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Nanoparticles of eight-arm PEG (polyethylene glycol)-oleanolic acid drug carrier and preparation

A technology of oleanolic acid and polyethylene glycol, which is applied in the field of nanoparticle preparation, can solve the problem that the pharmacokinetic index does not reach the clinical standard, the anti-inflammatory and anti-tumor activity of oleanolic acid is weak, and the water solubility is poor. problem, achieve the effect of prolonging the half-life of circulation, improving water solubility and stability, and reducing toxicity

Inactive Publication Date: 2017-09-01
BEIJING FORESTRY UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, due to the weak anti-inflammatory and anti-tumor activities of oleanolic acid, and there are defects such as pharmacokinetic indicators that do not meet clinical standards and poor water solubility, it affects its clinical application.

Method used

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  • Nanoparticles of eight-arm PEG (polyethylene glycol)-oleanolic acid drug carrier and preparation
  • Nanoparticles of eight-arm PEG (polyethylene glycol)-oleanolic acid drug carrier and preparation
  • Nanoparticles of eight-arm PEG (polyethylene glycol)-oleanolic acid drug carrier and preparation

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] Synthesis of Eight-armed Polyethylene Glycol (10 KDa)-Oleanolic Acid Conjugate: Into a Dry Three-necked Flask 2 ; Dissolve 0.5 g oleanolic acid, 1.25 g eight-arm carboxypolyethylene glycol (Mw 10,000) in 20 mL of dichloromethane, then add 0.1 g EDC, 0.13 g DMAP, stir to dissolve at 0 ° C, and stir to react 1 hour, then stirred at room temperature and reacted for 24 h; after the reaction was completed, the solvent was removed by rotary evaporation, precipitated with glacial ether, and filtered to obtain the crude product of the eight-armed polyethylene glycol-oleanolic acid conjugate; with DMF / IPA (1: 4 (v / v)) recrystallization, filter out insoluble matter, the product is precipitated with ether, filters, and the product is vacuum-dried to obtain an eight-arm polyethylene glycol-oleanolic acid conjugate with a purity of more than 95%;

[0030] Preparation of nanoparticles: Precipitation method is used to prepare nanoparticles; eight-arm polyethylene glycol-oleanolic acid...

Embodiment 2

[0032] Synthesis of Eight-armed Polyethylene Glycol (20 KDa)-Oleanolic Acid Conjugate: Into a Dry Three-necked Flask 2 ; Dissolve 0.25 g oleanolic acid, 1.25 g eight-arm carboxypolyethylene glycol (Mw 20,000) in 20 mL of dichloromethane, then add 0.05 g EDC, 0.06 g DMAP, stir to dissolve at 0 ° C, and stir to react 1 hour, then stirred at room temperature and reacted for 24 h; after the reaction was completed, the solvent was removed by rotary evaporation, precipitated with glacial ether, and filtered to obtain the crude product of the eight-arm polyethylene glycol-oleanolic acid conjugate; with DMF / IPA (1:4 (v / v)) recrystallization, filter off insoluble matter, product is precipitated with ether, filters, and product is vacuum-dried, obtains the eight-arm polyethylene glycol-oleanolic acid conjugate that purity is more than 95%;

[0033] Preparation of nanoparticles: Precipitation method is used to prepare nanoparticles; eight-arm polyethylene glycol-oleanolic acid conjugate ...

Embodiment 3

[0035] Synthesis of Eight-armed Polyethylene Glycol (40 KDa)-Oleanolic Acid Conjugate: Into a Dry Three-necked Flask 2 ; Dissolve 0.12 g oleanolic acid, 1.25 g eight-arm carboxypolyethylene glycol (Mw 20,000) in 20 mL of dichloromethane, then add 0.03 g EDC, 0.03 g DMAP, stir to dissolve at 0 °C, and stir to react 1 hour, then stirred at room temperature and reacted for 24 h; after the reaction was completed, the solvent was removed by rotary evaporation, precipitated with glacial ether, and filtered to obtain the crude product of the eight-arm polyethylene glycol-oleanolic acid conjugate; with DMF / IPA (1:4 (v / v)) recrystallization, filter off insoluble matter, product is precipitated with ether, filters, and product is vacuum-dried, obtains the eight-arm polyethylene glycol-oleanolic acid conjugate that purity is more than 95%;

[0036] Preparation of nanoparticles: Precipitation method is used to prepare nanoparticles; eight-arm polyethylene glycol-oleanolic acid conjugates ...

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Abstract

The invention discloses a preparation method of nanoparticles of an eight-arm PEG (polyethylene glycol)-oleanolic acid drug carrier. The preparation method comprises steps as follows: eight-arm PEG and oleanolic acid are subjected to an esterification reaction, and a conjugate of eight-arm PEG-oleanolic acid is obtained; 10-hydroxycamptothecine is wrapped with eight-arm PEG-oleanolic acid through self-assembly, and the nanoparticles are obtained. The nanoparticles have a double-layer structure, the outer layer is hydrophilic PEG, and the inner layer is hydrophobic oleanolic acid drug and 10-hydroxycamptothecine. The preparation method has the advantages that the drug loading capacity is greatly increased with the adoption of PEG; the water solubility and stability of oleanolic acid are increased, and the half-life period of oleanolic acid is prolonged; pH sensitive release of the drug in tumor cells can be realized; the toxic and side effects on normal tissue are reduced; the preparation process is simple and easy to operate.

Description

technical field [0001] The invention relates to a preparation method of nanoparticles with eight-armed polyethylene glycol-oleanolic acid as a drug carrier. Background technique [0002] Cancer has become a major disease that endangers human health. One of the important methods to treat cancer is chemical drug therapy. However, many anticancer drugs have defects such as insoluble in water and poor stability. In addition, poor selectivity of anticancer drugs, large adverse reactions, and drug resistance of tumors have greatly affected the efficacy of tumor treatment, and severe toxic reactions often even force treatment to be discontinued. Therefore, how to solubilize insoluble anticancer drugs, improve the selectivity to cancer cells and reduce the adverse reactions of drugs is very important. [0003] Oleanolic acid is a pentacyclic triterpenoid compound widely distributed in Chinese herbal medicines in the form of free or combined glycosides. Oleanolic acid has a wide ra...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A61K9/51A61K47/60A61K31/56A61K31/4745A61P35/00
CPCA61K9/5031A61K9/0002A61K31/4745A61K31/56
Inventor 王英飒何静雷建都朱蓬勃马芸芸
Owner BEIJING FORESTRY UNIVERSITY
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