Hydrophilic anthracene fluorescent dye and synthesis method thereof

A technology of fluorescent dyes and synthesis methods, applied in the field of hydrophilic anthracene fluorescent dyes and their synthesis, can solve the problems of reduced quantum efficiency, poor water solubility, etc., and achieve the effects of increased self-stability, easy storage, and widened selection range.

Active Publication Date: 2021-02-02
CYGNUS BIOSCI BEIJING CO LTD
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

In the dye sequencing experiment, it was found that the original fluorescent dyes had poor water solubility, and their quantum efficiency was lower than that of xanthene compounds; in

Method used

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  • Hydrophilic anthracene fluorescent dye and synthesis method thereof
  • Hydrophilic anthracene fluorescent dye and synthesis method thereof
  • Hydrophilic anthracene fluorescent dye and synthesis method thereof

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Embodiment Construction

[0035] Exemplary embodiments of the present disclosure are described in more detail below. It should be understood that the present disclosure can be implemented in various forms and should not be limited by the embodiments set forth herein. Rather, these embodiments are provided for more thorough understanding of the present disclosure and to fully convey the scope of the present disclosure to those skilled in the art.

[0036] Unless otherwise specified, the words involved in the present invention are common words in this field.

[0037] The anthracene compounds involved in the present invention refer to compounds having a triphenylcyclanthracene-like structure. This term is not a special term.

[0038] In the reaction involved in the present invention, there are other products in certain steps, but on the basis of the description of the present invention, those skilled in the art can easily obtain the target product. The specific structure of the by-product does not belo...

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Abstract

The invention provides a hydrophilic anthracene fluorescent dye and a synthesis method thereof. By introducing a sulfonic acid group and a difluoro substituent group, the hydrophilicity and stabilityof the anthracene fluorescent dye are improved. The synthesis method mainly comprises the following steps: reacting halogenated benzaldehyde with a phenyl Grignard reagent to generate a benzhydrol derivative; oxidizing an alcoholic hydroxyl group into a keto carbonyl group to obtain a benzophenone derivative with a phenolic hydroxyl group protecting group; converting the keto carbonyl group into dithioketal by using ethanedithiol for protection; carrying out fluorination by using a fluorine reagent to obtain an anthrone difluoride compound; conducting reacting by using a lithium reagent to achieve conversion into a lithium Grignard reagent; conducting oxidizing to obtain benzophenone; removing a protecting group from benzophenone, and carrying out cyclization reaction under an acidic condition; and carrying out sulfonation reaction on the obtained fluorinated fluorescent dye to obtain the fluorinated fluorescent dye.

Description

technical field [0001] The invention relates to a hydrophilic anthracene fluorescent dye and a synthesis method thereof, belonging to the field of synthesis of biochemical fluorescent dyes. Background technique [0002] Anthracene fluorescent dyes belong to a class of fluoresceins containing anthracyclines. Some of these compounds have the characteristics of long wavelength, fluorescence switching, and high molar absorption coefficient. Such compounds are particularly useful in gene sequencing. The applicant's previous patent CN201510155218.9 also disclosed the synthesis method of anthracene compounds. In the dye sequencing experiment, it was found that the original fluorescent dyes have poor water solubility, and their quantum efficiency is lower than that of xanthene compounds; in order to improve the water solubility of dyes and improve the optical stability of dyes; a specially developed one containing Bifluoro and sulfonate fluorescent dyes. It was further found tha...

Claims

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Application Information

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IPC IPC(8): C09B1/00C09K11/06G01N1/30
CPCC09B1/00C09K11/06G01N1/30G01N2001/302C09K2211/1011C09K2211/1007Y02P20/55
Inventor 段海峰张甲强陈子天
Owner CYGNUS BIOSCI BEIJING CO LTD
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