Preparation and application of zinc ion fluorescence probe based on Schiff base

A fluorescent probe and zinc ion technology, applied in the field of fluorescent probes, can solve the problems of cumbersome synthesis steps, low probe selectivity, and low sensitivity, and achieve the effects of simple synthesis steps, simple synthesis methods, and simple pretreatment

Inactive Publication Date: 2017-07-21
UNIV OF JINAN
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] In the existing fluorescent probe technology, some reported zinc ion fluorescent probes still have defects, for example, these synthetic steps are relatively cumbersome, the probe has low selectivity, low sensitivity, and the required detection time is relatively long
For example, HNAPP is a publicly reported fluorescent probe for detecting zinc ions. However, the fluorescent probe is a fluorescence quenching probe, which limits its use in vivo.

Method used

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  • Preparation and application of zinc ion fluorescence probe based on Schiff base
  • Preparation and application of zinc ion fluorescence probe based on Schiff base
  • Preparation and application of zinc ion fluorescence probe based on Schiff base

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1、II

[0041] The synthesis of embodiment 1, III

[0042] Under nitrogen protection, 6.24 g of cyanobiphenol, 4.56 g of anhydrous magnesium chloride, and 16.32 mL of triethylamine were dissolved in 80 mL of anhydrous acetonitrile, and then an excess of 12.3 g of dry paraformaldehyde was added. Refluxed for 8 hours, the reaction was cooled to room temperature, then quenched with a small amount of water, acidified with 6M hydrochloric acid, and the above crude product was treated with CH 2 Cl 2 Extracted 3 times, the extract was subjected to anhydrous MgSO 4 Dry, filter and remove the solvent in vacuo, and purify by column chromatography to obtain 3.5 g of white solid III, the yield is about 50%.

Embodiment 2、II

[0043] The synthesis of embodiment 2, II

[0044] Methyl 2-aminobenzoate (1.51g) and hydrazine hydrate (6mL) were dissolved in ethanol (50mL) and refluxed for 6h. The reaction mixture was cooled to obtain a solid, which was suction filtered and washed with cold water. The crude product was recrystallized from ethanol to obtain 1.28 g of solid compound II with a yield of 85%.

Embodiment 3

[0045] Embodiment 3, the synthesis of probe 1

[0046] Compound II (0.15g) and Compound III (0.22g) were dissolved in 20mL of dry ethanol under a nitrogen atmosphere, and refluxed for 4h. After the reaction was completed, the crude product was obtained by suction filtration, and recrystallized from ethanol to obtain 0.26g of yellow probe I, with a yield of 75 %.

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PUM

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Abstract

The invention relates to preparation and application of a zinc ion fluorescence probe based on Schiff base. A zinc ion fluorescence probe compound has the structure shown by a formula I. The preparation method comprises the steps that 2-aminobenzoic acid (methyl anthranilate) and hydrazine hydrate are subjected to heating reflux in ethyl alcohol to obtain a white solid II, cyanophenyl phenol, anhydrous magnesium chloride and paraformaldehyde are subjected to heating reflux in a triethylamine-containing acetonitrile solution to obtain a white solid III, the white solid II and the white solid III are subjected to heating reflux in ethyl alcohol to a yellow solid I. The probe compound has very good selectivity and sensitivity on zinc ions, is low in detection limit and can be applied to determination of the content of zinc ions in a water body.

Description

technical field [0001] The invention relates to the preparation and application of a Schiff base-based zinc ion fluorescent probe, belonging to the technical field of fluorescent probes. [0002] technical background [0003] As an important transition metal, zinc ion plays an important role in the natural environment and organisms. Zinc ions exist in natural water in the form of soluble complexes or ions, which will inevitably cause a large loss of zinc ions in soil, especially acidic soil. Conversely, the presence of excess zinc ions will also reduce soil microbial activity. In organisms, zinc ions are the second most abundant metal cations after iron ions. Zinc ions play a very important role in brain function, gene transfer, and immune function; It is closely related to various diseases such as stroke. Therefore, it is of great significance to monitor zinc ions in the environment and biological systems. [0004] At present, the detection methods for zinc ions mainly i...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C255/66C07C253/30C09K11/06G01N21/64
CPCC07C241/04C07C253/30C07C255/66C09K11/06C09K2211/1007C09K2211/1014G01N21/643C07C255/56C07C243/38
Inventor 吕正亮范文龙范春华孟可馨张陆艳
Owner UNIV OF JINAN
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