Ruthenium(ii) complexes and their preparation methods and their application as cell fluorescent dyes

A technology for fluorescent dyes and complexes, which is applied in the direction of azo dyes, organic dyes, and luminescent materials. It can solve the problems of polypyridine ruthenium complexes and other problems, so that the fluorescent color is not easy to quench, the price is simple and easy to obtain, and the fluorescent color is easy to obtain. The effect of observation

Active Publication Date: 2017-09-26
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) complexes and their preparation methods and their application as cell fluorescent dyes
  • Ruthenium(ii) complexes and their preparation methods and their application as cell fluorescent dyes
  • Ruthenium(ii) complexes and their preparation methods and their application as cell fluorescent dyes

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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, the structure of which is as follows:; also discloses the preparation method of the compound, including the steps: first use o-phenanthroline 5,6-dione and X-diketone as raw materials to prepare X- RPIP, and then use X‑RPIP and cis‑Ru(L)2Cl2 as raw materials to prepare the product. Alternatively, X-RPIP is first prepared from X-BrPIP and X-RPIP, and then X-RPIP and cis-Ru(L)2Cl2 are used as raw materials to prepare the product. Alternatively, the ruthenium precursor Ru(L)2Cl2 and X‑R'''PIP are reacted as raw materials to prepare Ru(L)2(X‑R'''PIP)2+, and then Ru(L)2( X‑R'''PIP) 2+, the product is prepared as raw material. The synthesis method of the present invention is simple, especially the synthesized Λ-[Ru(bpy)2(p-BEPIP)]2+ is non-toxic to living cells, transmembrane rapidly, the fluorescent color is strong and easy to observe and not easy to quench, and the fluorescence excitation and The emission bands do not overlap and can be enriched in the nucleus.

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 Patents(China)
IPC IPC(8): C07F15/00C09B57/10C09K11/06G01N21/64
Inventor 梅文杰
Owner GUANGDONG PHARMA UNIV
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