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Coumarin-acridone fluorescent probe, and preparation method and application thereof

A fluorescent probe and acridone technology, applied in the field of coumarin-acridone fluorescent probe and its preparation, can solve the problems of unsuitable real-time and on-site detection, expensive equipment, complicated operation, etc., and achieve short reaction time , low detection limit and high anti-interference ability

Active Publication Date: 2020-06-02
GUANGXI UNIV OF CHINESE MEDICINE
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although these methods are effective and sensitive for the quantitative detection of iron ions in samples, however, these methods usually have the disadvantages of expensive instruments, time-consuming, complicated operations, and not suitable for real-time and on-site detection.

Method used

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  • Coumarin-acridone fluorescent probe, and preparation method and application thereof
  • Coumarin-acridone fluorescent probe, and preparation method and application thereof
  • Coumarin-acridone fluorescent probe, and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0038] Preparation of coumarin-acridone fluorescent probe:

[0039] Put o-bromobenzoic acid (1mmoL) and 1-amino-4-methylcoumarin (2moL) into a 100mL three-neck flask, add DMFmL, after the dissolution is complete, add copper powder and potassium carbonate, and the temperature rises to 180°C Stir and reflux the reaction for 8 hours. After the reaction is completed, suction filter while it is hot. Add 400 mL of pure water to the filtrate, then add an appropriate amount of hydrochloric acid to adjust the pH to 2, and let it stand overnight. After suction filtration, a yellow solid is obtained, and chloroform is recrystallized to obtain intermediate 1. .

[0040] Dissolve Intermediate 1 (1moL) in Eaton’s reagent (1.14moL), heat up to 90°C and stir under reflux for 4h. After the reaction is complete, pour the reaction solution into saturated NaHCO 3 The solution was extracted with chloroform, the upper layer liquid was suction-filtered, recrystallized with acetic acid, and the coum...

Embodiment 2

[0043] Preparation of coumarin-acridone fluorescent probe:

[0044] Put o-bromobenzoic acid (1mmoL) and 1-amino-4-methylcoumarin (1.5moL) into a 100mL three-necked flask, add DMFmL, after the dissolution is complete, add copper powder and potassium carbonate, and the temperature rises to 180 Stir and reflux at ℃ for 8 hours. After the reaction is over, filter while hot. Add 400mL of pure water to the filtrate, then add an appropriate amount of hydrochloric acid to adjust the pH to 5, and let it stand overnight. After suction filtration, a yellow solid is obtained, and chloroform is recrystallized to obtain an intermediate 1.

[0045] Dissolve Intermediate 1 (1moL) in Eaton’s reagent (2moL), raise the temperature to 90°C and stir under reflux for 4h. After the reaction is complete, pour the reaction solution into saturated NaHCO 3 The solution was extracted with chloroform, the upper layer liquid was suction-filtered, recrystallized with acetic acid, and the coumarin-acridone ...

Embodiment 3

[0047] Selective detection of iron ions by coumarin-acridone fluorescent probe S

[0048] Use acetonitrile: buffer solution=8:2 (v / v) solution to configure molar concentration 2×10 -5 moL / L of coumarin-acridone fluorescent probe, adding Mn 2+ , Mg 2+ 、Ag + 、Na + 、Ni 2+ , Ca 2+ 、Cd 2+ 、Co 2+ 、 Cu 2+ , Fe 3+ , Zn 2+ , Pb 2+ Mix 10 ul of the acetonitrile solution of ion perchlorate, let it react for 5 minutes, and measure its fluorescence emission spectrum with 355 nm as the excitation wavelength.

[0049] Such as figure 1 As shown, the fluorescent probe has an emission peak at 420-450nm, when adding Fe 3+ After that, the emission peak of the fluorescent probe solution at 420-450nm was significantly weakened, and when other cations were added, such as Mn 2+ , Mg 2+ , Ag + 、Na + 、Ni 2+ , Ca 2+ 、Cd 2+ 、Co 2+ 、Cu 2+ , Fe 3+ , Zn 2+ , Pb 2+ After ionization, the fluorescent probe solution has no obvious change at 420-450nm. Therefore, the experimental result...

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Abstract

The invention discloses a coumarin-acridone fluorescent probe, and a preparation method and an application thereof. The chemical name of the coumarin-acridone fluorescent probe is 4-methyl-2H-pyrano[2,3a]acridin-2,12(7H)-dione acetate. The preparation method is characterized in that o-bromobenzoic acid and 1-amino-4-methylcoumarin which are taken as initial raw materials undergo a Cu-catalyzed Ullmann reaction and a ring closing reaction to synthesize the coumarin-acridone fluorescent probe. The fluorescent probe has specific selectivity to iron ions, basically has no change with other commonmetal ion fluorescence signals, and has high sensitivity and low detection limit. The coumarin-acridone fluorescent probe can be applied to in-vitro fluorescence detection of iron ions.

Description

technical field [0001] The invention relates to the technical field of fluorescent molecular probes, more specifically, the invention relates to a coumarin-acridone fluorescent probe and its preparation method and application. Background technique [0002] One of the most important trace elements in the iron life system, it is widely involved in various physiological processes of the human body, including enzyme catalysis, proton transfer, cell metabolism, nucleic acid synthesis, oxygen transport, etc., and plays an irreplaceable role in the life system. However, excessive or insufficient iron intake can cause many diseases, such as cancer, Parkinson's disease, mental retardation and iron deficiency anemia, etc. Therefore, effective detection of iron ion content in biological samples or environmental samples has become a research focus in related fields in recent years. [0003] In recent decades, scientists have established a variety of analytical methods for the detection...

Claims

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Application Information

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IPC IPC(8): C07D491/052C09K11/06G01N21/64
CPCC07D491/052C09K11/06G01N21/643C09K2211/1033C07B2200/13G01N2021/6443G01N2021/6432
Inventor 霍丽妮黄嘉咏贾智若丘佩玲严振硕陈睿
Owner GUANGXI UNIV OF CHINESE MEDICINE
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