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Dibromofluorescein derivative as well as synthetic method and application thereof

A technology of dibromofluorescein and its synthesis method, which is applied in the application field of dibromofluorescein derivatives and its synthesis, and detection of Al3+, achieving the effects of high sensitivity, high specificity and simple synthesis steps

Active Publication Date: 2019-11-26
SHANXI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, too much aluminum can lead to various physiological and biochemical problems, such as Alzheimer's disease, amyotrophic lateral sclerosis and other diseases

Method used

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  • Dibromofluorescein derivative as well as synthetic method and application thereof
  • Dibromofluorescein derivative as well as synthetic method and application thereof
  • Dibromofluorescein derivative as well as synthetic method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] Synthesis and characterization of embodiment 1 fluorescent probe NDH

[0030] (1) Weigh 3.4g (9.1mmol) of dibromofluorescein and 1mL (20mmol) of hydrazine hydrate solution and dissolve it in 10mL of methanol, react at 65°C for 4 hours, cool to room temperature after the reaction is complete, then rotary evaporate and vacuum Drying and recrystallization from methanol gave a pink solid.

[0031] (2) Weigh 0.019g (0.05mmol) of the product obtained above and 0.0075g (0.05mmol) of 2-hydroxy-5-nitrobenzaldehyde into 10mL of absolute ethanol, and ultrasonically dissolve it for 5min, then stir for 65 Reflux at °C for 4 hours, cool to room temperature after the reaction is complete, then rotary evaporate and vacuum-dry, and then recrystallize with methanol to obtain off-white solid powder. 1H NMR(600MHz,DMSO)δ12.23(s,1H),9.97(s,2H),9.11(s,1H),8.72(d,J=2.8Hz,1H),8.28(d,J=9.1Hz ,1H),7.99(d,J=32.5Hz,1H),7.18(d,J=9.1Hz,1H),7.00(d,J=9.3Hz,1H),6.68(d,J=8.8Hz,1H ), 6.43 (q, J=8.6Hz,...

Embodiment 2

[0032] Embodiment 2 fluorescent probe NDH is used for Al 3+ UV absorbance determination

[0033] Take 20 μL of the storage solution of the fluorescent probe NDH in a clean colorimetric tube, dilute it to 2 mL with THF:phosphate buffer solution (9:1), and scan the absorption spectrum on a UV-visible spectrophotometer. It can be observed that in the visible region There is absorption at 443nm, adding Al 3+ After that, the absorption peak at 443nm disappears see figure 1 , and the color of the solution changed from yellow to colorless, and the presence of aluminum ions could be judged with the naked eye.

Embodiment 3

[0034] Embodiment 3 fluorescent probe NDH is used for Al 3+ Fluorescence spectrometry

[0035] Take 20 μL of the storage solution of the fluorescent probe NDH in a clean colorimetric tube, dilute it to 2 mL with THF:phosphate buffer solution (9:1), and detect it on a fluorescence photometer. When the excitation wavelength is 445 nm, dibromofluorescein The derivative has an emission peak at 600nm, when adding Al 3+ After that, the intensity of the fluorescence emission peak at 600nm decreased gradually. figure 2 .

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Abstract

The invention discloses a dibromofluorescein derivative as well as a synthetic method of the derivative and an application of the derivative in detecting Al<3+>, and belongs to the technical field ofdetection of fluorescein derivatives and aluminum ions. The synthetic method of the dibromofluorescein derivative comprises the following steps: 1) dissolving hydrazine hydrate and dibromofluoresceininto methanol, and performing heating reflux to obtain a crude product; and performing rotary evaporation on the crude product, performing vacuum drying, and performing recrystallization by using methanol to obtain dibromofluorescein hydrazide; and 2) dissolving the dibromofluorescein hydrazide and 2-hydroxy-5-nitrobenzaldehyde into an absolute ethanol solution, performing heating reflux to obtaina crude product, performing rotary evaporation on the crude product, performing vacuum drying, performing recrystallization by using methanol, and performing drying to obtain the off-white solid powder 5-nitrosalicylaldehyde dibromofluorescein hydrazone (NDH). The invention also provides a method for detecting the aluminum ions. The method comprises the following step of quantitatively detectingthe content of the Al<3+> in a THF:H2O (9:1, v / v) solution by using the dibromofluorescein derivative as a probe. The detection method provided by the invention can detect the aluminum ions with highselectivity and high sensitivity, is simple and convenient to operate, and can be applied to cell imaging.

Description

technical field [0001] The present invention relates to the detection of fluorescein and metal ions, in particular to a dibromofluorescein derivative and its synthesis method and its ability to detect Al 3+ in the application. Background technique [0002] The content of aluminum in the earth's crust is about 8%, second only to oxygen and silicon, and is the most abundant metal element in the earth's crust. Aluminum compounds are closely related to our lives, such as food packaging, medicine, and catering utensils, which all contain aluminum compounds. However, too much aluminum can lead to various physiological and biochemical problems, such as Alzheimer's disease, amyotrophic lateral sclerosis and other diseases. According to the report of the World Health Organization, the average daily aluminum intake per capita is about 3-10mg, and the weekly aluminum intake of the human body accounts for about 7mg kg of human body weight. -1 . Therefore, quantitative detection of A...

Claims

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Application Information

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IPC IPC(8): C07D491/107C09K11/06G01N21/31G01N21/33G01N21/78G01N21/64
CPCC07D491/107C09K11/06C09K2211/1007C09K2211/1029C09K2211/1088G01N21/31G01N21/33G01N21/6428G01N21/78
Inventor 刘洋李明璐双少敏宋胜梅董川
Owner SHANXI UNIV
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