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Hemicyanine-based reactive Hg<2+> fluorescent probe Cy-PT and preparation method and application thereof

A fluorescent probe and reactive technology, applied in the direction of fluorescence/phosphorescence, chemical instruments and methods, luminescent materials, etc., can solve the problems of tedious sample preparation and high cost, achieve high selectivity and sensitivity, short response time, good The effect of developing potential

Inactive Publication Date: 2019-03-08
HUBEI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the above test methods not only require high-cost test instruments, but also require tedious sample preparation

Method used

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  • Hemicyanine-based reactive Hg&lt;2+&gt; fluorescent probe Cy-PT and preparation method and application thereof
  • Hemicyanine-based reactive Hg&lt;2+&gt; fluorescent probe Cy-PT and preparation method and application thereof
  • Hemicyanine-based reactive Hg&lt;2+&gt; fluorescent probe Cy-PT and preparation method and application thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0040] A reactive Hg based on hemicyanine of this embodiment 2+ The fluorescent probe Cy-PT, the chemical structure formula of the fluorescent probe Cy-PT is shown in Formula 1 in the summary of the invention.

[0041] The above-mentioned reactive Hg based on hemicyanine 2+ The fluorescent probe Cy-PT is prepared by the following method, including the following steps:

[0042] (1) Preparation of intermediate Cy-OH: Resorcinol (332mg, 3.0mmol) and K 2 CO 3 (413mg, 3.0mmol) was dissolved in 20mL of anhydrous acetonitrile, reacted for 30 minutes at 35°C under nitrogen conditions, and then an acetonitrile solution containing IR-780 (1g, 1.5mmol) was added to the mixture. The reaction was carried out at 50°C for 4 hours, and the progress was detected by TCL. After the reaction, the solvent was evaporated in vacuo, and the crude product was purified by column chromatography (V DCM / V MeOH =40:1), 0.41g Cy-OH is obtained as a dark green powdery product with a yield of 65%.

[0043] (2) P...

Embodiment 2

[0050] Example 2Hg 2+ Influence on the ultraviolet absorption and fluorescence spectra of Cy-PT probe

[0051] (1)Hg 2+ Effect on the UV absorption spectrum of Cy-PT probe: The absorption and fluorescence spectrum of Cy-PT probe are measured in DMSO / HEPES (2:8, v / v, pH7.4) solution, the final concentration of Cy-PT is 10 -5 M, Hg 2+ The concentration is 100 μM. Such as figure 1 As shown in (a), when mercury ions are present in the compound Cy-PT, the strongest absorption peak at 587nm is rapidly weakened, two absorption peaks that did not exist before appear at 660nm and 693nm, and one at 601nm appears Extinction point, indicating the probe Cy-PT and Hg 2+ It worked. Will add Hg 2+ The latter absorption spectrum was compared with that of Cy-OH, and it was found that the absorption spectra of the two were very similar, which confirmed the reaction mechanism of the Cy-PT probe to identify mercury ions.

[0052] (2)Hg 2+ Influence on the fluorescence spectrum of the probe Cy-PT: the...

Embodiment 3

[0053] Example 3: Selectivity experiment of probe Cy-PT

[0054] Probe selectivity experiment: In order to find out whether the probe Cy-PT is positive for Hg 2+ With specific identification, we have different common metal cations (Fe 3+ , Mn 2+ , Cu 2+ , Zn 2+ , Pb 2+ , Co 2+ , Hg 2+ , Ni 2+ , Cr 3+ And Mg 2+ , K + , Al 3+ , Na + , Fe 2+ ) Conducted selective experiments. Such as figure 2 As shown in (a), when the probe solution is mixed with 10 equivalents of other common metal ion solutions, only Hg 2+ As a result, the fluorescence is significantly enhanced, and other metal ions hardly change the fluorescence spectrum. And it was observed with the naked eye that only 10 equivalents of Hg were added 2+ When the color of the probe solution changes significantly, such as figure 2 As shown in middle (b), it is proved that the probe Cy-PT is against Hg 2+ With specific recognition.

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Abstract

The invention discloses a reactive Hg<2+> fluorescent probe Cy-PT and a preparation method and application thereof. In the reactive Hg<2+> fluorescent probe Cy-PT, phenyl thiochloroformate serving asan identification unit is coupled to a stable hemicyanine framework via an ester bond to form the fluorescent probe Cy-PT; and generated thioester is hydrolyzed under the catalysis of Hg<2+>, and theester bond is broken to expose a hydroxyl group. The probe fluorescence is enhanced due to an intramolecular ICT mechanism. The probe can specifically recognize Hg<2+> in a physiological pH environment, and can be used for colorimetric detection of Hg<2+> as the solution turns from indigo to lake blue. In addition, the cytotoxicity test of the reactive Hg<2+> fluorescent probe Cy-PT proves that the probe has low biotoxicity, and a cell imaging experiment shows that the probe can detect mercury ions in a living complex biological system, which indicate that the reactive Hg<2+> fluorescent probeCy-PT has a development potential in living body detection.

Description

Technical field [0001] The present invention belongs to the technical field of organic synthesis, and specifically relates to a fluorescent probe for detecting metal ions. More specifically, the present invention relates to a hemicyanine-based, identifying and detecting Hg 2+ The reactive fluorescent probe Cy-PT and its preparation method and application. Background technique [0002] As we all know, compared with many other metal ions, mercury is one of the most toxic metals because of its durability, easy transferability and high bioaccumulation. Due to human activities such as coal-fired power plants and gold mines, mercury and mercury species are continuously released into the environment, which poses a non-negligible threat to human health and the living environment. Therefore, the development of selective and sensitive detection methods for mercury is still urgently needed. Traditionally, atomic absorption spectroscopy, inductively coupled plasma mass spectrometry and capi...

Claims

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Application Information

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IPC IPC(8): C07D405/06C09K11/06G01N21/64
CPCC07D405/06C09K11/06C09K2211/1029C09K2211/1088G01N21/6428G01N21/643
Inventor 何汉平吕贺红袁刚常钢任子奇张修华王升富
Owner HUBEI UNIV
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