A small molecule fluorescent probe for rapid recognition of superoxide, its preparation method and application

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

Inactive Publication Date: 2018-12-18
UNIV OF JINAN
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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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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  • A small molecule fluorescent probe for rapid recognition of superoxide, its preparation method and application
  • A small molecule fluorescent probe for rapid recognition of superoxide, its preparation method and application
  • A small molecule fluorescent probe for rapid recognition of superoxide, its preparation method and application

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 once, under nitrogen atmosphere After heating and refluxing for 5 hours, the reaction was detected by dot plate until the raw materials disappeared, the solvent was spin-dried under reduced pressure to obtain a crude product, and the probe compound NS-O was separated by silica gel column. 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 chart see figure 1 .

Embodiment 2

[0025] Probe NS-O with O 2 - Add its visible light absorption change

[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 30μL 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. See the spectrogram figure 2 Shown. by figure 2 It can be seen that after adding probe NS-O, directly add O 2 - , The absorption change can be detected instantaneously, and O 2 - Detection.

Embodiment 3

[0028] Probe compound NS-O fluorescent probe with O 2 - Change of fluorescence spectrum with increase in equivalent

[0029] Take 30μL from the stock solution of Example 2 and add it to a 5mL centrifuge tube, add different equivalents (0-70equiv) of O 2 - The standard solution was diluted to 3 mL with a 1:1 volume ratio of PBS buffer solution (0.1mol / L, pH=7.4) and DMSO, and 400nm was used as excitation light to measure its fluorescence properties. Fluorescence spectra such as image 3 Shown. by image 3 It can be seen that with O 2 - Fluorescence gradually increased with the increase of the added equivalent.

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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 and a preparation method and application thereof, belonging to the field of organic small molecule fluorescent probes. Background technique [0002] Active oxygen species are produced by oxidative energy metabolism, and are generally considered to be active oxygen free radicals or other species that can be converted into active oxygen free radicals. They play a very important role in cell function, allowing the immune system to defend against attacks by foreign microorganisms, such as bacteria, viruses and parasites. The reactive oxygen species mainly include: superoxide radical (O 2 - ), hydrogen peroxide (H 2 O 2 ), hydroxyl radical (●OH) and nitrate (NO 3 - )Wait. Although some reactive oxygen species are necessary in the organism, the imbalance of reactive oxygen species can also cause a series of diseases, such as: central nervous system disorders, ...

Claims

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Application Information

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Patent Type & Authority Patents(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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