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Polyethylene glycol-distearoyl phosphatidyl ethanolamine derivant and preparation method thereof

A technology of stearoyl phosphatidyl ethanolamine and polyethylene glycol is applied in the field of derivatives of novel polyethylene glycol-distearoyl phosphatidyl ethanolamine, which can solve the problems of limited tumor cell affinity and the like

Active Publication Date: 2011-12-21
北京中海康医药科技发展有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] Although liposomes containing RGD ligands have the effect of targeting tumors, most of them are monovalent ligands with limited affinity with tumor cells

Method used

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  • Polyethylene glycol-distearoyl phosphatidyl ethanolamine derivant and preparation method thereof
  • Polyethylene glycol-distearoyl phosphatidyl ethanolamine derivant and preparation method thereof
  • Polyethylene glycol-distearoyl phosphatidyl ethanolamine derivant and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] Synthesis of PEG2000 mono-tert-butyldimethylsilyl ether (compound (II))

[0030] Take 5g (2.5mmol) PEG2000, 0.45g (3mmol) tert-butyldimethylsilyl chloride, 0.41g (6mmol) imidazole, add 30ml dichloromethane to dissolve. After stirring at room temperature for 24 hours, a small amount of water was added to separate the layers. The organic phase was washed with saturated sodium bicarbonate solution, and washed with water until neutral. The organic phase was dried with anhydrous sodium sulfate, filtered, and the filtrate was concentrated. Pressurized column chromatography (petroleum ether-ethyl acetate=10:1) yielded 5.27 g of white solid PEG2000 mono-tert-butyldimethylsilyl ether, which was stirred.

Embodiment 2

[0032] Synthesis of RGD Benzyl Ether (Compound (III))

[0033] Take 0.5g (1.39mmol) RGD, benzyl bromide (0.52mL, 4.46mmol), potassium carbonate (0.76g, 5.56mmol) in THF-H 2 O (40:1, 20 mL) was stirred overnight at room temperature. After filtration, the filtrate was evaporated to dryness under reduced pressure and subjected to silica gel column chromatography (petroleum ether-ethyl acetate=8:1) to obtain 0.73 g of a white amorphous solid.

Embodiment 3

[0035] 1-O-(ω-O-tert-butyldimethylsilyl)polyethylene glycol-2,3,4,6-tetra-O-acetyl-β-D-glucose (compound (V)) Synthesis

[0036] Take 1 g (0.47 mmol) of PEG2000 mono-tert-butyldimethylsiloxane, the product of Example 1, and 0.37 g (0.94 mmol) of compound (IV) into 10 ml of dichloromethane to dissolve. Join BF 3 ·Et 2 O solution 0.06ml (0.47mmol), stirred at room temperature for 2 hours, and the filtrate was concentrated to dryness. Pressurized column chromatography (ethyl acetate-petroleum ether=5:1) gave 1.1 g of the title compound.

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Abstract

The invention discloses a polyethylene glycol (PEG)- distearoyl phosphatidyl ethanolamine (DSPE) derivant shown in a formula (I) and a preparation method thereof (n in the formula is an integral number from 0 to 9). The RDG modified DSPE-PEG derivant can increase tumour affinity to meet the requirement of treatment.

Description

technical field [0001] The invention relates to a novel polyethylene glycol-distearoylphosphatidylethanolamine derivative and a preparation method thereof. Background technique [0002] Polyethylene glycol-distearoylphosphatidylethanolamine (hereinafter referred to as PEG-DSPE) is a new type of liposome carrier auxiliary material, and the liposome prepared by using this auxiliary material has the property of long circulation. A preparation using this substance as an auxiliary material has been marketed in the United States in 1995, with a trade name of DOXIL. The application of polyethylene glycol-distearoylphosphatidylethanolamine in the field of medicine has been reported in many documents, such as: [1]Influence of preparation path on the formation of discs and threadlike micelles inDSPE-PEG2000 / lipid systems.Biophysical Chemistry , 2008, 132, 97; [2] Effects of phospholipidhydrolysis on the aggregate structure in DPPC / DSPE-PEG2000liposome preparations after gel toliquid ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08G65/48A61K47/34
Inventor 徐庆春宋华先黄海
Owner 北京中海康医药科技发展有限公司
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