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Fluorescence probe based on 1, 3, 4-oxadiazole derivative, and synthetic method and applications thereof

A technology of fluorescent probes and synthesis methods, applied in the direction of fluorescence/phosphorescence, chemical instruments and methods, luminescent materials, etc., can solve the problems of interference of measurement results, complex synthesis process of zinc ion fluorescent probes, inaccurate detection data, etc., to achieve Promote charge transfer, facilitate fluorescent signal detection, and detect accurate effects

Active Publication Date: 2014-03-19
BOHAI UNIV
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  • Abstract
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  • Claims
  • Application Information

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Problems solved by technology

However, this kind of fluorescent probe is easily affected by external conditions such as probe concentration, excitation light wavelength and detection environment, which will interfere with the measurement results, resulting in inaccurate detection data.
In addition, the synthesis process of many zinc ion fluorescent probes is complicated

Method used

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  • Fluorescence probe based on 1, 3, 4-oxadiazole derivative, and synthetic method and applications thereof
  • Fluorescence probe based on 1, 3, 4-oxadiazole derivative, and synthetic method and applications thereof
  • Fluorescence probe based on 1, 3, 4-oxadiazole derivative, and synthetic method and applications thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034] (1) Synthetic recognition of Zn 2+ The reaction formula of the ratiometric fluorescent probe:

[0035]

[0036] (2) Synthesis and recognition of Zn 2+ The specific steps of the ratiometric fluorescent probe:

[0037] Weigh out 300mg N -[2-(5-phenyl-1,3,4-oxadiazol-2-yl)phenyl]-2-chloroacetamide (compound 1 ) and 573mg of bis-(pyridylmethylene)amine (compound 2 ), 1.53ml N,N -Diisopropylethylamine, 57mg potassium iodide, added to 50ml of acetonitrile, stirred and heated to reflux for 10h under nitrogen protection; evaporated the solvent under reduced pressure, and used ethyl acetate and petroleum ether with a volume ratio of 3:1 as the eluent The residue was separated by column chromatography to obtain a fluorescent probe N -[2-(5-Phenyl-1,3,4-oxadiazol-2-yl)phenyl]-2-bis(2-pyridinemethylamino)acetamide (compound L ), the yield was 72%.

[0038] Fluorescent probe of the present invention N Basic data for -[2-(5-phenyl-1,3,4-oxadiazol-2-yl)phenyl]-2-bis(2-py...

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Abstract

The invention discloses a fluorescence probe based on 1, 3, 4-oxadiazole derivative, and a synthetic method and applications thereof. Chemical formula of the fluorescence probe is represented in the invention. The synthetic method comprises following steps: N-[2-(5-phenyl-1, 3, 4-oxadiazole-2-yl)phenyl]-2-chloroacetamide, di-(pyridylmethylene)amine, N, N-diisopropylethylamine and potassium iodide are added into acetonitrile so as to obtain a mixture; the mixture is stirred, and is subjected to heating reflux under protection of nitrogen; solvent removing is realized via reduced pressure distillation, and obtained residues are subjected to column chromatography for separation so as to obtain the fluorescence probe N-[2-(5-phenyl-1, 3, 4-oxadiazole-2-yl)phenyl]-2-di(2-pyridylmethylene) acetamide. The raw materials are easily available; the synthetic method is simple; product separation and purification processes are easy; and the fluorescence probe possesses excellent water solubility, can be used for Zn<2+> monitoring analysis and tracer analysis in water environmental systems and biological cell systems, and possesses excellent sensitivity and relatively strong anti-interference capability on detection of Zn<2+>.

Description

technical field [0001] The invention relates to a fluorescent probe based on 1,3,4-oxadiazole derivatives and its synthesis method and application. Background technique [0002] Zinc ions are the second most abundant transition metal ions in the human body, and they play a role in many basic biological processes, such as cell metabolism, gene expression, apoptosis, neurotransmission, metalloenzyme regulation, and DNA binding and recognition processes. extremely important role. Most zinc ions are closely combined with enzymes or proteins, and are the main components of dozens of enzymes in the human body. They are also related to the body's sexual development, germ cell generation, brain development and intelligence. However, excessive intake of zinc ions by the human body can cause certain neurodegenerative diseases, such as Alzheimer's disease, Parkinson's disease, epilepsy and ischemic stroke. Due to the wide application of zinc ions in industry, it is also common for na...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09K11/06C07D413/14G01N21/64
Inventor 汤立军代鑫钟克利侯淑华边延江
Owner BOHAI UNIV
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