Zinc ion fluorescent probe, preparation method and method for detecting zinc ion content

A fluorescent probe and zinc ion technology, applied in the field of fluorescence detection, can solve the problems of unstable detection results, limited popularization and application, complicated preparation process, etc., achieve good spatial control effect, increase fluorescence intensity, and simple detection method

Active Publication Date: 2017-12-29
XUZHOU MEDICAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, most of the zinc ion probes developed so far have poor structural stability, and the detection results are very unstable; and the preparation process is complicated, the environmental pollution is heavy, and the production rate is not high, which greatly limits its popularization and application in the market.

Method used

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  • Zinc ion fluorescent probe, preparation method and method for detecting zinc ion content
  • Zinc ion fluorescent probe, preparation method and method for detecting zinc ion content
  • Zinc ion fluorescent probe, preparation method and method for detecting zinc ion content

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] Preparation process: (1) Add 2-naphthol (0.144g, 1mmol), m-bromobenzaldehyde (0,185g, 1mmol), aniline (91μL, 1mmol) in sequence in a 50mL round bottom flask, stir and mix evenly; take TBAB ( 1mmol, 0.322g) and ammonium acetate (1mmol, 0.077g), dissolved in distilled water (10mL), stirred to form a transparent and clear solution, and added to the above mixture, reacted under microwave conditions at 60°C and 1atm for 4h. After the reaction solution was cooled, it was suction-filtered and washed with distilled water; the filter cake was recrystallized with 95vol% ethanol. Dry in an infrared oven at 200° C. for 20 minutes to obtain 0.345 g of a yellow solid, with a yield of 93%. The structural formula of the prepared fluorescent probe is:

[0034] The structure of the fluorescent probe is characterized as follows: IR(KBr,ν,cm -1 ):3334.97(s), 2887.41(w), 1601.03(s), 1496.65(m), 1229.43(s), 744.37(m); 1 H NMR (400MHz, CDCl 3 )δ (ppm): 11.34 (s, 1H, Ar-OH), 7.82-7.72 (m...

Embodiment 2

[0047] Preparation process: (1) Add 2-naphthol (0.144g, 1mmol), m-nitrobenzaldehyde (0.151g, 1mmol), aniline (91μL, 1mmol) in sequence in a 50mL round bottom flask, stir and mix evenly; TBAB (1mmol, 0.322g) and ammonium acetate (1mmol, 0.077g) were dissolved in distilled water (10mL), stirred to form a transparent and clear solution, added to the above mixture, and reacted under microwave conditions at 60°C and 1atm for 4h . After the reaction solution was cooled, it was suction filtered and washed with distilled water; the filter cake was recrystallized with 95% ethanol. Dry in an infrared oven at 300° C. for 20 minutes to obtain 0.336 g of a yellow solid, with a yield of 93%. The structural formula of the prepared fluorescent probe is:

[0048] The structure of the fluorescent probe is characterized as follows: IR(KBr, ν, m-1): 3609.56, 2936.45, 2896.23, 1603.21, 149.89, 1356.45, 1196.78; 1 H NMR (400MHz, CDCl 3 )δ (ppm): 8.40 (s, 1H, O-H), 8.06 (m, 1H, C-H), 7.93 (s, ...

Embodiment 3

[0054] Preparation process: (1) Add 2-naphthol (0.144g, 1mmol), m-nitrobenzaldehyde (0.151g, 1mmol) and hexahydropyridine (98μL, 1mmol) into a 50mL round bottom flask in sequence, and stir to mix evenly; Then take TBAB (1mmol, 0.322g) and ammonium acetate (1mmol, 0.077g), dissolve in distilled water (10mL), stir to form a transparent and clear solution, and add to the above mixture, at 60 ° C, 1 atm under microwave conditions Reaction 4h. After the reaction solution was cooled, it was suction filtered and washed with distilled water; the filter cake was recrystallized with 95% ethanol. Dry in an infrared drying oven at 250° C. for 30 min to obtain 0.355 g of a yellow solid, with a yield of 93%. The structural formula of the prepared fluorescent probe is:

[0055] The structure of the fluorescent probe is characterized as follows: IR(KBr,ν,cm -1 ):3626.29(w), 2953.47(w), 2811.51(w), 1620.41(m), 1449.05(m), 1343.15(s), 1237.06(m); 1 H NMR (400MHz, CDCl 3 )δ(ppm):8.40(s,1H...

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Abstract

The invention discloses a zinc ion fluorescent probe, a preparation method and a method for detecting zinc ion content. The chemical formula of the fluorescent probe is as shown in the specification, wherein R1 is -Cl, -Br, -I, -NO2 or NH2; R2 is -Cl, -Br, -I, -NO2 or NH2. The preparation method is characterized in that ammonium acetate and TBAB are used as the catalysts, 1, 3-amino alcohol, a aniline derivative and a benzaldehyde derivative are used as the raw materials, and a series of Zn<2+> fluorescent probes in a water phase under microwave conditions. The zinc ion fluorescent probe is good in structural stability. The preparation method is simple and easy to operate, high in product yield and free of pollutant generation. The detection method has the advantages that the detection method is simple, the Zn<2+> content can be detected in a quantified manner only by detecting fluorescence intensity, and the method is good in detection accuracy; a used solvent is an ethanol solution which is nontoxic and environmentally friendly; the method is wide in detection linear range, detection limit of the method is 1*10<-6>mol / L, and the method is applicable to the detection of the trace Zn<2+> content of environments and food and the in-vivo and in-vitro trace Zn<2+> content.

Description

technical field [0001] The invention relates to a zinc ion fluorescent probe, a preparation method and a method for detecting zinc ion content, belonging to the field of fluorescence detection. Background technique [0002] Zinc is a trace element in the human body. It is a key component of various proteins and participates in the regulation of synthesis and metabolism of proteins and enzymes. As a signal molecule, zinc also participates in cell signal transmission and plays a role in the process of cell signal transduction. important role. In addition, the content of zinc ions in the body is closely related to the occurrence and development of various malignant tumors such as esophageal cancer and breast cancer; studies have shown that Zn 2+ It can affect the growth and metastasis of tumor cells by affecting the expression of tumor necrosis factor-related inducible ligand (TRAIL). Zinc deficiency can affect growth and development, induce diabetes and heart failure; and whe...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09K11/06C07C213/02C07C215/50C07D295/096G01N21/64
CPCC07C213/02C07C215/50C07D295/096C09K11/06C09K2211/1007C09K2211/1011C09K2211/1014C09K2211/1029G01N21/643
Inventor 牟杰刘杰张志浩高干裴冬生
Owner XUZHOU MEDICAL UNIV
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