A novel organic ligand and its preparation method, novel ruthenium complexes and fluorescent probes

A technology of organic complexes and organic ligands, applied in ruthenium organic compounds, platinum group organic compounds, organic chemistry, etc., can solve the problems of unstable fluorescence emission lifetime, short water solubility, etc., and achieve excellent optical properties and excited state lifetime Long-lasting, biocompatible effect

Inactive Publication Date: 2018-12-18
GUANGDONG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] However, the existing fluorescent molecular probes generally have the problems of unstable fluorescence emission, short lifetime and poor water solubility, which cannot be well applied to fluorescent bioimaging in biomedical research.

Method used

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  • A novel organic ligand and its preparation method, novel ruthenium complexes and fluorescent probes
  • A novel organic ligand and its preparation method, novel ruthenium complexes and fluorescent probes
  • A novel organic ligand and its preparation method, novel ruthenium complexes and fluorescent probes

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Experimental program
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preparation example Construction

[0046] The preparation method of fpic is as follows: add 5-fluoroindolecarboxylic acid to benzene or pyridine, slowly add thionyl chloride dropwise, heat to reflux, concentrate until crystals are precipitated, and then add 5-amino-1,10-phenanthroxine morphine, stirred, and the precipitate was collected and dried. Its chemical reaction formula is:

[0047]

[0048] The ligand fpic, the organic complex of ruthenium, and the reaction solvent ethanol were mixed, refluxed for 6h under nitrogen, cooled to room temperature, filtered, and NaClO was added to the filtrate 4 Aqueous solution, precipitated, suction filtered, washed, dried to obtain the ruthenium complex.

[0049]When the organic complex of ruthenium is bis(1,10-phenanthroline)-dichloro-ruthenium dihydrate, the molecular structure of the novel ruthenium complex is as shown in formula (a):

[0050]

[0051] The organic complex of ruthenium is bis(2,2'-bipyridine)-dichloro-ruthenium dihydrate, and the molecular struc...

Embodiment 1

[0055] The synthesis of embodiment 1 organic ligand fpic

[0056] 5-fluoroindole-2-carboxylic acid (1.27g, 9.0mmol) was added to benzene, heated to reflux, slowly added thionyl chloride dropwise, and the suspension was heated to reflux for min; then, the mixture was concentrated in vacuo until light Yellow-green crystals precipitated to give 5-fluoroindole-2-yl chloride. A benzene solution of 5-fluoroindole-2-acyl chloride was added dropwise to a solution of 5-amino-1,10-phenanthroline (1.9 g, 9.0 mmol) in pyridine, and the resulting mixture was stirred at room temperature Overnight; let the precipitate stand, filter and collect the precipitate, and then crystallize in ethanol solution to obtain a khaki solid with a yield of 2.918 g and a yield of 91%.

[0057] Fpic- 1 H NMR(400MHz,DMSO,ppm):δ12.04(3H,s),10.96(3H,s),9.25(4H,d,J=3.3Hz),9.22-9.14(3H,m),8.97-8.72 (7H,m),8.35(3H,s),8.16-7.95(7H,m),7.62(3H,d,J=1.5Hz),7.57-7.40(8H,m),7.26(1H,d,J =17.4Hz),7.20-6.99(4H,m),5.37-2.0...

Embodiment 2

[0058] Example 2 Complex Ru[(phen) 2 (fpic)] (ClO 4 ) 2 2H 2 Preparation of O

[0059] 0.568g (1mmo1) of Ru(phen) 2 Cl 2 2H 2 O. 0.356g (1mmol) of fpic was added to a three-necked flask, and then ethanol was added, and the resulting mixture was refluxed for 6h under nitrogen, cooled to room temperature, and filtered. Add NaClO to the filtrate 4 , stand still, filter with suction, wash the precipitate with water and diethyl ether for several times, and then dry it in vacuum to obtain an orange-red solid product with a yield of 2.918 g and a yield of 75%.

[0060] Ru[(phen) 2 (fpic)] - 1 H NMR (400MHz, DMSO, ppm): δ11.98 (22H, d, J = 18.2Hz), 10.95 (20H, s), 8.93-8.73 (129H, m), 8.62 (23H, s), 8.40 (84H ,s),8.23-8.00(126H,m),7.99-7.70(130H,m),7.67-7.38(79H,m),7.28(7H,s),7.13(28H,dtd,J=24.7,9.2, 2.5Hz), 3.35(629H, s), 2.47(303H, d, J=29.2Hz), 2.36-1.23(33H, m), 1.61(21H, d, J=304.8Hz), 1.23(11H, s) , 1.00 (9H,d,J=118.3).

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Abstract

The invention belongs to the technical field of complex, and in particular relates to a novel organic ligand, a preparation method thereof, a novel ruthenium complex and a fluorescent probe. The invention provides the novel organic ligand and the preparation method thereof. The invention also provides the novel ruthenium complex which comprises a compound as shown in Ru[M2(fpic)]X2 and / or hydrate thereof, wherein fpic refers to the novel organic ligand. The invention also provides the fluorescent probe and a pharmaceutical composition. The novel ruthenium complex has preferable water solubility, fine optical properties, long lifetime of excited state, good biocompatibility and simple synthesis steps, and can be used as a novel fluorescent molecular probe to be applied in the field of fluorescent biological imaging in research of life science.

Description

technical field [0001] The invention belongs to the technical field of complexes, and in particular relates to an organic ligand and a preparation method thereof, a novel ruthenium complex and a fluorescent probe. Background technique [0002] Fluorescent probes refer to those molecules that can selectively bind to an analyte, and the fluorescence spectrum of the system will change accordingly. In the design of molecular probes, the luminescent signal is regulated through the changes of chemical structure, environment and intermolecular interaction, so as to play a role in the detection of the analyte. Re(I), Ru(II), Ir(III), and Pt(II) complexes are a kind of transition metal complexes, which are often used for the luminescence of molecular probes due to their good application value in fluorescent bioimaging Due to their special photophysical and photochemical properties, this kind of fluorescent probe has the advantages of low consumption, high sensitivity and wide dynami...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D471/04C07F15/00C09K11/06G01N21/64A61K49/00
CPCA61K49/0021C07D471/04C07F15/0053C09K11/06C09K2211/185G01N21/6486
Inventor 符淑钗于会娟
Owner GUANGDONG UNIV OF TECH
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