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Synthesis of Arylimidazophenanthroline Fluorescent Dye and Its Recognition of Metal Ions

An arylimidazo and imidazo technology is applied in the field of synthesizing arylimidazo[4,5-f]phenanthroline-type oxacrown ethers, and achieves simple synthesis route, simple and convenient post-processing, and great foundation. effect of action

Active Publication Date: 2022-03-18
FUJIAN MEDICAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Arylimidazo[4,5-f]phenanthrolines have strong fluorescence and are easy to synthesize, but fluorescent crown ethers containing arylimidazo[4,5-f]phenanthrolines are rarely reported

Method used

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  • Synthesis of Arylimidazophenanthroline Fluorescent Dye and Its Recognition of Metal Ions
  • Synthesis of Arylimidazophenanthroline Fluorescent Dye and Its Recognition of Metal Ions
  • Synthesis of Arylimidazophenanthroline Fluorescent Dye and Its Recognition of Metal Ions

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] Example 1: Synthesis of fluorescent probes for phenylimidazo[4,5-f]phenanthroline oxacrown ethers

[0031] (1) Synthesis of intermediate compound I (triethylene glycol di-p-toluenesulfonate):

[0032]

[0033] Dissolve triethylene glycol (10 mmol) and p-toluenesulfonyl chloride (10 mmol) in 150 mL tetrahydrofuran (THF), add potassium hydroxide (70 mmol) solution, and stir at room temperature for 7 h. After the reaction, extract with dichloromethane, use MgSO 4 Dried, spin-dried dichloromethane, crude product was purified through chromatographic column, with (V 乙酸乙酯 :V 石油醚 =1: 2) to obtain compound Ⅰ (triethylene glycol di-p-toluenesulfonate) with a yield of 90%;

[0034] (2) Synthesis of intermediate compound II (benzo-12-crown-4)

[0035]

[0036] In a 100 ml flask, catechol (5 mmol), 2.5 mmol of tetrabutylammonium bromide (TBAB) were dissolved in 30 mL of toluene solution, and 50 wt% NaOH aqueous solution (10 mL) was added. The mixture was stirred at 50-60 ...

Embodiment 2

[0052] Embodiment 2: the mensuration of ultraviolet spectrum and fluorescence spectrum

[0053] The N-(4-(1H-imidazole-[4,5-f]phenanthroline)benzo-12-crown-4 (abbreviation: phenylimidazo[4,5-f] ] phenanthroline oxa crown ether compounds) concentration diluted to 2 × 10 -5 mol / L, select 13 different metal ions (Ag + , Cu 2+ , Al 3+ , Fe 3+ , Hg 2+ , K+, Mg 2+ , Mn 2+ , Zn 2+ , Li + , Ni + , Ca 2+ and Na + ) configured as 1×10 -5 mol / L solution. Add 1 mL of different metal ion solutions to the cuvette, measure its fluorescence spectrum under the action of different metal ions, and screen out the probes that can specifically recognize a certain metal ion, see figure 1 , figure 1 It is the ultraviolet spectrum and fluorescence spectrum of aryl imidazo[4,5-f]phenanthroline oxa crown ether compounds and metal ions of the present invention. The abscissa is the wavelength, and the ordinate is the light intensity. The concentration of the compound is 10 μM, metal ion...

Embodiment 3

[0054] Example 3: Determination of UV Titration Spectrum and Fluorescent Titration Spectrum of Phenylimidazo[4,5-f]phenanthroline Oxacrown Fluorescent Probe and Metal Ion Recognition

[0055]By screening out the metal ions with the best response to different compounds, and then weighing an appropriate amount of metal ions to prepare 10 concentration gradient solutions (1μM, 2μM, 3μM, 4μM, 5μM, 6μM, 7μM, 8μM, 9μM, 10μM) for detection. Take the N-(4-(1H-imidazole-[4,5-f]phenanthroline)benzo-12-crown-4 compound (abbreviation: phenylimidazo[4 , 5-f] phenanthroline oxa crown ether compounds) and the best response of the compound to different concentrations of metal ions to measure its fluorescence emission spectra, see figure 2 .

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Abstract

The invention discloses the synthesis of an aryl imidazophenanthroline fluorescent dye and the recognition of metal ions. It is a method for synthesizing aryl imidazo[4,5-f]phenanthroline oxa-crown compounds from cheap and easy-to-obtain 1,10-phenanthroline as a raw material through a series of steps. Through screening the fluorescence properties of aryl imidazo[4,5‑f]phenanthroline compounds, through the screening experiments of different metal ions, and the ion concentration experiments to verify the complexation performance of the compounds with metal ions , to achieve the metal ion Zn in tumor cells 2+ identification. The technical effect of the fluorescent probe of the present invention is as follows: 1, the compound respectively shows on a wide range of metal ions to Zn 2+ High selectivity; 2, can be realized in MCF‑7 cells to Zn 2+ The corresponding fluorescent quenching molecular switch has played a great role in paving the way for the system to be applied in more fields such as biological recognition.

Description

technical field [0001] The invention discloses a method for synthesizing aryl imidazo[4,5-f]phenanthroline oxa crown ether compounds with cheap and easy-to-obtain 1,10-phenanthroline as a raw material. The fluorescence properties of 4,5-f]phenanthroline compounds were screened, and their fluorescence properties were used to identify metal ions. Background technique [0002] As a chelating ligand, o-phenanthroline, many of its derivatives can be widely used as important chelating agents in many fields such as analytical chemistry and homogeneous catalysis, and its complexes are also important electron transfer agents in life sciences . Many complexes of o-phenanthroline exhibit good electrochemical, photochemical and catalytic properties, and have certain application prospects in antitumor activity. From the structural point of view, o-phenanthroline is an aromatic conjugated system composed of three six-membered rings. The two nitrogen atoms at the 1 and 10 positions have ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D471/14C09K11/06G01N21/64
CPCC07D471/14C09K11/06G01N21/6428C09K2211/1007C09K2211/1029C09K2211/1044C09K2211/1088G01N2021/6432
Inventor 张志强侯慧青柯方周孙英许贻文林媚陈艳
Owner FUJIAN MEDICAL UNIV