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Fluorescence probe compound, and preparation method and application thereof

A technology of fluorescent probes and compounds, applied in the field of fluorescent probes, can solve problems such as memory loss, damage to the central nervous system, and impact on memory, and achieve the effects of consistent reaction conditions, simple and convenient post-processing, and simple synthetic routes

Inactive Publication Date: 2018-03-30
NANJING UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

But in recent years, more and more evidences have proved that aluminum ions are very harmful to the central nervous system of the human body. E. Altschuler reported that aluminum-containing antacids can cause primary Parkinson's disease, and from Parkinson's Aluminum was found in the hippocampal nerve of the patient. B.Wang et al. found that long-term exposure to aluminum will affect memory through various signal transmissions, resulting in varying degrees of decline in memory

Method used

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  • Fluorescence probe compound, and preparation method and application thereof
  • Fluorescence probe compound, and preparation method and application thereof
  • Fluorescence probe compound, and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] Embodiment 1: detect the preparation of the fluorescent probe of aluminum ion, basic synthesis process is as follows:

[0030] (1) Synthesis of 7-acetoxycoumarin (compound 2): 10mmol 7-hydroxycoumarin was added to a 100mL single-mouth bottle, 50mL chloroform was added dropwise to dissolve it, and then 10mmol acetic anhydride and 1mmol pyridine Added dropwise to compound 1 dissolved in chloroform and reacted for 6 hours to obtain a yellow clear solution, which was evaporated by rotary evaporation and separated by column chromatography to obtain compound 2 as a white solid. The eluent was petroleum ether: dichloromethane=1:4, and the yield was 85%. The proton spectrum data of gained compound 2 are as follows: 1 H-NMR (400MHz, CDCl 3 ): δ=7.69(d, J=9.6Hz, 1H), 7.49(d, J=8.4Hz, 1H), 7.11(d, J=2.1Hz, 1H), 7.05(dd, J=8.4, 2.2Hz ,1H),6.39(d,J=9.6Hz,1H),2.34(s,3H)

[0031] (2) Synthesis of 7-hydroxy-8-formyl coumarin (compound 3): at 0°C, dissolve 5 mmol of compound 2 obtain...

Embodiment 2

[0033] Embodiment 2: detect the preparation of aluminum ion fluorescent probe, basic synthesis process is as follows:

[0034](1) Synthesis of 7-hydroxy-8-formyl coumarin (compound 2): 50mmol 7-hydroxycoumarin was added in a reaction flask, and 100mL dichloromethane was added dropwise to dissolve it; then 100mmol acetic acid Anhydride and 25mmol pyridine were added dropwise to compound 1 dissolved in chloroform and reacted for 10 hours to obtain a yellow clear solution, which was evaporated by rotary evaporation and separated by column chromatography to obtain compound 2 as a white solid. The eluent was petroleum ether: dichloromethane = 1:4 , and the yield is 87%. The hydrogen spectrum data of the obtained compound 2 are as follows: 1 H-NMR (400MHz, CDCl 3 ): δ=7.69(d, J=9.6Hz, 1H), 7.49(d, J=8.4Hz, 1H), 7.11(d, J=2.1Hz, 1H), 7.05(dd, J=8.4, 2.2Hz ,1H),6.39(d,J=9.6Hz,1H),2.34(s,3H)

[0035] (2) Synthesis of 7-hydroxy-8-formyl coumarin (compound 3): at 5°C, 25 mmol of compo...

Embodiment 3

[0037] Embodiment 3: the fluorescence spectrometry of probe molecule

[0038] Get 3mL concentration among the example 1 and be the probe ethanol water mixed solution of 10 μ mol / L in the quartz cuvette, then add 3 μ L concentration respectively and be the various metal ions of 10 mmol / L (Na + , K + , Ag + ,Mg 2+ ,Cu 2+ ,Cd 2+ ,Pb 2+ ,Zn 2+ ,Mn 2+ ,Co 2+ , Ni 2+ , Fe 3+ ,Al 3+ ) solution, shake well, and measure its fluorescence emission spectrum at an excitation wavelength of 475nm (such as image 3 ), the results show that when aluminum ions are added, an emission peak occurs at 475nm, and when other metal ions are added, there is no obvious emission peak.

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Abstract

The invention discloses a fluorescence probe compound, and a preparation method and an application thereof. The fluorescence probe is characterized in that the fluorescence probe is a coumarin derivative, and the structural formula of the fluorescence probe is shown in the description. The preparation method comprises the following steps: synthesizing 7-acetoxycoumarin, and then synthesizing 7-hydroxy-8-formylcoumarin; and synthesizing the fluorescence probe compound. The coumarin derivative synthesized in the invention has multiple functions, can realize the identification and the quantitative determination of Al<3+> through fluorescence spectrometry, can be used as the Al<3+> fluorescence probe, and has excellent interference resistance, high selectivity and high sensitivity in the presence of other ions.

Description

Technical field: [0001] The invention relates to a fluorescent probe compound and its preparation and application, in particular to a fluorescent probe compound for detecting aluminum ions and its preparation and application, belonging to the technical field of fluorescent probes. technical background: [0002] In recent years, with the rapid development of chemical sensors, fluorescent probes have the advantages of high sensitivity, good selectivity, and real-time response, especially through the use of fluorescent confocal microscopy imaging technology to detect the concentration of molecules or ions in living cells in real time. As well as the change process of the structure of biological macromolecules, it has received more and more attention in many fields such as chemistry, biology, medicine, and environment, and has become a major research hotspot. [0003] Aluminum is the metal element with the highest content in the earth's crust, and is widely used in aerospace, au...

Claims

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Application Information

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IPC IPC(8): C07D311/18C09K11/06G01N21/64
CPCG01N21/643C09K11/06C07D311/18
Inventor 胡永红樊世敏杨文革郝建峰李红杰张健赵王丹
Owner NANJING UNIV OF TECH
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