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Fluorescent probe for detecting Fe < 3 + > and preparation method and application thereof

A technique for fluorescent probes and compounds, applied in the field of fluorescent probes for detecting Fe3+ and their preparation, can solve the problems of expensive and precise instruments, time-consuming, complicated and cumbersome sample processing processes, etc.

Inactive Publication Date: 2021-03-16
YANTAI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, these methods generally take a long time, involve complex and tedious sample processing procedures, or require expensive precision instruments, etc.

Method used

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  • Fluorescent probe for detecting Fe &lt; 3 + &gt; and preparation method and application thereof
  • Fluorescent probe for detecting Fe &lt; 3 + &gt; and preparation method and application thereof
  • Fluorescent probe for detecting Fe &lt; 3 + &gt; and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] Embodiment 1: the synthesis of fluorescent probe

[0034] The present invention detects Fe 3+ The BODIPY type fluorescent probe is synthesized as follows:

[0035] Under anhydrous and oxygen-free conditions, dissolve 0.6798g of p-chloromethylbenzaldehyde and 0.7ml of 2,4-dimethylpyrrole in dichloromethane and stir evenly, add 0.15ml of trifluoroacetic acid and react for three hours to obtain intermediate product, then add 1.98g 2,3-dichloro-5,6-dicyanophenylquinone (DDQ), stir for one hour, add 10ml triethylamine to react for one hour, add 10ml boron trifluoride diethyl ether to react for three hours . Add 50ml of water to start the extraction, separate the organic phase, add 5g of anhydrous sodium sulfate to dry, filter with suction, rotary evaporate, and separate by column chromatography (the eluent is a mixed solution of petroleum ether / ethyl acetate=3 / 1) to obtain Product red solid 105mg (yield: 68%), as figure 2 As shown, it was confirmed that the following co...

Embodiment 2

[0038] Embodiment 2: Fluorescent detection of probes to iron ions

[0039] Dissolve the fluorescent probe prepared above in a mixed solution of water and acetonitrile, and prepare a 2 μM probe solution, add 2 mL of the prepared 2 μM probe solution of the present invention to a cuvette, and then add different concentrations of Fe 3+ After uniform mixing, the fluorescence spectrum was tested, and it was found that the fluorescence intensity increased with Fe 3+ The concentration increases and decreases, the results are as follows image 3 Shown, show that the fluorescent intensity of the fluorescent probe of the present invention varies with Fe 3+ concentration increases and decreases.

[0040] The fluorescence emission intensity of the solution at 512nm for Fe 3+ Concentration plotted, Fe 3+ When the concentration is in the range of 0–120μM, there is a good linear relationship between the two ( Figure 4 ), indicating that the probe of the present invention can realize Fe ...

Embodiment 3

[0045] Embodiment 3: Anti-interference test of probe

[0046] Add 400 μM different ion Na to the prepared 2 μM probe solution of the present invention respectively + 、K + , Li + , Mg 2+ 、Al 3+ 、Ba 2+ , Ca 2+ , Zn 2+ , Hg 2+ 、Cd 2+ 、Ni 2+ 、Co 2+ 、Cr 2+ 、Cu 2+ , Pb 2+ Afterwards, 200 μM Fe was added to the fluorescent probe solution and the fluorescent probe solution with different ions, respectively. 3+ After that, the change of the fluorescence emission intensity at 512 nm; the abscissa is the interference ion of the blank and the test, and the ordinate is the fluorescence intensity.

[0047] like Figure 8 As shown, the addition of Fe to the fluorescent probe 3+ In contrast to adding other metal ions to the fluorescent probe followed by the addition of Fe 3+ The degree of weakening of the fluorescence intensity is similar, indicating that the fluorescent probe of the present invention has excellent anti-interference, and can be used to detect iron ions in the...

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Abstract

The invention discloses a fluorescent probe for detecting Fe < 3 + > and a preparation method and application of the fluorescent probe. According to the preparation method, p-chloromethyl benzaldehyde, 2, 4-dimethyl pyrrole and boron trifluoride diethyl ether react to generate the BODIPY type fluorescent probe molecule, the preparation process of the material adopted by the fluorescent probe molecule is simple and easy to operate, the raw material source is sufficient, the production cost is low, the yield is high, the repeatability is good, the molecule can be complexed with Fe < 3 + >, an the charge structure is changed, so that the fluorescence is weakened or even disappears; according to the characteristics, the fluorescence probe can be used for detecting Fe < 3 + > and can be used for biological imaging so as to detect biological cell Fe < 3 + >, and a research method is provided for researching the effect of Fe < 3 + > in human life activities.

Description

technical field [0001] The invention belongs to the field of organic fluorescent probes, in particular to a method for detecting Fe 3+ Fluorescent probes and their preparation methods and applications. Background technique [0002] Iron is an important metal element in the earth's crust, its content occupies the fourth place, and it is also an essential trace element with the highest content in the human body. Biological and chemical processes at the multicellular level require the participation of iron ions. Iron is the main substance for sustaining life. Heme and myoglobin, the necessary substances to promote the metabolism of vitamin B family, participate in the transportation and storage of oxygen, and play a very important physiological role in enhancing the immune function of the body. Iron element participates in the synthesis of cytochrome and other enzymes, and participates in the transport of oxygen, but if the human body absorbs too much iron, it may also lead to...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F5/02C09K11/06G01N21/64
CPCC07F5/022C09K11/06G01N21/643C09K2211/1055G01N2021/6417
Inventor 冷俊强于淇刘振波宋奎柱成文帅苑林颖刘爽
Owner YANTAI UNIV
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