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Ferric ion fluorescent probe compound as well as preparation method and application thereof

A technology of fluorescent probes and compounds, applied in the field of fluorescent probes, can solve the problems such as the failure to apply detection and imaging of fluorescent probes, the non-linearity of the response of fluorescent probes, and the inability to quantitatively test the concentration of iron ions, etc. Beneficial for observation and detection, good selectivity and sensitivity, and good promotion prospects

Inactive Publication Date: 2015-04-08
UNIV OF JINAN
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

But it has the following disadvantages: 1. The response of the fluorescent probe of this technology to iron ions does not have a linear rule, and the concentration of iron ions cannot be quantitatively tested; 2. The detection limit of the fluorescent probe of this technology is only 10 -6 mol / L, which cannot meet the test of lower iron ion concentration; 3. The fluorescent probe of this technology cannot be applied to the detection and imaging of iron ion in biology

Method used

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  • Ferric ion fluorescent probe compound as well as preparation method and application thereof
  • Ferric ion fluorescent probe compound as well as preparation method and application thereof
  • Ferric ion fluorescent probe compound as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0046] Embodiment 1, the preparation method of ferric ion fluorescent probe compound, route is as follows:

[0047]

[0048] (a) Take 2.4 grams of rhodamine B, dissolve it in 20 milliliters of ethanol, add 2.5 milliliters of anhydrous ethylenediamine, stir and reflux for 15 hours, until the red color of the solution fades. The solvent was evaporated to dryness, 20 ml of water was added, extracted with dichloromethane, dried over anhydrous sodium sulfate, and the solvent was evaporated to obtain the rhodamine amide product shown in formula II.

[0049] (b) Under nitrogen protection, 2.5 g of binaphthol was dissolved in 100 ml of tetrahydrofuran, the solution was cooled to 0° C., and 0.88 g of sodium hydride was slowly added, and stirred for 15 minutes. 1.65 ml of 98% chloromethyl methyl ether was slowly added, the mixture was warmed to room temperature and reacted for 4 hours, then quenched by adding water. It was extracted with ethyl acetate, dried over anhydrous sodium su...

Embodiment 2

[0054] Embodiment 2, fluorescence experiment

[0055] The fluorescent probe compound prepared in Example 1 was dissolved in an aqueous solution containing 30% tetrahydrofuran, and the pH was adjusted to 7.0 with HEPES buffer solution (Zhangjiagang Changhua Chemical Co., Ltd.); the fluorescent probe solution was obtained for future use.

[0056] 1. Take the fluorescent probe solution, divide it into 13 groups, each group (bottle) 10 ml, add the solution containing Fe 3+ 、Cd 2+、 Pb 2+ , Hg 2+ 、Na 2+ 、Ba 2+ 、K + , Mn 2+ , Li + 、Cu 2+ , Zn 2+ 、Ag + 、Ni 2+ solution, so that the concentration of the probe compound contained in each group of solutions is 50 μM, and the metal ion concentration is 500 μM, so that the molar ratio of the metal ion to the probe compound is 10:1; the excitation wavelength is 510 nm, and its fluorescence intensity is tested by a fluorescence photometer ,Such as figure 1 As shown, the results show that: the solution added with iron ions has a st...

Embodiment 3

[0058] Embodiment 3: Fluorescent probes of the present invention are used in cell imaging experiments

[0059] The fluorescent probe compound prepared in Example 1 was used for cell imaging, and the obtained cell micrograph is shown in Figure 3. In the figure, a, b, c are images of HeLa cells cultured and treated with this fluorescent probe, and it can be seen that there is no obvious fluorescence; d, e, f are HeLa cells cultured and treated with ferric ions In the figure, there is no fluorescence; g, h, and i are HeLa cells treated with ferric ions, and then added this fluorescent probe compound for culture, and obvious fluorescence imaging can be seen.

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Abstract

The invention relates to a ferric fluorescent probe compound as well as a preparation method and application thereof. The ferric fluorescent probe compound has the structure in formula I in the specification. The preparation method comprises the following steps: mixing rhodamine B with anhydrous ethanediamine and refluxing in ethyl alcohol to prepare amide of rhodamine; protecting hydroxyl of binaphthol by chloromethyl methyl ether, reacting with N,N-dimethylformamide under the action of butyl lithium, and removing methyl of methyl ether by hydrochloric acid to obtain binaphthol with aldehyde group; finally refluxing the amide of rhodamine and the binaphthol with aldehyde group in ethyl alcohol and washing to obtain the pure ferric fluorescent probe compound. The probe compound has favorable selectivity and sensitivity for the ferric ions, is simple to treat before sample detection and free of causing toxicity to cells, and is used for detecting the ferric ions in the water environment or the biological cells.

Description

technical field [0001] The invention relates to a ferric ion fluorescent probe compound and its preparation and application, belonging to the technical field of fluorescent probes. technical background [0002] Iron is an essential trace element for animals and plants. It plays an important role in cell metabolism. Iron can serve as an oxygen carrier for hemoglobin and catalyze various enzyme reactions. In the human body, the lack of ferric ions can lead to anemia, diabetes, heart disease, and liver and kidney damage. However, although iron is an important element for maintaining good health, once its content exceeds the safe range of the organism, it may promote the oxidation of fats, proteins and other components in cells and become toxic. Excess ferric ions in the body are closely related to certain cancers and organ dysfunction. Therefore, detecting the iron content in the body can be used to guide the prevention of certain diseases. [0003] Common methods for qualit...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D491/107C09K11/06G01N21/64
CPCC07D491/107C09K11/06C09K2211/1022C09K2211/1033G01N21/64
Inventor 吕正亮黄曦明范春华
Owner UNIV OF JINAN
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