Small-molecule fluorescent probe, and preparation method and application thereof

A technology of fluorescent probes and small molecules, which is applied in the fields of fluorescence/phosphorescence, chemical instruments and methods, and analytical materials, and can solve problems such as unsatisfactory recognition ability and selectivity, and few reports on dual-functional recognition probes. Achieve the effect of good application prospect, simple synthesis method and convenient operation

Active Publication Date: 2019-11-19
WENZHOU MEDICAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In recent years, many small molecule probes have been reported to selectively recognize hypochlorous acid. Although so many hypochlorous acid recognition probes have been reported, there are few reports on fluorescent and visual dual-functional recognition probes. The probe's recognition ability and selectivity for hypochlorous acid are not very ideal. In view of this, this study invented a dual-functional hypochlorous acid recognition fluorescent probe with high selectivity and high sensitivity.

Method used

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  • Small-molecule fluorescent probe, and preparation method and application thereof
  • Small-molecule fluorescent probe, and preparation method and application thereof
  • Small-molecule fluorescent probe, and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] Example 1 Synthesis of Small Molecular Probes

[0030] Dissolve triphenylamine oxime (0.238g, 0.83mmol) and spiropyranaldehyde (0.300g, 0.83mmol) in 30mL ethanol solution, wherein triphenylamine oxime and spiropyranaldehyde are customized by Anaiji Chemical, and the structural formula is as follows figure 1 shown in , and stirred at room temperature for 16 hours to obtain a light yellow precipitate; the above light yellow precipitate was filtered, washed repeatedly with ethanol, and dried to obtain 0.183g of a yellow solid powder, abbreviated as SPTPA, with a yield of 35%. And mass spectrometry can confirm that the product is the target small molecule probe. The route for the synthesis of small molecule probes is figure 1 , figure 1 Represents the roadmap for the synthesis of small molecule fluorescent probes, where EtOH is ethanol and RT is room temperature.

[0031] NMR characterized as figure 2 , the mass spectrum is characterized by image 3 And the model of t...

Embodiment 2

[0036] Example 2 Ultraviolet and Fluorescent Spectrum of Small Molecular Probes Recognizing Hypochlorous Acid

[0037] Prepare 1 mL of small molecule probes (10 µM and 2.0 µM) in DMSO / HO 2 O (v / v=5:1) solution. The same concentration of ClO - The solution was added dropwise to the probe solution,

[0038] Such as Figure 5 As shown in (a), adding ClO to the probe solution - Afterwards, the absorption bands at 298nm and 408nm gradually decrease, and there is a new absorption peak at 350nm~600nm, and the maximum absorption peak appears at 530nm, and its absorption intensity varies with ClO- The concentration was increased and gradually increased, and finally the stoichiometric ratio of the two was 1:3. For fluorescence titration experiments, prepare 1 mL of small molecule probes (2.0 μM) in DMSO / HO 2 O (v / v=5:1) solution. The same concentration of ClO - The solution was added dropwise to the probe solution, and the fluorescence value of the probe from 400nm to 700nm was m...

Embodiment 3

[0039] Example 3 verifies the selectivity and competitiveness of small molecule probes to hypochlorous acid.

[0040] Prepare 5.0mL molecular probe (5.0×10 -6 mol / L) of DMSO / H 2 O (v / v=1:1) solution. Solutions of various anions were prepared by dissolving the corresponding salts in deionized water [F - , Cl - , NO 2 - , ClO 4 - , HCO 3 - , H 2 PO 4 - , SO 4 2- , S 2 o 3 2- , CO 3 - , H 2 o 2 ,ClO - ](1.0×10 -3 mol / L). Subsequently, an equivalent equivalent of the anion solution was added to the probe solution. Detection is carried out by fluorescence spectroscopy, the experimental results are shown in Figure 10 (a). Take the fluorescence maximum absorption wavelength for comparison, such as Figure 10 As shown in (b), the ions include F - , Cl - , NO 2 - , ClO 4 - , HCO 3 - , H 2 PO 4 - , SO 4 2- , S 2 o 3 2- , CO 3 - , H 2 o 2 , ClO - . Except for hypochlorite ion, none of these anions produced significant changes in the fluor...

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Abstract

The invention discloses a small-molecule fluorescent probe, and a preparation method and application thereof. According to the invention, a parent structure formed by connection of triphenylamine oxime and a spiropyran aldehyde structure through nitrogen-nitrogen bonds has strong conjugate pi electrons; a spiropyrane ring is easy to open, and after the spiropyrane ring in the structure is opened,strong fluorescent light can be emitted; the small-molecule fluorescent probe can realize precise detection of hypochlorous acid via a fluorescence technology and can detect endogenous hypochlorous acid in living cells, bacteria and zebra fish bodies; so the small-molecule fluorescent probe has good application prospects in the hypochlorous acid detection. The preparation method of the invention is simple in process and convenient to operate and does not need harsh conditions.

Description

technical field [0001] The invention relates to the field of fluorescent imaging molecular probes, in particular to a method for detecting ClO using fluorescent imaging technology - The ion probe specifically relates to a molecular probe, a preparation method and an application. Background technique [0002] Hypochlorous acid is an unstable, weak acid commonly used as a main ingredient in disinfectants and bleaches. Moreover, it has important physiological functions in organisms, such as antibacterial and antiviral functions in the immune system. In addition, hypochlorous acid plays an important role in maintaining the environment in living organisms, such as balancing redox processes in the body. However, once the amount of hypochlorous acid in the body exceeds the normal range required by the body, it will cause certain damage to the internal environment of the body. For example, excessive hypochlorous acid may also cause serious damage to the following phospholipids, pr...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D491/107G01N21/64A61K49/00
CPCA61K49/0021C07D491/107C09K11/06G01N21/6428G01N21/643
Inventor 何晓俊沈建良
Owner WENZHOU MEDICAL UNIV
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