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Fluorescent probe for detecting zinc ions as well as preparation method and application of fluorescent probe

A fluorescent probe, zinc ion technology, applied in the field of fluorescent probes, to achieve the effects of low cost, high improvement cost and good stability

Pending Publication Date: 2022-04-15
WUHAN INSTITUTE OF TECHNOLOGY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] At present, many probes capable of detecting zinc ions have been reported, but few are fluorescence-enhanced probes that can detect in aqueous solution and are not interfered by other metal ions, especially cadmium ions.

Method used

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  • Fluorescent probe for detecting zinc ions as well as preparation method and application of fluorescent probe
  • Fluorescent probe for detecting zinc ions as well as preparation method and application of fluorescent probe
  • Fluorescent probe for detecting zinc ions as well as preparation method and application of fluorescent probe

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0037] A preparation method of a fluorescent probe for detecting zinc ions:

[0038] (1) Take 3,8 dibromo-10-phenanthroline-5,6-dione (0.75g, 2.0475mmol), ammonium acetate (2.3625g, 60mmol), p-hydroxybenzaldehyde (0.2497g, 2.0475mmol) Dissolve in glacial acetic acid (26.25ml), keep at 90°C for two hours, then increase the temperature to 120°C for reaction, stop the reaction, add water (200ml) to dilute, adjust the pH to neutral with concentrated ammonia, and filter to obtain the crude product Compound 1 was obtained by purification on a silica gel chromatography column (developing solvent: ethanol: dimethyl sulfoxide = 40: 1).

[0039] (2) Dissolve compound 1 (0.1753g, 0.3mmol) and tetraphenylethylene borate (0.1410g, 0.3mmol) prepared in step (1) in DMF (10ml), then add the catalyst tetrakis (triphenyl Phosphine) palladium (4mg), 2M K 2 CO 3 (2ml) solution, the temperature was maintained at 120 degrees Celsius under the protection of nitrogen, and the reaction was carried ...

Embodiment 2

[0041] Ion selectivity tests for target products, such as figure 1 . P and metal ions were added to the water-ethanol solution (1:1, v / v), and the concentration of P in the test solution was 1×10 -6 mol / L, add 5 times the equivalent of sodium ions (Na + ), magnesium ions (Mg 2 + ), calcium ions (Ca 2+ ), cadmium ions (Cd 2+ ), chromium ions (Cr 2+ ), lithium ion (Li + ), barium ion (Ba 2+ ), manganese ions (Mn 2+ ), potassium ions (K + ), ferrous ions (Fe 2+ ), ferric ions (Fe 3+ ), cobalt ions (Co 2+ ), nickel ions (Ni 2+ ), copper ions (Cu 2+ ), cesium ions (Sr 2+ ), aluminum ions (Al 2+ ). It can be seen from the figure that the emission peaks of the system are basically unchanged except for zinc ions. After adding zinc ions, the fluorescence intensity is significantly enhanced (about 15 times), accompanied by an obvious blue shift. It shows that the fluorescent probe P has better fluorescence selective recognition ability for zinc ions.

Embodiment 3

[0043] Fluorescent titration test of target compounds against zinc ions, such as figure 2 . Dissolve P in ethanol to a concentration of 1×10 -6 mol / L standard solution, then dropwise add zinc ion solution with a molar ratio of 0-10eq, and test the fluorescence spectrum at room temperature. From the test results, it can be found that after adding 0.001 times the equivalent of zinc ions, the fluorescence emission peaks are significantly enhanced and blue-shifted. And with the increase of zinc ion concentration in the test system, the fluorescence emission intensity also increases. This indicates that the fluorescent probe P has a high sensitivity for the recognition of zinc ions.

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Abstract

The invention belongs to the technical field of fluorescent probes, and particularly relates to a fluorescent probe for detecting zinc ions as well as a preparation method and application of the fluorescent probe. The method comprises the following steps: 1) reacting 3, 8-dibromo-10-phenanthroline-5, 6-diketone with p-hydroxybenzaldehyde, and synthesizing to obtain a compound 1; and 2) reacting the compound 1 obtained in the step 1) with tetraphenyl ethylene borate to obtain the fluorescent probe compound P for detecting the zinc ions. The fluorescent probe provided by the invention realizes fluorescence detection of zinc ions by virtue of a fluorescence enhancement and blue shift phenomenon, and has the advantages of high selectivity, high sensitivity, wide detection concentration range, good biological safety, low cost, simplicity in operation and the like.

Description

technical field [0001] The invention belongs to the technical field of fluorescent probes, and in particular relates to a fluorescent probe for detecting zinc ions, a preparation method and application thereof. Background technique [0002] Fluorescence recognition methods have been widely studied due to their high sensitivity, good selectivity, easy operation, low cost, high sensitivity, and rapid in situ on-line detection in vivo. [0003] Zinc is the second most abundant transition metal element in the human body. Related studies have shown that zinc ions participate in and actively regulate many physiological and chemical processes. At the same time, zinc ions are also closely related to the pathological changes of many organisms, such as ischemic stroke, Alzheimer's disease, amyotrophic lateral sclerosis, Parkinson's syndrome, epilepsy, diabetes, prostate cancer, etc. Therefore, the development of simple and sensitive fluorescent sensing materials has practical signifi...

Claims

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Application Information

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IPC IPC(8): C07D471/14C07D519/00C09K11/06G01N21/64
CPCC07D471/14C07D519/00C09K11/06G01N21/6428G01N2021/6439C09K2211/1074
Inventor 李辉涂曼汪锋孙磊肖宇
Owner WUHAN INSTITUTE OF TECHNOLOGY
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