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Small-molecular fluorescent HClO probe, as well as preparation method and application thereof

A small molecule, fluorescent technology, applied in the field of preparation and small molecule fluorescent probes, can solve problems such as insufficient exploration of biological or environmental detection application potential, unsatisfactory sensitivity and/or selectivity, and complex HClO probe synthesis procedures. , to achieve the effect of good application prospect, low detection limit and convenient operation

Active Publication Date: 2021-10-22
WENZHOU MEDICAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] In addition, some of the currently available HClO probes suffer from complex synthetic procedures, unsatisfactory sensitivity and / or selectivity, poor water solubility, and insufficient exploration of potential applications in biological or environmental detection.
Moreover, most HClO probes rely on fluorescence enhancement or quenching of fluorophore units to achieve detection, which is obviously inferior to those relying on ratiometric fluorescence responses, since they are not easily affected by other environmental factors.
Taken together, these deficiencies urge us to continue developing new HClO probes

Method used

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  • Small-molecular fluorescent HClO probe, as well as preparation method and application thereof
  • Small-molecular fluorescent HClO probe, as well as preparation method and application thereof
  • Small-molecular fluorescent HClO probe, as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] Example 1: Synthesis of Small Molecule Fluorescent Probes

[0032] The chemical formula of the synthetic small molecule fluorescent probe is as follows figure 1 Shown, wherein EtOH is ethanol, RT is room temperature.

[0033] The specific synthesis process is as follows: Dissolve 7-(diethylamino)coumarin-3-carbaldehyde (500mg, 2.04mmol) in 30mL ethanol solution, and add 2-hydrazinobenzothiazole (336mg, 2.04 mmol) and stirred at room temperature for 16 h, the reactant was filtered through a Buchner funnel, washed and dried with ethanol to obtain a green target probe solid. Such as figure 2 , 3 As shown, the product can be determined to be the target small molecule fluorescent probe by means of mass spectrometry, NMR and spectroscopy.

Embodiment 2

[0034] Example 2: Ultraviolet, fluorescence spectrum and fluorescence colorimetric analysis of small molecule fluorescent probes in response to hypochlorous acid to test HClO

[0035] Prepare 0.5mL small molecule fluorescent probe (10.0×10 -6 mol / L) in EtOH / PBS (v / v=2 / 8, pH-7.4) solution. 0-30 μM hypochlorous acid solution was added dropwise to the probe solution, as Figure 4 As shown in (A), after adding hypochlorous acid to the probe solution, the main absorption band at 450nm gradually weakens, and there is a new absorption peak at ~550nm, and its absorption intensity increases gradually with the concentration of HClO ions. The inner figure shows that the color of the fluorescent probe solution changes from green to colorless after adding hypochlorous acid, so that the colorimetric detection of hypochlorous acid can be realized.

[0036] In the fluorescence titration experiment, prepare 3mL small molecule probe (10.0×10 -6 mol / L) in EtOH / PBS (v / v=2 / 8, pH-7.4) solution. ...

Embodiment 3

[0037] Embodiment 3: verification small molecule fluorescent probe is to hypochlorous acid selectivity, response speed and pH adaptability

[0038] Prepare 5mL molecular probe (10.0×10 -6mol / L) in EtOH / PBS (v / v=2 / 8, pH-7.4) solution. Various interfering media solutions (1: HNAP-hdbt, 2: OH, 3: AcO - ,4:SO 3 2- ,5:O 2 - ,6:SO 4 2- ,7:HClO,8:NO 3 - ,9:H 2 o 2 ,10:Cys,11:GSH,12:PO 4 2- , 30.0×10 -6 mol / L). Subsequently, equal equivalents of hypochlorous acid solution and these interfering media were added to the probe solution, respectively. Detection is carried out by fluorescence spectrum, and the ratio of fluorescence emission wavelength (F 478 / F 528 )comparing. The results show( Figure 5 A), these interfering media have no obvious changes in the fluorescence of the probe as hypochlorous acid, which belong to the ROS series OH, H 2 o 2 There was also no noticeable impact. Only after adding hypochlorous acid, the fluorescence ratio of the probe solution ...

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Abstract

The invention discloses a small-molecular fluorescent HClO probe as well as a preparation method and application thereof. The small-molecule fluorescent probe is synthesized from 7-(diethylamino) coumarin-3-formaldehyde and a 2-hydrazinobenzothiazole group, the 2-hydrazinobenzothiazole group falls off after a connecting part of the 7-(diethylamino) coumarin-3-formaldehyde and the 2-hydrazinobenzothiazole group is easily oxidized by hypochlorous acid, so that another coumarin derivative is generated, meanwhile, the fluorescence of the probe is also converted from green to blue, therefore, the hypochlorous acid or hypochlorite ions can be accurately and rapidly detected in a colorimetric and fluorescence ratio mode, and the method can be used for detecting exogenous and endogenous hypochlorous acid or hypochlorite ions in living cells. In addition, the probe can also be used for detecting exogenous hypochlorous acid or hypochlorite ions in solutions, plant bean sprouts and test paper. The synthesis method disclosed by the invention is simple and convenient to operate, does not need harsh conditions, and is very high in synthesis yield and purity. Therefore, the probe has a good application prospect in the aspect of hypochlorous acid or hypochlorite ion detection.

Description

technical field [0001] The invention belongs to the field of fluorescent imaging molecular probes, and in particular relates to a small molecular fluorescent probe, a preparation method and an application thereof. Background technique [0002] Together with hydroxyl radicals, singlet oxygen, nitric oxide, superoxide, etc., HClO or its anionic form (ClO - ) constitute the family of reactive oxygen species (ROS). ROS play important roles in nearly every type of life process, from cell signaling to cancer progression to autophagy. HClO is an important player in various ROS and also helps keep our immune system functioning well. Low concentrations of HClO can kill invading microorganisms or pathogens. On the other hand, excess HClO has been shown to cause DNA damage and lead to various diseases. These complex situations require us to develop highly sensitive and selective HClO probes to monitor its subtle changes within all systems. [0003] Over the years, several HClO pro...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D417/12C09K11/06G01N21/64
CPCC07D417/12C09K11/06G01N21/6428C09K2211/1037C09K2211/1088
Inventor 丁峰戴立上张积太孙鹏陈洪
Owner WENZHOU MEDICAL UNIV
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