Xanthene-hemicyanine near-infrared fluorescent dye as well as synthesis method and application thereof

A technology of fluorescent dyes and synthesis methods, applied in the field of its synthesis, xanthene-semicyanine near-infrared fluorescent dyes, can solve the problems of fluorescence quenching, molar extinction coefficient, low fluorescence quantum yield, and poor photostability. Achieve good water solubility, increase molar extinction coefficient and fluorescence quantum yield

Active Publication Date: 2022-06-07
DALIAN UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, these dyes have defects to some extent that affect their application
For example: 1. The absorption wavelength and emission wavelength are relatively short, and it is easy to receive interference from biological background fluorescence during imaging and analysis; 2. The water solubility is generally poor, and it is easy to aggregate in aqueous solvents to cause fluorescence quenching; 3. The photostability is poor, which increases the cost of large-scale storage and

Method used

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  • Xanthene-hemicyanine near-infrared fluorescent dye as well as synthesis method and application thereof
  • Xanthene-hemicyanine near-infrared fluorescent dye as well as synthesis method and application thereof
  • Xanthene-hemicyanine near-infrared fluorescent dye as well as synthesis method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0056] Example 1 Production of Compound 1

[0057] The structural formula of compound 1:

[0058]

Embodiment 11

[0060]

[0061] 9 mL of phosphorus tribromide was slowly added dropwise to a mixed solution of 12 mL of DMF and 25 mL of chloroform at 0°C, stirred for 1 h, then warmed to room temperature, added with 4 mL of cyclohexanone, and the reaction was stopped after stirring for 12 h. The solution was poured into 100 mL of ice water, and NaHCO was added 3 Make the solution neutral with CH 2 Cl 2 Extraction, washed with saturated brine, anhydrous Na 2 SO 4 After drying, the solvent was evaporated to give the title compound 1.1 (6.0 g, 31.74 mmol, Y=73.8%).

Embodiment 12

[0063]

[0064] At room temperature, the compound of Example 1.1 (2.93g, 15.5mmol, 1.0eq) and 4-diethylaminosalicylaldehyde (3.0g, 15.5mmol, 1.0eq) were added to 15mL of DMF, stirred for 16h and then stopped Reaction, pour the solution into 100 mL of water, use CH 2 Cl 2 Extraction, washed with saturated brine, anhydrous Na 2 SO 4 The organic phase was dried, concentrated, and purified by silica gel column to obtain yellow-brown compound 1.2 (1.4 g, 4.94 mmol, Y=31.9%).

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Abstract

The invention discloses a xanthene-hemicyanine near-infrared fluorescent dye as well as a synthesis method and application thereof. The dye has longer absorption and emission wavelengths, the water solubility of the dye is improved, and the change of spectral properties after the dye interacts with biomacromolecules is avoided by reasonably introducing active groups. Experiments prove that the dye has good photophysical properties and bioluminescence imaging potential, and can be applied to the aspects of biological recognition imaging, cell imaging, protein labeling, specific recognition of antibodies, nucleic acid labeling, DNA sequencing, tumor photodynamic therapy and the like.

Description

technical field [0001] The invention belongs to the technical field of organic dyes, and relates to a class of xanthene-hemicyanine near-infrared fluorescent dyes, a synthesis method thereof, and applications thereof. Background technique [0002] For a long time, fluorescent dyes have been widely used in the field of biomarkers and identification, and play an important role in the sequencing of biologically specific proteins, tumor markers and DNA recognition genes. [0003] Compared with the isotope labeling method, the fluorescence analysis method has the advantages of simple equipment, convenient operation, high sensitivity and fast response. The fluorescent dyes used in fluorescence analysis play a pivotal role in the entire analysis process, and the performance of the fluorescent dyes will directly affect the accuracy and sensitivity of the analysis. At present, the common commercial fluorescent dyes are mainly coumarin, fluorescein, rhodamine, indocyanine green and s...

Claims

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Application Information

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IPC IPC(8): C09B23/10C09K11/06C07D405/14C07D405/06G01N21/64A61K41/00A61P35/00C12Q1/6869C07K1/13
CPCC09B23/105C09B23/0091C09K11/06C07D405/06C07D405/14C12Q1/6869G01N21/6428G01N21/6456A61K41/0057A61P35/00C07K1/13C09K2211/1029C09K2211/1088C12Q2563/107C12Q2563/173Y02P20/55
Inventor 杜健军韩富平李鑫樊江莉彭孝军
Owner DALIAN UNIV OF TECH
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