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Preparation and application of cyclometalated iridium complex ratio type carbon monoxide fluorescent probe

An iridium complex, carbon monoxide technology, applied in fluorescence/phosphorescence, indium organic compounds, platinum group organic compounds, etc., can solve the problems of inability to track biological samples for a long time, poor spectral stability, etc., and achieve good selectivity and reproducibility , high sensitivity and good stability

Inactive Publication Date: 2021-11-09
ANHUI UNIVERSITY OF TECHNOLOGY
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] As a new type of non-invasive diagnostic technology, fluorescence imaging technology has been more and more applied to the diagnosis of biological diseases. Due to the advantages of convenience, non-invasiveness, low background signal and high sensitivity, fluorescence imaging has attracted widespread attention. , but currently most of the molecules used for fluorescence imaging are small organic molecules. Small molecule fluorescent probes have poor spectral stability during use and cannot track biological samples for a long time, while metal complex fluorescent probes can make up for the above At the same time, the advantages of large Stokes shift and simple synthesis of metal complex fluorescent probes are very promising to be applied to biological imaging. However, there are few reports on the use of metal complexes to dynamically monitor intracellular viscosity changes. Therefore, development A novel metal complex-based fluorescent probe is of great significance for dynamic monitoring of viscosity changes in lipid droplets

Method used

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  • Preparation and application of cyclometalated iridium complex ratio type carbon monoxide fluorescent probe
  • Preparation and application of cyclometalated iridium complex ratio type carbon monoxide fluorescent probe
  • Preparation and application of cyclometalated iridium complex ratio type carbon monoxide fluorescent probe

Examples

Experimental program
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Effect test

Embodiment 1

[0044] Synthesis of fluorescent probes for o-hydroxynitrobenzene-o-phenanthroline-iridium complexes:

[0045] Weigh 200 mg of iridium trichloride and 52 mg (48 μL) of 2-aminopyridine into a 100 ml round-bottomed flask, add 15 ml of ethylene glycol ether and 5 ml of water as a solvent, the reaction temperature is 135 ° C, and condense to reflux. The reaction time is 24h. After the reaction, cool to room temperature, ultrasonic and suction filter to obtain a yellow-green solid, which is finally washed with distilled water and dried to obtain a cyclometal iridium complex;

[0046] Weigh 150mg of 4-hydroxy-3-nitrobenzaldehyde, 158mg of 1,10-phenanthroline-5,6-dione, and 1160mg of ammonium acetate in a flask, add 15ml of glacial acetic acid as a solvent, and the reaction temperature is 118°C, condensing reflow. The reaction time is 5 hours. After the reaction, cool to room temperature, add a small amount of distilled water, slowly drop ammonia water into the flask, adjust the pH to...

Embodiment 2

[0050] Fluorescence intensities of o-hydroxynitrobenzene-o-phenanthroline-iridium complex fluorescent probes in different solvents:

[0051] Weigh 0.5 mg o-hydroxyiridium complex and dissolve it in 615 μL dimethyl sulfoxide to obtain 1 mmol / L o-hydroxyiridium complex mother solution. Take 4 μL o-hydroxyiridium complex mother solution (1 mmol / L) in a centrifuge tube, add dichloromethane, acetonitrile, dimethyl sulfoxide, dioxane, methanol, and dilute to 100 μL, and the liquid in the centrifuge tube Transfer to a 96-well black plate for analysis using a microplate reader (fixed excitation: 405nm, emission start: 450nm, stop: 700nm, step: 2nm). Among them, the solution in which the solvent is dichloromethane is extremely corrosive, and the 96-well plate is severely corroded, so the detection of dichloromethane is canceled. After detecting the fluorescence intensity, immediately transfer the liquid in the black plate to a transparent 96-well transparent plate to test the UV absor...

Embodiment 3

[0054] Fluorescence and UV absorption spectrometry of o-hydroxynitrobenzene-o-phenanthroline-iridium complex stimulated by carbon monoxide:

[0055] Weigh 0.5 mg of the o-hydroxyiridium complex and dissolve it in 615 μL of methanol to obtain a 1 mmol / L mother solution of the hydroxyiridium complex. Take 5 mg of ruthenium tricarbonyl dichloride dimer and dissolve it in 974 μL of dimethyl sulfoxide to obtain a 10 mmol / L mother solution of ruthenium tricarbonyl dichloride dimer solution.

[0056] 1. For different concentrations, take three 1.5ml centrifuge tubes, numbered 1, 2, and 3. Add 20 μL o-hydroxyiridium complex mother solution, 30 μL methanol, 50 μL dimethyl sulfoxide and 400 μL distilled water to number 1; add 20 μL hydroxyl iridium complex mother solution, 30 μL methanol, 2 μL tricarbonyl dichlororuthenium dimer to number 2 (10mmol / L), 48μL dimethyl sulfoxide and 400μL distilled water; add 20μL hydroxyiridium complex mother solution, 30μL methanol, 20μL tricarbonyl dic...

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Abstract

The invention belongs to the technical field of organic metal complex molecular fluorescent probes, and particularly relates to preparation and application of a cyclometalated iridium complex ratio type carbon monoxide fluorescent probe. The preparation method comprises the following steps: firstly, taking iridium trichloride and 2-aminopyridine as raw materials, and glycol ether and water as solvents to synthesize a cyclometalated iridium complex ; taking 4-hydroxy-3-nitrobenzaldehyde, 1, 10-phenanthroline-5, 6-diketone and ammonium acetate as raw materials and glacial acetic acid as a solvent, and reacting to obtain a phenanthroline-cinnamyl aldehyde ligand; and taking a phenanthroline-cinnamyl aldehyde ligand as a raw material, taking a metal iridium complex and the phenanthroline-cinnamyl aldehyde ligand as reactants, taking dichloromethane and methanol as reaction solvents, reacting to obtain an o-hydroxynitrobenzene-phenanthroline-iridium complex product, and separating and purifying to obtain the o-hydroxynitrobenzene-phenanthroline-iridium complex. The fluorescence spectrum of the o-hydroxy iridium complex disclosed by the invention generates red shift in a carbon monoxide system, the fluorescence intensity is gradually increased along with the concentration, and the fluorescence does not change along with the polarity of a solvent, amino acid and in-vivo common ions.

Description

technical field [0001] The invention belongs to the technical field of organometallic complex molecular fluorescent probes, in particular to the preparation and application of a cyclometal iridium complex ratio-type carbon monoxide fluorescent probe. Background technique [0002] Viscosity is ubiquitous in nature. According to different viscosities, liquids are divided into Newtonian fluids and non-Newtonian fluids. The value of viscosity directly affects the rate of fluid expansion. The intercellular and intracellular fluids in organisms have different fluidity due to their different viscosities, especially the different organic content in the liquid between the various organelles in the cell, resulting in great differences in the fluidity of the fluid between the various organelles, while the intracellular The transport and synthesis of biomolecules such as amino acids and nucleotides almost all require the fluidity of the fluid between the various organelles as the drivin...

Claims

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Application Information

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IPC IPC(8): C07F15/00C09K11/06G01N21/64
CPCC07F15/0033C09K11/06G01N21/6428G01N21/643C09K2211/185C09K2211/1029C09K2211/1074
Inventor 杨刚刚胡晓军徐霞张楷
Owner ANHUI UNIVERSITY OF TECHNOLOGY
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