Norharman-ruthenium (II) polypyridine complex with antitumour activity

A technology of anti-tumor activity and anti-tumor drugs, applied in the field of new Norharman-ruthenium polypyridine complexes, to achieve the effects of inhibiting tumor proliferation, enhancing cell transmembrane ability, and stabilizing molecular structure

Inactive Publication Date: 2014-01-01
SUN YAT SEN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

They found that although the complexes were inactive in vitro, they had a significant inhibitory effect on the metastatic tumors of mice

Method used

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  • Norharman-ruthenium (II) polypyridine complex with antitumour activity
  • Norharman-ruthenium (II) polypyridine complex with antitumour activity
  • Norharman-ruthenium (II) polypyridine complex with antitumour activity

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0021] Complex [Ru(tpy)(Norharman) 3 ]·(CF 3 SO 3 ) 2 Synthetic method:

[0022] (1)Ru(tpy)Cl 3 Synthesis

[0023] The synthesis of this compound can be prepared by referring to existing literature (B.P.Sullivan, D.J.Salmn and T.J.Meyer, Inorg.Chem., 1978, 17, 3334). Weigh RuCl 3 ·nH 2 O2.62g (about 10mmol), 2,2':6',2''-terpyridine 2.33g (10mmol), at 250cm 3 In absolute ethanol, heat to reflux for about 3 hours. After cooling to room temperature, filter with suction, wash the precipitate with ice water and cold acetone, and dry in vacuo to obtain purple-black microcrystals. The average yield is 80%.

[0024] (2) Synthesis of Norharman

[0025]The synthesis of this compound can be prepared by referring to existing literature (H.R.Snyder, H.G.Walker and F.X.Werber.J.Am.Soc.Chem., 1949, 71, 527-529). Weigh 10.0g (about 49mmol) of L-tryptophan and 4.0g (about 100mmol) of sodium hydroxide in 500cm 3 In ultrapure water, stir until completely dissolved. Then add 40% met...

Embodiment 2

[0029] [Ru(tpy)(Norharman) 3 ]·(CF 3 SO 3 ) 2 The confocal laser experiment of HeLa cells and complexes is taken as an example in this example.

[0030] Cell culture: HeLa cells were cultured in DMEM medium containing 10% fetal bovine serum, cells (5×l0 8 / L) inoculated in a special glass bottom petri dish for confocal microscopy, the diameter of the petri dish is 35mm, the thickness of the cover glass is 0.085-0.13mm, the diameter of the micropore in the center of the petri dish is 10mm, and 5% CO 2 and 95% air conditions, cultured at 37°C, and grown adherently for 24 hours.

[0031] Confocal Microscopy-Cell Imaging: HeLa cells with [Ru(tpy) (Norharman) 3 ]·(CF 3 SO 3 ) 2 (5μM) incubate for 30min, 1h, 1.5h and 2h, aspirate the culture solution, and then wash with PBS buffer for 3-4 times, image on a Leica TCS SP5 laser scanning confocal microscope, use a 63× / 1.4 oil lens, and use a 350nm Light is used as an excitation light source to collect fluorescence in the range...

Embodiment 3

[0033] [Ru(tpy)(Norharman) 3 ]·(CF 3 SO 3 ) 2 In this example, the ICP-MS experiment of HeLa cells and complexes is taken as an example.

[0034] Cell culture: HeLa cells were cultured in DMEM medium containing 10% fetal bovine serum, cells (5×l0 8 / L) inoculated in a cell culture dish with a diameter of 100 mm and 5% CO 2 and 95% air conditions, cultured at 37°C, and grown adherently for 24 hours.

[0035] Inductively coupled plasma mass spectrometry (ICP-MS): HeLa cells and [Ru(tpy) (Norharman) 3 ]·(CF 3 SO 3 ) 2 (5μM) incubate for 30min, 1h, 1.5h and 2h, suck out the culture medium, and then wash with PBS buffer 3 to 4 times. Digest into single cells with 0.25% trypsin and divide the cells into 4 parts. The first was used for cell counting, the second was used to isolate the cytoplasm using the Thermo's Cytoplasm Isolation Kit, and the third was used to isolate the nuclei using the Thermo's Nuclei Isolation Kit. Disperse the fourth cell, the isolated cytoplasm an...

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Abstract

The invention discloses a preparation method for a Norharman-ruthenium (II) polypyridine complex and the antitumour activity thereof. The chemical formula of the Norharman-ruthenium (II) polypyridine complex disclosed by the invention is [Ru(tpy)(Norharman)3]<2+>(tpy=2,2':6',2''- terpyridyl, Norharman=9H-pyridino-[3,4-b] indol), and prepared by taking ruthenium trichloride and Norharman as raw materials, and performing the steps of heating reflux reaction, cooling and filtering, washing, drying and the like. The influence of the complex on tumour cells is researched in in-vitro antitumour activity test, and the complex is found to be strong in an inhibition effect on the growth of tumour cells HeLa, HepG2, A549, MCF-7, NCI-H460, Bel-7402 and HCT-116. The complex is indicated to be good in a tumour inhibition effect by animal test data, and expected to be a novel antitumour medicinal member, and wide in application prospect.

Description

technical field [0001] The invention relates to the field of new anti-tumor small molecule compounds, in particular to a new Norharman-ruthenium (II) polypyridine complex, its preparation method and application. Background technique [0002] As the second leading cause of death among diseases, cancer seriously threatens human health. About 7 million people die from cancer every year in the world, of which 1.5 million people die from cancer every year in my country. Cancer has become the number one killer of various causes of death in my country. . Therefore, it is particularly urgent to develop new anti-tumor drugs that can selectively act on tumor cells and have no toxicity to normal cells. Chemotherapy is currently one of the three major means of clinical treatment of cancer, but for a long time, the drugs used for tumor treatment are mainly organic compounds; until 1969, biophysicist Barnett Rosenberg of Michigan State University in the United States accidentally discover...

Claims

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Application Information

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IPC IPC(8): C07F15/00A61K31/28A61P35/00
Inventor 徐安龙陈禹覃梦颖王磊巢晖计亮年
Owner SUN YAT SEN UNIV
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