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Preparation method and application of anthraquinone polypyridine ligand and binuclear ruthenium complexes

A technology of anthraquinone polypyridine and anthraquinone dinuclear ruthenium polypyridine, which is applied in the field of preparation of anthraquinone polypyridine ligands and their dinuclear ruthenium complexes, can solve the limitations of clinical application, severe toxicity and drug resistance of platinum complexes In order to achieve the effect of simple synthesis method, inhibition of tumor cell migration and stable structure

Inactive Publication Date: 2014-02-05
SUN YAT SEN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] At present, metal complex anticancer drugs widely used in clinic are mainly platinum complexes such as cisplatin, carboplatin, oxaliplatin, etc., but platinum complexes Severe toxicity and drug resistance limit its clinical application (Hartinger CG, Chem Biodivers, 2008, 5:2140-2155.)

Method used

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  • Preparation method and application of anthraquinone polypyridine ligand and binuclear ruthenium complexes
  • Preparation method and application of anthraquinone polypyridine ligand and binuclear ruthenium complexes

Examples

Experimental program
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Effect test

Embodiment 1

[0031] Example 1 Synthesis of Anthraquinone Polypyridine Ligands and Binuclear Ruthenium Complexes

[0032]The general formula of the binuclear ruthenium complex is: [(bpy) 2 Ru (X-biipad)Ru(bpy) 2 ](ClO 4 ) 4 ,in X Anthraquinone polypyridine ligands, specifically: 1,4-bis(imidazo[4,5-f][1,10]phenanthroline-2-)anthracene-9,10-dione (ligand 1); 1,5-bis(imidazo[4,5-f][1,10]phenanthroline-2-)anthracene-9,10-dione (ligand 2); 2,6-bis( imidazo[4,5-f][1,10]phenanthroline-2-)anthracene-9,10-dione (ligand 3); 2,7-bis(imidazo[4,5-f] [1,10]phenanthroline-2-)anthracene-9,10-dione (ligand 4). The binuclear ruthenium complexes prepared from ligands 1-4 correspond to complexes 1-4 respectively.

[0033] (1) Synthesis of 1,4-bis(imidazo[4,5-f][1,10]phenanthroline-2-)anthracene-9,10-dione (1,4-biipad)

[0034] (a) Synthesis of 2-(2',5'-dimethylbenzoyl)benzoic acid

[0035] Can refer to ( Journal of Jiangxi Normal University, 2008, 32 , 1, 94-97) Synthetic method, add 34...

Embodiment 2

[0076] Example 2 Binuclear ruthenium complexes inhibit the migration of MHCC97H tumor cells

[0077] The principle of cell scratch method: refer to the in vitro cell wound healing experimental model to measure the motility characteristics of tumor cells, scratch and wound the monolayer cells cultured in vitro, and then add drugs to observe its ability to inhibit tumor cell migration. If the drug can inhibit the ability of cell migration, the scratch cannot be covered by the migration movement of the cell, and the degree of healing of the scratch can reflect the strength of the ability of the drug to inhibit cell migration. Experimental steps: set the density to 5 × 10 5 Cells / mL of human hepatoma cell MHCC97H cells were plated on a 24-well plate (0.5 mL / well), added with 10% fetal bovine serum, and cultured for 24 hours to form a monolayer of cells. Then use the tip of a pipette to scratch the monolayer of cells in a straight line, wash with PBS three times, replace with DM...

Embodiment 3

[0078] Example 3 Binuclear Ruthenium Complex Inhibits MHCC97H Tumor Cell Invasion

[0079] Tumor cell invasion test principle: Matrigel is a matrix component extracted from mouse EHS sarcoma, containing LN, type IV collagen, contact protein and heparin sulfate polysaccharide, spread on polycarbonate filter membrane without polyvinylpyrrolidone, can The membrane structure is reconstituted in DMEM medium, which is very similar to the natural matrix structure. The pore size of the filter membrane is generally 8 μm, and the membrane pores are covered by Matrigel. Cells cannot pass through freely. They must secrete hydrolytic enzymes and deform to pass through the filter membrane covered with Matrigel, which is similar to the situation in vivo. The filter membrane covered with Martrigel is placed between the upper and lower chambers of the Blind Well chamber or MICS chamber, and the side covered with Martrigel faces the upper chamber. Chemotactic agents such as a certain concentr...

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Abstract

The invention discloses a novel anthraquinone polypyridine ligand and a preparation method thereof. The anthraquinone polypyridine ligand is simple in synthetic method and can be further used for preparing binuclear ruthenium complexes. The prepared anthraquinone polypyridine binuclear ruthenium complexes as shown in a general formula of [(bpy) 2Ru (X-biipad) Ru (bpy) 2] (ClO4)4 have the advantages of stable structure and high water solubility, can effectively inhibit the migration of tumor cells and cell invasion according to the results of cell wound scratch assay and cell invasion assay, and can be used for preparing novel antineoplastic drugs for inhibiting tumor metastasis.

Description

technical field [0001] The invention belongs to the field of antitumor drugs, and in particular relates to a preparation method and application of a novel anthraquinone polypyridine ligand and a dinuclear ruthenium complex. Background technique [0002] Cancer seriously threatens human life and health. According to WHO statistics, about 7 million people died of cancer worldwide in 2010. With the aggravation of population aging worldwide and the aggravation of environmental pollution, the number of people dying from cancer continues to increase every year, and it is estimated that 9 million people will die of cancer in 2015 (Tang ZY, J Cancer Res Clin Oncol, 2004, 130(4):187-196.). According to clinical statistics, most cancer patients have actually metastasized when they see a doctor. Invasion and metastasis are the basic biological characteristics of malignant tumors, an important link in the prevention and treatment of tumors, and the main factors of poor prognosis in...

Claims

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Application Information

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IPC IPC(8): C07D519/00C07F15/00A61K31/555A61P35/00A61P35/04
CPCC07D519/00C07F15/0053
Inventor 巢晖王金全寇军锋张平玉计亮年
Owner SUN YAT SEN UNIV
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