Rhodamin B double-sulfur fluorescence probe for detecting aqueous mediums and intracellular mercury ions, preparation and application thereof

A fluorescent probe, a technology for detecting water, applied in fluorescence/phosphorescence, luminescent materials, chemical instruments and methods, etc., can solve the problems of unsatisfactory selectivity, sensitivity and biocompatibility of fluorescent probes, and achieve good detection. Sensitivity, good cell permeability effect

Active Publication Date: 2015-04-01
SOUTH CHINA NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although a variety of rhodamine-based fluorescent probes have been developed and reported for the detection of mercury ions, the selectivity, sensitivity and biocompatibility of these fluorescent probes are not ideal at present.

Method used

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  • Rhodamin B double-sulfur fluorescence probe for detecting aqueous mediums and intracellular mercury ions, preparation and application thereof
  • Rhodamin B double-sulfur fluorescence probe for detecting aqueous mediums and intracellular mercury ions, preparation and application thereof
  • Rhodamin B double-sulfur fluorescence probe for detecting aqueous mediums and intracellular mercury ions, preparation and application thereof

Examples

Experimental program
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Embodiment 1

[0035] (1) The synthetic steps of a fluorescent probe for detecting mercury ions in aqueous media and cells provided by the present invention are as follows: figure 1 As shown, the details are as follows: at room temperature, 1.99g (1.0mmol) 2-bromoacetophenone and 1.64g (1.0mmol) 1-pyrrolidine ammonium dithiocarboxylate were dissolved in 30mL of acetone, and stirred at room temperature to The termination of the reaction was detected by TLC, and the solvent was evaporated to obtain a yellow solid, which was recrystallized from absolute ethanol to obtain a white disulfide intermediate-I with a yield of 75%;

[0036] Characterization data: 1 HNMR (400M, CDCl 3 ):δ=1.96(m,2H),2.08(m,2H),3.74(t,J=7.2Hz,2H),3.91(t,J=7.2Hz,2H),4.92(s,2H),7.48 (t, J=7.6Hz, 2H), 7.81(t, J=6.4Hz, 1H), 8.08(m, 2H); 13 CNMR (101M, CDCl 3 ): δ=24.39, 26.18, 44.51, 50.82, 55.50, 128.59, 128.71, 136.08, 191.00, 193.44; FAB-MS: m / z=265.

[0037] The structural formula is as shown in formula II:

[0038...

Embodiment 2

[0047] (1) The synthetic steps of a fluorescent probe for detecting mercury ions in aqueous media and cells provided by the present invention are as follows: figure 1 Shown, specifically as follows: at room temperature, 1.99g (1.0mmol) 2-bromoacetophenone and 1.97g (1.2mmol) 1-pyrrolidine ammonium dithiocarboxylate were dissolved in 30mL acetone, stirred at room temperature to The termination of the reaction was detected by TLC, and the solvent was evaporated to obtain a yellow solid, which was recrystallized from absolute ethanol to obtain a white disulfide intermediate-I with a yield of 77%;

[0048] (2) Under nitrogen protection, 1.00 g of the disulfide intermediate obtained in step (1) was dissolved in a mixed solvent of 20 mL of tetrahydrofuran and absolute ethanol (volume ratio 1:1), and then 1.60 mL (disulfide intermediate) was added. 8 times the molar equivalent of body-I) hydrazine hydrate, the mixed solution was refluxed until the reaction was terminated by TLC metho...

Embodiment 3

[0051] (1) The synthetic steps of a fluorescent probe for detecting mercury ions in aqueous media and cells provided by the present invention are as follows: figure 1 As shown, the details are as follows: at room temperature, 1.99g (1.0mmol) 2-bromoacetophenone and 2.50g (1.5mmol) 1-pyrrolidine ammonium dithiocarboxylate were dissolved in 30mL acetone, and stirred at room temperature until The termination of the reaction was detected by TLC, and the solvent was evaporated to obtain a yellow solid, which was recrystallized from absolute ethanol to obtain a white disulfide intermediate-I with a yield of 78%;

[0052] (2) Under the protection of nitrogen, 1.00 g of the disulfide intermediate obtained in step (1) was dissolved in a mixed solvent of 20 mL of tetrahydrofuran and absolute ethanol (volume ratio 1:1), and then 2.00 mL (disulfide intermediate 10 times the molar equivalent of body-I) hydrazine hydrate, the mixed solution was refluxed until the reaction was terminated by ...

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Abstract

The invention discloses a rhodamin B double-sulfur fluorescence probe for detecting aqueous mediums and intracellular mercury ions, preparation and application thereof. According to rhodamin B double-sulfur fluorescence probe, molecular closed loops in the rhodamin fluorescence probe are opened in the aqueous mediums by chelating and coordinating the mercury ions, so that fluorescence is generated; the fluorescence intensity is in a good linear relation with the initial concentration of the mercury ions; the color change can be seen by naked eyes when a probe solution is changed from colorless to pink; meanwhile, the fluorescence probe is high in specific selectivity on the mercury ions; in addition, the fluorescence probe is high in biocompatibility and cell permeability and low in cytotoxicity, can be used for detecting the intracellular mercury ions and is high in detection sensitivity of the mercury ions. The preparation of the rhodamin B double-sulfur fluorescence probe is characterized by taking the rhodamin B as the raw material, and enabling the rhodamin B to react with phosphorus oxychloride to prepare a rhodamin B acyl chloride intermediate; the acyl chloride intermediate is further condensed with a double-sulfur intermediate to obtain a mercury ion probe with high sensitivity and high selectivity.

Description

technical field [0001] The invention belongs to the field of environmental detection and biological diagnosis, and particularly relates to a rhodamine B disulfide fluorescent probe for detecting aqueous medium and intracellular mercury ions, a preparation method and application thereof. Background technique [0002] Mercury ion is one of the most threatening and toxic metal ions to human health. It has important toxic effects on the central nervous system, digestive system and kidneys of the human body, and also has certain effects on the respiratory system, skin, blood and eyes. Mercury and its pollutants are widely distributed in water, air and soil through volcanic activities, mining, solid waste incineration and other methods, and can be further enriched in the human body through the food chain, and the toxic effect on the human body is continuously enhanced , thereby posing a serious threat to human health. Based on this, the detection of low-concentration mercury ion...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09K11/06C07D491/107G01N21/64
Inventor 张涛邢达吴宝艳黄伟国
Owner SOUTH CHINA NORMAL UNIVERSITY
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