Small-molecule fluorescent probe for rapidly identifying superoxide radicals, preparation method and application thereof

A fluorescent probe and superoxide technology, applied in the direction of fluorescence/phosphorescence, chemical instruments and methods, analytical materials, etc., can solve the problems of long detection time and inability to realize cell imaging, and achieve simple post-processing process and resistance to other molecules Strong interference ability and good selectivity

Inactive Publication Date: 2017-04-19
UNIV OF JINAN
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, there are shortcomings such as long detection time and inability to realize cell imaging.

Method used

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  • Small-molecule fluorescent probe for rapidly identifying superoxide radicals, preparation method and application thereof
  • Small-molecule fluorescent probe for rapidly identifying superoxide radicals, preparation method and application thereof
  • Small-molecule fluorescent probe for rapidly identifying superoxide radicals, preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0021] Synthesis of probe compound NS-O:

[0022]

[0023] Compound 1 (0.5mmol, 86.0mg) and compound 2 (1.1equiv, 68.8mg) were added to the reaction flask under a nitrogen atmosphere, and then ethanol (5.0mL) was added to the above reactor at one time, and the After heating to reflux for 5 hours, the reaction was detected by spotting until the raw materials disappeared, and the solvent was spin-dried under reduced pressure to obtain a crude product, which was separated with a silica gel column to obtain the probe compound NS-O, the silica gel particle size was 200-300 mesh, and the yield was 63%. 1 H-NMR (400MHz, DMSO-d 6 )δ10.12(s,1H),8.56(s,1H),8.17-8.01(m,4H),7.86(d,J=8.8Hz,1H),7.58-7.45(m,2H),7.22-7.18 (m,2H). The probe's 1 H NMR spectrum see figure 1 .

Embodiment 2

[0025] Probe NS-O with O 2 - The addition of its visible light absorption changes

[0026] The probe NS-O prepared in Example 1 was dissolved in N,N-dimethylformamide (DMF) to prepare a 1 mmol / L stock solution. Take 30 μL from the stock solution and add it to a 5mL centrifuge tube, measure its absorption spectrum, and then add O 2 - (10equiv) standard solution, diluted to 3mL (10μM) with DMSO / PBS (1:1, v / v), and measure its absorption spectrum. Spectrum see figure 2 shown. Depend on figure 2 It can be seen that after adding probe NS-O, directly add O 2 - , the change in absorption can be detected instantaneously, realizing the O 2 - detection.

Embodiment 3

[0028] Probe compound NS-O fluorescent probe with O 2 - The change of fluorescence spectrum with the increase of equivalent

[0029] Take out 30 μ L and join among the centrifuge tube of 5mL from the stock solution of embodiment 2, add different equivalent (0-70equiv) O 2 - The standard solution was diluted to 3mL with PBS buffer solution (0.1mol / L, pH=7.4) and DMSO at a volume ratio of 1:1, and its fluorescence properties were measured with 400nm as excitation light. Fluorescence spectra such as image 3 shown. Depend on image 3 It can be seen that with O 2 - Fluorescence gradually increased with the addition of equivalents.

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Abstract

The invention discloses a small-molecule fluorescent probe for rapidly identifying superoxide radicals, a preparation method and the application thereof, and belongs to the field of organic small-molecule fluorescent probes. The structural formula of the probe molecule is shown in formula (I). The designed small-molecule fluorescent probe for rapidly identifying superoxide radicals is simple to prepare, and mature in synthesis route. By means of the small-molecule fluorescent probe, O<2-> in cells can be rapidly and accurately detected, and fluorescence imaging studies can be performed. Therefore, the fluorescent probe can be used as a simple, rapid and sensitive O<2->-specific detection reagent and has a wide application prospect in the field of biological molecule detection.

Description

technical field [0001] The invention relates to a small-molecule fluorescent probe for quickly identifying superoxide radicals, a preparation method and application thereof, and belongs to the field of organic small-molecule fluorescent probes. Background technique [0002] ROS species are produced by oxidative energy metabolism and are generally considered to be ROS radicals or other species that can be converted into ROS radicals. They play a very important role in cellular function and enable the immune system to defend against the attack of foreign microorganisms, such as: bacteria, viruses and parasites. Active oxygen species mainly include: superoxide (O 2 - ), hydrogen peroxide (H 2 o 2 ), hydroxyl radical ( OH ) and nitrate (NO 3 - )Wait. Although some reactive oxygen species are necessary in living organisms, the imbalance of reactive oxygen species can also cause a series of diseases, such as: central nervous system disorders, cancer, arthritis, arterioscler...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D277/66C09K11/06G01N21/64G01N21/29
CPCC07D277/66C09K11/06C09K2211/1037G01N21/293G01N21/6428G01N21/6486
Inventor 林伟英王建勇刘展榕
Owner UNIV OF JINAN
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