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Micromolecular fluorescent probe taking 3-hydroxyflavone as fluorophore as well as preparation method and application of micromolecular fluorescent probe

A technology of fluorescent probes and hydroxyflavones, which is applied in the field of fluorescent imaging molecular probes, can solve the problems of simultaneous detection of fluorescent probes, and achieve the effects of simple synthesis methods, good application prospects, and convenient operation

Active Publication Date: 2019-12-13
WENZHOU MEDICAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

There is no fluorescent probe that can simultaneously detect these three metal ions (especially trivalent metal ions) in the prior art

Method used

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  • Micromolecular fluorescent probe taking 3-hydroxyflavone as fluorophore as well as preparation method and application of micromolecular fluorescent probe
  • Micromolecular fluorescent probe taking 3-hydroxyflavone as fluorophore as well as preparation method and application of micromolecular fluorescent probe
  • Micromolecular fluorescent probe taking 3-hydroxyflavone as fluorophore as well as preparation method and application of micromolecular fluorescent probe

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] The spectroscopic properties of 3-hydroxyflavone after recognizing the third main group metal ion in Example 1

[0025] 3-Hydroxyflavone (3-HF), as a sensitive fluorescent probe for group IIIA ions including Ga(III), Al(III) and In(III) ions, has a common The fluorophores of the conjugated system are used for the selective detection of group IIIA ions. figure 1 a and b show the molecular structures of 3-HF and 3-HF-Group IIIA complexes, respectively. The spectroscopic properties of 3-HF exhibit an excited-state intramolecular proton transfer (ESIPT) reaction, accompanied by a clear band separation between the normal and photopolymeric forms in the emission spectrum, which is believed to be indicative of the interaction. 3-HF-solvent and 3-HF-cation in the corresponding complexes. Furthermore, we present a proposed 3-HF sensing mechanism with Ga(III), Al(III) and In(III) ions, as figure 2 as shown in a. The C=O ans-OH group of 3-HF plays an important role in the coo...

Embodiment 2

[0026] 3-hydroxyflavone recognition metal ion spectrometric titration in embodiment 2

[0027] The concentration dependence of the 3-HF response to group IIIA ions was studied. UV-Vis spectra of 3-HF in different amounts of Ga(III), Al(III) and In(III) ions ( image 3a, 3b, 3c). After adding the concentration of metal ions, the dark yellow solution system was obtained from light yellow, and the absorption peaks of 3-HF around 307nm and 347nm gradually decreased, and the specific absorption peak at 409nm was formed with a red shift (62nm). And, to examine the symbolic 3-HF fluorescence response to Ga(III), Al(III) and In(III) ions, as image 3 d, 3e, 3f, free 3-HF shows sign fluorescence at 535. When excited at 350 nm, the emission spectrum of 3-HF shows a large blue shift at 75 nm (from 535 nm to 460 nm), with an iso-emission point at 516 nm. With DMSO-H 2 The ratio of emission intensity (I460nm / I535nm) increases sharply with the increase of metal ion concentration in O(5...

Embodiment 3

[0028] Example 3 verifies the selectivity and competitiveness of small molecule probes to Ga(III), Al(III) and In(III).

[0029] Prepare 5.0mL molecular probe (5.0×10 -6 mol / L) of DMSO / H 2 O (v / v=1:1) solution. Various metal cation solutions [K(I), V(IV), Fe(III), Ca(II), Dy(III), Er(III), Al(III) were prepared by dissolving the corresponding salts in deionized water ), Cr(III), Ga(III), Bi(III), Ni(II), Zn(II), Co(II), In(III), Mn(II) and Cu(II)] (1.0× 10 -3 mol / L). Subsequently, an equivalent equivalent of the metal cation solution was added to the probe solution. Detection is carried out by fluorescence spectroscopy, the experimental results are shown in Figure 8 (a). Take the fluorescence maximum absorption wavelength for comparison, such as Figure 8 As shown in (b, c), ions include K(I), V(IV), Fe(III), Ca(II), Dy(III), Er(III), Al(III), Cr(III), Ga(III), Bi(III), Ni(II), Zn(II), Co(II), In(III), Mn(II) and Cu(II). Except for Ga(III), Al(III) and In(III) ions,...

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Abstract

The invention discloses a small-molecule fluorescent probe taking 3-hydroxyflavone as a fluorophore and application of the small-molecule fluorescent probe. An excited state intramolecular proton transfer (ESIPT) strategy system is adopted in a DMSO / H2O (5: 1, v / v) solution, high-selectivity response to group IIIA metal ions is shown relative to other cations, green fluorescence is converted intoblue fluorescence, ultraviolet absorption peaks are subjected to red shift, and along with the increase of the concentrations of Ga, Al and In ions, the metal ions are strongly combined with the probe, so that the Ga, Al and In ions are accurately detected by a fluorescence technology, and endogenous and exogenous Ga, Al and In ions in living cells can be detected. Therefore, the method has a goodapplication prospect in the aspect of Ga, Al and In ion detection, and meanwhile, the synthesis method disclosed by the invention is simple 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 probe for detecting Ga, Al and In ions using fluorescent imaging technology, and in particular to a molecular probe and its application. Background technique [0002] Gallium, aluminum and indium belong to group IIIA of the periodic table of elements, have similar physical and chemical properties, are double-edged swords for living organisms, and also bring harm when they participate in physiological processes. Aluminum is a trace element in living organisms, widely used in medicine, food processing and daily life. However, aluminum is toxic in the form of Al(III) and is closely related to various diseases. Excessive rates accumulate in organisms and have a greater impact on nervous system lesions. Therefore, it is particularly important to detect the content of free Al(III) ions in organisms. Gallium is the active metal after aluminum in group IIIA and has...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D311/30C09K11/06G01N21/64A61K49/00
CPCA61K49/0021C07D311/30C09K11/06C09K2211/1007C09K2211/1029G01N21/6428G01N21/643G01N2021/6417G01N2021/6432
Inventor 沈建良何晓俊
Owner WENZHOU MEDICAL UNIV
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