Dibromofluorescein derivative as well as synthetic method and application thereof

By developing the reaction of dibromofluorescein derivatives and 2-hydroxy-5-nitrobenzaldehyde, the fluorescent probe NDH was produced, which solved the selectivity and interference problems of Al3+ detection in the existing technology and achieved high sensitivity and economy. detection effect and showed low toxicity in cell imaging.

CN110498802AActive Publication Date: 2019-11-26SHANXI UNIV
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Patent Information

Application Number
CN201910594168.2
Authority / Receiving Office
CN · China
Patent Type
Applications(China)
Current Assignee / Owner
Filing Date
2019-07-03
Publication Date
2019-11-26
Estimated Expiration
2039-07-03

AI Technical Summary

Technical Problem

Existing technology is difficult to efficiently and selectively detect and quantitatively analyze aluminum ions (Al3+) in organisms, and it interferes with other ions, affecting detection accuracy.

Method used

Develop a dibromofluorescein derivative and its synthesis method. By reacting with 2-hydroxy-5-nitrobenzaldehyde under THF:H2O (9:1, v/v) conditions, a dibromofluorescein derivative with high selectivity and The sensitive fluorescent probe NDH is used to detect Al3+ by UV-visible absorption and fluorescence spectroscopy, and is used in cell imaging.

Benefits of technology

It achieves highly selective, sensitive and economical Al3+ detection, avoids interference from other ions, has naked-eye recognition and rapid analysis capabilities, and exhibits low cytotoxicity in cell imaging.

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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.
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