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

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

Inactive Publication Date: 2013-02-13
DALIAN UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] In recent years, 2-(2'-hydroxyphenyl) benzoxazoles (HBX, X=O, S, NH) and their modified compounds have been used as Zn2+ fluorescent probes have been widely studied, but these HBX-based Zn2+ fluorescent probe compounds are usually fluorescence-enhancing probes, and most of them are in The detection of Zn2+ is carried out in non-aqueous solvents. For example, Tian et al. designed a kind of structurally symmetrical Zn2+ fluorescent probe containing two HBX functional groups. Therefore, the detection of Zn2+ in water-soluble Zn2+ ratiometric probes has limited application in biological and clinical medicine. big

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

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] (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, stirring at 0 ℃ Add 5.7 g of chloroacetyl chloride dropwise, and the dropwise addition will end within 20 minutes;

[0027] (2) Continue to stir for 2 hours at room temperature, stand still for layering, take the water layer and set aside;

[0028] (3) Extract the aqueous layer solution with dichloromethane three times, combine the organic layers, and use 5% HCl and 5% NaHCO for the organic layers respectively. 3 The aqueous solution and water wash 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%.

[0029] (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, then distill off the acetonitrile to obtain Zn 2+ Ratio ...

Embodiment 2

[0031] (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 while stirring at 0 ℃. Add 7.4g of chloroacetyl chloride, and the dripping ends within 40 minutes;

[0032] (2) Continue to stir at room temperature for 1 hour, stand still for layering, take the water layer and set aside;

[0033] (3) Extract the aqueous layer solution with dichloromethane three times, combine the organic layers, and use 5% HCl and 5% NaHCO for the organic layers respectively. 3 The aqueous solution and water wash 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%.

[0034] (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, remove the acetonitrile by distillation, and obtain Zn 2+ ...

Embodiment 3

[0036] (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 while stirring at 5 ℃. Add 6.3g of chloroacetyl chloride, and the dripping ends within 33 minutes;

[0037] (2) Continue to stir for 2 hours at room temperature, stand still for layering, take the water layer and set aside;

[0038] (3) Extract the aqueous layer solution with dichloromethane three times, combine the organic layers, and use 5% HCl and 5% NaHCO respectively for the organic layers. 3 The aqueous solution and water wash 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%.

[0039] (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 hours, and then distill off the acetonitrile to obtain Zn 2+ R...

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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

[0001] technical field [0002] 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 [0003] 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 pl...

Claims

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Application Information

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IPC IPC(8): C09K11/06C07D413/12G01N21/64
Inventor 贾颖萍卢烨崔颖娜尹静梅李慎敏
Owner DALIAN UNIVERSITY
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