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Double-color fluorescent probe as well as synthesis method and application thereof

A dual-color fluorescent probe and fluorophore technology, applied in the field of dual-color fluorescent probes and their synthesis, achieves the effects of low cytotoxicity, simple preparation and simple operation

Active Publication Date: 2020-04-07
SHANDONG NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

In recent years, many detection methods have been developed to detect O 2 ·- or Zn 2+ fluorescent probes, but these probes are used for single-component detection and imaging at the cellular level. Due to the complex biological background of the brain and the existence of the blood-brain barrier, they are used for the simultaneous detection of O in vivo 2 ·- and Zn 2+ probes have not been reported

Method used

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  • Double-color fluorescent probe as well as synthesis method and application thereof
  • Double-color fluorescent probe as well as synthesis method and application thereof
  • Double-color fluorescent probe as well as synthesis method and application thereof

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preparation example Construction

[0033] In another specific embodiment of the present invention, a preparation method of the above-mentioned dual-color fluorescent probe is provided, and the preparation method includes the following reactions:

[0034]

[0035] In another specific embodiment of the present invention, the step a is specifically:

[0036] Under the protection of inert gas, bromopropylamine, DPA and potassium carbonate are mixed and stirred to obtain a light yellow solid A. A.

[0037] In another specific embodiment of the present invention, the step b is specifically:

[0038] Under the protection of inert gas, mix caffeic acid, DMAP, DCC, triethylamine and DMF, and stir under ice bath conditions to obtain an activated caffeic acid solution;

[0039] Under the protection of inert gas, after mixing ethylenediamine and DMF, the activated caffeic acid solution was added dropwise, stirred at room temperature to obtain a brown turbid liquid, and thin layer chromatography to obtain a light yellow solid B.

[0...

Embodiment 1

[0052] A detection cell and in vivo O 2 ·- And Zn 2+ The preparation method of the new fluorescent probe is as follows:

[0053]

[0054] Step a: Under nitrogen protection, add 2.18g bromopropylamine, 1.99gDPA, 0.50g K 2 CO 3 Put 30ml of acetonitrile into a two-necked flask, stir at room temperature for 12h, filter, and rotate to obtain a light yellow solid A. Mass spectrum see Figure 4A .

[0055]

[0056] Step b: Under the protection of nitrogen, put 1.8g caffeic acid, 1.2g DMAP, 2g DCC, 1.4ml triethylamine and 12ml DMF into a two-necked flask, and stir for 30 minutes under ice bath conditions to obtain an activated caffeic acid solution. Under nitrogen protection, 670 microliters of ethylenediamine and 5ml DMF were added to the three-necked flask, and then the activated caffeic acid solution was added dropwise to the three-necked flask, and stirred at room temperature for 12h to obtain a brown cloudy liquid. Thin layer chromatography (eluent: dichloromethane: methanol = 10:1) ...

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Abstract

The invention provides a double-color fluorescent probe as well as a synthesis method and application thereof, the double-color fluorescent probe is especially suitable for simultaneously detecting O2. <-> and Zn < 2 + > in a living body, the double-color fluorescent probe is composed of dipyridylmethylamine(DPA), caffeic acid and 4-bromo-1, 8-naphthoic anhydride, the double-color fluorescent probe has the advantages of simple preparation, sensitive detection, good selectivity and the like. According to the method, the change of the O2. <-> and Zn < 2 + > in the brain of the mouse with depression is successfully imaged and analyzed at the living body level for the first time, and the method has good practical application value.

Description

Technical field [0001] The invention belongs to the technical field of biological detection and fluorescent probe preparation, and specifically a dual-color fluorescent probe and its synthesis method and application. Background technique [0002] The information disclosed in the background of the present invention is only intended to increase the understanding of the overall background of the present invention, and is not necessarily regarded as an acknowledgement or any form of suggestion that the information constitutes the prior art known to those of ordinary skill in the art. [0003] As a type of mental illness, depression has a very high morbidity and mortality rate, which brings serious harm to human health. However, the current understanding of the pathophysiology of depression is still very imperfect. In order to effectively prevent and treat depression, we must thoroughly understand the occurrence and development of depression. Fluorescence imaging technology has obvious...

Claims

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Application Information

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IPC IPC(8): C07D401/14C09K11/06A61K49/00
CPCA61K49/0021C07D401/14C09K11/06C09K2211/1029
Inventor 唐波丁琪李平王昕
Owner SHANDONG NORMAL UNIV
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