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Carbazole hemicyanine fluorescent dye and application thereof

A fluorescent dye, carbazole-based technology, applied in the field of carbazole-based semicyanine fluorescent dyes

Active Publication Date: 2012-10-31
DALIAN UNIV OF TECH +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, there has been no literature report so far that carbazole-based hemicyanine dyes are used to design molecular rotors sensitive to environmental viscosity to detect the viscosity of solutions or intracellular environments.

Method used

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  • Carbazole hemicyanine fluorescent dye and application thereof
  • Carbazole hemicyanine fluorescent dye and application thereof
  • Carbazole hemicyanine fluorescent dye and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0067] Synthesis of Compound Hcaz

[0068] The synthesis flow method of compound Hcaz is as follows:

[0069]

[0070] (1) The synthesis of 2,3,3-trimethyl-3H-indoline (compound 1) follows the fisher indole synthesis method:

[0071] Weigh 54g (0.5mol) of phenylhydrazine and add it to a 250mL two-necked bottle, slowly add 43g (0.5mol) of 3-methyl-2-butanone dropwise under stirring, heat to 70~80°C, react for 4 hours, and separate to remove the water layer , the aqueous layer was extracted with ether, combined with the ether layer, dried and filtered with anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure to obtain 70 g of crude hydrazone with a yield of 80%.

[0072] Mix 70g (0.4mol) of the crude hydrazone from the previous step with 150mL of glacial acetic acid, react in an oil bath at 90°C for 3 hours, cool to room temperature, neutralize the water layer with saturated aqueous sodium carbonate solution until neutral, separate the water ...

Embodiment 2

[0085] Synthesis of Compound Qcaz

[0086] The synthetic method of compound Qcaz is as follows:

[0087]

[0088] (1) Synthesis of N-ethyl-3,6-dialdehyde carbazole (compound 5):

[0089] Accurately measure 18 mL of dry DMF with a pipette and place it in a dry 100 mL single-necked flask, place the single-necked flask in an ice-water bath, and drop 15 mL of phosphorus oxychloride into the single-necked flask. Analytical balance Accurately weigh N-ethylcarbazole (2.8g, 14.3mmol) dissolved in 40mL of chlorobenzene, place in a constant pressure dropping funnel, and install a constant pressure dropping funnel. After 0.5h, the chlorobenzene solution of N-ethylcarbazole was slowly dropped into a one-necked flask, and stirred and reacted in an oil bath at 90~95°C for 60h. After the reaction was completed, cool, adjust the pH to neutral with 10% sodium bicarbonate solution, extract with chloroform, dry with anhydrous sodium sulfate, remove the solvent under reduced pressure, and recr...

Embodiment 3

[0097] Viscosity test of compounds Qcaz and Hcaz

[0098] The preparation concentration is 1×10 -3 The DMSO solution of the compounds Qcaz and Hcaz of M, accurately measure 10 μL of the solution and add it to 10mL glycerol-water solution, ultrasonic for 10 minutes, remove the air bubbles and let it stand for 1 hour, and measure it on the ultraviolet spectrophotometer and fluorescence photometer. Absorption and emission spectra. The excitation wavelength chosen was 330 nm. The instruments used are ultraviolet-visible spectrophotometer, model: Hp8453; fluorescence spectrophotometer, model: FP-6500, fluorescence lifetime tester: Horiba Jobin Yvon Fluoromax-4p. The excitation source of the two-photon excitation fluorescence spectrum is a mode-locked femtosecond titanium sapphire exciter, and the fluorescence detection is detected by a Leica confocal microscope fluorescence detection system.

[0099] Wherein, the glycerol-ethanol solution includes glycerol, ethanol and V 甘油 :V ...

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Abstract

The invention relates to a carbazole hemicyanine fluorescent dye and application thereof. The carbazole hemicyanine fluorescent dye has a structural general formula I, in which R1 and R2 are independently slected from hydrogen and C1-6 alkyl, C1-6 hydroxy instead of alkyl and C1-6 alkoxy; R3 is H or a formaldehyde radical; and Y is a halogen negative ion. The dye provided by the invention has sensitive response to the change of environment viscosity, the influence on the fluorescent property caused by solvent polarities is very little, and the dye has a two-photon property and can detect the environment viscosity by a ratio method. Therefore, the dye provided by the invention can be used for detecting the change of microenvironment viscosity of cells and tissues.

Description

technical field [0001] The invention relates to a class of carbazole-based semicyanine fluorescent dyes and a method for using the fluorescent dyes as viscosity-sensitive fluorescent probes to detect the viscosity of the microenvironment in living cells. Background technique [0002] Viscosity is the main factor to measure the fluidity and diffusibility of a thick fluid, and it is also the main reference index of the fluid diffusion rate. For viscous fluids with large macroscopic volumes, the methods and instruments for measuring fluid viscosity have been developed relatively maturely. For the determination of microenvironment, such as viscosity at tissue and cell levels, the existing methods often cannot achieve the purpose of testing. It is of great significance to accurately measure the viscosity of the microenvironment at the cellular level. [0003] In cells, viscosity affects the transmission of substances and signals, the interactions between biomacromolecules, and ...

Claims

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Application Information

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IPC IPC(8): C09B23/10C09K11/06G01N11/00C12Q1/02
Inventor 彭孝军刘飞樊江莉王静云吴彤
Owner DALIAN UNIV OF TECH
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