 1. Dissolve 20 mmol of trityl (Trt)-protected mercaptopropionic acid in 50 ml of dimethyl sulfoxide, add 20 mmol of CDI and 10 mmol of DBU, add 10 mmol of glycerophosphocholine (GPC) , stirred and reacted at room temperature for 6 hours; after the reaction was completed, 50 milliliters of distilled water was added, extracted with 100 milliliters of dichloromethane, the extract was dried over magnesium sulfate, concentrated and purified by silica gel column chromatography to obtain bis-trityl mercaptopropane Glycerylphosphocholine;

[0054] 2. Dissolve 8 mmoles of the above-mentioned bis-trityl mercaptopropionate glycerol phosphorylcholine in 50 ml of dichloromethane, add ...

Embodiment 2

[0058] Embodiment 2 bis-n-decyl dithiopropionate glycerophosphocholine

[0059] A kind of phospholipid compound, this compound is bis-n-decyl dithiopropionate glycerophosphocholine (in the formula, m gets 2, n gets 9), and its structure is:

[0060]

[0061] 1. Dissolve 20 mmol of trityl (Trt)-protected mercaptopropionic acid in 50 ml of dimethyl sulfoxide, add 20 mmol of CDI and 10 mmol of DBU, add 10 mmol of glycerophosphocholine (GPC) , stirred and reacted at room temperature for 12 hours; after the reaction was completed, 50 milliliters of distilled water was added, extracted with 100 milliliters of dichloromethane, the extract was dried over magnesium sulfate, concentrated and purified by silica gel column chromatography to obtain bis-trityl mercaptopropane Glycerylphosphocholine;

[0062] 2. Dissolve 8 mmoles of bis-trityl mercaptopropionin glycerol phosphorylcholine in 50 ml of dichloromethane, add 0.3 ml of trifluoroacetic acid and 0.3 ml of triethylsilane, stir at...

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Abstract

The invention discloses a phospholipid compound and a preparation method thereof. The structural general formula of the phospholipid compound is shown in the specification. In the formula, m is a positive integer from 2 to 10, and n is a positive integer from 7 to 15. The compound contains a disulfide bond easy to break and can be quickly broken and degraded in a reducing medium. The method comprises the following steps: (1) dissolving triphenylmethyl protected mercapto n-alkanoic acid into dimethyl sulfoxide, adding N,N'-carbonyl diimidazole, 1,8-diazabicyclo[5.4.0]undecane-7-ene and choline glycerophosphate, and carrying out a reaction to obtain bis-triphenylmethyl mercapto n-alkanoic acid choline glycerophosphate; 2) dissolving the bis-triphenylmethyl mercapto n-alkanoic acid choline glycerophosphate in dichloromethane, adding trifluoroacetic acid and triethylsilane, and carrying out a reaction to obtain bis-mercapto-alkanoic acid choline glycerophosphate; and 3) dissolving the bis-mercapto-alkanoic acid choline glycerophosphate in dichloromethane, adding n-alkyl dithiopyridine, and carrying out a reaction to obtain the bis-n-alkyl dithio-n-alkanoic acid choline glycerophosphate.

Description

technical field [0001] The invention relates to a phospholipid compound and a preparation method thereof, belonging to the technical field of phospholipid compounds. Background technique [0002] Phospholipids are an important class of surfactants, and are also important materials for the preparation of drug carriers such as liposomes, nanomicelles, microemulsions, and solid lipid nanoparticles. The degradation of ordinary phospholipids depends on the hydrolysis of ester bonds, and it is difficult to degrade quickly. Common phospholipids have no special functions, which limits its application range, especially the inability to construct functional nanoparticles. [0003] The concentration of glutathione in inflammatory tissues, tumor tissues, especially tumor cells is much higher than that in normal tissues, and the use of its microenvironment can promote the cleavage of molecules or carriers containing reduction-sensitive bonds. [0004] In view of the above, it is necess...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F9/10
CPCC07F9/10
Inventor 李新松杜亚伟何伟
Owner SOUTHEAST UNIV
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