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New use of glyoxal bis (thiosemicarbazone) compound

A technology of glyoxal-based bisthiosemicarbazone and dialdehyde-based bisthiosemicarbazide is applied in the directions of medical preparations, drug combinations, and pharmaceutical formulations containing active ingredients, and achieves low toxic and side effects, strong killing effect, The effect of broad application prospects

Inactive Publication Date: 2009-11-04
PEKING UNIV +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

So far, there is no research report on the targeted inhibition of human tumors by glyoxal bisthiosemicarbazone compounds

Method used

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  • New use of glyoxal bis (thiosemicarbazone) compound
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  • New use of glyoxal bis (thiosemicarbazone) compound

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Effect test

Embodiment 1

[0064] Embodiment 1, compound and preparation thereof

[0065] 1. 2-Oxobutyraldehyde bisthiosemicarbazone (IMMLG-597) and its preparation

[0066] (1) Preparation method: the preparation process is as follows: figure 1 shown.

[0067] Step 1: Synthesis of 2-oxobutyraldehyde: In a 250 mL round bottom flask, add equimolar amounts of 2-butanone and selenium dioxide (0.25 mol), and then add 180 mL of dioxane and 12 mL of deionized water. Heating to reflux for 6 hours (until the precipitation of selenium close to the theoretical amount). Selenium was removed by filtration while it was hot, and after the solvent was evaporated, an oil pump was distilled under reduced pressure to obtain 6.4 g of golden yellow liquid 2-oxobutyraldehyde, with a yield of 30%. Step 2: Synthesis of 2-oxobutyraldehyde bisthiosemicarbazone (IMMLG-597): Add 2.2mol thiosemicarbazide and 10mL 5% glacial acetic acid-95% ethanol (v / v) solution in a 50mL round bottom flask , control the reaction temperature a...

Embodiment 2

[0081] Embodiment 2, five kinds of compounds are to the inhibitory activity of tumor cell

[0082] BEL7402 liver cancer cells and HepG2 liver cancer cells overexpressing the LAPTM4B gene and its encoded LAPTM4B-35 protein were used to screen 1697 small compounds in the combinatorial chemical library for their killing effect on cancer cells. A normal human fetal liver cell line with low expression of the LAPTM4B gene and its encoded LAPTM4B-35 protein was used as a control. Acid phosphatase assay (APA) was used to measure the rate of viable cells to detect the inhibitory / killing activity of each compound on tumor cells.

[0083] Use DMEM medium containing 10% newborn bovine serum (10% fetal bovine serum for fetal liver cells) for the cells to be tested, at saturated humidity, 37°C, 5% CO 2 cultured in an incubator. Cells in the logarithmic growth phase cultured in vitro were digested with 0.25% crude trypsin to make a single cell suspension (adjust the cell concentration to 3...

Embodiment 3

[0089] Example 3, IMMLG-597 compound's in vitro killing effect on tumor cells and in vivo tumor inhibiting effect

[0090] 1. In vitro tumor cell killing activity of IMMLG-597

[0091] 1. Calcein AM / EthD-1 fluorescence double staining simultaneously detects dead cells (red fluorescence) and living cells (green fluorescence) and cells entering middle / late stage apoptosis (red fluorescence):

[0092] HepG2 liver cancer cell line and FLC fetal liver cell line were used as experimental cells. The above-mentioned cells in the logarithmic growth phase were digested with 0.25% crude trypsin, washed with PBS, and made into a single-cell suspension with DMEM medium containing 10% newborn bovine serum, and adjusted the cell density (according to different cell types, it can be between 3-6 ×10 4 cells / ml) in 96-well plate (3~6×10 3 cells / 100 μl / well); normal human fetal liver FLC cells were cultured in DMEM medium containing 10% fetal bovine serum. Cells to be tested in 5% CO 21. Af...

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Abstract

The invention discloses new use of glyoxal bis (thiosemicarbazone) compound. The new use relates to an application of glyoxal bis (thiosemicarbazone) compound or salt or a solvate of the compound in antineoplastic drug preparation. The glyoxal bis (thiosemicarbazone) compound of the invention can effectively kill a large number of tumour cells and dosage-effect relation and time-effect relation are obvious. Thus, the invention provides a new way for practice and research of tumour treatment and / or relapse prevention and also can be taken as reagent used for experimental researches relevant to cell cycle, cell proliferation, and apoptosis as well as a certain of signal passage regulation and control. The invention has wide application in tumour treatment and relapse prevention.

Description

technical field [0001] The invention relates to a new application of glyoxal-based bisthiosemicarbazone compounds or salts or solvates thereof. Background technique [0002] Malignant tumors (commonly known as cancer) are one of the most important diseases that endanger human health. According to the latest report of the WHO, the number of new cancer cases in the world has reached 10 million each year, and 6 million deaths have occurred, and the trend is on the rise. It is expected that by 2020, the annual number of new cases will reach 20 million. According to the latest epidemiological survey, since 2003, the number of deaths from malignant tumors in my country has ranked first in all kinds of deaths in both urban and rural areas, and has become the greatest threat to people's health. In 2000, there were 1.8 to 2 million cancer cases and 1.4 to 1.5 million deaths. In my country, liver cancer (hepatoma) accounts for 50% to 55% of the world's morbidity population, and it ...

Claims

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Application Information

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IPC IPC(8): A61K31/175A61P35/00
Inventor 周柔丽刘刚李茂进李莉单毅王琳杨华
Owner PEKING UNIV
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