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A kind of ruthenium complex fluorescent probe, preparation method and application

A technology of fluorescent probes and ruthenium complexes, applied in the fields of ruthenium organic compounds, fluorescence/phosphorescence, chemical instruments and methods, etc., can solve the problems of undeveloped and designed ruthenium antitumor drugs, unfavorable naked eye detection, poor selectivity, etc. Achieve the effect of excellent selectivity, good selectivity and simple material structure

Active Publication Date: 2020-09-25
GUANGZHOU YUEWANG AGRI CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0006] Research progress on the interaction between ruthenium complexes and G-quadruplex DNA, Zhao Xiaolong et al., Chemical Bulletin, Volume 78, No. 10, 2015, reported that various ruthenium complexes can stabilize G-quadruplex DNA, and also reported A variety of ruthenium complexes that can be used as molecular optical switches, but it also pointed out that the selectivity and specificity of the interaction between ruthenium complexes and G-quadruplex DNA needs to be improved. Ruthenium complexes can be used as G-quadruplex DNA in vivo Structural probes, ruthenium anti-tumor drugs targeting G-quadruplex DNA have not been developed yet, and its compounds 23, 24, 25 show certain selectivity to G-quadruplex DNA
Although these complexes exhibit photoswitching effects, they have poor selectivity for G-quadruplex DNA recognition, and they have a strong fluorescent background, which is not conducive to naked eye detection

Method used

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  • A kind of ruthenium complex fluorescent probe, preparation method and application
  • A kind of ruthenium complex fluorescent probe, preparation method and application
  • A kind of ruthenium complex fluorescent probe, preparation method and application

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Experimental program
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Effect test

Embodiment 1

[0032] The present invention comprises the steps:

[0033] (1)Cis-[Ru(bpy) 2 Cl 2 ].2H 2 o

[0034] Weigh RuCl at a molar ratio of 1:1:2 3 ·3H 2 O. Lithium chloride monohydrate and auxiliary ligand 2,2'-bipyridyl, add DMF to dissolve to obtain a solution, heat under reflux at 140°C to obtain a solid-liquid mixture, add acetone after cooling to room temperature, and store at -4°C for 15 to 30 hours. Suction filtration to obtain purple black crystals, set aside;

[0035] (2) O-phenanthroline 5,6-dione

[0036] Add 4g of o-phenanthroline and 4g of potassium bromide, add a mixed solution of 40ml of ice-cold concentrated sulfuric acid and 20ml of concentrated nitric acid under magnetic stirring, add the mixed acid within 20 minutes, keep at 80-85°C, and reflux for 3h. After the reaction was complete, let the bromine escape, add ice to the completely cooled orange-yellow reaction product, neutralize it with NaOH until the pH was less than 7, extract the neutralized mixture di...

Embodiment 2

[0046] Adopt the preparation method similar to embodiment 1, specifically comprise the following steps:

[0047] (1)Cis-[Ru(phen) 2 Cl 2 ].2H 2 o

[0048] Weigh RuCl at a molar ratio of 1:1:2 3 ·3H 2 O. Lithium chloride monohydrate and the auxiliary ligand o-phenanthroline were dissolved in DMF to obtain a solution, heated at reflux at 140°C to obtain a solid-liquid mixture, cooled to room temperature, added acetone, stored at -4°C for 15 to 30 hours, and obtained by suction filtration Purple black crystal, for use;

[0049] (2) O-phenanthroline 5,6-dione

[0050] Add 4g of o-phenanthroline and 4g of potassium bromide, add a mixed solution of 40ml of ice-cold concentrated sulfuric acid and 20ml of concentrated nitric acid under magnetic stirring, add the mixed acid within 20 minutes, keep at 80-85°C, and reflux for 3h. After the reaction was complete, let the bromine escape, add ice to the completely cooled orange-yellow reaction product, neutralize it with NaOH until t...

Embodiment 3

[0058] Applications of Probe Molecules

[0059] 1. Tris-HCl buffer:

[0060] Buffer A: 10mM Tris, 100mM KCl, pH=7.0;

[0061] General preparation method: Accurately weigh 0.303g Tris salt, 1.865g KCl l, dissolve completely with 60mL sterilized triple distilled water, slowly adjust the pH value to 7.0 with dilute hydrochloric acid, transfer to a 250ml volumetric flask, constant volume with triple distilled water, mix well Backup.

[0062] 2. Preparation of complex solution:

[0063] Accurately weigh 2 to 3 mg of the complex (depending on the molecular weight of the complex, the expected concentration of the ruthenium complex prepared in this paper is 200 μM, the volume is 10 mL, and the preparation container is a 10 mL volumetric flask, so the theoretical value to be weighed is: molecular weight / 1000*2mg), first dissolved in 50-100μL DMSO, then distilled to 10mL with pure water to obtain a 200μM stock solution of the complex.

[0064] 3. There are two types of double-stran...

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Abstract

The invention belongs to the field of biological detection, and specifically relates to a ruthenium complex fluorescence probe, a preparation method and application. 2-(3-methyl, 4-nitro)phenyl-imidazo[1,10]-phenanthroline is used as a main ligand, and 2,2'-bipyridyl or 1,10-phenanthroline is used as an auxiliary ligand. The invention initially discovers that when G-quadruplex DNA is combined witha nitro-substituted ruthenium complex, four base planes can effectively protect nitro groups on the complex from attack of water molecules, thereby restoring fluorescence of the complex; and when thenitro-substituted ruthenium complex is combined with other single-stranded and double-stranded DNAs, small base planes cannot effectively protect the nitro groups, and the fluorescence of the complexis reduced due to the water molecules, thereby realizing selective detection of the G-quadruplex DNA.

Description

technical field [0001] The invention belongs to the field of biological detection, and in particular relates to a fluorescent probe of a ruthenium complex, a preparation method and an application. Background technique [0002] The G-quadruplex DNA structure is a non-traditional nucleic acid structure, which is composed of single-stranded DNA rich in guanine bases (Guanine) in monovalent cations (such as K + and Na + ) stabilized by the Hoogsteen hydrogen bond between G bases to form a G-plane and further stacked to form a quadruplex helical structure. G-quadruplexes are usually located in many important biological functional regions of the genome, such as the promoter regions of some important proto-oncogenes. The G-quadruplex plays an important role in regulating the transcription, replication and recombination of these genes and regulating the stability of telomeres. Therefore, the G-quadruplex structure is considered to function as a molecular switch, and its formation...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F15/00C09K11/06G01N21/64
CPCC07F15/0046C09K11/06C09K2211/185G01N21/6428
Inventor 刘学文唐裕才张慧
Owner GUANGZHOU YUEWANG AGRI CO LTD
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