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Conjugate containing cancer cell targeting molecules and preparation method and application thereof

A technology for targeting molecules and cancer cells, applied in the field of conjugates containing cancer cell targeting molecules and their preparation, can solve the problems of poor solubility, weak anti-tumor activity of GAA, and low bioavailability, and overcome the poor solubility. , Enhance the activity and targeting of anticancer drugs, and remove cancer cells

Inactive Publication Date: 2017-11-03
FOSHAN UNIVERSITY
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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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  • Conjugate containing cancer cell targeting molecules and preparation method and application thereof
  • Conjugate containing cancer cell targeting molecules and preparation method and application thereof
  • Conjugate containing cancer cell targeting molecules and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] Glycyrrhetinic acid (1.1mmole) and folic acid (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 (2-9):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):

[0026]

Embodiment 2

[0028] 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.

[0029] 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 with folic acid GAA-FA (ie the target compound obtained in Example 1), glycyrrhetinic acid GAA, folic acid FA and an equimolar mixture of the two GAA+FA. 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 field of natural drugs and drug therapy and discloses a conjugate containing cancer cell targeting molecules and a preparation method and application thereof. The conjugate is formed by coupling glycyrrhetinic acid and folic acid, and a structural formula is shown as a formula (I). The preparation method comprises the steps that the glycyrrhetinic acid and the folic acid are dissolved in anhydrous dichloromethane, room temperature reaction is performed for one night under the catalysis of pyridine and 4-dimethylamino pyridine, filtration is performed, processing is performed through a silica gel chromatographic column, and rotary evaporation and drying are performed to obtain a target compound. It is found through an in-vitro MTT detection experiment that the conjugate has the very good inhibiting effect on tumor cell strains (MCF-7, BC-3 and HepG2 cells), is 4-7 times stronger than the glycyrrhetinic acid in IC50 value and is low toxicity to normal liver cells L-O2. The compound treats cancers in the mode that two pharmaceutical molecules are coupled into a prodrug, the problem of poor solubleness, antitumor activity and targeting of the glycyrrhetinic acid are solved, and the effect of clearing cancer cells through a cell apoptosis enhancing way is achieved.

Description

technical field [0001] The invention belongs to the field of natural medicine and drug treatment, and in particular relates to a conjugate containing cancer cell targeting molecules, a preparation method and application thereof. 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-inf...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07J63/00A61K31/58A61P29/00A61P35/00A61K47/54A61K8/63A61Q19/00
CPCC07J63/008A61K8/63A61K2800/10A61Q19/00
Inventor 刘连刘腾彭咏波邱桥春黄文柱陈仰新严文
Owner FOSHAN UNIVERSITY