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Small-molecule probe H4L and preparing method and application thereof

A technology of small molecule probes and molecular probes, which is applied in the field of fluorescent imaging molecular probes, can solve problems such as gallium ion recognition ability and selectivity are not very ideal, and achieve good application prospects, convenient operation, and simple synthesis methods

Active Publication Date: 2019-05-21
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 different metal ions, especially zinc ions, copper ions, iron ions, and mercury ions. There are few reports on the recognition probes, and the recognition ability and selectivity of such probes to gallium ions are not very ideal. In view of this, it is of far-reaching significance to explore a new gallium ion recognition probe

Method used

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  • Small-molecule probe H4L and preparing method and application thereof
  • Small-molecule probe H4L and preparing method and application thereof
  • Small-molecule probe H4L and preparing method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034] Example 1 Synthesis of Small Molecular Probes

[0035] Put salicylaldehyde (3.05g, 25mmol) and 3,3'-diaminobenzidine (1.07g, 5mmol) into a 100mL round bottom flask, add 50mL of absolute ethanol, and stir at room temperature for 20 minutes to make all solids All dissolved, and a light yellow transparent liquid was obtained, and then the above transparent solution was heated to 353K and refluxed for 8 hours. During the reaction, the color of the solution gradually changed from light yellow to dark red, and orange solid powder was precipitated, cooled and filtered, and vacuum dried to obtain Orange solid powder 2.520g, yield 80%, then weigh 1.0g of the above orange solid powder and dissolve it in 15mL of DMF, then heat at 80°C and stir for 10 minutes to filter while hot, place the filtrate in a beaker, and partially seal it with filter paper, After slowly volatilizing for 2 days, a red crystal was obtained, which was confirmed to be the target small molecule probe by mass ...

Embodiment 2

[0041] Example 2 Ultraviolet and fluorescence spectra of small molecule probes in response to gallium ions

[0042] Prepare 1mL small molecule probe (2.0×10 -6 mol / L) of DMSO / H 2 O (v / v=9:1) solution. Gallium ion solution of the same concentration was added dropwise to the probe solution,

[0043] Such as figure 2 As shown in (a), after adding gallium ions to the probe solution, the absorption bands at 275nm and 350nm gradually decrease, and there is a new absorption peak at 350nm-450nm, and the maximum absorption peak appears at 410nm. As the concentration of gallium ions increases and gradually increases, the final stoichiometric ratio of the two is 1:2.

[0044]In the fluorescence titration experiment, prepare 1mL small molecule probe (2.0×10 -5 mol / L) of DMSO / H 2 O (v / v=9:1) solution. The same concentration of gallium ion solution was added dropwise to the probe solution, and the fluorescence value of the probe from 400nm to 650nm was measured with 350nm as the exc...

Embodiment 3

[0045] Example 3 Verifying the Selectivity and Competitiveness of Small Molecular Probes to Gallium Ions

[0046] Prepare 5mL molecular probe (2.0×10 -6 mol / L) of DMSO / H 2 O (v / v=9:1) solution. Various anion solutions (Ga 3+ ,Cr 3+ ,Al 3+ , Fe 3+ , Ca 2+ ,Cd 2+ , Co 2+ ,Mn 2+ , Ni 2+ ,Zn 2+ , Fe 2+ ,Cu 2+ , Ag + , K + , Li + and Na + , 1.0×10 -3 mol / L). Subsequently, an equivalent equivalent of the metal ion solution was added to the probe solution.

[0047] Detection is carried out by fluorescence spectroscopy, the experimental results are shown in image 3 (a). Take the fluorescence maximum absorption wavelength for comparison, such as image 3 As shown in (b), the ions include Ga 3+ ,Cr 3+ ,Al 3+ , Fe 3+ , Ca 2+ ,Cd 2+ ,Co 2+ ,Mn 2+ , Ni 2+ ,Zn 2+ , Fe 2+ ,Cu 2+ , Ag + , K + , Li + and Na + . In addition to Ga 3+ In addition, these metal ions did not produce significant changes in the fluorescence of the probe. in Ga 3+ After the ad...

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Abstract

A small-molecule probe H4L and a preparing method and application thereof are disclosed. The parent structure of the probe is salicylaldehyde and a 3,3'-diaminobenzidine group. The probe can accurately detect gallium ions with ultraviolet and fluorescence, and can also be used for detecting gallium ions in solutions, live cells and exogenous gallium ions in zebra fish. The method is simple and convenient to operate, and does not need harsh conditions, the synthetic yield and purity are high, and the probe has a good application prospect in gallium ion detection.

Description

technical field [0001] The present invention relates to the field of fluorescent imaging molecular probes, in particular to a probe for detecting gallium ions using fluorescent imaging technology, and in particular to a preparation method and application of a molecular probe. Background technique [0002] Among the analytical methods designed so far, fluorescence imaging is an important method for detecting ions. However, this method has certain limitations in terms of sample requirements and working environment. In addition, the selectivity and sensitivity of most probes have certain limitations, and developing a probe with high selectivity and sensitivity is a technical challenge. In order to gain insight into the relevant information of deep fluorescence imaging, the development of metal fluorescence imaging has become an option. However, due to the difference in fluorescence intensity, the maximum imaging effect of fluorescence imaging is not ideal, and this imaging ef...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C249/02C07C251/24C09K11/06G01N21/64
Inventor 何晓俊沈建良
Owner WENZHOU MEDICAL UNIV
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