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Cyanine fluorescent dye

A technology of fluorescent dyes and cyanines, which is applied in the field of cyanine fluorescent dyes, can solve the problems of low fluorescence quantum efficiency, affect the accuracy of detection results, and long synthesis routes, and achieve simple purification methods, avoid fluorescence background interference, and improve synthesis conditions. mild effect

Inactive Publication Date: 2014-12-17
太原瑞盛生物科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The fluorescent quantum efficiency of these dyes is low, which reduces the degree of fluorescence enhancement and affects the accuracy of the test results. At the same time, due to the need to measure red blood cells, white blood cells and platelets, some abnormal red blood cells such as large red blood cells will affect the accurate count of white blood cells.
[0007] Currently used cyanine fluorescent dyes, such as the asymmetric cyanine dyes TOTO (thiazole orange dimer), YOYO (oxazole yellow dimer), TOTAB, TOTIN (thiazole orange dimer) developed by Glazer et al. dimer), and the asymmetric monomethylene cyanine dyes TO-PRO-3, PO-PRO-2 and BO-PRO-2 derived on this basis [K.M. Sovenyhazy, J.A. Bordelon, J.T. Petty. Nucleic Acids Res, 2003, 31, 2561], their absorption and emission are in the near-infrared region (670-1000 nm), but the molecular structure of this type of dye is complex, the synthesis route is long, the purification process takes a long time and the yield is low , so the price is high, which limits its scope of use

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0043] Embodiment 1 Preparation and purification of cyanine fluorescent dye I

[0044]

[0045]Add 4.0mmol of 3-benzyl-5-hydroxy-2-(2-(N-phenylacetamido)-vinyl)benzothiazole bromide salt and 4.1mmol of 7-propylamino- To 4-methyl-1-(propenyl)quinoline bromide, 10ml of pyridine and 2ml of acetic anhydride were added, and the reaction was stopped after 4.5 hours of magnetic stirring at room temperature to obtain a crude product of the reaction product. The crude product was poured into anhydrous ether and stirred, and the product precipitated out. The crude product was filtered, washed with 3×25ml ethyl acetate, and then recrystallized with an appropriate amount of methanol to obtain the title compound. The product yield is 72%.

[0046] Maximum absorption peak: 630nm (methanol / ethylene glycol)

[0047] MS (EI) C 32 h 32 BrN 3 OS m / z: 506.6 [M-Br] + .

Embodiment 2

[0048] Example 2 Preparation and purification of cyanine fluorescent dye II

[0049]

[0050] Add 4.0mmol of 3-(hexen-2-yl)-5-hydroxy-2-(2-(N-phenylacetamido)-vinyl)benzothiazole bromide salt and 4.1 Mmol 7-butylamino-4-methyl-1-(hexen-2-yl) quinoline bromide salt, add 10ml pyridine and 3ml acetic anhydride to it, and stop after 5 hours of magnetic stirring at room temperature to obtain the reaction Crude product. The crude product was poured into anhydrous ether and stirred, and the product precipitated out. The crude product was filtered, washed with 3×25ml ethyl acetate, and then recrystallized with an appropriate amount of methanol to obtain the title compound. The product yield is 65%.

[0051] Maximum absorption peak: 632nm (methanol / ethylene glycol)

[0052] MS (EI) C 33 h 44 BrN 3 OS m / z: 539.3 [M-Br] + .

Embodiment 3

[0053] Example 3 Preparation and Purification of Cyanine Fluorescent Dye III

[0054]

[0055] Add 4.0mmol of 6-hydroxy-3,3-dimethyl-2-(2-(N-phenylacetamido)-vinyl)-1-(propyn-2-yl) into a dry and clean 50mL three-necked flask )-benzothiazole iodide salt and 4.1mmol 7-N,N-diethylamino-4-methyl-1-benzyl-quinoline iodide salt, add 10ml pyridine and 0.8ml acetic anhydride to it, at room temperature The magnetic stirring reaction was stopped after 8 hours, and the crude product of the reaction product was obtained. The crude product was poured into anhydrous ether and stirred, and the product precipitated out. The crude product was filtered, washed with 3×25ml ethyl acetate, and then recrystallized with an appropriate amount of methanol to obtain the title compound. The product yield is 78%.

[0056] Maximum absorption peak: 635nm (methanol / ethylene glycol)

[0057] MS (EI) C 36 h 38 IN 3 O m / z: 528.7 [M-I] + .

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Abstract

The invention discloses a cyanine fluorescent dye used for biological fluorescence labelling. The fluorescent dye has a general formula shown in formula I and the characteristics of little synthetic steps, mild reaction conditions, simple purification processing mode, high yield and high light stability. Also, the fluorescent dye has a certain abilities to permeate cell membrane and the characteristics of low fluorescence background and specific recognizability to nucleic acid at the same time. When used as a nucleic acid stain in a flow cytometer, the fluorescent dye can effectively reduce the interference of the background fluorescence and increase the accuracy of the detection. The fluorescent dye provided by the invention can be used as leucocyte and reticulocyte stains in the blood.

Description

technical field [0001] The invention relates to a cyanine fluorescent dye which can be used for biological fluorescent labeling, in particular, the invention relates to a fluorescent dye which can be prepared under mild reaction conditions, its preparation method and its application in biological sample dyeing. Background technique [0002] Fluorescent dyes have been widely used in life science research and clinical medical diagnosis. In flow cytometry analysis, after the fluorescent dye is combined with the nucleic acid material in the cell, it emits fluorescence and multi-angle scattered light when it passes through the laser irradiation area. Through the detection of these fluorescent and scattered light signals, a wealth of information about the structure and physicochemical parameters of cells can be obtained. [0003] In clinical medical diagnosis, normal white blood cells in human peripheral blood are usually divided into lymphocytes, neutrophils, monocytes, eosinoph...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C09B23/06C09K11/06C12Q1/68G01N1/30G01N21/64
Inventor 阎晓敏赵军
Owner 太原瑞盛生物科技有限公司
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