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Preparation method and application of anthraquinone polypyridine ligand and ruthenium-anthraquinone complex

A technology of anthraquinone polypyridine and anthraquinone ruthenium polypyridine is applied in the field of preparation of anthraquinone ligands and anthraquinone ruthenium complexes, can solve problems such as treatment failure, and achieves small molecular structure, good water solubility and simple synthesis method. Effect

Inactive Publication Date: 2015-10-07
SUN YAT SEN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Because oxygen-starved cells in cancer tissue resist radiation and chemotherapy, leading to treatment failure

Method used

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  • Preparation method and application of anthraquinone polypyridine ligand and ruthenium-anthraquinone complex
  • Preparation method and application of anthraquinone polypyridine ligand and ruthenium-anthraquinone complex
  • Preparation method and application of anthraquinone polypyridine ligand and ruthenium-anthraquinone complex

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034] Example 1 Ligands and Complexes Preparation Methods

[0035] (1) Synthesis of 2-formaldehyde-9,10-anthraquinone

[0036] You can refer to ( J. Org. Chem . 1997, 62 , 5690-5695) synthetic method, in a 150 mL round bottom flask, add 2.0 g (8 mmol) of 2-hydroxymethylanthraquinone, 100 mL of dichloromethane, and then add 2.6 g (12 mmol) of pyridinium chlorochromate Om salt (PCC), stirred at room temperature for 12 h. The excess PCC was filtered off, and the solvent was evaporated under reduced pressure. First wash with 75 mL of distilled water, and then extract with dichloromethane (3×75 mL) three times. The solvent was distilled off under reduced pressure, passed through a silica gel column, and eluted with toluene:dichloromethane=1:5. Yield 98%.

[0037] (2) Synthesis of 2-(phenylimidazo[4,5-f][1,10]phenanthroline-2-)anthraquinone (a)

[0038] Weigh 1,10-phenanthroline dione (0.212 g, 1 mmol), 2-formaldehyde-9,10-anthraquinone (0.236 g, 1 mmol), aniline (0.25 ...

Embodiment 2

[0050] Example 2 Cytotoxicity MTT assay

[0051] Take the tumor cells in the logarithmic growth phase and adjust the cell density to 5×10 3 cells / ml, inoculated in 96-well culture plates, and each sample in the experiment had 6 concentrations of 100, 50, 25, 12.5, 6.25, and 3.125 μM. Four replicate wells were set for each concentration, and more than eight replicate wells were set for the control. Experimental samples were dissolved with DMSO and diluted with DMEM culture medium. After 24 hours of loading, cells were still placed at 37°C, 5% CO 2 , 1%O 2 Continue culturing in an anaerobic incubator for 48 hours, then add MTT, continue culturing for another 4 hours, absorb the supernatant, add 150 μL DMSO to each well, measure the absorbance of each well at a wavelength of 490 nm with an enzyme-linked immunosorbent assay instrument, and calculate the inhibition of cell proliferation Rate. find IC 50 value (drug concentration at which the inhibition rate is equal to 50...

Embodiment 3

[0053] Example 3 Fluorescence imaging experiments of complexes 1a, 1b, 1c in hypoxic cells

[0054] Cell culture: Hela cells were cultured in DMEM medium containing 10% fetal bovine serum, cells (5×10 8 / L) in 6-well plates, 5% CO 2 and 1%O 2 Under anaerobic conditions, 37 o C culture, adherent growth for 24 hours. Then Hela cells were incubated with complexes 1a, 1b, 1c (7.5μM) for 0, 0.5h, 1h, 3h, respectively. Aspirate the culture medium, then wash 2-3 times with PBS buffer, and image under a fluorescent microscope. The result is as Figure 4 shown. With the increase of the incubation time between the complex and the cells, the amount of the complex entering the cells increases, and thus the fluorescence increases.

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Abstract

The invention discloses a synthesis method and application of an anthraquinone polypyridine ligand and anthraquinone-ruthenium polypyridine complex. The anthraquinone-ruthenium polypyridine complex has good inhibition activity on the growth of hypoxic cells, and generates obvious fluorescence through reduction in the hypoxic cells; and thus, the compound is a novel biological reduction type hypoxic cell anti-cancer drug and a specific fluorescence probe as well as a drug with application value and taking tumor hypoxia as a target point and a fluorescence probe.

Description

technical field [0001] The invention relates to the application of anticancer drugs and fluorescent imaging probes in hypoxic cells, in particular to the preparation method and application of a new class of anthraquinone ligands and anthraquinone ruthenium complexes. Background technique [0002] Hypoxia in solid tumors has always been a difficult problem for medical scientists. Because hypoxic cells in cancer tissue resist radiation and chemotherapy, leading to treatment failure. According to the characteristics of hypoxic tumor cells, many methods have been developed to achieve specific killing, among which bioreductant drugs are a class of drugs that can use the intracellular oxygen environment to specifically kill hypoxic tumor cells. After being reduced and activated in the body, this kind of drugs can generate active oxygen groups or alkylating groups, and then damage intracellular biomacromolecules such as DNA and proteins, thereby killing cancer cells. Among them, ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D471/14C07F15/00A61K31/4375A61K49/00A61P35/00
Inventor 巢晖张平玉计亮年
Owner SUN YAT SEN UNIV
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