Ruthenium (II) complex, preparation method thereof, and application of complex as cell fluorescent dye

A complex and reaction technology, applied in azo dyes, organic dyes, luminescent materials, etc., can solve the problems of polypyridine ruthenium complexes, etc., and achieve the effects of not easy quenching of fluorescent color, simple synthesis method, and good application prospects.

Active Publication Date: 2014-04-09
GUANGDONG PHARMA UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Due to its problems in the transmembrane barrier of cellular uptake, the further application of polypyridine ruthenium complexes as fluorescent probes in cells has been limited.

Method used

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  • Ruthenium (II) complex, preparation method thereof, and application of complex as cell fluorescent dye
  • Ruthenium (II) complex, preparation method thereof, and application of complex as cell fluorescent dye
  • Ruthenium (II) complex, preparation method thereof, and application of complex as cell fluorescent dye

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preparation example Construction

[0040] The synthetic method of above-mentioned formula (D compound comprises following three kinds of preparation methods:

[0041] Method one includes the following steps:

[0042] (1) Mix o-phenanthroline 5,6-dione and alkyne-modified benzaldehyde, dissolve in acetic acid solvent, heat and reflux under the catalysis of ammonium acetate, and adjust the acidity and alkalinity to precipitate the target compound X-RPIP after the reaction.

[0043] (2) X-RPIP prepared in step (1) and Λ-[Ru(bpy) 2 (py) 2 ][o,o'-dibenzoyl-D-tartrate]·12H 2 O or Δ-[Ru(bpy) 2 (py) 2 ][o,o'-dibenzoyl-D-tartrate]·12H 2 O is heated and reacted under the protection of argon. After the reaction is completed, it is cooled to room temperature, diluted with water, filtered to remove insoluble matter, an excessive amount of acid or salt containing Y ions is added to the filtrate, allowed to stand overnight, filtered, and purified by filter cake column chromatography to obtain Compound Λ-[Ru(L) 2 (X-RPI...

Embodiment 1C

[0078] Embodiment 1Cis-[Ru(bpy) 2 (Cl) 2 ]·2H 2 O synthesis

[0079] In a 50mL three-necked flask, add: bipyridyl (1.87g, 12mmol), lithium chloride (2.43g, 57.6mmol), ruthenium trichloride (1.57g, 6mmol), after adding DMF and water, under argon protection Heated at 140°C to reflux for 8h. After stopping the reaction, cool to room temperature, add acetone, and filter with suction to obtain black crystals. After washing the filter cake several times with ice water and acetone, dry it in a vacuum desiccator to obtain purple-black crystals with a yield of 75.5%.

Embodiment 2C

[0080] Embodiment 2Cis-[Ru(bpy) 2 (py) 2 ]·2H 2 O synthesis

[0081] Add in a 150mL three-necked bottle: Cis-[Ru(bpy) 2 (py) 2 ]·2H 2 O (2.01g, 3.85mmol), pyridine, and distilled water were reacted under reflux at 100°C for 4h under the protection of argon. After stopping the reaction, cool to room temperature, distill off all solvents under reduced pressure, dissolve in methanol to obtain a red solution, then add ether, filter with suction, wash the filter cake with ether several times, and dry it in a vacuum desiccator to obtain red crystals. Yield 89.5%.

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Abstract

The invention discloses a ruthenium (II) complex, of which the structure is as shown in the specification, and also discloses a preparation method of the complex. The method comprises the following steps: firstly, preparing X-RPIP from phenanthroline 5,6-diketone as a raw material, and then preparing a product, namely the ruthenium (II) complex from the X-RPIP and cis-Ru(L)2Cl2 as the raw materials; or firstly, preparing the X-RPIP from X-BrPIP as a raw material, and then preparing the product from the X-RPIP and cis-Ru(L)2Cl2 as the raw materials; or firstly, preparing Ru(L)2(X-R'''PIP)<2+> from Ru(L)2Cl2 and X-R'''PIP as the raw materials, and then preparing the product from the Ru(L)2(X-R'''PIP)<2+> as the raw material. The synthetic method disclosed by the invention is simple, especially the synthetic lambda-[Ru(bpy)2(p-BEPIP)]<2+> is free of toxicity on a living cell, quick to stride across a film, strong in fluorescence color, easy to observe, and not easy to quench, fluorescence excitation does not overlap with an emission waveband, and cell nucleus enrichment can be carried out.

Description

technical field [0001] The invention relates to a ruthenium (II) complex, a preparation method thereof and an application as a cell fluorescent dye. Background technique [0002] Fluorescent dyes generally refer to substances that absorb light waves of a certain wavelength and emit light waves of another wavelength greater than the absorbed light. Most of the reported fluorescent dyes are compounds containing benzene rings or heterocycles and conjugated double bonds. Due to its high sensitivity and convenient operation, it has gradually replaced radioactive isotopes as detection labels. It is widely used in fluorescent immunology, fluorescent probes, cell staining, etc., including specific DNA staining, chromosome analysis, cell cycle, and apoptosis. and other related research fields. With the continuous deepening of the basic theoretical research on fluorescent dyes, the counterstaining agent applied to the multi-color staining system can be used as a background control to...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F15/00C09B57/10C09K11/06G01N21/64
Inventor 梅文杰
Owner GUANGDONG PHARMA UNIV
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