Fluorescent probe for detecting bivalent copper ions, and preparation method and application of fluorescent probe

A technology of diethylamino and reflux reaction, applied in fluorescence/phosphorescence, chemical instruments and methods, luminescent materials, etc., can solve the problems of low detection sensitivity, poor selectivity, sensitivity to pH value, etc., and achieve high sensitivity and low detection limit , the effect of fewer synthesis steps

Inactive Publication Date: 2017-10-10
SHANXI DATONG UNIV
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Problems solved by technology

[0004] Aiming at the problems of low detection sensitivity, poor selectivity, and sensitivity to pH value in fluorescent molecular probes for detecting copper ions in the prior art, the main purpose of the present invention is to provide a method that can detect divalent copper ions and has high sensitivity, good selectivity and A fluorescent molecular probe that is insensitive to pH; another purpose is to provide the preparation method and application of the fluorescent molecular probe

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  • Fluorescent probe for detecting bivalent copper ions, and preparation method and application of fluorescent probe
  • Fluorescent probe for detecting bivalent copper ions, and preparation method and application of fluorescent probe
  • Fluorescent probe for detecting bivalent copper ions, and preparation method and application of fluorescent probe

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Embodiment 1

[0044] Embodiment 1: the preparation of fluorescent probe I

[0045] Step 1: Compound II was synthesized according to the literature Bioorganic & Medicinal Chemistry Letters, 2013, 23, 2916–2919.

[0046] Step 2: Add 300.0 mg of compound II to 20 mL of absolute ethanol, then add 2.0 mL (1.7 g) of 85% hydrazine hydrate, and then reflux the reaction under the protection of nitrogen; after the reaction, cool the solution to room temperature and rotate Remove ethanol by evaporation, then add 50 parts of dichloromethane and 150 parts of saturated sodium chloride solution; separate with a separatory funnel, dry the organic phase with anhydrous sodium sulfate, and spin to dry the solvent; use petroleum ether (bp 60-90 °C ) / ethyl acetate (v:v)=5:1 as the developing solvent, separated by silica gel column chromatography, and dried in vacuo to obtain 273.1 mg of compound Ⅰ as a yellow solid. Yield: 89.2%.

[0047] Since the compound II synthesized in step 1 has some impurities, it is ...

Embodiment 2

[0052] Embodiment 2: compound I and different concentration Cu 2+ Spectral changes after action

[0053] Compound I was added to acetonitrile / water solution at a concentration of 10 μM, and then the concentration of copper ions was gradually increased (0-70 μM), and the corresponding UV and fluorescence spectra were recorded. The test results are shown in image 3 In a and 3b, it can be seen from the figure that with the increase of the concentration of copper ions, the ultraviolet absorption intensity at 562 nm and the fluorescence emission intensity at 571 nm gradually increase. 2+ When it reaches 60 μM, the UV absorption and fluorescence intensity are saturated, and then increase Cu 2+ concentration, the intensity of both will no longer increase.

Embodiment 3

[0054] Embodiment 3: the selectivity of compound I to common cation

[0055] The selectivity to copper ions was evaluated using compound I, which was added at a concentration of 10 μM to acetonitrile aqueous solution containing 50 μM divalent copper ions and various common cations (respectively, compound I and divalent copper ions in acetonitrile aqueous solution, compound I and any common cation in acetonitrile aqueous solution), the test results are shown in Figure 4 Medium (UV and fluorescence spectra). It can be seen from the figure that compound I (probe) has a high selectivity for divalent copper ions, and the addition of copper ions significantly enhances the fluorescence intensity of compound I, while the addition of other common cations has no significant change.

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Abstract

The invention relates to a fluorescent molecular probe for detecting Cu<2+> in the field of fine chemical engineering, in particular to a preparation method of a Cu<2+> fluorescent molecular probe based on rhodamine dyes and an application of the fluorescent molecular probe to biocellular imaging and water system copper ion detection. A preparation method of a compound I includes the steps: adding 1 part of (E)-2-((3', 6'-bis (diethylamino)-3-oxaspiro [isoindazole-1, 9'-xanthene]-2-alkene) imine) ethylal and 6 parts of hydrazine hydrate into a reaction vessel, heating and stirring mixture, performing rotary evaporation to remove ethyl alcohol after reaction, and adding 50 parts of methylene dichloride and 150 parts of saturated sodium chloride solution; separating mixture by the aid of a separating funnel, drying a organic phase by the aid of anhydrous sodium sulfate, performing spin drying on solvents, and separating coarse products by a column chromatography to obtain the compound I. The preparation method is mild in reaction condition, less in synthesis step and high in product yield, and raw materials are low in cost and easily acquired.

Description

technical field [0001] The invention relates to Cu in the field of fine chemical industry 2+ Fluorescent molecular probes for detection, specifically a rhodamine dye-based Cu 2+ Preparation of fluorescent molecular probes and their applications in biological cell imaging and detection of copper ions in water systems. Background technique [0002] Copper is one of the basic trace elements in living organisms, and copper plays an important role as a catalytic cofactor in different physiological processes. However, excessive copper intake in organisms can also be toxic and can cause neurological diseases such as Wilson's, Menkes and Alzheimer's. Due to the long-term excessive use of copper by humans, copper has also become an important pollutant in the environment. The U.S. Environmental Protection Agency (EPA) stipulates that the maximum limit of copper ions in drinking water is 20 μmol L -1 . Since copper is of great significance to the survival and development of human ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D491/107C09K11/06G01N21/64
CPCC07D491/107C09K11/06C09K2211/1029C09K2211/1088G01N21/6428G01N21/6486
Inventor 袁跃华朱永军田茂忠白云峰冯锋
Owner SHANXI DATONG UNIV
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