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Xanthene fluorescent dye molecular fluorescent probe as well as preparation method and application thereof

A technology of fluorescent dyes and fluorescent probes, which is applied in the field of xanthene fluorescent dye molecular fluorescent probes and its preparation, can solve the problems of poor cell research effect, easy photobleaching, and poor specific selectivity, and achieve a simple and easy preparation method , Economic and technical effects are obvious, and the effect of good biofilm permeability

Inactive Publication Date: 2015-04-01
TIANJIN UNIVERSITY OF TECHNOLOGY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the peak shapes of absorption and emission spectra of rhodamine-based fluorescent dyes are relatively narrow, and the Stokes shift is also small, which limits their application in in vivo fluorescence imaging.
At the same time, the fluorescence is relatively greatly interfered by the sample background, the fluorescence quantum yield is sensitive to pH, the fluorescence quantum yield is reduced in the physiological environment of the organism, and it is sensitive to light. It is prone to photobleaching under strong light detection and has poor lipophilicity. , it is not easy to penetrate into cells, so the effect of cell research is poor, and the specific selectivity is poor
Although cyanine dyes with near-infrared absorption and emission are widely used in cell imaging, cyanine dyes still have the disadvantages of low quantum yield and easy photobleaching.

Method used

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  • Xanthene fluorescent dye molecular fluorescent probe as well as preparation method and application thereof
  • Xanthene fluorescent dye molecular fluorescent probe as well as preparation method and application thereof
  • Xanthene fluorescent dye molecular fluorescent probe as well as preparation method and application thereof

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Effect test

Embodiment 1

[0030] A Molecular Fluorescence Probe of Xanthene Fluorescent Dye 3 The preparation route for is as follows:

[0031] ,

[0032] Concrete preparation steps are as follows:

[0033] 1) Add 10 mL of 98 wt% sulfuric acid dropwise to 626 mg (2 mmol) of 2-(4-diethylamino-2-hydroxybenzoyl)benzoic acid and 1,5-dihydroxynaphthalene cooled in an ice-water bath 160 mg (1 mmol) of the mixed solution was heated in a dark oil bath, reacted at a temperature of 85 °C for 5 hours, and then cooled to room temperature to obtain a reaction solution;

[0034] 2) Pour the above reaction solution into 150 mL deionized water, stir and adjust to neutrality with saturated aqueous sodium bicarbonate solution, extract three times with 120 mL ethyl acetate, dry the organic phase with anhydrous sodium sulfate, distill under reduced pressure, and remove the solvent get crude product;

[0035] 3) Separation and purification by silica gel column chromatography to obtain the target product 13,15-(3',3''-d...

Embodiment 2

[0046] A preparation route of a xanthene fluorescent dye molecular fluorescent probe 1 is as follows:

[0047]

[0048] Concrete preparation steps are as follows:

[0049] 1) Add 10 mL of 98 wt% sulfuric acid dropwise to 626 mg (2 mmol) of 2-(4-diethylamino-2-hydroxybenzoyl)benzoic acid and 110 mg (1 mmol) in a mixed solution, heated in a dark oil bath, reacted for 5 hours at a temperature of 85 ° C, and then cooled to room temperature to obtain a reaction solution;

[0050] 2) Pour the above reaction solution into 150 mL deionized water, stir and adjust to neutrality with saturated aqueous sodium bicarbonate solution, extract three times with 120 mL ethyl acetate, dry the organic phase with anhydrous sodium sulfate, distill under reduced pressure, and remove the solvent get crude product;

[0051] 3) Separation and purification by silica gel column chromatography to obtain the target product 1 , is 478 mg of purple solid, the yield is 72%; melting point: > 300 ℃.

[00...

Embodiment 3

[0061] A preparation route of a xanthene fluorescent dye molecular fluorescent probe 2 is as follows:

[0062] ,

[0063] Concrete preparation steps are as follows:

[0064]1) Add 10 mL of 98 wt% sulfuric acid dropwise to 626 mg (2 mmol) of 2-(4-diethylamino-2-hydroxybenzoyl)benzoic acid and 2,6-dihydroxynaphthalene cooled in an ice-water bath 160 mg (1 mmol) of the mixed solution was heated in a dark oil bath, reacted at a temperature of 85 °C for 5 hours, and then cooled to room temperature to obtain a reaction solution;

[0065] 2) Pour the above reaction solution into 180 mL deionized water, stir and adjust to neutrality with saturated aqueous sodium bicarbonate solution, extract three times with 140 mL ethyl acetate, dry the organic phase with anhydrous sodium sulfate, distill under reduced pressure, remove the solvent get crude product;

[0066] 3) Separation and purification by silica gel column chromatography to obtain the target product xanthene fluorescent dye ...

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Abstract

The invention discloses a xanthene fluorescent dye molecular fluorescent probe. Under different acid and alkali conditions, a fluorescent dye is transformed between isomers of a single loop coil open loop and a double-loop coil open loop, and the structure transformation ensures that a conjugated system of the dye is changed, and the color of a corresponding solution, the wavelengths for absorption and emission peaks and the fluorescence intensity are changed; and a xanthene fluorescent dye is used for preparing a xanthene fluorescent dye esterification derivative which can be used as a fluorescent molecular probe material to realize fluorescent detection of NADH. The xanthene fluorescent dye molecular fluorescent probe disclosed by the invention has the advantages that the molecular fluorescent probe has a double-loop coil hexatomic ring condensing system, the release of optical signals of the dye is controlled by the double-loop coil structure, and a switch of the loop coil structure is used for adjusting and controlling a fluorophore xanthene conjugated system in the whole molecular structure, and widening the adsorption and emission wavelengths of the conjugated system to ensure that the optical signal intensity is changed correspondingly; and the probe material is quick in response to NADH, high in selectivity and good in biological membrane permeability, and a preparation method of the probe material is simple and feasible, low in cost and obvious in economic and technical effects.

Description

technical field [0001] The invention relates to the technical field of dye molecular fluorescent probes, in particular to a xanthene fluorescent dye molecular fluorescent probe and its preparation method and application. Background technique [0002] As an important method in modern analytical chemistry, fluorescence analysis technology is an analysis and detection technology that uses fluorescent molecular probes as optical signal reagents to change the fluorescence optical signals such as fluorescence intensity or wavelength through the combination of probe materials and targets. . 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 molecular probe materials that meet various dete...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09K11/06C07D493/22G01N21/64
Inventor 曾宪顺刘畅
Owner TIANJIN UNIVERSITY OF TECHNOLOGY
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