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Beta-sitosterol and epalrestat conjugate, preparation method and application of conjugate

A technology of epalrestat and sitosterol, which is applied in the field of β-sitosterol and epalrestat conjugates and their preparation, can solve the problems of weak anti-tumor activity of BST, and achieves eliminating cancer cells and enhancing cell apoptosis. Effect

Inactive Publication Date: 2017-11-24
GUANGDONG FOOD & DRUG VOCATIONAL COLLEGE
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the natural anti-tumor activity of BST is relatively weak. In order to further improve the anti-tumor activity of BST, it has been modified and transformed to obtain some highly active BST derivatives, which has become a hot topic.

Method used

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  • Beta-sitosterol and epalrestat conjugate, preparation method and application of conjugate
  • Beta-sitosterol and epalrestat conjugate, preparation method and application of conjugate
  • Beta-sitosterol and epalrestat conjugate, preparation method and application of conjugate

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Experimental program
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Effect test

Embodiment 1

[0024] β-sitosterol (1.2mmole) and epalrestat (1.2eq) were dissolved in anhydrous dichloromethane (30ml), under the catalysis of pyridine (0.5g) and 4-dimethylaminopyridine (0.5g) , react overnight at room temperature 25-30°C, filter, pass through a silica gel chromatographic column (the elution solvent used is ethyl acetate and petroleum ether with a volume ratio (3-15): 8), rotary evaporation, and drying to obtain white Solid target compound. 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):

[0025]

Embodiment 2

[0027] 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.

[0028] 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 1-150 μM for tumor cells, concentration 5-250 μM for LO2 cells), β-sitosterol coupled to epalrestat BST-EPA (i.e. the target compound obtained in Example 1), β-sitosterol BST, epalrestat EPA and an equimolar mixture of the two BST+EPA. Set 4 to 6 multiple wells in each group, culture for 24 hours, discard the supernatant, add 100 μl of MTT (tetrazolium salt) serum-free culture solution conta...

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Abstract

The invention belongs to the field of natural medicines and discloses a beta-sitosterol and epalrestat conjugate, a preparation method and application of the conjugate. The conjugate is formed by coupling beta-sitosterol with epalrestat. The structure is shown as formula (I) described in the specification. The preparation method comprises the following steps: dissolving beta-sitosterol and epalrestat in anhydrous dichloromethane, reacting under room temperature overnight under the catalytic effect of pyridine and 4-dimethylamino pyridine, filtering, pouring onto a silica gel chromatographic column, performing rotary steaming and drying, thereby acquiring a target compound. An in vitro MTT detection experiment proves that the beta-sitosterol and epalrestat conjugate has an excellent restraining effect on tumor cell lines, has an IC50 value being 3-6 times that of beta-sitosterol but has low toxicity to normal liver cells L-O2. The compound is used for treating tumor in the manner of conjugating two drug molecules into prodrug, the problems of insufficient antitumor capacity of beta-sitosterol and synergic targeted inhibition for cancer cell aldose reductase target are solved and the effect of clearing away tumor cells in the manner of enhancing cell apoptosis can be achieved.

Description

technical field [0001] The invention belongs to the field of natural medicines, in particular to a conjugate of β-sitosterol and epalrestat, 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] β-sitosterol (β-sitosterol, BST) is the main component of animal and plant cell membranes. Currently, more than 200 phytosterols have been identified, among which β-sitosterol, brassicasterol, and stigmasterol are the most abundant and common. About a hundred kinds of plants have been reported to contain β-sitosterol. β-Sitosterol exhibits a wide range of pharmacological activities, mainly including: antibacterial, anti-inflammatory, anti-cancer (breast cancer, rectal cancer, prostate can...

Claims

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Application Information

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IPC IPC(8): C07J43/00A61K31/58A61P35/00A61P29/00
CPCC07J43/003
Inventor 夏黎段启张树潘谢小霞刘佳周国洪
Owner GUANGDONG FOOD & DRUG VOCATIONAL COLLEGE
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