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Polyacrylic acid-cystamine dihydrochloride-vitamin E succinate polymer, and preparation method and application thereof

A technology of cystamine dihydrochloride and succinate, applied in the direction of active ingredients of heterocyclic compounds, pharmaceutical formulations, medical preparations of non-active ingredients, etc., can solve the problems of large side effects and low drug bioavailability, and achieve Mild conditions, low critical micelle concentration, improved safety and efficacy

Active Publication Date: 2016-08-24
LIAONING UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] However, the current anti-cancer chemotherapy drugs are not stable and are released before reaching the tumor cell site, resulting in low bioavailability of the drug and high side effects

Method used

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  • Polyacrylic acid-cystamine dihydrochloride-vitamin E succinate polymer, and preparation method and application thereof
  • Polyacrylic acid-cystamine dihydrochloride-vitamin E succinate polymer, and preparation method and application thereof
  • Polyacrylic acid-cystamine dihydrochloride-vitamin E succinate polymer, and preparation method and application thereof

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preparation example Construction

[0040] The synthetic method of this polyacrylic acid-cystamine dihydrochloride-vitamin E succinate polymer, comprises the steps:

[0041] (1) Synthesis of cystamine dihydrochloride-vitamin E succinate: dissolve vitamin E succinate in anhydrous N,N-dimethylformamide, add 1-(3-dimethylaminopropyl base)-3-ethylcarbodiimide hydrochloride (EDCI), 1-hydroxybenzotriazole (HOBT), stirred at room temperature for 2-4h, and then added cystamine dihydrochloride, triethyl Amine, under room temperature, avoid light and stir for 12 hours. After the reaction is completed, add the reaction solution dropwise into a beaker containing ice water under the condition of stirring. After the addition, a white solid precipitates out, which is filtered and freeze-dried to obtain cystamine di Hydrochloride - Vitamin E succinate product.

[0042] (2) Synthesis of polyacrylic acid-cystamine dihydrochloride-vitamin E succinate: dissolve polyacrylic acid in anhydrous N,N-dimethylformamide, add 1-(3-dimethyl...

Embodiment 1

[0051] Embodiment 1. the synthesis of cystamine dihydrochloride-vitamin E succinate

[0052] 1) Dissolve vitamin E succinate (VES, 0.53g, 1mmol) in 20mL of anhydrous N,N-dimethylformamide, put it in a 50mL round bottom flask, and after dissolving, add 1-(3 -Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDCI, 0.23g, 1.2mmol), 1-hydroxybenzotriazole (HOBT, 0.18g, 1.2mmol), stirring at room temperature React for 2-4h, then add cystamine dihydrochloride (0.675g, 3mmol), 1mL triethylamine, and stir for 12h at room temperature in the dark. Add it into a beaker containing 200mL of ice water. After the addition, a white solid precipitates out. After filtering and freeze-drying, the cystamine dihydrochloride-vitamin E succinate solution is obtained.

[0053] The structure of the compound in Example 1 is determined by proton nuclear magnetic resonance spectroscopy, and the solvent is CDCl 3 , the result is as figure 1 shown. The chemical shift is 6.5ppm for the H in -NH-CO...

Embodiment 2

[0054] Embodiment 2. the synthesis of polyacrylic acid-cystamine dihydrochloride-vitamin E succinate

[0055] 2) Dissolve polyacrylic acid (0.18g, 2.5mmol) in 20mL of anhydrous N,N-dimethylformamide, add 1-(3-dimethylaminopropyl)-3-ethylcarbodiethylene Amine hydrochloride (EDCI, 0.115g, 0.6mmol), 1-hydroxybenzotriazole (HOBT, 0.09g, 0.6mmol), stirred and reacted at room temperature for 6h to obtain a mixed solution, and then added 5mL to the mixed solution dropwise A solution of cystamine dihydrochloride-vitamin E succinate (0.332 g, 0.5 mmol) in N,N-dimethylformamide was stirred and reacted at room temperature for 12 h in the dark. After the reaction, the reaction solution was transferred to a dialysis bag, dialyzed at room temperature for 3-5 days, and freeze-dried to obtain a white powder, that is, polyacrylic acid-cystamine dihydrochloride-vitamin E succinate.

[0056] Determination by NMR 1 HNMR determines the combination of compound in embodiment 2, adopts DMSO-d6 as s...

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Abstract

The invention discloses a polyacrylic acid-cystamine dihydrochloride-vitamin E succinate polymer. The polymer is formed by bridging vitamin E succinate onto the main chain polyacrylic acid through diamino group, and the structural formula of the polymer is disclosed as Formula (I). The polyacrylic acid-cystamine dihydrochloride-vitamin E succinate polymer is hydrophilic and is responsive to GSH reduction, and can be used as an excellent antineoplastic drug carrier. The preparation method is simple, and is mild in conditions. The used materials are novel, and have the advantages of lower critical micelle concentration, favorable biocompatibility and favorable biodegradability. The carrier material can be self-assembled to form a micelle in water, and can be used for increasing the solubility of water-insoluble drugs and improving the distribution in vivo.

Description

technical field [0001] The invention belongs to the technical field of polymer synthesis and nanometer materials, and in particular relates to a polyacrylic acid-cystamine dihydrochloride-vitamin E succinate polymer and its preparation method, as well as its application on antitumor drug loading. Background technique [0002] At present, a large number of anticancer drugs have poor water solubility, short half-life, frequent and large doses, and poor targeting, resulting in many toxic and side effects. Therefore, drug carriers have begun to be widely studied. Drugs that are poorly soluble in water are loaded on a suitable carrier to change the absorption and distribution of the drug, and deliver the drug to the target organ, so as to achieve a better anti-cancer effect. [0003] However, the current anti-cancer chemotherapy drugs are not stable and are released before reaching the tumor cell site, resulting in low bioavailability of the drug and high side effects. Therefore...

Claims

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Application Information

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IPC IPC(8): C08F20/06C08F8/34A61K9/107A61K31/355A61K31/44A61K47/32A61K47/48
CPCA61K9/1075A61K31/355A61K31/44A61K47/32C08F8/34C08F20/06A61K2300/00
Inventor 陈立江刘宇杨佳王欣刘举
Owner LIAONING UNIVERSITY
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