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Fluorescent dye compound and preparation method and application thereof

A technology of fluorescent dyes and compounds, applied in the field of fine chemicals, can solve the problems of complex structure, impermeability of living cells, large molecules, etc., and achieve the effects of high sensitivity, good cell membrane permeability, and low toxicity

Inactive Publication Date: 2014-05-21
南京博炫生物科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[A.Furstenberg, M.D.Julliard, T.G.Deligorgiec, N.I.Gadjev.J.AM.CHEM.SOC., 2006, 128, 7661-7669] Some varieties of such dyes have been commercialized, such as: SYTOXBlue, TOTO, POPO , BOBO, YO-PRO, etc., but most of these commercial dyes have large molecules and complex structures, which are impermeable to living cells and can only be used for the identification and detection of nucleic acids in vitro

Method used

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  • Fluorescent dye compound and preparation method and application thereof
  • Fluorescent dye compound and preparation method and application thereof
  • Fluorescent dye compound and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] preparation of

[0025] 1) The first quaternary ammonium salt intermediate III (n=3) is obtained by reacting the benzothiazole aromatic heterocyclic compound of the formula II compound with propane sultone; the reaction temperature is 150°C, the reaction time is 20 hours, and the reaction solvent Selected from: dichloromethane, chloroform, the molar ratio of formula II compound and propane sultone or butane sultone is 1:1;

[0026] 2) Condensate the first quaternary ammonium salt intermediate III with N,N,-dibenzamidine to obtain the compound of formula IV; the reaction temperature is 150°C, the reaction time is 24 hours, the reaction solvent is acetic anhydride, and acetic acid is a protonic acid Catalyst, the mol ratio of the first quaternary ammonium salt and benzamidine is 1:3;

[0027] 3) Reaction of compound IV with compound of formula V (m=2) to obtain compound of formula VI: the reaction temperature is 150°C, the reaction time is 24 hours, the reaction solven...

Embodiment 2

[0029] preparation of

[0030] 1) The first quaternary ammonium salt intermediate III (n=4) is obtained by reacting the compound of formula II, benzothiazole aromatic heterocyclic compound and butane sultone; the reaction temperature is 200°C, the reaction time is 10 hours, and the reaction solvent Selected from: ethanol, acetonitrile, the molar ratio of formula II compound and propane sultone or butane sultone is 1:3;

[0031] 2) Condensing the first quaternary ammonium salt intermediate III with N,N,-dibenzamidine to obtain the compound of formula IV; the reaction temperature is 50°C, the reaction time is 20 hours, the reaction solvent is acetic anhydride, and acetic acid is a protonic acid Catalyst, the mol ratio of the first quaternary ammonium salt and benzamidine is 1:2;

[0032] 3) Reaction of compound IV with compound of formula V (m=2) to obtain compound of formula VI: the reaction temperature is 10°C, the reaction time is 48 hours, the reaction solvent is acetic a...

Embodiment 3

[0034] preparation of

[0035] 1) The first quaternary ammonium salt intermediate III (n=3) is obtained by reacting the compound of formula II, benzothiazole aromatic heterocyclic compound and propane sultone; the reaction temperature is 10°C, the reaction time is 48 hours, and the reaction solvent Selected from: ethyl acetate, toluene, the molar ratio of the compound of formula II to propane sultone or butane sultone is 1:5;

[0036]2) Condensing the first quaternary ammonium salt intermediate III with N,N,-dibenzamidine to obtain the compound of formula IV; the reaction temperature is 100°C, the reaction time is 10 hours, the reaction solvent is acetic anhydride, and acetic acid is a protonic acid Catalyst, the mol ratio of the first quaternary ammonium salt and benzamidine is 1:1;

[0037] 3) Reaction of compound IV with compound of formula V (m=3) to obtain compound of formula VI: the reaction temperature is 85°C, the reaction time is 24 hours, the reaction solvent is a...

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PUM

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Abstract

The invention discloses a fluorescent dye compound, the structural formula of which is shown as the formula I described in the specification, wherein X is C(CH3)2, S or O; n is 3 or 4; m is 2 or 3. The invention further discloses a method of preparing the fluorescent dye compound. The invention further discloses an application of the fluorescent dye compound. Aiming at the deficiencies in the prior art, by improvement on the basis, the invention provides novel compounds which are simple in structure, high in sensitivity and long in wavelength and have good membrane permeability. The fluorescent dye compound disclosed by the invention mainly reflects very good water solubility, and is simple in structure, easy to get raw materials and low in toxicity. A target molecule can be synthesized by 4-5 steps ordinarily, so that the fluorescent dye compound is easy to industrialize.

Description

technical field [0001] The invention belongs to the technical field of fine chemicals, and in particular relates to a fluorescent dye compound and its preparation method and application. Mainly the preparation and application of nitrogen-containing cyanine fluorescent dye and the application of this fluorescent dye or its composition in biological dyeing. Background technique [0002] Fluorescent dyes, as functional pigments, are widely used in various fields of science and technology, especially in life sciences, clinical medical diagnosis, cotton-padded clothes analysis and detection, etc., which have attracted worldwide attention. At present, commercial fluorescent dyes such as phenanthridines (EP, PI), acridines (AO), imidazoles (Hoechst, DAPI) and cyanine family (Cy, TOTO, SYTO) are widely used in genomics technology, nucleic acid quantitative detection, It has played an important role in blood cell analysis and other fields. However, each of these dyes has limitation...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D417/06C07D413/06C07D403/06C09K11/06C09B23/06C12Q1/68G01N21/64
CPCC09B23/06C07D417/06C07D403/06C07D413/06C09K11/06C09K2211/1029C09K2211/1033C09K2211/1037
Inventor 李忠顾玉龙马飞飞金智成周国岩
Owner 南京博炫生物科技有限公司
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