Ruthenium complex and preparation method thereof and purpose of product as histone deacetylase inhibitor

A technology of ruthenium complexes and compounds, applied in the field of ruthenium complexes with excellent anti-tumor activity and its preparation, can solve the problems of histone hypoacetylation and achieve good anti-tumor activity

Inactive Publication Date: 2013-09-04
SUN YAT SEN UNIV
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  • Abstract
  • Description
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  • Application Information

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Problems solved by technology

However, in the state of cell transformation, the activity of HDACs is significantly enhanced. Current studies have confirmed that there are overe

Method used

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  • Ruthenium complex and preparation method thereof and purpose of product as histone deacetylase inhibitor
  • Ruthenium complex and preparation method thereof and purpose of product as histone deacetylase inhibitor
  • Ruthenium complex and preparation method thereof and purpose of product as histone deacetylase inhibitor

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Experimental program
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[0053] Example 1

[0054] (1) Preparation of ligand:

[0055] Add 5-amino-1,10-phenanthroline (0.629 g, 3.226 mmol) and methyl 8-chloro-8-oxooctanoic acid (1 g, 4.839 mmol) into the reaction flask, add a catalytic amount of DMAP After stirring for 12 h at room temperature in 45 ml DMF solvent, rotary steam to remove most of DMF, add a large amount of ether, filter to obtain a light yellow solid, then add 50% hydroxylamine aqueous solution (the amount of the substance added to the hydroxylamine aqueous solution is light yellow 20 times of solid), methanol as solvent (4 mL), add 1N NaOH solution (2 mL) and stir at room temperature for 30 min, adjust the pH to neutral with 1N HCl, you can see the formation of light yellow precipitate, filter The ligand is obtained with a yield of 40%.

[0056] Elemental Analysis C 20 H 22 N 4 O 3 (Molecular weight is 366.4), theoretical value: C 65.56%, H 6.05%, N 15.29%; experimental value: C 65.17%, H 6.01%; N 14.96%. ESI-MS: [(L+H) + ] Theoretical...

Example Embodiment

[0066] Example 2 Inhibition test of Ru(Ⅱ) complex on histone deacetylase

[0067] HDAC enzyme activity test: The ability of ruthenium complexes to inhibit histone deacetylase is mainly detected by the HDAC activity analysis kit of fluorescence method. The operation steps are roughly as follows. Add 0.5 μL of HeLa nuclear extract to a 96-well culture plate , Then add HDAC substrate, 100 μL HDAC analysis buffer, negative control without HeLa nuclear extract and HDAC substrate, and add 1 μM Trichostatin A as positive control. Incubate the above reaction mixture in a 37°C incubator for 30 min, then add 10 μL of lysine developer to stop the reaction, continue to incubate in a 37°C incubator for 30 minutes, take it out, and place the plate on a multifunctional microplate reader for measurement Fluorescence value, excitation wavelength is set to 340 nm, emission wavelength is 460 nm. The activity of histone deacetylase is expressed as the relative fluorescence value per microgram of pr...

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Abstract

The invention discloses a ruthenium complex and preparation method thereof and purpose of product as histone deacetylase inhibitor, specifically speaking, the invention discloses a ruthenium complex with histone deacetylase inhibitor effect [Ru(N-N)2L](PF6)2, wherein, L is N1-hydroxy-N8-(1,10 phenanthroline) octanedioyl amine, N-N=2,2 ' -dipyridine is the complex 1, N-N=1, 10-phenanthroline is the complex 2, N-N=4, 7-dibenzyl-1, 10-orthophenanthrolene is the complex 3 and the structural formula is shown in the formula (I). The anticancer activity and histone deacetylase activity of the ruthenium complex are researched, and the complex 3 not only can inhibit the activity of the histone deacetylase, but also has an excellent antineoplastic activity.

Description

technical field [0001] The invention relates to a ruthenium complex with histone deacetylase inhibitor function and a preparation method thereof, in particular to a ruthenium complex with excellent antitumor activity and a preparation method thereof. Background technique [0002] Epigenetics is the study of heritable phenotypic changes in gene expression without changes in the genomic DNA sequence. There are many epigenetic phenomena, such as DNA methylation, histone modification, genome imprinting, chromosome inactivation, and non-coding RNA. As an important part of epigenetics, histone modification has attracted more and more attention in recent years. The disorder of histone modification can lead to abnormal gene expression, which affects the important physiological functions of cells, and then leads to the formation of tumors. Among them, the acetylation level of histones is closely related to the occurrence and proliferation of tumors, and the expression levels of onc...

Claims

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Application Information

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IPC IPC(8): C07D471/04C07F15/00A61K31/4745A61P35/00
Inventor 谭彩萍叶瑞绒毛宗万黄华珍计亮年
Owner SUN YAT SEN UNIV
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