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A preparation method of near-infrared emitting xanthene fluorescent dye with large Stokes shift

A fluorescent dye and near-infrared technology, applied in the field of preparation of molecular fluorescent dyes, can solve problems such as background interference and harsh synthesis conditions, and achieve the effects of wide pH value range, low cost, and simple and easy preparation method.

Active Publication Date: 2019-05-14
TIANJIN UNIVERSITY OF TECHNOLOGY
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Problems solved by technology

Since the Stokes shift is as small as traditional rhodamine (<30nm), it can be expected that this kind of dye will cause some background interference, and the synthesis conditions of this kind of dye are harsh

Method used

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  • A preparation method of near-infrared emitting xanthene fluorescent dye with large Stokes shift
  • A preparation method of near-infrared emitting xanthene fluorescent dye with large Stokes shift
  • A preparation method of near-infrared emitting xanthene fluorescent dye with large Stokes shift

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Experimental program
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Embodiment 1

[0028] Preparation of a near-infrared emitting xanthene fluorescent dye TJ730

[0029]

[0030] Concrete preparation steps are as follows:

[0031] 1) 2-(4-diethylamino-2-hydroxybenzoyl) benzoic acid (626mg, 2mmol) and N-ethyl-2-methoxyphenothiazine (516mg, 2mmol) were added to methanesulfonic acid ( 4mL). Heat the oil bath at 70°C in the dark and react for 12 hours; then cool to room temperature to obtain a reaction solution;

[0032] 2) The above reaction solution was cooled to room temperature, poured into 80 mL of deionized water and stirred, and the pH of the reaction solution was adjusted to neutral (pH=7.0) with saturated aqueous sodium bicarbonate solution. Then, the mixed solution was extracted three times with dichloromethane (50 mL). After the organic phase was dried with anhydrous sodium sulfate, the solvent was distilled off under reduced pressure to obtain a crude product. The crude product was separated and purified by column chromatography on silica gel,...

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Abstract

The invention discloses a preparation method and application of near-infrared emission xanthene fluorescent dye with large Stokes shift. The preparation method has the advantages that xanthene fluorescent dye with maximum absorption wavelength exceeding 600 nm, maximum fluorescent emission wavelength exceeding 730 nm and Stokes shift exceeding 100 nm is designed and synthesized through a strategy of prolonging a xanthene conjugated system linearly, and the xanthene fluorescent dye is one of the fluorescent dyes with largest Stokes shift in the existing known rhodamine fluorescent dyes. According to a cell imaging experiment, the dye has good water solubility, biocompatibility, small biotoxicity and is used for positioning lysosome in a targeted mode. Besides, the dye structurally contains a spirolactone structure, and can be used as a near-infrared emission dye fluorescence reporter group to design various near-infrared emission fluorescence opening type biological fluorescent probes. In a word, the invention provides a design and synthesis method for the novel near-infrared emission xanthene fluorescent dye with large Stokes shift, and the novel near-infrared emission xanthene fluorescent dye is used for novel fluorescence probe design and development.

Description

technical field [0001] The invention relates to the preparation of molecular fluorescent dyes in optical sensing imaging detection technology, in particular to a preparation method and application of a near-infrared emitting xanthene fluorescent dye molecule with a large Stokes shift. Background technique [0002] Fluorescence analysis technology is an important method in modern analytical chemistry. It uses fluorescent molecular probes as optical signal labeling reagents to analyze and detect fluorescent optical signals such as fluorescence intensity or wavelength through the combination of probe materials and targets. technology. With the rapid development of computer science, optical imaging technology and new probe labeling technology, it has greatly promoted the development of fluorescence analysis technology in the fields of molecular biology, cell biology, medicine and new drug development, and the key to this technology is It is to design and synthesize fluorescent ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D513/04C09B57/00C09K11/06G01N21/64
CPCC07D513/04C09B57/00C09K11/06C09K2211/1037C09K2211/1088G01N21/6486
Inventor 曾宪顺刘畅
Owner TIANJIN UNIVERSITY OF TECHNOLOGY
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