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Preparation of amphiphilic ursolic acid-polysaccharide conjugate and its application in tumor therapy

An ursolic acid and amphiphilic technology is applied in the field of preparation and application in tumor treatment, can solve the problems of difficult preparation of preparations, low bioavailability and the like, and achieves improved water solubility and stability, high drug loading, The effect of enhanced antitumor activity

Active Publication Date: 2016-03-02
南京泽恒医药技术开发有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, ursolic acid is insoluble in water, which leads to the difficulty in preparation of its preparations and low bioavailability. Therefore, improving the solubility of insoluble ursolic acid and then improving its bioavailability has become a hot and difficult point

Method used

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  • Preparation of amphiphilic ursolic acid-polysaccharide conjugate and its application in tumor therapy
  • Preparation of amphiphilic ursolic acid-polysaccharide conjugate and its application in tumor therapy
  • Preparation of amphiphilic ursolic acid-polysaccharide conjugate and its application in tumor therapy

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0057] Embodiment 1 The synthesis of amphiphilic ursolic acid-low molecular weight heparin conjugate

[0058] 300mg of ursolic acid was dissolved in dichloromethane, and gradually dropped into the dichloromethane solution in which 280mg of pyridinium chlorochromate was dissolved at 10°C. After the dropwise addition was completed, stir at room temperature for 1.5h. The reaction solution was filtered, washed, washed with water, dried, filtered and concentrated, followed by silica gel column chromatography, eluted and concentrated to obtain a white solid. Take 59.2mg of the white solid and 80mg of hydroxylamine hydrochloride and dissolve it in 7ml of pyridine, connect it to a drying tube, and reflux at 115°C for about 6h. After the reaction solution was cooled to room temperature, it was washed with distilled water, filtered, washed with water, and dried to obtain a white solid. Take 120 mg of the white solid, 1.03 g of sodium cyanoborohydride, and 1.03 g of sodium acetate, and...

Embodiment 2

[0059] Example 2 Synthesis of amphiphilic ursolic acid-desulfated heparin conjugate

[0060] 250mg of ursolic acid was dissolved in dichloromethane, and gradually dropped into the dichloromethane solution in which 270mg of pyridinium chlorochromate was dissolved at 12°C. After the dropwise addition was completed, stir at room temperature for 5 h. The reaction solution was filtered, washed, washed with water, dried, filtered and concentrated, followed by silica gel column chromatography, eluted and concentrated to obtain a white solid. Take 61.3mg of the white solid and 81mg of hydroxylamine hydrochloride and dissolve it in 8ml of pyridine, connect it to a drying tube, and reflux at 110°C for about 7h. After the reaction solution was cooled to room temperature, it was washed with distilled water, filtered, washed with water, and dried to obtain a white solid. Take 150 mg of the white solid, 1.2 g of sodium cyanoborohydride, and 1.2 g of sodium acetate, and dissolve it in meth...

Embodiment 3

[0061] Example 3 Synthesis of amphiphilic ursolic acid-unfractionated heparin conjugate

[0062] 250mg of ursolic acid was dissolved in dichloromethane, and gradually dropped into the dichloromethane solution in which 270mg of pyridinium chlorochromate was dissolved at 5°C. After the dropwise addition, stir at room temperature for 4h. The reaction solution was filtered, washed, washed with water, dried, filtered and concentrated, followed by silica gel column chromatography, eluted and concentrated to obtain a white solid. Take 61.3mg of the white solid and 81mg of hydroxylamine hydrochloride and dissolve it in 8ml of pyridine, connect it to a drying tube, and reflux at 90°C for about 13h. After the reaction solution was cooled to room temperature, it was washed with distilled water, filtered, washed with water, and dried to obtain a white solid. Take 150 mg of the white solid, 1.2 g of sodium cyanoborohydride, and 1.2 g of sodium acetate, and dissolve it in methanol. The re...

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Abstract

The invention relates to preparation and application of an amphiphilic ursolic acid-polysaccharide coupled substance with antitumor activity. The ursolic acid is chemically modified to substitute C3 site carboxyl group with amino group, the generated aminated ursolic acid is chemically coupled to a polysaccharide framework to form the amphiphilic ursolic acid-polysaccharide coupled substance, and the amphiphilic ursolic acid-polysaccharide coupled substance can be self-assembled into a nano micelle in water. The method is characterized in that the antitumor activity of the chemically modified ursolic acid is obviously enhanced; the hydrophobic inner core formed by the hydrophobic group can physically wrap the antineoplastic drug to obviously improve the solubility of the antineoplastic drug; and the antineoplastic drug which is physically wrapped by the chemically coupled ursolic acid can implement combined chemotherapy, has higher antitumor activity, has the combined synergetic action, and lowers the toxicity. The preparation method is simple and easy to operate, has the advantage of higher yield, and can easily implement industrialization.

Description

technical field [0001] The invention belongs to the field of pharmaceutical preparations, and in particular relates to the preparation of amphiphilic ursolic acid-polysaccharide conjugates and their application in tumor treatment. Background technique [0002] Cancer has become the leading cause of human death worldwide today. According to the World Health Organization, cancer currently kills more than 7 million people worldwide every year, and this number will continue to rise. Therefore, the treatment and research of cancer is urgent, and it is a difficult problem that human beings urgently need to solve in the new century. At present, the treatment methods for cancer are mainly surgical treatment and chemical drug treatment, but surgical treatment can only remove tumors visible to the naked eye. Chemotherapy drugs have poor water solubility, low oral bioavailability, fast metabolism in the body, and lack of target for cancer cells. tropism, with greater toxicity and sid...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): A61K47/48A61K31/56A61K9/107A61P35/00C08B37/00C08B37/10C08B37/08C08B37/02C08B37/04
Inventor 姚静李园珂周建平
Owner 南京泽恒医药技术开发有限公司
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