3,8-bis-(5-methyl-2-thienyl)-1,10-phenanthroline and its preparation method and application in zinc ion fluorescence sensing and cell imaging

A phenanthroline and thiophene-based technology, applied in the 3,8-position of 1,10-phenanthroline to expand the field of bis-5-methylthiophene compounds, can solve time-consuming and labor-intensive, difficult to achieve real-time detection of living body detection, etc. question

Inactive Publication Date: 2014-10-01
NANJING UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] Traditional detection methods, such as titration, atomic absorption spectroscopy (AAS), gas phase or liquid chromatography, etc., are not only time-consuming and labor-intensive, but also difficult to achieve real-time detection or even live detection

Method used

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  • 3,8-bis-(5-methyl-2-thienyl)-1,10-phenanthroline and its preparation method and application in zinc ion fluorescence sensing and cell imaging
  • 3,8-bis-(5-methyl-2-thienyl)-1,10-phenanthroline and its preparation method and application in zinc ion fluorescence sensing and cell imaging
  • 3,8-bis-(5-methyl-2-thienyl)-1,10-phenanthroline and its preparation method and application in zinc ion fluorescence sensing and cell imaging

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0021] Example 1. Synthesis of 3,8-bis-(5-methyl-2-thienyl)-1,10-phenanthroline

[0022]Add 0.71 g (29.21 mmol) of activated magnesium chips, 5 mL of anhydrous tetrahydrofuran and a catalytic amount of iodine into a 100 mL dry three-necked flask, and keep stirring at room temperature under the protection of argon. Dissolve 1.7 mL (15.10 mmol) of 2-bromo-5-methylthiophene in 5 mL of anhydrous tetrahydrofuran to make a solution, then slowly drop about 10% solution into the above-mentioned three-necked bottle, and continue to drop in after the reaction is triggered remaining solution, and keep the reaction system at a slight boil. After dripping, heat to reflux for 30 min. The reaction solution was cooled to room temperature, poured into a 50 mL dropping funnel, and then slowly dropped into Ni(dppp)Cl 2 and 50 mL of dry tetrahydrofuran in a three-necked flask, stirred at room temperature for 2 h after dropping, then heated to reflux for 12 h, cooled to room temperature, and...

Embodiment 2

[0028] Example 2. Imaging of HL-60 cells

[0029] HL-60 (human acute leukemia cells) suspension was used in DMEM medium, plus 10% FBS (fetal calf serum), penicillin (100 μg·mL -1 ), streptomycin (100 μg·mL -1 ), at 37°C and 5% CO 2 Cultivated under atmosphere. In the experiment, the suspension was centrifuged and washed with Hank's balanced salt solution (HBSS), then resuspended with HBSS, and incubated with 50 μM PHT1 at 37 °C for 45 min. After incubation, the remaining PHT1 was washed away with HBSS, and divided into two culture flasks, with 1 mL of cell suspension in each flask. One of the bottles added Zn 2+ Solution ([Zn 2+ ] = 50 μM), and then the two bottles of suspension were incubated at 37 °C for 20 min. Cell imaging of the two vials of suspension was performed separately using a laser confocal scanning microscope (TCS SP5, Leica, Germany): a 405 nm laser diode was used for the excitation light source, and a 450 nm–500 nm filter was used for emission light co...

Embodiment 3

[0031] Example 3. Imaging of HepG-2 cells

[0032] HepG-2 (human liver cancer cell) suspension was used in DMEM medium, plus 10% FBS (fetal calf serum), penicillin (100 μg·mL -1 ), streptomycin (100 μg·mL -1 ), at 37°C and 5% CO 2 Cultivated under atmosphere. Before staining, wash twice with DMEM medium, resuspend with 10 μM PHT1 solution, and incubate at room temperature for 30 min. After incubation, the remaining PHT1 was washed away with DMEM, and divided into two culture flasks, with 1 mL of cell suspension in each flask. One of the bottles added Zn 2+ Solution ([Zn 2+ ] = 10 μM) and incubated at room temperature for 30 min. Finally, HepG-2 cells were treated with zinc ion chelator (TPEN). Cell imaging was performed using a laser confocal scanning microscope: a 405 nm laser diode was used for the excitation light source, and a 450 nm-500 nm filter was used for emission light collection.

[0033] The experimental results and conclusions of HepG-2 cell imaging are ...

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Abstract

A 1,10-phenanthroline derivative, which is 3,8-bis-(5-methyl-2-thienyl)-1,10-phenanthroline (PHT1), has the following structural formula:. In ethanol-water mixed solution, it can selectively chelate free zinc ions to form a zinc ion complex ([Zn(PHT1)2]2+) with a stoichiometric ratio of 2:1, and the stability constant of the complex is as high as 3.4×1012M -1, and produced a 51-fold fluorescence enhancement in the blue light region (455-490nm). This fluorescence enhancement is neither affected by alkali metal ions (such as Na+, K+), alkaline earth metal ions (such as Ca2+, Mg2+) and most transition metal ions (such as Hg2+, Pb2+, Ag+), nor is it affected by pH. The detection limit of free zinc ions can reach 5ppb. Imaging experiments on HL-60 cells and HepG-2 cells show that PHT1 has good cell permeability and low cytotoxicity, and can label trace amounts of zinc ions in organelles, which can be applied to zinc ion sensors. The invention discloses its preparation method.

Description

technical field [0001] The invention relates to a 3,8-position extended bis-5-methylthiophene compound of 1,10-phenanthroline and its application in high-sensitivity zinc ion fluorescence sensing, cell imaging and the like. Background technique [0002] Some important cations, especially heavy metal ions such as Hg 2+ Ions can be converted into neurotoxic methylmercury in nature, causing environmental pollution and damage to human and animal cell metabolism and nerve tissue through bioaccumulation. Another example is Cd 2+ Ions are also highly toxic and can damage lungs, kidneys, spleen and other organs and tissues; Pb 2+ Ions can cause anemia, muscle paralysis, and mental retardation; Cu 2+ Ions can not only participate in important basic physiological processes in many organisms, but excessive Cu 2+ The presence of ions can produce toxicity to organisms; Zn 2+ Ions can participate in many important cellular activities, such as neurotransmission, signal transduction an...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D471/04C09K11/06G01N33/52G01N21/64
Inventor 黄伟尹桂张波曹扣森
Owner NANJING UNIV
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