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Polyoxyalkylene chain-containing lipid derivative and lipid film structure containing such derivative

A technology of lipid derivatives and polyoxyalkylene chains, which can be used in liposome delivery, oil/fat/wax non-active ingredients, drug combinations, etc., and can solve the problem of drug activity reduction

Inactive Publication Date: 2008-08-06
UNIVERSITY OF TOKUSHIMA +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] However, although these methods improve the retention of the drug in the blood and the transferability to the target site, etc., there are problems such as a decrease in the activity of the drug because polysaccharides and the like are directly bonded to the drug.

Method used

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  • Polyoxyalkylene chain-containing lipid derivative and lipid film structure containing such derivative
  • Polyoxyalkylene chain-containing lipid derivative and lipid film structure containing such derivative
  • Polyoxyalkylene chain-containing lipid derivative and lipid film structure containing such derivative

Examples

Experimental program
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Effect test

Embodiment 1

[0152] Synthesis of Methylpolyoxyethylene Carbamoyl-Glycyl-Glycyl-Glycyl-Dioleoyl Phosphatidylethanolamine (DOPE-GGG-PEG2000)

[0153] (1) Synthesis of methyl polyoxyethylene carbamoyl-glycyl-glycyl-glycine 5g (2.5mmol) methoxy polyethylene glycol p-nitrophenyl carbonate (trade name: SUNBRIGHT MENP- 20H, weight average molecular weight 2,000, manufactured by NOF Co., Ltd.) was dissolved in 15 mL of acetonitrile. To this solution, an aqueous solution of 946 mg of glycyl-glycyl-glycine dissolved in 10 mL of water was added, stirred, and 0.5 g of triethylamine was added, followed by stirring at room temperature for 3 hours. After the reaction, the insoluble matter was removed by filtration, and then the solvent was removed under reduced pressure using an evaporator. Next, 50 mL of ethyl acetate was added to dissolve, and after adding sodium sulfate and stirring, it was filtered and dehydrated. Next, 100 mL of hexane was added to the filtrate, cooled to below 0° C., and filtered...

Embodiment 2

[0159] Methylpolyoxyethylenecarbamoyl-glycyl-lysine (methylpolyoxyethylenecarbamoyl)-glycyl-glycyl-glycyl-distearoylphosphatidylethanolamine (DSPE-GGG Synthesis of -K(PEG2000)-G-PEG2000)

[0160] (1) Synthesis of methyl polyoxyethylene carbamoyl-glycyl-lysine (methyl polyoxyethylene carbamoyl)-glycyl-glycyl-glycyl

[0161] Dissolve 10 g (5 mmol) of methoxypolyethylene glycol-p-nitrophenyl carbonate (SUNBRIGHTMENP-20H, weight average molecular weight 2,000, manufactured by NOF Corporation) in 30 mL of acetonitrile, and add 1.6 An aqueous solution of g glycyl-lysine-glycyl-glycyl-glycine (sequence number 11) dissolved in 18 mL of water was stirred, and 1 g of triethylamine was added, and stirred at room temperature for 3 hours. After the reaction, the insoluble matter was removed by filtration, and then the solvent was removed under reduced pressure using an evaporator. Next, 50 mL of ethyl acetate was added and dissolved, and sodium sulfate was added and stirred, followed by ...

Embodiment 3

[0167] Methylpolyoxyethylene carbamoyl-cysteine ​​(methylpolyoxyethylene maleimide)-glycyl-glycyl-distearoylphosphatidylethanolamine (DSPE-GGC(-PEG2000)- PEG5000) synthesis

[0168] (1) Synthesis of methyl polyoxyethylene carbamoyl-cysteine

[0169]Add 150 ml (0.1 M, pH 9.5) of boric acid buffer solution to 2.5 g of L-cystine, and stir until completely dissolved. Dissolve 50 g (10 mmol) of methoxypolyethylene glycol-p-nitrophenyl carbonate (trade name: SUNBRIGHT MENP-50H, average molecular weight 5000, produced by NOF Corporation) in 50 mL of water, and add to the previous L - In cystine, keep the pH at 9.5 and react at room temperature for 2 hours. After the reaction, the pH was adjusted to 5.5 with dilute hydrochloric acid, and cooled to 2°C. Next, insoluble matter was removed by filtration, and the filtrate was dialyzed 5 times against 2 L of ion-exchanged water using a dialysis tube. After the dialysis, the pH was adjusted to 7.5, the solution was cooled to 2° C., and ...

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Abstract

Disclosed is a polyoxyalkylene chain-containing lipid derivative represented by the following general formula (1). In the formula, L, Y, W, X<1>, X<2>, X<3>, OA, Z, m1, m2, m3, n1, n2 and n3 are as defined in the description.

Description

technical field [0001] The present invention relates to lipid derivatives containing polyoxyalkylene chains and lipid membrane structures containing the derivatives. Background technique [0002] In order to reduce the side effects of physiologically active substances such as drugs and improve the selective delivery of drugs to target sites, drug delivery systems (DDS) are being developed. For example, there are methods of modifying polypeptides in protein preparations, and methods of encapsulating pharmaceuticals in microparticles such as liposomes or polymer micelles using copolymers of hydrophilic polymers and hydrophobic polymers. Early liposome formulations have the problem of poor blood retention and easy capture by the reticuloendothelial system (hereinafter referred to as "RES") such as the liver and spleen when administered intravenously. Therefore, the existence of the RES is a huge obstacle to the use of fine particle drug carriers as target preparations that del...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07K5/04A61K9/127A61K47/44A61K47/48C07K7/06
CPCC07K5/0806C07K7/06C07K5/1008A61K47/48215A61K47/48238A61K9/1271A61K47/60A61K47/62A61P35/00
Inventor 际田弘志石田龙弘伊藤智佳久保和弘坂上研二菊池宽
Owner UNIVERSITY OF TOKUSHIMA
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