Amide-substituted azaindole-pentamethine cyanine dye as well as synthesis method and application thereof

An azaindole and cyanine dye technology, which is applied in the field of biological identification reagents, can solve the problems of difficulty in entering biological tissues, reduced detection efficiency, limited excitation time, etc., and achieves flexible labeling methods, strong applicability, and good water solubility. Effect

Active Publication Date: 2021-08-06
DALIAN UNIV OF TECH
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, each of these dyes has its own application limitations
1. The excitation light of a considerable part of fluorescent dyes is in the ultraviolet region. Since ultraviolet light can cause serious damage to nucleic acid, protein and other components in cells, the use of this type of fluorescence in fluorescence microscopy is limited by the time of light excitation. limits
In addition, when performing fluorescence detection in the ultraviolet region, the absorption of biological samples in this range makes it difficult for light to enter the interior of biological tissues. At the same time, the autofluorescence of certain components in biological samples forms strong background interference, which greatly reduces the detection efficiency.

Method used

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  • Amide-substituted azaindole-pentamethine cyanine dye as well as synthesis method and application thereof
  • Amide-substituted azaindole-pentamethine cyanine dye as well as synthesis method and application thereof
  • Amide-substituted azaindole-pentamethine cyanine dye as well as synthesis method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0055] Embodiment 1 manufactures compound 1

[0056]

[0057] The structural formula of compound 1

Embodiment 11

[0059]

[0060] To a solution of p-hydrazinobenzenesulfonic acid (5.00 g, 26.6 mmol, 1.0 eq) in acetic acid at room temperature, was added 3-methyl-2-butanone (5.70 mL, 53.1 mmol, 2.0 eq), refluxed After 4h, stop the reaction, filter, wash with ethyl acetate three times, dissolve the solid in 30mL of methanol, slowly add dropwise to a solution of potassium hydroxide (1.50g, 26.6mmol, 1.0eq) dissolved in 30mL of propanol, at room temperature Stir for 24h. After filtration, the target compound 1.1 (6.04 g, 21.8 mmol, Y=82%) was obtained.

Embodiment 12

[0062]

[0063] The compound of Example 1.1 (1.00g, 3.6mmol, 1.0eq) and 6-bromo-n-hexanoic acid (1.40g, 7.2mmol, 2.0eq) were dissolved in 10mL o-dichlorobenzene, refluxed for 24h under nitrogen, and the reaction was stopped . Add isopropanol and filter to obtain target compound 1.2 (1.14 g, 2.4 mmol, Y=67%).

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PUM

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Abstract

The invention discloses an amide-substituted azaindole-pentamethine cyanine dye as well as a synthesis method and application thereof, and mainly relates to synthesis of the amide-substituted azaindole-pentamethine cyanine dye and application of the amide-substituted azaindole-pentamethine cyanine dye in the aspects of biological recognition imaging, nucleic acid labeling, DNA sequencing and the like. The dye has an active group and a water-soluble group for further amidation reaction. The dye has near-infrared absorption and high fluorescence quantum yield, can be used for biological recognition and detection of amino compounds, and is applied to the fields of protein labeling, nucleic acid detection, DNA sequencing and the like.

Description

technical field [0001] The invention belongs to the technical field of biological recognition reagents, and relates to the synthesis of a class of amide-substituted azaindole-pentamethine dyes and their application in biological dyeing. Background technique [0002] Fluorescent dyes are an important tool for biomarking and identification, and are of great significance in the sequencing of biologically specific proteins, tumor markers, and DNA recognition genes. [0003] In recent years, with the continuous advancement of laser technology and fluorescent dyes, fluorescence analysis has some advantages, such as simple equipment, convenient operation, high sensitivity and fast response, which are particularly prominent compared with isotope labeling methods. Therefore, fluorescence response technology has become a a very important research tool. At present, commercial fluorescent dyes such as fluorescein, rhodamine, coumarin, 7-nitrobenzofurazanaminocaproic acid (NBD), tetrame...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09B23/08C07D471/04C09K11/06G01N21/64
CPCC09B23/083C07D471/04C09K11/06G01N21/6486G01N21/6428C09K2211/1029C09K2211/1044G01N2021/6439
Inventor 彭孝军黄海桥丁俊莹李怡坤杜健军樊江莉
Owner DALIAN UNIV OF TECH
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