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Multifunctional polyethylene glycol-dual vitamin E succinate derivative and application thereof in drug delivery

A polyethylene glycol, succinate technology, applied in the direction of drug delivery, pharmaceutical formulations, etc., can solve the problems of inefficiency, high toxicity, etc., and achieve the effects of high encapsulation efficiency, easy operation and good stability

Inactive Publication Date: 2013-12-25
SHENYANG PHARMA UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] At present, in order to avoid the efflux of internalized drugs and better overcome the multidrug resistance of tumors, many multidrug resistance inhibitors are used in combination with anticancer drugs, but they are limited by low efficiency and high toxicity.

Method used

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  • Multifunctional polyethylene glycol-dual vitamin E succinate derivative and application thereof in drug delivery
  • Multifunctional polyethylene glycol-dual vitamin E succinate derivative and application thereof in drug delivery
  • Multifunctional polyethylene glycol-dual vitamin E succinate derivative and application thereof in drug delivery

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0037] Example 1 Preparation of monomethoxy polyethylene glycol 2000-lysine-bis-vitamin E succinate block copolymer

[0038] (A) Dissolve 2.1 g of vitamin E succinate in dichloromethane, add 1 g of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride and 0.6 g of 1-Hydroxybenzotriazole, magnetically stirred at 0°C under ice bath for 1 h. 1.3 g benzyloxy lysine ester hydrochloride sulfonate was mixed with 3 mL triethylamine, and then added to the above activation solution, N 2 Magnetic stirring at 30°C for 24 h under protection. After the reaction is completed, wash and dry. After purification, benzyloxy lysine divitamin E succinate (structure formula I) is obtained.

[0039]

[0040] (B) Dissolve the product of step (a) in ethyl acetate, in palladium on carbon (Pd / C) and H 2 Under the action, magnetic stirring was carried out at 30℃ for 6 h. Filter, collect the filtrate, and rotate to obtain lysine divitamin E succinate (the structural formula is as formula II).

[0041...

Embodiment 2

[0045] Example 2 Preparation of polyethylene glycol 5000-lysine-bis-vitamin E succinate block copolymer

[0046] (A) Dissolve 2.1 g of vitamin E succinate in dichloromethane, add 1 g of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride and 0.6 g of 1-Hydroxybenzotriazole, magnetically stirred at 0°C in an ice bath for 1 h. 1.3 g benzyloxy lysine ester hydrochloride sulfonate was mixed with 3 mL triethylamine, and then added to the above activation solution, N 2 Magnetic stirring at 30°C for 24 h under protection. After the reaction is completed, wash and dry. After purification, benzyloxy lysine divitamin E succinate (structure formula I) is obtained.

[0047]

[0048] (B) Dissolve the product of step (a) in ethyl acetate, and stir magnetically at 30°C for 6 h under the action of palladium carbon and hydrogen. Filter, collect the filtrate, and rotate to obtain lysine divitamin E succinate (the structural formula is as formula II).

[0049]

[0050] (C) 1.2g Step (b)...

Embodiment 3

[0053] Example 3 Preparation of monomethoxy polyethylene glycol amidation-lysine-bis-vitamin E succinate block copolymer

[0054] (A) Dissolve 2.1 g of vitamin E succinate in dichloromethane, add 1 g of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDCI) and 0.6 g of 1-hydroxybenzotriazole (HOBT) was stirred magnetically for 1 h in an ice bath at 0°C. 1.3 g benzyloxy lysine ester hydrochloride sulfonate was mixed with 3 mL triethylamine, and then added to the above activation solution, N 2 Magnetic stirring at 30°C for 24 h under protection. After the reaction is completed, wash and dry. After purification, benzyloxy lysine divitamin E succinate (structure formula I) is obtained.

[0055]

[0056] (B) Dissolve the product of step (a) in ethyl acetate, in palladium on carbon (Pd / C) and H 2 Under the action, magnetic stirring was carried out at 30℃ for 6 h. Filter, collect the filtrate, and rotate to obtain lysine divitamin E succinate (the structural formula is...

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Abstract

The invention relates to a multifunctional polyethylene glycol-dual vitamin E succinate derivative and application thereof in drug delivery. An amphiphilic block copolymer utilizes polyethylene glycol as a hydrophyllic end to be combined with bimolecular hydrophobic vitamin E succinate under bridging of lysine, so that the AB2 type two-arm amphiphilic block copolymer is obtained. The polymer has potential antineoplastic activity and P-gp inhibitory action, and is capable of synergetically and effectively overcoming multidrug resistance to increase chemotherapeutic effect. Besides, the block copolymer can be self-assembled to form a micelle in aqueous medium, and can serve as a reservoir of poorly water-soluble drug, protein and gene-based drug, and the micelle is safe and high in stability and encapsulation, can be used for intravenous injection and oral ingestion, and has bright market application prospects.

Description

Technical field [0001] The invention belongs to the field of new excipients and new dosage forms for pharmaceutical preparations, and relates to an amphiphilic polyethylene glycol divitamin E succinate derivative with anti-tumor effects, P-gp inhibition and long circulation functions and the preparation of the carrier. And its application as a drug carrier in drug delivery. Background technique [0002] For the clinical treatment of cancer, chemotherapy is the main method to treat cancer. However, due to the high toxicity of chemotherapeutics in application, tumor non-specificity and multi-drug resistance limit their clinical efficacy and application. Therefore, the development of new anti-tumor drug delivery systems has attracted more and more attention. Amphiphilic polymer micelles are particularly interesting in drug delivery systems. Amphiphilic block copolymers self-assemble in water to form nanomicelles with a core-shell structure, and poorly soluble drugs (such as tax...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08G65/48A61K47/34A61K9/00
Inventor 何仲贵孙进王金铃王永军孙英华刘晓红
Owner SHENYANG PHARMA UNIVERSITY
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