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Xanthone fluorochrome and application

A technology of xanthone and heterocyclic aryl, which is applied in the direction of luminescent materials, organic dyes, fluorescence/phosphorescence, etc., can solve the problems of poor tissue permeability and short emission wavelength, and achieve the effect of simple synthesis and easy-to-obtain products

Inactive Publication Date: 2018-11-23
成都必凯科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, due to its relatively short excitation and emission wavelengths, it has poor tissue permeability when performing live cell imaging studies.

Method used

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  • Xanthone fluorochrome and application
  • Xanthone fluorochrome and application
  • Xanthone fluorochrome and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0051]

[0052] (E)-3-(4-(dimethylamino)styryl)-9H-xanthen-9-one

[0053] Preparation of Compound (E)-3-(4-(dimethylamino)styryl)-9H-xanthen-9-one

[0054]

[0055] o-Nitrobenzaldehyde (20.0g, 0.13mol), m-cresol (18.6g, 0.17mol), anhydrous copper chloride (890mg, 6.6mmol), triphenylphosphine (2.6g, 10mmol) and anhydrous Potassium phosphate (62.0g, 0.29mol) was dissolved in 100 ml of redistilled toluene, and the reaction solution was refluxed at 110°C; after 24 hours of reaction, the reaction solution was cooled to room temperature, filtered with diatomaceous earth, and washed with ethyl acetate several times. The filter cake was cleaned; then the solvent was evaporated to dryness by distillation under reduced pressure. After dissolving the residue with 150 ml of ethyl acetate, add an equal amount of water and wash it several times until the color of the water phase becomes clear from dark brown; then wash it several times with 40% aqueous sodium hydroxide solution until...

Embodiment 2

[0059]

[0060] (E)-3-(4-hydroxystyryl)-9H-xanthen-9-one

[0061] Preparation of Compound (E)-3-(4-hydroxystyryl)-9H-xanthen-9-one

[0062]

[0063] According to Example 1, compound c was prepared. Compound c (224mg, 0.1mmol), p-hydroxybenzyltriphenylphosphonium salt (434mg, 0.1mmol), sodium ethoxide (20.4mg, 0.3mmol) were added to a 50ml round bottom reaction flask, dissolved in 10ml of DMF, at room temperature Under stirring reaction for 24 hours, the reaction solution changed from initial dark rose red to light yellow, adding 10 milliliters of water to quench the reaction, extracting with 20 milliliters of ethyl acetate, separating the aqueous phase, and washing with 10 milliliters of water 5 to 8 times, fully DMF was removed, and finally dried over anhydrous sodium sulfate; the organic phase was distilled under reduced pressure, purified by column chromatography, and loaded by dry method (PE: EA = 20: 1) to obtain 240 mg of the target compound in the form of light y...

Embodiment 3

[0065]

[0066] (E)-3-(4-nitrostyryl)-9H-xanthen-9-one

[0067] Preparation of Compound (E)-3-(4-nitrostyryl)-9H-xanthen-9-one

[0068] According to Example 1, compound c was prepared. Compound c (224mg, 0.1mmol), p-nitrobenzyltriphenylphosphonium salt (434mg, 0.1mmol), sodium ethoxide (20.4mg, 0.3mmol) were added to a 50ml round bottom reaction flask, dissolved in 10ml of DMF, Stirring and reacting at room temperature for 24 hours, the reaction solution changed from initial dark rose red to light yellow, adding 10 milliliters of water to quench the reaction, extracting with 20 milliliters of ethyl acetate, separating the aqueous phase, and washing with 10 milliliters of water for 5 to 8 times. DMF was fully removed, and finally dried over anhydrous sodium sulfate; the organic phase was distilled under reduced pressure, purified by column chromatography, and loaded by dry method (PE: EA = 20: 1) to obtain 240 mg of the target compound as a light yellow powder, with a yield...

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Abstract

The invention provides xanthone fluorochrome and application therefore to design synthesis of a fluorescence probe. The Xanthone fluorochrome has the following structure general formulas I, II, III and IV shown in the description, wherein R1, R2, R3 and R4 are respectively selected from hydrogen, halogen, hydroxyl, NH2, sulfydryl, cyano-group, nitryl, N,N-bis-C1-4 alkyl amino group, aldehyde group, carboxyl, amido, sulfoamido, C5-10 aryl, C2-8 heterocyclic aryl, C1-6 alkyl, boric acid, boronic acid pinacol ester and OR (wherein R is C1-4 saturated alkyls or unsaturated alkyls).

Description

1. Technical field [0001] The invention relates to a class of xanthone fluorescent dyes and their application in the preparation of living cell dyes and subcellular organelle dyes. 2. Technical background [0002] Fluorescent probes have received widespread attention in recent years due to their non-invasive, easy-to-operate, and visual detection capabilities. At present, with the advancement of fluorescence imaging and detection methods, the application of fluorescent probes to study the distribution and function of intracellular proteins has become one of the very important means of life science research, and has received much attention from biochemistry, medicinal chemistry, and zymomics. attention of researchers in many fields. [0003] Fluorescent dyes play a key role in the development and application of fluorescence technology. The development of laser confocal fluorescence imaging technology and super-resolution fluorescence technology all depend on the development ...

Claims

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Application Information

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IPC IPC(8): C07D405/06C07D311/86C07D455/04C07D519/00C07F5/02C09K11/06C09B23/10G01N21/64C12Q1/02
CPCC07D311/86C07D405/06C07D455/04C07D519/00C07F5/025C09B23/102C09B23/105C09K11/06G01N21/643G01N33/5076
Inventor 孙健王超
Owner 成都必凯科技有限公司
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