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Azaindole-squarylium cyanine dye as well as synthesis method and application thereof

A technology of azaindole and squaraine, which is applied in its synthesis, azaindole-squarine dyes, biological and medical applications, can solve the problem of affecting the spectral performance of dyes, poor dye stability, and affecting biological Application and other issues, to achieve the effect of good biocompatibility, large molar extinction coefficient, and good survival rate

Active Publication Date: 2022-07-22
DALIAN UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] However, in the study of cyanine dyes, it was found that the longer the conjugated methine chain of the molecule, the longer the maximum absorption wavelength of the dye, but the worse the photostability of the dye. Compared with other dyes, the photostability of cyanine dyes is limited. its application
Since the fine structure of the dye can affect the spectral properties of the dye, thereby affecting its biological application

Method used

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  • Azaindole-squarylium cyanine dye as well as synthesis method and application thereof
  • Azaindole-squarylium cyanine dye as well as synthesis method and application thereof
  • Azaindole-squarylium cyanine dye as well as synthesis method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0052] Example 1 Production of Compound 1

[0053] To 2-hydrazinopyridine (2.182 g, 20 mmol) dissolved in 60 mL of toluene was added 3-methyl-2-butanone (3.445 g, 40 mmol) at room temperature. The mixture was stirred and heated to reflux under nitrogen protection, and the reaction was stopped after 12 h. Cool to room temperature. Most of the toluene was removed, 12 mL of polyphosphoric acid was added to the residue, the reaction was heated and stirred at 140 ° C for 45 min, the mixture was poured into 200 mL of ice water, ammonia water was added dropwise, the pH was adjusted to weakly alkaline, extracted with ethyl acetate Anhydrous Na 2 SO 4 After drying, the solvent was evaporated and purified by silica gel column to obtain compound 1.1 (1.280 g, 8 mmol, Y=40%) as a pale yellow solid.

[0054] The structural formula of compound 1.1 is as follows:

[0055]

[0056] Compound 1.1 (1.00 g, 4 mmol, 1.0 eq) and iodomethane (1.77 g, 8 mmol, 2.0 eq) were added to a 100 mL tw...

Embodiment 2

[0062] Example 2 Production of Compound 2

[0063] To 2-hydrazino-4-bromopyridine (1.00 g, 5.32 mmol, 1.0 eq) dissolved in 20 mL of toluene was added 3-methyl-2-butanone (0.92 g, 10.64 mmol, 2.0 eq) at room temperature ). The mixture was stirred and heated to reflux under nitrogen protection, and the reaction was stopped after 12 h. Cool to room temperature. Most of the toluene was removed, 12 mL of polyphosphoric acid was added to the residue, the reaction was heated and stirred at 140 ° C for 45 min, the mixture was poured into 200 mL of ice water, ammonia water was added dropwise, the pH was adjusted to weakly alkaline, extracted with ethyl acetate Na 2 SO 4 After drying, evaporating the solvent and purifying with silica gel column, a pink solid compound 2.1 was obtained (0.760 g, 3.18 mmol, Y=59.8%). The structural formula of compound 2.1 is as follows:

[0064]

[0065] Compound 2.1 (1.00 g, 4.2 mmol, 1.0 eq) and iodomethane (1.19 g, 8.4 mmol, 2.0 eq) were added ...

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Abstract

The invention discloses an azaindole-squarylium cyanine dye as well as a synthesis method and application thereof. Compared with a conventional squarylium cyanine dye, the dye of the type has the advantages that the molecular charge separation degree and the electron mobility are increased by changing the position of quaternary ammonium nitrogen and the type of an electron-donating group, so that the dye has a larger molar extinction coefficient. Related experiments verify that novel dye molecules change photophysical properties compared with traditional squarylium cyanine dyes, and verify that the dyes have good biocompatibility and can be applied to the aspects of biological recognition imaging, nucleic acid labeling, DNA sequencing, tumor photodynamic therapy and the like.

Description

technical field [0001] The invention relates to the technical field of organic dyes, in particular to a class of azaindole-squaric acid cyanine dyes, a synthesis method thereof, and applications in biology and medicine. Background technique [0002] As a commercial dye that can be used for biofluorescence labeling, cyanine dyes have been discovered since 1856. Quinoline blue dyes have wide absorption wavelength range (about 500-1000nm), large molar extinction coefficient and absorption peak. And the position of the emission peak can be adjusted, the solubility in organic solution is high, and the synthesis is easy. In the early research, the main function of cyanine dyes is to expand the photosensitive range of silver halide particles to improve their sensitivity, and they are widely used in photosensitive fields. With the in-depth study of its properties, cyanine dyes have gradually been widely used in solar cell photosensitizers, photodynamic therapy, photothermal therapy...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09B57/00C09K11/06G01N21/64A61K41/00A61K49/00A61P35/00
CPCC09B57/007C09K11/06A61K41/0057A61P35/00A61K49/0032G01N21/6428G01N21/6456C09K2211/1044C09B23/0066
Inventor 杜健军刘圆潘静巍张晓雪樊江莉彭孝军
Owner DALIAN UNIV OF TECH
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