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Glutathione response type double-loading medicine polymer micelle and preparation method and application thereof

A technology of glutathione and polymers, applied in the field of biomedical engineering materials

Active Publication Date: 2018-11-02
JINAN UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

So far, there has been no report on glutathione-responsive double drug-loaded polymer micelles prepared by Michael addition reaction using non-covalent bonds to embed DOX in the hydrophobic core of micelles

Method used

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  • Glutathione response type double-loading medicine polymer micelle and preparation method and application thereof
  • Glutathione response type double-loading medicine polymer micelle and preparation method and application thereof
  • Glutathione response type double-loading medicine polymer micelle and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0088] Example 1: Synthesis of dihydroxypolycaprolactone (PCL) with disulfide bonds

[0089] Dissolve cystamine and ε-caprolactone with a disulfide bond in dry toluene, slowly add the catalyst stannous isooctanoate dropwise for 20 minutes under anhydrous and anaerobic conditions, and after the dropwise addition, place at 110°C in a nitrogen atmosphere Condensation and reflux reaction for 18 hours, magnetic stirring during the reaction, the rotation speed was 300rpm; after the reaction was completed, the toluene solvent was removed by rotary evaporation at 40°C, and then precipitated with cold ether, and then vacuum-dried at 40°C for 12h to obtain dihydroxypolycaprolactone with disulfide bonds Esters (PCL).

[0090] The mol ratio of described cystamine, epsilon-caprolactone, stannous isooctanoate is 1:132:0.05; The quality of described cystamine is 200mg; The total volume of described dried toluene is 10mL; Used cold The volume ratio of diethyl ether and reaction system soluti...

Embodiment 2

[0091] Example 2: Synthesis of dihydroxypolycaprolactone (PCL) with disulfide bonds

[0092] Dissolve cystamine and ε-caprolactone with a disulfide bond in dry toluene, slowly add the catalyst stannous isooctanoate dropwise for 50 minutes under anhydrous and anaerobic conditions, and after the dropwise addition, place at 110°C in a nitrogen atmosphere Condensation and reflux reaction for 24 hours, magnetic stirring during the reaction, the rotation speed was 600rpm; after the reaction was completed, the toluene solvent was removed by rotary evaporation at 60°C, and then precipitated with cold ether, and then vacuum-dried at 40°C for 24h to obtain dihydroxypolycaprolactone with disulfide bonds Esters (PCL).

[0093] The mol ratio of described cystamine, epsilon-caprolactone, stannous isooctanoate is 1:132:0.1; The quality of described cystamine is 100mg; The total volume of described dried toluene is 10mL; Used cold The volume ratio of diethyl ether to the reaction system solu...

Embodiment 3

[0094] Embodiment 3: NMR characterization of dihydroxy polycaprolactone (PCL) with disulfide bonds

[0095] The dihydroxy polycaprolactone (PCL) having a disulfide bond obtained in Example 1 was dissolved in deuterated chloroform for H NMR characterization. Such as figure 1 As shown, the peaks with chemical shifts at 4.08, 2.33, 1.40, and 1.67ppm are the characteristic peaks of the five methylene hydrogens after caprolactone ring opening, and 4.08ppm represents the characteristic peaks of the methylene hydrogens connected with oxygen , 2.33ppm represents the characteristic peak of methylene hydrogen linked to carbonyl; the peak at 3.55ppm is the hydrogen peak of methylene linked to cystamine. figure 1 The results proved that the step reaction successfully synthesized dihydroxypolycaprolactone (PCL) with disulfide bonds.

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Abstract

The invention discloses glutathione response type double-loading medicine polymer micelle and a preparation method and application thereof and belongs to the field of biological medical engineering materials. The preparation method disclosed by the invention is mild and simple and avoids special treatment. The prepared double-loading medicine polymer micelle disclosed by the invention has the advantages of good water solubility and good biocompatibility; furthermore, metabolite of the double-loading medicine polymer micelle is easy to degrade and has smaller toxicity; ingredients of the double-loading medicine polymer micelle are simple, the raw materials are easy to obtain, and the double-loading medicine polymer micelle is hopeful to be widely applied to the field of biological and medical engineering materials. The micelle can be used for wrapping hydrophobic drug; meanwhile, a positive-electricity high molecular material can carry gene medicine through electrostatic interaction toform a double-loading medicine carrier to give play to a synergistic effect. As polypeptide has a modifying effect, the polypeptide has the ability of entering tumor cells; furthermore, gene medicineand hydrophobic medicine can inhibit growth of tumor cells through different mechanisms, so that a treating effect of the polymer micelle to the tumor cells is improved; thus, the double-loading medicine polymer micelle has a wide application prospect in compound chemotherapy for malignant tumors.

Description

technical field [0001] The invention belongs to the field of biomedical engineering materials, and in particular relates to a glutathione-responsive double-loaded drug polymer micelle and its preparation method and application. Background technique [0002] At present, among numerous drug carriers, polymer micelles are suitable for a wide range of drugs due to their core-shell nanomaterial structure and core with high drug loading capacity, small particle size and very narrow distribution, and excellent biophasic properties. Capacitance, biodegradability, and easy surface modification have attracted widespread attention. Therefore, it has excellent performance in controlling drug release and achieving targeted release, and has great development prospects. In addition, the concentration of glutathione with reducing mercapto groups in tumor tissues is much higher than that in normal tissues. In recent years, glutathione-responsive smart drug carriers have also attracted attent...

Claims

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Application Information

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IPC IPC(8): A61K9/19A61K9/107A61K48/00A61K38/17A61K31/704A61P35/00
CPCA61K9/107A61K9/19A61K31/704A61K38/177A61K47/34A61K47/42A61K48/00A61K2300/00
Inventor 郭瑞薛巍冯龙宝刘璇
Owner JINAN UNIVERSITY
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