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

A technology of polyethylene glycol and succinate, applied in drug delivery, medical preparations of non-active ingredients, pharmaceutical formulations, etc., can solve the problems of high toxicity and low efficiency, and achieve easy operation and high encapsulation rate , the effect of easy preparation

Inactive Publication Date: 2012-07-25
SHENYANG PHARMA UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] 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

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Experimental program
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Effect test

Embodiment 1

[0041] The preparation of embodiment 1 monomethoxypolyethylene glycol 2000-lysine-double vitamin E succinate block copolymer

[0042] (a) Dissolve 2.1 g vitamin E succinate in dichloromethane, add 1 g of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride and 0.6 g of 1-Hydroxybenzotriazole, magnetically stirred in an ice bath at 0°C for 1 h. 1.3 g of benzyloxylysine ester hydrochloride sulfonate was mixed with 3 mL of triethylamine, then added to the activation solution above, N 2 Under the protection of 30 ℃ magnetic stirring for 24 h. After the reaction, wash and dry. Purified to obtain benzyloxylysine di-vitamin E succinate (structural formula as formula Ⅰ).

[0043]

[0044] (b) Dissolve the product of step (a) in ethyl acetate, in palladium carbon (Pd / C) and H 2 Under the action of magnetic stirring at 30 °C for 6 h. Filtrate, collect the filtrate, and rotate to evaporate to obtain lysine di-tocopherol succinate (structural formula as formula II).

[...

Embodiment 2

[0049] Preparation of embodiment 2 polyethylene glycol 5000-lysine-double vitamin E succinate block copolymer

[0050] (a) Dissolve 2.1 g vitamin E succinate in dichloromethane, add 1 g of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride and 0.6 g of 1-Hydroxybenzotriazole, magnetically stirred in an ice bath at 0°C for 1 h. 1.3 g of benzyloxylysine ester hydrochloride sulfonate was mixed with 3 mL of triethylamine, then added to the activation solution above, N 2 Under the protection of 30 ℃ magnetic stirring for 24 h. After the reaction, wash and dry. Purified to obtain benzyloxylysine di-vitamin E succinate (structural formula as formula Ⅰ).

[0051]

[0052] (b) The product of step (a) was dissolved in ethyl acetate, and stirred magnetically at 30°C for 6 h under the action of palladium carbon and hydrogen. Filtrate, collect the filtrate, and rotate to evaporate to obtain lysine di-tocopherol succinate (structural formula as formula II).

[0053] ...

Embodiment 3

[0057] Embodiment 3 Preparation of monomethoxypolyethylene glycol amidation-lysine-double vitamin E succinate block copolymer

[0058] (a) Dissolve 2.1 g 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 magnetically stirred in an ice bath at 0 °C for 1 h. 1.3 g of benzyloxylysine ester hydrochloride sulfonate was mixed with 3 mL of triethylamine, then added to the activation solution above, N 2 Under the protection of 30 ℃ magnetic stirring for 24 h. After the reaction, wash and dry. Purified to obtain benzyloxylysine di-vitamin E succinate (structural formula as formula Ⅰ).

[0059]

[0060] (b) Dissolve the product of step (a) in ethyl acetate, in palladium carbon (Pd / C) and H 2 Under the action of magnetic stirring at 30 °C for 6 h. Filtrate, collect the filtrate, and rotate to evaporate to obtain lysine di-tocopherol succinate (structural formula ...

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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

[0001] technical field [0002] The invention belongs to the field of new excipients and new dosage forms of pharmaceutical preparations, and relates to the preparation of an amphiphilic polyethylene glycol divitamin E succinate derivative with anti-tumor effect, P-gp inhibition and long-circulation function and the carrier. and its application as a drug carrier in drug delivery. [0003] Background technique [0004] For the clinical treatment of cancer, chemotherapy is the main means of treating cancer. However, the clinical efficacy and application of chemotherapy drugs are limited due to their high toxicity, tumor non-specificity and multidrug resistance. Therefore, the development of new anti-tumor drug delivery systems has attracted more and more attention. Amphiphilic polymer micelles are of particular interest in drug delivery systems. Amphiphilic block copolymers self-assemble in water to form core-shell nanomicelles, and encapsulate poorly soluble drugs (such...

Claims

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Application Information

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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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