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Application for thiazolidone derivative in preparation for broad-spectrum anti-cancer medicine

A technology of thiazolidinone and anticancer drugs, which is applied in the field of application of thiazolidinone derivatives in the preparation of broad-spectrum anticancer drugs, and can solve problems such as neurotoxicity and adverse reactions of chemotherapy drugs

Inactive Publication Date: 2013-04-24
SHANDONG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Second, chemotherapy drugs have serious adverse reactions, such as gastrointestinal reactions, bone marrow suppression, neurotoxicity, etc. (quoted from Song Enfeng et al., Toxic and side effects of chemical anticancer drugs and treatment with traditional Chinese medicine, "Journal of Guiyang College of Traditional Chinese Medicine", 2008 Year 01)
However, 4-thiazolidinone is used to develop broad-spectrum anticancer drugs, evaluate drug efficacy and pharmacology research, and has been retrieved by authoritative organizations (SCI / SSCI / A&HCI / ESI, BIOSIS / Inspec / JCR database and CNKI database). Not yet reported

Method used

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  • Application for thiazolidone derivative in preparation for broad-spectrum anti-cancer medicine
  • Application for thiazolidone derivative in preparation for broad-spectrum anti-cancer medicine
  • Application for thiazolidone derivative in preparation for broad-spectrum anti-cancer medicine

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] Example 1: Preparation of 2-(4-hydroxyphenylimino)-5-(3-methoxybenzylidene)-4-thiazolidinone

[0034] by HCl:H 2 The ratio of O (1:4) is made into hydrochloric acid solution. Weigh 11.4g (150mmol) of ammonium thiocyanate and dissolve it in 50mL of hydrochloric acid solution, add 10.9mL (100mmol) of 4-hydroxyaniline, and heat to 85°C with stirring, the mixture becomes clear. After 12 hours of reaction, TLC monitors the reaction. After the reaction, the mixture was cooled to room temperature, and a viscous oily liquid appeared, which was extracted with ethyl acetate, and the extract was washed with 10% hydrochloric acid solution, saturated sodium chloride solution, and water successively, and the solvent was evaporated off the extract under reduced pressure to obtain Viscous oily liquid, 4-hydroxyphenylthiourea.

[0035] Add 4.24g of 4-hydroxyphenylthiourea and 9.15g of anhydrous sodium acetate into 35mL of ethanol, add 5.13g of ethyl chloroacetate under stirring condit...

Embodiment 2

[0040] Example 2: Determination of the half inhibitory concentration of 2-(4-hydroxyphenylimino)-5-(3-methoxybenzylidene)-4-thiazolidinone on cancer cell growth by SRB method

[0041] 5% CO at 37°C 2 Three cancer cells, Hela, HCT-116, and RD, were cultured in DMEM / 10% fetal bovine serum medium under the condition of . Three kinds of cancer cells in the logarithmic phase were collected and seeded in 96-well plates respectively, and incubated for 24 hours. Add different concentrations (20, 10, 5, 1, 0.1, 0.01 μM) of 2-(4-hydroxyphenylimino)-5-(3-methoxybenzylidene)-4-thiazolidinone ( Compound I) After incubation for 48 hours, 50 μL of trichloroacetic acid solution (30%) was added and fixed at 4°C for one hour. Shake off the solution, rinse with high-purity water five times, add 100 μL sulforhodamine B to stain for 30 minutes after drying, rinse with 1% acetic acid solution five times after drying. After drying, add 100 μL of Tris solution to fully dissolve, and measure the ab...

Embodiment 3

[0042] Example 3: Determination of the effect of 2-(4-hydroxyphenylimino)-5-(3-methoxybenzylidene)-4-thiazolidinone on cancer cell cycle by PI staining flow cytometry

[0043] Hela, HCT-116, and RD cancer cells in the logarithmic growth phase were inoculated into 6 cm culture dishes at an amount of 200,000 cells per 3 mL of medium volume. After culturing for 24 hours, each cancer cell group was treated with DMSO and 5.0 μM 2-(4-hydroxyphenylimino)-5-(3-methoxybenzylidene)-4-thiazolidinone (Compound I) deal with. After incubation for 24 h, the cells were digested on ice, and the cell suspension was collected, washed twice with PBS after centrifugation. Add 10 mL of 70% ice ethanol to suspend at -20°C overnight. Centrifuge the cell suspension, wash twice with PBS, add 500 μL PI / 5 μL RNAaseA to the cell mass and stain at 4°C for half an hour in the dark. The DMSO group was used as a negative control, and the cell cycle was detected by flow cytometry with standard procedures. ...

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Abstract

The invention discloses an application for thiazolidone derivative in preparation for a broad-spectrum anti-cancer medicine, wherein the thiazolidone derivative is 2-(4-hydroxyphenylimino)-5-(3-metoxybenzylidene)-4-thiazolidone; and the broad-spectrum anti-cancer medicine preferably is a medicine with good anti-cancer activity for cervical cancer, colon cancer and rhabdomyosarcoma. Tests confirm that the thiazolidone compound disclosed by the invention can effectively inhibit the proliferations of cervical cancer Hela cells, colon cancer HCT-116 cells and rhabdomyosarcoma RD cells and induce apoptosis; and inspections for the action target of the thiazolidone compound found that the compound acts on microtubulin, obviously inhibits microtubule formation, and has a prospect of being developed into a broad-spectrum anti-cancer medicine.

Description

technical field [0001] The present invention relates to the application of a novel thiazolidinone derivative in the preparation of broad-spectrum anticancer drugs, in particular to a 2-(4-hydroxyphenylimino)-5-(3-methoxybenzylidene Application of )-4-thiazolidinone in the preparation of broad-spectrum anti-cancer (anti-cervical cancer, colon cancer, rhabdomyosarcoma) drugs. Background technique [0002] Cancer, also known by other terms as malignant tumor or neoplasm, is a group of diseases that can affect any part of the body. A defining feature of cancer is the rapid production of abnormal cells that extend beyond the boundaries of their normal growth and can invade adjacent parts of the body and spread to other organs. Cancer is an important cause of death in humans, accounting for about 13% of all deaths among the 7.6 million people who died in 2008, and about 70% of cancer deaths occurred in low- and middle-income countries like China (data cited from the Internationa...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A61K31/426A61P35/00
Inventor 闫兵田聪穆岩吴金梅张斌
Owner SHANDONG UNIV
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