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 molecu

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

Example Embodiment

[0066] Example 1

[0067] Synthesis of Compound Hcaz

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

[0069]

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

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

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

Example

[0084] Implementation 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] Pipette accurately measure 18 mL of dry DMF and place it in a 100 mL dry 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. An analytical balance accurately weighed N-ethylcarbazole (2.8 g, 14.3 mmol) and dissolved it in 40 mL of chlorobenzene, placed it in a constant pressure dropping funnel, and mounted the constant pressure dropping funnel. After 0.5 h, the solution of N-ethylcarbazole in chlorobenzene was slowly dropped into the single-necked flask, and the reaction was stirred for 60 h in an oil bath at 90-95 °C. After the reaction was completed, cooled, adjusted to neutral pH with 10% sodium bicarbonate solution, extracted with chloroform, dried over anhydrous sodium...

Example Embodiment

[0096] Example 3

[0097] Viscosity test for compounds Qcaz and Hcaz

[0098] The preparation concentration is 1×10 -3 The DMSO solutions of M compounds Qcaz and Hcaz, respectively, accurately measure 10 μL of the solutions and add them to 10 mL of glycerol-water solution, ultrasonicate for 10 minutes, remove air bubbles, and let stand for 1 hour. Absorption and emission spectra. The selected excitation wavelength was 330 nm. The instruments used are UV-Vis spectrophotometer, model: Hp8453; fluorescence spectrophotometer, model: FP-6500, and fluorescence lifetime tester: Horiba Jobin Yvon Fluoromax-4p. The excitation source of the two-photon excitation fluorescence spectrum is a mode-locked femtosecond Ti: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 水 They are 1:9, 2:8, 3:7, 4:6, 5:5, 6:4, 7:3, 8:2, 9:1 two-p...

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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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