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Novel Alexa Fluor fluorescent cyanine dye as well as preparation method and application thereof

A fluorescent cyanine and dye technology, applied in the field of new Alexa Fluor fluorescent cyanine dye and its preparation, can solve the problems of poor photostability and thermal stability, affecting analysis reliability, etc., and achieve the effect of improving photostability and thermal stability

Inactive Publication Date: 2014-03-19
NANJING XIAOZHUANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The Alexa Fluor series of fluorescent dyes developed by Molecular Probes have long linear conjugated double bonds in their molecular structures, resulting in poor photostability and thermal stability, which directly or indirectly affect their analysis as fluorescent markers reliability

Method used

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  • Novel Alexa Fluor fluorescent cyanine dye as well as preparation method and application thereof
  • Novel Alexa Fluor fluorescent cyanine dye as well as preparation method and application thereof
  • Novel Alexa Fluor fluorescent cyanine dye as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] The synthetic method of embodiment 1 dye 8

[0028] 1) [5-sulfo-2-(2-ethoxy-3,4-dioxo-cyclobut-1-enyl-methenyl)-3-methyl-1-(γ-sulfopropyl base) synthesis of indol-3-yl]hexanoic acid.

[0029] In a 50ml three-necked flask equipped with a reflux condenser, add 3-(5-pentylcarboxy)-2,3-dimethyl-5-sulfonic acid-1-(γ-sulfopropyl) indole betaine (References for synthetic methods [1] , 1.0g, 2.17mmol), 0.5ml (2.78mmol) of 3,4-diethoxy-3-cyclobutene-1,2-dione and 20ml of anhydrous methanol, then dropwise added sodium methoxide 3ml, heated to 70-80°C and maintained for 5 minutes, then rotary evaporated to remove the solvent, and the residual solid was washed with ether and chloroform to obtain [5-sulfonic acid-2-(2-ethoxy-3,4-dioxo-cyclobutane- 0.52 g of 1-alkenyl-methenyl)-3-methyl-1-(γ-sulfopropyl)indol-3-yl]hexanoic acid, which can be used in the next reaction without complete purification.

[0030] 2) 5-sulfo-2-{3-[5-sulfo-3-(ζ-carboxypentyl)-3-methyl-1-(γ-sulfopropyl)-l,...

Embodiment 2

[0032] The synthetic method of embodiment 2 dye 10

[0033] 1) [5-sulfo-2-(2-ethoxy-3,4-dioxo-cyclobut-1-enyl-methenyl)-3-methyl-1-(δ-sulfobutyl base) synthesis of indol-3-yl]hexanoic acid.

[0034] In a 50ml three-necked flask equipped with a reflux condenser, add 3-(5-pentylcarboxy)-2,3-dimethyl-5-sulfonic acid-1-(γ-sulfobutyl) indole betaine (References for synthetic methods [2] , 1.0g, 2.10mmol), 0.5ml (2.78mmol) of 3,4-diethoxy-3-cyclobutene-1,2-dione and 20ml of anhydrous methanol, then dropwise added sodium methoxide 3ml, heated to 70-80°C and maintained for 5 minutes, then rotary evaporated to remove the solvent, and the residual solid was washed with ether and chloroform to obtain [5-sulfonic acid-2-(2-ethoxy-3,4-di Oxy-cyclobut-1-enyl-methenyl)-3-methyl-1-(δ-sulfobutyl)indol-3-yl]hexanoic acid 0.49g, can be used in the next reaction without complete purification .

[0035]2) 5-sulfo-2-{3-[5-sulfo-3-(ζ-carboxypentyl)-3-methyl-1-(δ-sulfobutyl)-l,3-di Hydrogen-ind...

Embodiment 3

[0037] The photostability comparison of embodiment 3 dyes [3]

[0038] Dye 8 (prepared in Example 1), dye 10 (prepared in Example 2) and Alexa fluor647 were prepared at a concentration of 10 -5 mol / L dye aqueous solution, the dye sample solution is placed in a 1cm thick quartz cuvette, and after a certain period of time is irradiated under a 500W iodine tungsten lamp, the absorbance value of the sample before and after irradiation is measured with a UV-Vis spectrophotometer. The photostability of the samples was compared according to the decrease speed of the absorbance value (the position of the maximum absorption peak) with the illumination time. The calculation formula of fading rate is as follows: calculate according to the following formula:

[0039]

[0040] In the formula, A 0 is the maximum absorbance value of the dye before illumination, A t is the maximum absorbance value of the dye after illumination.

[0041] The photostability results of the three dyes are...

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Abstract

The invention discloses a novel Alexa Fluor fluorescent cyanine dye as well as a preparation method and application thereof. The structural general formula (I) of the novel Alexa Fluor fluorescent cyanine dye is as shown in the specification, wherein n1 is equal to 1 or 2, n2 is equal to any integer ranging from 1 to 5. A squaric acid bridge ring is successfully introduced into the fluorescent cyanine dye Alexa Fluor to obtain a series of improved Alexa Fluor fluorescent cyanine dyes, and the heat stability is obviously improved in comparison with that of the existing fluorescent cyanine dye Alexa Fluor, the Alexa Fluor fluorescent cyanine dye can be applied to marking and positioning tissues, cells and biomolecules in biological chemistry analysis or preparing a fluorescence mark reagent.

Description

technical field [0001] The invention belongs to the field of chemical synthesis, and relates to a novel Alexa Fluor fluorescent cyanine dye and a preparation method and application thereof. Background technique [0002] Alexa Fluor series dyes are a series of fluorescent cyanine dyes developed by Molecular Probes, a subsidiary of Life technologies. Its invention is an important breakthrough in the application of fluorescent labeling reagents. The spectrum of this dye Excellent dyes that span the spectrum from blue to far-infrared including a range of near-ultraviolet, visible and near-infrared. The conjugates formed by these reagents are without exception the best and brightest ever experimentally detected, offering multiple options for multicolor detection and fluorescence resonance energy transfer in the blue and far-red range. In addition, these dyes have been carefully selected and optimized to have excellent water solubility, minimize dye-dye interactions, and allow a ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09B23/04C09K11/06G01N33/52
Inventor 张敦林薛蒙伟唐宁刘光祥周业飞
Owner NANJING XIAOZHUANG UNIV