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Small-molecule fluorescent probe with TS as fluorophores and preparation method and application of small-molecule fluorescent probe

A technology of fluorescent probes and small molecules, which is applied in the field of fluorescent imaging molecular probes, can solve problems such as the influence of probe molecular charge transfer, changes in ultraviolet and fluorescent spectra, and achieve good application prospects, simple synthesis methods, and convenient operation.

Active Publication Date: 2019-08-13
WENZHOU MEDICAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, when the recognition process occurs with the guest, the charge transfer in the probe molecule will be affected, and its UV and fluorescence spectra will change.

Method used

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  • Small-molecule fluorescent probe with TS as fluorophores and preparation method and application of small-molecule fluorescent probe
  • Small-molecule fluorescent probe with TS as fluorophores and preparation method and application of small-molecule fluorescent probe
  • Small-molecule fluorescent probe with TS as fluorophores and preparation method and application of small-molecule fluorescent probe

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0035] Example 1 Synthesis of Small Molecule Fluorescent Probes

[0036] Synthesis of small molecule fluorescent probes with TS as fluorophore: Dissolve 4-dianilinobenzaldehyde (500mg, 1.83mmol) in 30mL ethanol solution, and add salicylic acid hydrazide (278mg, 1.83mmol) at room temperature Stirring, stirring at room temperature for 20 h, the reaction gave a green solid, which was washed and dried with ethanol. The small molecule fluorescent probe can be recrystallized with absolute ethanol to obtain a sample with higher purity, and the yield of the final sample is: 80%. The route diagram for synthesizing the small molecule fluorescent probe is shown in figure 1 as shown, figure 1 Represents the roadmap for the synthesis of small molecule fluorescent probes, where EtOH is ethanol and RT is room temperature.

[0037] It can be determined that the product is the target small molecule fluorescent probe by mass spectrometry, NMR and spectroscopic methods, and its mass spectromet...

Embodiment 2

[0044] Example 2 Ultraviolet and fluorescence spectra of small molecule fluorescent probes in response to copper ions

[0045] Prepare 1.0mL small molecule fluorescent probe (1.0×10 -5 mol / L) of DMSO / H 2 O (v / v=1:1) solution. 0.5 times the normal concentration of copper ion solution was added dropwise to the probe solution, such as Figure 5 As shown in (a), after copper ions are added to the TS probe solution, the absorption bands at 298nm and 372nm gradually decrease, and there is a new absorption peak at 400nm-500nm, and the maximum absorption peak appears at 398nm. The intensity gradually increases with the ion concentration, and the final stoichiometric ratio of the two is 2:1.

[0046] In the fluorescence titration experiment, prepare 3.0mL small molecule probe (5.0×10 -6 mol / L) of DMSO / H 2 O (v / v=1:1) solution. 0.5 times the equivalent concentration of copper ion solution was added dropwise to the probe solution. For the TS probe, the fluorescence value of the pro...

Embodiment 3

[0047] Example 3 verifies the selectivity and competitiveness of small molecule fluorescent probes for copper ions.

[0048] Prepare 5.0mL molecular probe (5.0×10 -6 mol / L) of DMSO / H 2 O (v / v=1:1) solution. Various cationic solutions [Fe(III), Al(III), Cr(III), Zn(II), Ni(II), Co(II), Mg(II) were prepared by dissolving the corresponding salts in deionized water , Ca(II), Cd(II), Mn(II), Ag(I), K(I) and Na(I)] (1.0×10 -3 mol / L). Subsequently, an equivalent equivalent of the metal ion solution was added to the probe solution. Detection is carried out by fluorescence spectroscopy, the experimental results are shown in Figure 6 (a). Take the fluorescence maximum absorption wavelength for comparison, such as Figure 6 As shown in (b), ions include Fe(III), Al(III), Cr(III), Zn(II), Ni(II), Co(II), Mg(II), Ca(II), Cd( II), Mn(II), Ag(I), K(I) and Na(I). Except for Cu(II), none of these metal ions produced significant changes in the fluorescence of the probes. After adding...

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Abstract

The invention discloses a small-molecule fluorescent probe with TS as a fluorophore and a preparation method and application of the small-molecule fluorescent probe. The triphenylamine is used as thefluorophore, salicylhydrzidate is used as a basis, and the small-molecule fluorescent probe has strong conjugate pi electronics, wherein the salicylhydrzidate and aldehyde groups are condensed to serve as chelation sites of metal ions, and after the small-molecule fluorescent probe is combined with copper ions, the fluorescence can be quenched; in the presence of the copper ions, the small-molecule fluorescent probe blocks transfer of the electronics in probe molecules, so that the fluorescence is from appearance to disappearance, ultraviolet absorption peaks shift to red, new absorption appears at the wavelength of 398 nanometers, along with increasing of the concentration of the copper ions, absorption peaks are gradually increased and transferred, it is shown that the metal ions are highly combined with the probe, it is achieved that the copper ions are precisely detected by using the fluorescence technology, and the ectogenic copper ions in living cells can be detected. Therefore,the small-molecule fluorescent probe has a good application prospect in the aspect of copper ion detection, besides, the synthesis method is simple, operation is convenient, and no harsh conditions are needed.

Description

technical field [0001] The invention relates to the field of fluorescent imaging molecular probes, in particular to a probe for detecting copper ions using fluorescent imaging technology, and in particular to a molecular probe, its preparation method and application. Background technique [0002] In living organisms, copper ions are the third most essential trace element after iron ions and zinc ions. A certain amount of copper ions plays a vital role in the basic physiological activities of plants and animals. However, excessive copper ions can generate reactive oxygen species, disrupt the balance of cell metabolism, and become toxic substances in biological systems. For example, excessive intake of copper ions may cause severe damage to the gastrointestinal tract, kidneys, and liver; some difficult-to-treat diseases, including Alzheimer's disease, amyotrophic lateral sclerosis, Menkes syndrome, Wilson's disease, and There is some association with excess copper ions. What...

Claims

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Application Information

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IPC IPC(8): C07C251/86C07C249/16C09K11/06G01N21/33G01N21/64
CPCC07C251/86C07C249/16C09K11/06G01N21/33G01N21/6428G01N21/643C09K2211/1007C09K2211/1014G01N2021/6432
Inventor 沈建良何晓俊
Owner WENZHOU MEDICAL UNIV
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