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Fluorescence dye using fluorescein as matrix, and preparation method and application thereof

A fluorescent dye, fluorescein technology, applied in the field of new fluorescent dyes

Active Publication Date: 2013-07-24
DALIAN UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the absorption and emission wavelengths of these reported probes are still around 480nm and 520nm, respectively

Method used

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  • Fluorescence dye using fluorescein as matrix, and preparation method and application thereof
  • Fluorescence dye using fluorescein as matrix, and preparation method and application thereof
  • Fluorescence dye using fluorescein as matrix, and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0162] Preparation of Fluorescent Dye Compound A 1

[0163]

[0164] (1) Synthesis of intermediate compound 1

[0165] DCF (6.30 g, 15.75 mmol) was dissolved in a round bottom flask containing 60 mL of 50% aqueous sodium hydroxide. This mixture was stirred, heated to 165°C, and stirred for 1 h, the mixture became viscous. Then the mixture was added to 400mL of ice water, neutralized with 100mL of concentrated hydrochloric acid until the acidic system became cloudy, and after standing for 2 hours, it was then filtered with a Buchner funnel, and the precipitate was washed with water for 3 times. After vacuuming, it was dried under an infrared lamp to obtain a red intermediate compound 1 as a solid (8.10 g).

[0166] (2) Synthesis of intermediate compound 2

[0167]Freshly distilled cyclohexanone (6.6 mL, 63.7 mmol) was added dropwise to concentrated sulfuric acid (7.0 mL), then cooled to 0°C. Then, intermediate compound 1 (32mmol) was added to the system in batches, the ...

Embodiment 2

[0171] Preparation of Fluorescent Dye Compound A 2 :

[0172]

[0173] (1) Dye Compound A 1 Synthesis

[0174] Prepare dye compound A according to the method of embodiment 1 1 . Obtained orange solid A 1 (1.95 g), used as starting material for the next step without further purification.

[0175] (2) Dye Compound A 2 Synthesis

[0176] Under nitrogen atmosphere, the A 1 (100mg, 0.41mmol) and malononitrile (ie vi) (40mg, 0.61mmol) were dissolved in acetonitrile (45mL, and this mixture was refluxed under nitrogen at 85°C for 4h. The reaction mixture was cooled to room temperature. Then in vacuum Solvent was distilled off under the conditions, and a dark purple solid product A was obtained on silica gel (dichloromethane as eluent: ethyl acetate=40 / 3, v / v) after purification by column chromatography 2 (0.0793g, 0.185mmol, yield 45%), R f =0.40, (5% CH 3 OH / dichloromethane). 1 H NMR (400MHz,MeOD)δ8.03(d,J=6.9Hz,1H),8.00(d,J=11.4Hz,1H),7.67–7.42(m,2H),7.10(dd,J=7.3, ...

Embodiment 3

[0178] Preparation of Fluorescent Dye Compound A 3 :

[0179]

[0180] (1) Dye Compound A 1 Synthesis

[0181] Prepare dye compound A according to the method of embodiment 1 1 . Obtained orange solid A 1 (1.95 g), used as starting material for the next step without further purification.

[0182] (2) Dye Compound A 3 Synthesis

[0183] Under nitrogen atmosphere, the A 1 (766mg, 2.0mmol) and 2-cyanoacetic acid (vii) (813mg, 7.2mmol) were dissolved in ethanol (45mL), and then 0.2mL piperidine (3.2mmol) and 0.4mL acetic acid solution were added to the reaction system, This mixture was refluxed for 10 h at 85 °C under nitrogen. The reaction mixture was cooled to room temperature. Then the solvent was distilled off under vacuum, and after purification by column chromatography, a deep red solid A was obtained on silica gel (dichloromethane / methanol=200 / 3, v / v as eluent). 3 (150mg, 0.33mmol, yield rate is 20%), Rf=0.30, (5% CH 3 OH / dichloromethane). 1 H NMR (400MHz,M...

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Abstract

The invention provides a fluorescence dye using fluorescein as matrix, and a preparation method and application thereof. The fluorescence dye using fluorescein as maternal has the structure in general formula I. The fluorescence dye is used for biological dyeing, and simultaneously one of the dyes is applied to external and internal detections of cysteine, and meanwhile is applied to in vivo detection and other fields. The compound has a certain level of water-solubility, and simultaneously has good cell membrane permeability. The compound of the present invention simultaneously has novel spectrum characteristics, and the fluorescein derivative dyes with good properties are applied to the aspect of the fluorescence imaging.

Description

technical field [0001] The invention relates to a class of novel fluorescent dyes with fluorescein as the parent, its preparation method and application, and the detection of biological sulfhydryl compounds in vitro and in vivo by using the fluorescent probe compounds, and the application of the dyes to cell imaging and in vivo experiments. Background technique [0002] As functional pigments, fluorescent dyes have been widely used in various fields of science and technology, especially in life sciences, clinical medical diagnosis, immunoassay and detection, etc., which have attracted worldwide attention. Among many fluorescent dyes, fluorescein is a class of dyes that are widely used. This kind of dye has the advantages of large molar extinction coefficient, good photostability, and high fluorescence quantum yield. [0003] Fluorescence imaging is one of the most powerful techniques for monitoring biomacromolecules in living systems, and dyes in the near-infrared (NIR) rang...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09B57/00C09K11/06G01N1/30G01N21/64
Inventor 彭孝军熊小庆宋锋玲樊江莉王静云孙世国张玉康
Owner DALIAN UNIV OF TECH
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