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A water-soluble cu based on rhodamine b 2+ 、hg 2+ Probe and its preparation method and application

A water-soluble, probe technology, applied in the field of metal ion analysis and detection, can solve the problems of poor selectivity, pH sensitivity, single detection ion, etc., and achieve the effect of good development prospects

Inactive Publication Date: 2016-08-24
ZHENGZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] Aiming at the problems that the fluorescent molecular probes for detecting copper ions or mercury ions in the prior art have single detection ions, low sensitivity, poor selectivity and sensitivity to pH value of most fluorescent molecular probes, the main purpose of the present invention is to provide a method that can simultaneously A metal ion fluorescent molecular probe that detects copper ions and mercury ions with high sensitivity, good selectivity, and insensitive to pH; another purpose is to provide a preparation method and application of the fluorescent molecular probe

Method used

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  • A water-soluble cu based on rhodamine b  <sup>2+</sup> 、hg  <sup>2+</sup> Probe and its preparation method and application
  • A water-soluble cu based on rhodamine b  <sup>2+</sup> 、hg  <sup>2+</sup> Probe and its preparation method and application
  • A water-soluble cu based on rhodamine b  <sup>2+</sup> 、hg  <sup>2+</sup> Probe and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] Example 1: Synthetic Probe L

[0028] Step 1: Raw material 1 was synthesized according to the method of literature Chem.Asian J.2011,6,1987-1991.

[0029] Step 2: Dissolve 55 mg of raw material 1 (0.0859 mmol) in 5 ml of acetonitrile, add 24 mg of potassium carbonate and 15 mg of potassium iodide, and add 19 mg of NH(CH 2 CH 2 SCH 2 CH 2 CH 3 ) 2 (0.0859mmol), continue the reflux reaction; after the reaction, the solution is cooled to room temperature, the precipitate is filtered off, and the filtrate is concentrated under reduced pressure; the developing agent is passed through column silica gel with dichloromethane / methanol 20:1, and vacuum-dried to obtain 35 mg probe needle L. Yield: 52%

[0030] 1 H NMR (400MHz, CDCl 3 ,ppm) δ=7.94(d,1H,J=6.3Hz),7.57(t,1H,J=15.4Hz),7.49(d,2H,J=1.6Hz),7.39(m,2H,J=19.9 Hz), 7.09(t, 1H, J=6.8Hz), 6.57(d, 2H, J=8.8Hz), 6.39(s, 2H), 6.30(s, 1H), 6.28(d, 1H, J=2.4 Hz), 4.90(s, 2H), 3.71(s, 2H), 3.35(m, 8H, J=6.9Hz), 2.73(t, 4H,...

Embodiment 2

[0033] Embodiment 2: the selectivity of the probe L of the present invention to copper ions:

[0034] The synthesized probe L was prepared with acetonitrile / water (1:1, V / V) to prepare 0.4mM mother solution, and deionized water was used to prepare 5mM solutions of various metal salts. Add 3ml of ethanol:water=4:1 (pH=7.4 buffer solution, V / V) solution in the cuvette, and then add 75 μL of 0.4mM solution of the probe molecule L of the present invention configured above , which was diluted to 10 μM. After mixing evenly, measure the absorbance value of the system in the range of 450nm-650nm. The probe molecule L has a weak absorbance value at 562nm. After adding copper ions, strong absorption occurs, and the absorbance increases by about 870 times. The color of the solution changes from colorless to For fuchsia, add other metal ions

[0035] K + , Na + , Ca 2+ ,Mg 2+ ,Mn 2+ , Ni 2+ ,Zn 2+ ,Cd 2+ ,Co 2+ ,Fe 2+ ,Fe 3+ ,Cr 3+ ,Hg 2+ ,Pb 2+ , Ag + ,Al 3+ (concentrat...

Embodiment 3

[0036] Example 3: The influence of coexisting metal ions on the ultraviolet detection of copper ions by probe molecules:

[0037] In the ethanol:water=4:1 (pH=7.4 buffer solution, V / V) solution with a concentration of 10 μM probe compound, the absorbance was significantly enhanced after adding 10 equivalents of copper ions, and then added to the probe-Cu 2+ Add other metal ions such as K to the solution + , Na + , Ca 2+ ,Mg 2+ ,Mn 2+ , Ni 2+ ,Zn 2+ ,Co 2+ ,Fe 2+ ,Fe 3+ ,Cr 3+ ,Hg 2+ ,Pb 2+ , Ag + ,Al 3+ (concentration and Cu 2+ Equivalent) after measuring the absorbance of the system, the results show that the presence of other metal ions does not affect the detection of the probe molecule L of the present invention for copper ions. It reflects the strong anti-interference performance of the probe molecule. See attached figure 1 ..

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Abstract

The invention discloses a water-soluble Cu<2+> and Hg<2+> probe based on Rhodamine B as well as a preparation method and application of the water-soluble Cu<2+> and Hg<2+> probe, and belongs to the technical field of metal ion analysis and detection. The water-soluble Cu<2+> and Hg<2+> probe has the structural formula shown in the description, and solves the problems of single detection ion existing in fluorescent molecular probes for detecting copper ions or mercury ions, low sensitivity of most of the fluorescent molecular probes, poor selectivity, high sensitivity to pH values, irreversibility and the like in the prior art. The molecular probe has the characteristic of strong anti-interference ability in the aspect of the detection of the copper ions and the mercury ions, is good selectivity and high in sensitivity, can be better widely applied to the detection of the copper ions and the mercury ions in environmental pollution and biological cell imaging and can also be reversibly operated.

Description

technical field [0001] The invention belongs to the technical field of metal ion analysis and detection, and in particular relates to a rhodamine B-based water-soluble Cu 2 + , Hg 2+ Preparation of probes and their applications in biological cell imaging and detection of environmental water samples. Background technique [0002] As we all know, copper is a transition metal ion. Excessive copper is harmful to the human body, animals and plants, but it is also a trace element necessary for life. It plays a role in different physiological processes such as mitochondrial respiration, iron absorption, and enzyme redox. play a very important role. However, if the metabolic balance of copper ions in the body is disrupted, it may cause oxidative stress and neurodegenerative diseases, such as Alzheimer's disease, Wilson's disease, and Menke's syndrome. In addition, copper has also become an important metal pollutant due to the large amount of copper ions mined and widely used. M...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D491/107C09K11/06G01N21/31G01N21/64
Inventor 臧双全李敏董喜燕路红琳徐虹
Owner ZHENGZHOU UNIV