2-arylimidazole-phenanthroline probe capable of recognizing cu<2+> in HL-60 and preparation method thereof

A technology of aryl imidazolo and o-phenanthroline, which is applied in the field of fluorescent probes for metal ions, can solve problems such as life safety threats, acute illness, and dangerous prognosis, and achieve high sensitivity, high response value, and good selectivity Effect

Inactive Publication Date: 2017-12-26
FUJIAN MEDICAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The disease is very harmful, and most cases are characterized by acute and severe conditions and a dangerous prognosis. If not treated in time, it will threaten life safety

Method used

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  • 2-arylimidazole-phenanthroline probe capable of recognizing cu&lt;2+&gt; in HL-60 and preparation method thereof
  • 2-arylimidazole-phenanthroline probe capable of recognizing cu&lt;2+&gt; in HL-60 and preparation method thereof
  • 2-arylimidazole-phenanthroline probe capable of recognizing cu&lt;2+&gt; in HL-60 and preparation method thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] Embodiment 1: This embodiment is a specific embodiment prepared according to the reaction scheme of the compound of formula (I).

[0032] Phenylimidazo[5,6-f]phenanthroline: Weigh 2.0g of 1,10-phenanthroline and 6.0g of selenium dioxide, mix them evenly in a flask, and make 20 mL of 18mol·L -1 Concentrated sulfuric acid, 10 mL concentration is 14mol•L -1Concentrated nitric acid is mixed and cooled in an ice-water bath to form a cooled mixed acid. Slowly add the cooled mixed acid dropwise along the wall of the flask. After the dropwise addition, heat to reflux, and a reddish-brown gas is gradually generated in the bottle. Stop heating to obtain a reddish-brown transparent solution; pour the reddish-brown transparent solution into ice water, and slowly neutralize the acid with NaOH until the pH of the reaction mixture is 7. During this process, many yellow flocculent precipitates are formed, and the yellow precipitate is obtained by suction filtration , extracted three ...

Embodiment 2

[0034] Embodiment 2: 2-(2-hydroxyl-5-nitrophenyl) imidazo[5,6-f] o-phenanthroline: the preparation method is the same as in Example 1, adding 5-nitrosalicylaldehyde to obtain light Yellow needle-point crystals, yield 57%. Its hydrogen nuclear magnetic resonance spectrum data are:

[0035] 1 H NMR (500 MHz, DMSO-d6): 9.06 (d, 2H, J = 8.2 Hz), 8.98 (d, 2H, J = 7.5 Hz), 7.87 (dd, 2H, J = 8.0 Hz), 7.43 (d ,1H, J =8.0 Hz), 6.84 (d, 1H, J =8.6 Hz),6.73—6.75 (m, 1H).

Embodiment 3

[0036] Embodiment 3: the ultraviolet absorption spectrum of the 2-(2-hydroxyl-5-nitrophenyl) imidazo[5,6-f] o-phenanthroline fluorescent probe that embodiment 2 makes (see figure 1 ) and fluorescence spectra (see Picture 1-1 ).

[0037] Accurately weigh 2-(2-hydroxy-5-nitrophenyl)imidazo[5,6-f]phenanthroline, transfer it into a 10 mL volumetric flask, dissolve it with absolute ethanol, and wait until the sample is completely dissolved After constant volume, prepare to a concentration of 1.0×10-5 mol•L -1 The solution was measured for its UV absorption spectrum and fluorescence excitation spectrum, respectively. Measurement results such as figure 1 , Picture 1-1 shown; figure 1 is the ultraviolet absorption spectrum of copper ion fluorescent probe 2-(2-hydroxyl-5-nitrophenyl)imidazo[5,6-f]phenanthroline; Picture 1-1 It is the fluorescence spectrum of the copper ion fluorescent probe 2-(2-hydroxyl-5-nitrophenyl)imidazo[5,6-f]phenanthroline for the detection of aggregati...

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Abstract

The invention discloses a 2-arylimidazole-phenanthroline probe capable of recognizing Cu<2+> in HL-60 and a preparation method thereof. The invention provides 2-arylimidazole[5,6-f] phenanthroline is applied to detection on Cu<2+> in HL-60 cells, has high sensitivity and high response value to Cu<2+>, and has obvious response to Cu<2+> when being used as a fluorescent probe. When being used for detecting Cu<2+> of different concentrations, the probe shows a good linear relationship, and has a good selectivity for Cu<2+> in HL-60 cells; after the HL-60 suspension cells stained with the compound 2-arylimidazole[5,6-F] phenanthroline are subjected to blue light excitation, the cells emit green fluorescence under the observation in a microscope, and the detection method is reliable; the reaction formula is as follows (shown in the description).

Description

technical field [0001] The invention relates to a method capable of recognizing Cu in HL-60 cells 2+ The 2-arylimidazo[5,6-f]phenanthroline fluorescent probe and its preparation method belong to the field of metal ion fluorescent probes. Background technique [0002] The content of copper in the human body is second only to iron and zinc, and is one of the trace metal elements necessary for the human body. It exists in plasma ceruloplasmin, superoxide dismutase, cytochrome C oxidase, and has many important physiological functions. Deficiency diseases can be caused when the body's copper intake is insufficient, but Cu 2+ Excessive amount will destroy the enzyme system of the organism, hinder the normal biochemical reaction and metabolism of the organism, and have great harm to the human body. Many literatures have reported that there are a lot of copper ions in HL-60 cells, which were isolated from the peripheral blood of patients with acute promyelocytic leukemia (APL), A...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D471/14C09K11/06G01N21/64
CPCC07D471/14C09K11/06C09K2211/1007C09K2211/1029C09K2211/1044G01N21/6486
Inventor 柯方张鹏许建华林小燕林晨刘洋
Owner FUJIAN MEDICAL UNIV
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