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A conjugate containing diclofenac, a preparing method thereof and uses of the conjugate

A technology of diclofenac and conjugates, which is applied in the field of natural medicine and drug therapy, can solve the problems of poor solubility, low bioavailability, weak anti-tumor activity of GAA, etc., so as to overcome poor solubility, remove cancer cells, and increase anti-cancer drugs active effect

Inactive Publication Date: 2017-12-15
佛山市第五人民医院 +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, due to the influence of solubility, the antitumor activity of natural GAA is relatively weak. In order to further improve the antitumor activity of GAA, people carry out structural modification and transformation to obtain some highly active GAA derivatives, which has become a hot topic.
At present, GAA has low activity, low absorption, poor solubility and low bioavailability in the body, these characteristics greatly limit its application

Method used

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  • A conjugate containing diclofenac, a preparing method thereof and uses of the conjugate
  • A conjugate containing diclofenac, a preparing method thereof and uses of the conjugate
  • A conjugate containing diclofenac, a preparing method thereof and uses of the conjugate

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] Glycyrrhetinic acid (1.1mmole) and diclofenac (1.3eq) were dissolved in anhydrous dichloromethane (30ml), under the catalysis of pyridine (0.5g) and 4-dimethylaminopyridine (0.5g), room temperature 25- React overnight at 30°C, filter, pass through a silica gel chromatography column (the elution solvent used is ethyl acetate and petroleum ether in a volume ratio (3-8):7), rotary evaporate, and dry to obtain the target compound as a white solid. Through liquid chromatography mass spectrometry and NMR analysis, the newly prepared white solid target compound is a conjugate with the structure shown in formula (I):

[0027]

Embodiment 2

[0029] In vitro anti-tumor effect evaluation of target compounds. In this example, breast cancer MCF-7, lymphoma BC-3 and liver cancer HepG2 cells were used to evaluate their efficacy, while LO2 liver cells were used to detect their toxicity.

[0030] Take the cells in the logarithmic growth phase and inoculate 4-40×10 cells according to the size of the cells 3 Each was placed on a 96-well plate, and after 24 hours of growth, the supernatant was discarded, and then administered in groups as follows: Tumor cells were set up with no drug addition group and drug addition group (concentration 1-100 μM for tumor cells, concentration 5-200 μM for LO2 cells), glycyrrhetinic acid coupled to diclofenac GAA-DC (i.e. the target compound obtained in Example 1), glycyrrhetinic acid GAA, diclofenac DC and an equimolar mixture of the two GAA+DC. Set up 4 to 6 multiple wells in each group, culture for 72 hours, discard the supernatant, add 100 μl of MTT (tetrazolium salt) serum-free culture ...

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Abstract

The invention belongs to the fields of natural medicines and medicine therapy, and discloses a conjugate containing diclofenac, a preparing method thereof and uses of the conjugate. The conjugate is formed by coupling glycyrrhetinic acid and the diclofenac and has a structure shown as a formula (I) as follows. The method includes reacting the glycyrrhetinic acid and the diclofenac in anhydrous dichloromethane at room temperature overnight under catalysis of pyridine and 4-dimethylaminopyridine, performing filtration, allowing a filtration product to pass through a silica gel chromatographic column, performing rotary evaporation, and performing drying treatment to obtain a product. In-vitro MTT detection experiments found that the conjugate has good inhibiting effects on tumor cell strains (MCF-7, BC-3 and HepG2 cells), the IC50 value of the conjugate is 3-4 times lower than that of the glycyrrhetinic acid, and the conjugate has low toxicity for normal liver cells L-O2. The compound can treat cancer in a manner that two medicine molecules are coupled to form a target prodrug, overcomes a problem that the glycyrrhetinic acid has low solubility, combines the diclofenac that is an anti-inflammatory drug to enhance anticancer activity, and achieves effects of removing cancer cells through a route of enhancing cell apoptosis.

Description

technical field [0001] The invention belongs to the field of natural medicine and drug treatment, in particular to a conjugate containing diclofenac and its preparation method and application. Background technique [0002] Cancer is a chronic disease that seriously endangers human health, and has become the second largest killer after cardiovascular disease. Therefore, it is of great significance to find safe, effective, and low-toxic antitumor drugs and study their mechanism of action. [0003] Licorice belongs to leguminous plants, mainly distributed in western my country and other regions, and is one of the commonly used Chinese herbal medicines in my country. Glycyrrhizic acid and its aglycon glycyrrhetinic acid (GAA for short) are the main pharmacological active substances of licorice. Its structural formula is as follows: [0004] [0005] Modern studies have shown that GAA has various pharmacological activities such as anti-inflammation, anti-ulcer, anti-virus, a...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07J63/00A61K31/56A61K47/55A61K8/63A61P35/00A61P29/00A61Q19/00
CPCA61K8/63A61K31/56A61Q19/00C07J63/008
Inventor 黄文柱刘连刘腾彭咏波王志军严文
Owner 佛山市第五人民医院
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