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

A technology of fluorescent dyes and semicyanines, applied in the field of fluorescent dyes, can solve problems such as inability to fully utilize light energy, small molar extinction coefficient, limit labeling and detection, etc., to increase the degree of molecular charge separation and electronic mobility, molar Increased extinction coefficient and fluorescence quantum yield, effects of long absorption and emission wavelengths

Pending Publication Date: 2022-08-09
DALIAN UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] However, the existing xanthene hemicyanine dyes also have a series of problems: 1. The molar extinction coefficient is relatively small, and the light energy cannot be fully utilized; 2. The fluorescence quantum yield is low, which limits the application of this type of dye; 3. The synthesis method is relatively simple, resulting in fewer sites that can be modified; 4. The water solubility is poor, which limits the labeling and detection in vivo and in vitro

Method used

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

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Effect test

Embodiment 1

[0050] Example 1 Production of Compound 1

[0051] The structural formula of compound 1:

[0052]

Embodiment 11

[0054]

[0055] 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 1 h, the mixture was poured into 150 mL of ice water, ammonia water was added dropwise, the pH was adjusted to weakly alkaline, extracted with ethyl acetate and then Anhydrous Na 2 SO 4 After drying, evaporating the solvent, and purifying with silica gel column, a nitrogen-yellow solid compound 1.1 was obtained (1.280 g, 8 mmol, Y=40%).

Embodiment 12

[0057]

[0058] To compound 1.1 (0.500g, 3.12mmol, 1.0eq) was added to 15mL of acetonitrile, benzyl bromide (1.07g, 6.24mmol, 2.0eq) was added, and the reaction was carried out at 70°C for 12h, the reaction was stopped, cooled to room temperature, It was added to 100 mL of ethyl acetate, and the precipitate was collected to obtain compound 1.2 (0.710 g, 2.14 mmol, Y=68.7%).

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Abstract

The invention discloses a novel hemicyanine near-infrared fluorescent dye as well as a synthesis method and application thereof. According to the type, the molar extinction coefficient and the fluorescence quantum yield of the dye can be effectively improved, and compared with the traditional hemicyanine fluorescent dye, the hemicyanine fluorescent dye has longer absorption and emission wavelengths. Experiments prove that the dye has good photophysical properties and bioluminescence imaging potential, can be used for cell imaging, protein labeling, specific recognition of antibodies, nucleic acid labeling, DNA sequencing, preparation of reagents for specific recognition and photodynamic therapy of tumors and the like, and can be applied to the fields of biology and medicine.

Description

technical field [0001] The invention belongs to the field of fluorescent dyes, and relates to the synthesis of a new type of hemicyanine near-infrared fluorescent dyes and its application in biological dyeing. Background technique [0002] In recent years, fluorescent dyes have been widely used to label, detect, and quantify components in biological samples. The mechanism of action is mainly to attach fluorescent dyes to biological ligands, such as proteins, antibodies, on enzymes, nucleotides, nucleic acids, and other molecules. The dye-labeled ligand is generally specific, so as to ensure the specific recognition of the dye to the biological sample, so as to achieve the purpose of labeling and detection. [0003] Hemicyanine fluorescent dyes, as a kind of cyanine dyes, have been widely studied. Especially the xanthene type hemicyanine dyes, whose absorption and emission wavelengths are in the near-infrared region, can effectively avoid the interference of biological auto...

Claims

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Application Information

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IPC IPC(8): C09B23/10A61K41/00A61K49/00A61P35/00C07K1/13C09K11/06C12Q1/6869G01N21/64
CPCC09B23/105C09K11/06A61K41/0057A61P35/00A61K49/0032G01N21/6428G01N21/6456C07K1/13C12Q1/6869C09K2211/1044C09K2211/1033C09K2211/1088C09K2211/1029C12Q2563/107Y02E10/52
Inventor 杜健军王书鹏韩富平樊江莉彭孝军
Owner DALIAN UNIV OF TECH