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M-bistetrahydrofuran annonaceous acetogenins compound with anti-tumor activity and preparation method and application thereof

A tetrahydrofuran-type, annona lactone technology, applied in the direction of antineoplastic drugs, organic active ingredients, medical preparations containing active ingredients, etc., can solve the problems of large toxic and side effects, high price, poor tolerance of patients, etc., to achieve Strong antitumor activity and low toxicity

Inactive Publication Date: 2017-03-29
NANJING UNIVERSITY OF TRADITIONAL CHINESE MEDICINE
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In many countries including China, especially moderately developed countries, the death caused by malignant tumors accounts for the first or second place among all causes of death, and the incidence rate is still on the rise worldwide. Among the four major therapies of chemotherapy, chemotherapy and biological therapy, chemotherapy is still the main treatment method, but as we all know, the existing chemotherapy drugs have limited anti-tumor activity, high toxicity and side effects, poor patient tolerance, and high prices

Method used

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  • M-bistetrahydrofuran annonaceous acetogenins compound with anti-tumor activity and preparation method and application thereof
  • M-bistetrahydrofuran annonaceous acetogenins compound with anti-tumor activity and preparation method and application thereof
  • M-bistetrahydrofuran annonaceous acetogenins compound with anti-tumor activity and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034] The preparation of embodiment 1 bistetrahydrofuran type annona lactone compound (annoscomotine C)

[0035] Take 10kg of dried custard apple seeds, percolate with chloroform after crushing, reclaim and combine the percolation liquid, filter, and reclaim the filtrate under reduced pressure to obtain 1 kg of concentrated solution, the concentrated solution is separated by column chromatography with normal phase silica gel, and separated by petroleum ether-ethyl acetate -Methanol gradient elution, a total of 500 fractions were collected and combined into twelve fractions (F1-F12) according to the thin-layer chromatography. F10 (23.7 g) was separated by medium-pressure column chromatography on reverse-phase silica gel, and was eluted with methanol-water (20:1-1:0) gradient, and should be divided into 8 parts (F13-F21) ). The precipitated product of F20 was recrystallized from ethyl acetate-methanol to obtain the compound Anoxamotine (1). The purity was 98.7% by HPLC detect...

Embodiment 2

[0040] Example 2. Acute toxicity test of m-bis-tetrahydrofuran type annona lactone compound (annoscometin).

[0041] Calculate the half lethal dose LD of mice according to Bliss method 50 value, and the results are as follows:

[0042] Table 2. Acute toxicity test data

[0043]

[0044] LD obtained from experiment 50 The value shows that the acute toxicity of Anoxetin C is relatively low. Among the three routes of administration, the toxicity of oral administration is the least. Because the drug reaches all organs quickly, intravenous injection presents a more sensitive dose-effect (death) relation.

Embodiment 3

[0045] Example 3: Inhibitory effect on human tumor cells in vitro.

[0046] Drug-resistant tumor strains: human breast cancer (MCF-7 / ADR), human liver cancer (SMMC-7721 / T), human lung cancer (A549 / T) three tumor strains, using thiazolium blue reduction method (MTT) for in vitro anti- For the tumor experiment, 6 concentrations of Anoxamotine C prepared in Example 1 were set, cisplatin was used as the positive control group, and dimethyl sulfoxide, the solvent of the sample, was used as the negative control group. From the experimental results in Table 3, it can be seen that Anoxamotrim C has different inhibitory effects on three strains of human tumor cells, and the data of in vitro anti-tumor experiments show that Anuosicometin C provided by the present invention shows a specific positive effect. The stronger cell selective inhibitory activity of cisplatin.

[0047] Table 3 Inhibitory effect of anoxostatin on 3 strains of drug-resistant tumor cells.

[0048]

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Abstract

The invention discloses an m-bistetrahydrofuran annonaceous acetogenins compound with anti-tumor activity. Shown by the spectral and mass spectral data analysis, the new m-bistetrahydrofuran annonaceous acetogenins compound is separated from seeds of annona squamosa by carrying out systematic in-depth study on the chemical composition of the seeds of annona squamosa; shown by in vivo and in vitro antineoplastic activity studies, the m-bistetrahydrofuran annonaceous acetogenins provided by the invention has strong anti-tumor activity on various tumor cells including lung cancer cells, breast cancer cells, liver cancer cells and the like, and also has obvious inhibition activity on solid tumors such as mice transplanted tumor HepG2 and mice sarcoma S180; and shown by toxicity experimental study, the m-bistetrahydrofuran annonaceous acetogenins compound provided by the invention has lower toxicity and is an excellent anti-tumor compound.

Description

technical field [0001] The invention relates to a compound with antitumor activity, in particular to a novel m-bistetrahydrofuran type anemone lactone compound with antitumor activity and its application in preventing and treating tumor diseases, belonging to the technical field of medicine. Background technique [0002] Malignant tumors are frequent and common diseases that seriously endanger human health and life. As early as 2000-3000 years ago, there were records about tumors in Egypt and my country. In many countries including China, especially moderately developed countries, the death caused by malignant tumors accounts for the first or second place among all causes of death, and the incidence rate is still on the rise worldwide. Among the four major therapies of chemotherapy, chemotherapy, and biological therapy, chemotherapy is still the main treatment method, but as we all know, the existing chemotherapy drugs have limited anti-tumor activity, large toxic and side e...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D307/58A61K31/365A61P35/00
CPCC07D307/58
Inventor 李祥马程遥陈建伟
Owner NANJING UNIVERSITY OF TRADITIONAL CHINESE MEDICINE
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