Zn<2+> ratiometric fluorescent probe compound and preparation method and use thereof

A ratiometric fluorescent probe and compound technology, applied in chemical instruments and methods, fluorescence/phosphorescence, luminescent materials, etc., can solve problems such as limited applications, and achieve the effects of increased sensitivity, elimination of system errors, and high selectivity

Inactive Publication Date: 2014-12-24
DALIAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] In recent years, 2-(2’-hydroxyphenyl) benzoxazoles (HBX, X=O, S, NH) and their modified compounds have been used as Zn 2+ Fluorescent probes have been extensively studied, but these HBX-based Zn 2+ Fluorescent probe compounds are usually fluorescence-enhancing probes, and in most cases Zn 2+ detection, such as Tian et al. designed a class of structurally symmetrical Zn containing two HBX functional groups 2+ Fluorescent probe, Zn in DMF 2+ detection, which limits the application in biology and clinical medicine testing, so the study of water-soluble Zn 2+ Ratiometric fluorescent probes make more sense

Method used

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  • Zn&lt;2+&gt; ratiometric fluorescent probe compound and preparation method and use thereof
  • Zn&lt;2+&gt; ratiometric fluorescent probe compound and preparation method and use thereof
  • Zn&lt;2+&gt; ratiometric fluorescent probe compound and preparation method and use thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] (1) Add 11.3 g of 2-(4'-amino-2'-hydroxyphenyl)benzoxazole, 100 ml of dichloromethane and 10 ml of 20% NaOH aqueous solution to a 250 mL three-neck flask, and stir at 0 °C Add dropwise 5.7 g of chloroacetyl chloride, and dropwise finishes within 20 minutes;

[0026] (2) Continue to stir at room temperature for 2 hours, let stand to separate layers, take the water layer, and set aside;

[0027] (3) The aqueous layer solution was extracted 3 times with dichloromethane, and the organic layers were combined, and the organic layers were successively washed with 5% HCl and 5% NaHCO 3 aqueous solution and washed with water to neutral, anhydrous MgSO 4 After drying, filtering, and evaporating the solvent under reduced pressure, 13.9 g of the intermediate compound was obtained with a yield of 92%.

[0028] (4) Dissolve 13.9 g of the intermediate compound in 50 mL of acetonitrile, then add 4.5 g of N-methylimidazole, heat to reflux for 24 h, distill off the acetonitrile to obta...

Embodiment 2

[0030] (1) Add 11.3 g of 2-(4'-amino-2'-hydroxyphenyl)benzoxazole, 100 mL of dichloromethane and 10 ml of 20% NaOH aqueous solution into a 250 mL three-neck flask, and drop them under stirring at 0 °C Add 7.4g of chloroacetyl chloride, and dropwise finish within 40 minutes;

[0031] (2) Continue to stir at room temperature for 1 hour, let stand to separate layers, take the water layer, and set aside;

[0032] (3) The aqueous layer solution was extracted 3 times with dichloromethane, and the organic layers were combined, and the organic layers were successively washed with 5% HCl and 5% NaHCO 3 aqueous solution and washed with water to neutral, anhydrous MgSO 4 After drying, filtering, and evaporating the solvent under reduced pressure, 14.2 g of the intermediate compound was obtained with a yield of 94%.

[0033](4) Dissolve 14.2 g of the intermediate compound in 50 mL of acetonitrile, then add 3.9 g of N-methylimidazole, heat to reflux for 18 h, distill off the acetonitrile...

Embodiment 3

[0035] (1) Add 11.3 g of 2-(4'-amino-2'-hydroxyphenyl)benzoxazole, 100 mL of dichloromethane and 10 ml of 20% NaOH aqueous solution into a 250 mL three-necked flask, and drop them under stirring at 5 °C Add 6.3g of chloroacetyl chloride, and the dropwise addition ends within 33 minutes;

[0036] (2) Continue to stir at room temperature for 2 hours, let stand to separate layers, take the water layer, and set aside;

[0037] (3) The aqueous layer solution was extracted 3 times with dichloromethane, and the organic layers were combined, and the organic layers were successively washed with 5% HCl and 5% NaHCO 3 aqueous solution and washed with water to neutral, anhydrous MgSO 4 After drying, filtering, and evaporating the solvent under reduced pressure, 12.6 g of the intermediate compound was obtained with a yield of 83%.

[0038] (4) Dissolve 12.6g of the intermediate compound in 50 mL of acetonitrile, then add 3.7g of N-methylimidazole, heat to reflux for 24 h, distill off the...

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Abstract

The invention provides a Zn<2+> ratiometric fluorescent probe compound and a preparation method and use thereof, and belongs to the field of fluorescent probe compounds and preparation thereof. According to the preparation method, the Zn<2+> ratiometric fluorescent probe compound prepared by using 2-(4'-amino-2'-hydroxyphenyl)benzoxazole as a raw material has high water solubility. The compound can be used to test Zn<2+> concentration in a water phase. A 1*10<-6> to 1*10<-4>mol / L aqueous solution of Zn<2+> ratiometric fluorescent probe compound can test the strength of the fluorescence peaks at 370nm and 454nm in fluorescence spectrum, and accordingly the Zn<2+> concentration of the aqueous solution can be worked out. The compound provided by the invention has high selectivity in Zn<2+> test and high reproducibility, and therefore is suitable for test the Zn<2+> concentration in water phases in biochemistry and environmental chemistry.

Description

technical field [0001] The invention belongs to the field of fluorescent probe compounds and their preparation, in particular to a method for Zn in aqueous solution 2+ Fluorescent probe compound for determination, preparation method and application. Background technique [0002] Zinc is an important trace element essential to the human body, widely distributed in the cells and body fluids of the human body. Zn 2+ It plays an important role in the synthesis of protein and nucleic acid, gene expression and metabolism. Any abnormal zinc intake will lead to growth and metabolism disorders, and even serious diseases and death. For example, insufficient zinc content in the human body can lead to loss of taste and low immunity. Zinc deficiency in developing children will cause dwarfism, but the human body Excessive intake of zinc will produce poisoning phenomenon, too much Zn in the environment 2+ It will also cause pollution and affect the growth and development of plants, so ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C09K11/06C07D413/12G01N21/64
Inventor 贾颖萍卢烨崔颖娜尹静梅李慎敏
Owner DALIAN UNIV
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