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Carbazole-based two-photon viscosity fluorescence probe as well as preparation method and application thereof

A fluorescent probe and two-photon technology, applied in fluorescence/phosphorescence, chemical instruments and methods, luminescent materials, etc., to achieve the effects of simple structure, increased permeability, and easy synthesis

Active Publication Date: 2018-09-04
ANHUI UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Currently, there are relatively few reports on mitochondria-targeted two-photon viscosity probes using carbazole as a fluorophore.

Method used

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  • Carbazole-based two-photon viscosity fluorescence probe as well as preparation method and application thereof
  • Carbazole-based two-photon viscosity fluorescence probe as well as preparation method and application thereof
  • Carbazole-based two-photon viscosity fluorescence probe as well as preparation method and application thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] Embodiment 1: the synthesis of intermediate MC

[0029] 3-iodo-6-formyl-N-ethylcarbazole (1.048g, 3mmol), cuprous iodide (0.029g, 0.15mmol), triphenylphosphine palladium dichloride (0.063g, 0.09mmol) Add it into a Schneck bottle, fill and discharge argon three times, then add an appropriate amount of solvent tetrahydrofuran (THF) and triethylamine (6mL) with a syringe, stir for 30 minutes at room temperature, and then inject 4-methoxyphenylacetylene (0.4757 g, 3.6mmol) THF solution, and reacted at 45°C for 1 day. After the reaction was finished, cool to room temperature, and use filter paper to remove excess salt from the reaction solution. The filtrate was placed in a round-bottomed flask, and rotary evaporation removed THF and a small amount of triethylamine. Sample preparation was separated by silica gel column chromatography (elution The liquid is petroleum ether: ethyl acetate=20:1 (v / v)) to obtain 0.6574 g of the target product. Yield 62%. 1 HNMR (400MHz, CDCl ...

Embodiment 2

[0030] Embodiment 2: the synthesis of fluorescent probe molecule MCB

[0031] Add 3-p-methoxyphenylethynyl-6-formyl-N-ethylcarbazole (0.3534g, 1mmol) into a 100mL round bottom flask, add 15mL of ethanol, heat and stir until the raw materials are dissolved, then add 2, 3-Dimethylbenzothiazol-3-ium iodide (0.2911 g, 1 mmol) was added dropwise with 2-3 drops of piperidine, and refluxed at 80° C. overnight. Stand to cool, separate layers and filter to obtain a red crude product, prepare a sample, and separate by silica gel column chromatography (eluent: dichloromethane: methanol = 100:1 (v / v)) to obtain 0.5012 g of the target product. Yield 80%. 1 H NMR (400MHz, DMSO-d 6 , ppm): δ9.04(s, 1H), 8.44(t, J=12.8Hz, 2H), 8.37(s, 1H), 8.22(t, J=17.6Hz, 2H), 8.07(d, J= 15.6Hz, 1H), 7.87(t, J=12.0Hz, 2H), 7.79(dd, J=8.0Hz, 2H), 7.71(d, J=8.8Hz, 1H), 7.54(d, J=8.4Hz ,2H),7.03(d,J=8.8Hz,2H),4.55(dd,J=14.6Hz,2H),4.38(s,3H),3.82(s,3H),1.40(t,J=14.2Hz ,3H). 13 C NMR (400MHz, DMSO-d 6 ,pp...

Embodiment 3

[0032] Embodiment 3: the spectroscopic test of fluorescent probe molecule

[0033] Dissolve the two-photon fluorescent probe of the present invention in DMSO to prepare a 2mM mother solution, prepare 5mL, take a 15μM mother solution in a 3mL sample tube, prepare a detection solution of 10μM, and excite at a wavelength of 480nm in various organic solvents. The fluorescence emission peak (at 566nm) intensity in glycerol was significantly enhanced, and its emission peak intensity had no significant change in other solvents ( figure 1 ). In order to illustrate the response of the probe molecule to the viscosity, the fluorescence spectrum under different ratios of methanol-glycerol (v / v) was tested: the fluorescence intensity at 566nm increases with the increase of the glycerol volume ratio, and the fluorescence of the probe MCB increases, and The fluorescence intensity and the viscosity value have a certain linear relationship ( figure 2 and image 3 ). In addition, in order ...

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PUM

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Abstract

The invention discloses a carbazole-based two-photon viscosity fluorescence probe as well as a preparation method and application thereof. The two-photon viscosity fluorescence probe takes carbazole as a matrix, and the structural formula is as follows: as shown in the specification. The two-photon viscosity fluorescence probe aims at different organic solvent systems, and only in a viscosity solvent (glycerin), the fluorescence is obviously enhanced. Through the adjustment of the ratio of methanol to glycerin and changing of the system viscosity, tests show that the viscosity fluorescence probe has a good linear relation with viscosity response. Cytotoxicity tests indicate that the probe has hardly any toxic and side effect on cell, and two-photon confocal fluorescence microscopic imagingexperiments indicate that the probe has good permeability for cytomembrane and can be applied to the qualitative detection of viscosity change in mitochondria.

Description

technical field [0001] The invention relates to a carbazole-based two-photon viscosity fluorescent probe and its preparation method and application, so as to realize the qualitative detection of the viscosity in cell mitochondria by two-photon confocal imaging. The probe has the advantages of large conjugated system and two-photon absorption cross section, sensitive and specific response to viscosity, low cytotoxicity and good biocompatibility. Background technique [0002] Cell viscosity is an important indicator of whether a cell is normal or not. Cell viscosity affects the transport of substances in the cell, the transmission of signals, the interaction between macromolecules such as proteins, nucleic acids, and polysaccharides, and the diffusion of various active metabolites (such as reactive oxygen species ROS and reactive nitrogen species RNS) in the cell. Viscosity can control the transfer rate between different substances in life activities and the transfer of subst...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D417/06C09K11/06G01N21/64
CPCC07D417/06C09K11/06C09K2211/1007C09K2211/1029C09K2211/1037G01N21/6486
Inventor 冯燕方国顺王文娟张佳琪孙澍钰张成宇连冲
Owner ANHUI UNIVERSITY
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