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Fluorochrome taking fluorescein as matrix, as well as preparation method and application thereof

A fluorescent dye and fluorescein technology, which is applied to a class of fluorescent dyes with fluorescein as the parent, its preparation and application fields, can solve the problems of prolonging the absorption and emission spectra, and achieve good photostability

Active Publication Date: 2013-05-08
DALIAN UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The reported literature mainly adopts derivatization by Mannich reaction at the 4', 5' position, but this method is not an effective method to extend the absorption and emission spectra effectively. Therefore, in order to obtain "red" Fluorescein needs to come up with a new synthetic method to modify fluorescein to extend its wavelength to the "red" region

Method used

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  • Fluorochrome taking fluorescein as matrix, as well as preparation method and application thereof
  • Fluorochrome taking fluorescein as matrix, as well as preparation method and application thereof
  • Fluorochrome taking fluorescein as matrix, as well as preparation method and application thereof

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preparation example Construction

[0043] Another aspect of the present invention provides the preparation method of the fluorescent dye with fluorescein as the parent, the method comprising the following steps: preparing the intermediate binary aldehyde respectively, and then combining the intermediate with compounds i, ii, iii, vi, v The compound is obtained by reacting under the action of an organic base (such as piperidine), and the specific synthesis scheme includes the following steps:

[0044] 1) The compound of formula II and the compound of urotropine are reacted at 10-180° C. for 4-48 hours according to the feeding molar ratio of 1:1-1:20, to prepare the compound of formula III;

[0045]

[0046] The reaction solvent is trifluoroacetic acid, dichloromethane, chloroform, ethanol, acetonitrile, ethyl acetate, toluene, xylene, o-dichlorobenzene or a mixture thereof;

[0047] In a preferred embodiment, the reaction temperature is 70-140°C, the reaction time is 2-36 hours, and the reaction solvent is se...

Embodiment 1

[0081] Preparation of probe compound A 1

[0082]

[0083] (1) Synthesis of intermediate 1

[0084] Dissolve DCF (6.30 g, 15.75 mmol, synthesized according to literature), urotropine (10.5 g, 75.1 mmol) in a round bottom flask containing 25 mL of trifluoroacetic acid. This mixture was stirred, heated to 90°C, and stirring was continued for 24h. The mixture became viscous and was treated with aqueous acetic acid (10 mL acetic acid dissolved in 200 mL water). The mixture was then stirred overnight at ambient temperature. A solid precipitated, which was then filtered using a Buchner funnel, and the precipitate was washed 3 times with water. After vacuuming, it was dried under an infrared lamp to obtain a red solid (8.10 g).

[0085] (2) Probe Compound A 1 Synthesis

[0086] Under nitrogen atmosphere, 2.5 mmol of piperidine (0.215 g) was added into absolute ethanol (50 mL) dissolved with DCF dihydric aldehyde (0.32 g, 0.67 mmol) and 2-methylbenzothiazole (339 μL, 2.66 mm...

Embodiment 2

[0088] Preparation of probe compound A 2 :

[0089]

[0090] (1) Synthesis of intermediate 1

[0091] Dissolve DCF (6.30 g, 15.75 mmol, synthesized according to literature), urotropine (10.5 g, 75.1 mmol) in a round bottom flask containing 25 mL of trifluoroacetic acid. This mixture was stirred, heated to 90°C, and stirring was continued for 24h. The mixture became viscous and was treated with aqueous acetic acid (10 mL acetic acid dissolved in 200 mL water). The mixture was then stirred overnight at ambient temperature. A solid precipitated, which was then filtered using a Buchner funnel, and the precipitate was washed 3 times with water. After vacuuming, it was dried under an infrared lamp to obtain a red solid (8.10 g).

[0092] (2) Probe Compound A 2 Synthesis

[0093] Under a nitrogen atmosphere, 2.5 mmol of piperidine (0.215 g) was added into a solution of DCF dihydric aldehyde (0.828 g, 1.82 mmol) and 2,6-dimethyl-4-pyranylidene malononitrile (0.828 g , 1.82 ...

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Abstract

The invention discloses a fluorochrome taking fluorescein as matrix, as well as a preparation method and application thereof. The fluorochrome taking the fluorescein as the matrix has the structure shown in a general formula I (figure 1); and the compound has a certain level of water-solubility, and has certain good membrane permeability. The compound disclosed by the invention has novel spectral characteristics; and dye of fluorescein derivative with good property is applied to the fluorescence imaging aspect.

Description

technical field [0001] The present invention relates to a preparation method and application of a novel long-wavelength fluorescent dye with special properties based on fluorescein, and the use of this type of fluorescent probe compound to detect bovine serum albumin in vitro and in vivo, and to apply the dye to cell imaging In experiment. 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] Fluorescein was first synthesized in 1871 and then became an important type of fluorophore. Due to its excellent quantum yield and photostability, fluor...

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
Owner DALIAN UNIV OF TECH
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