Two-photon fluorescent probe for detecting polarity and viscosity through two channels as well as preparation method and application thereof

A two-photon fluorescence, two-channel technology, applied in chemical instruments and methods, fluorescence/phosphorescence, material analysis by optical means, etc., to achieve the effect of low cytotoxicity and good cell permeability

Active Publication Date: 2020-06-09
ANHUI UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0006] The present invention aims to provide a two-photon fluorescent probe for dual-channel detection of polarity and viscosity and its preparation method and application. The technical problem to be solved is to A suitable fluorescent probe structure is designed, which has the advantages of excellent tw

Method used

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  • Two-photon fluorescent probe for detecting polarity and viscosity through two channels as well as preparation method and application thereof
  • Two-photon fluorescent probe for detecting polarity and viscosity through two channels as well as preparation method and application thereof
  • Two-photon fluorescent probe for detecting polarity and viscosity through two channels as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] Embodiment 1: the synthesis of fluorescent probe molecule Mito-PV

[0027] 3-Hexyl-2-methylbenzothiazole iodide salt (0.32g, 0.9mmol) and 3-(4-fluorophenylethynyl)-6-formyl-N-ethylcarbazole (0.3g, 0.9 mmol) were mixed in 50 mL of absolute ethanol; the mixture was refluxed for 12 hours under nitrogen protection, then cooled, and the solvent was removed by rotary evaporation; ), and the solvent was evaporated under vacuum, and the residue was purified by column chromatography (dichloromethane:methanol=50:1 as eluent) to obtain 0.36 g (59%) of Mito-PV.

[0028] 1 H NMR (400MHz, DMSO-d 6,ppm): δ9.00(s,1H),8.43(dd,J=21.2,13.9Hz,3H),8.27(t,J=9.0Hz,2H),8.03(d,J=15.6Hz,1H) ,7.87(dd,J=8.1,4.9Hz,2H),7.81-7.72(m,3H),7.66 (dd,J=8.1,5.7Hz,2H),7.31(t,J=8.7Hz,2H), 4.97(t, J=7.0Hz, 2H), 4.56(m, J=6.8Hz, 2H), 1.88(dd, J=15.0, 7.7Hz, 2H), 1.46(dd, J=14.9, 7.2Hz, 2H ),1.40-1.24(m,7H),0.84(t,J=7.0 Hz,3H). 13 C NMR(100MHz,DMSO,ppm):δ171.75,160.61,150.62,142.64,141.22,140.07, 133.49,13...

Embodiment 2

[0029] Embodiment 2: the spectroscopic test of fluorescent probe molecule

[0030] Dissolve the two-photon fluorescent probe of the present invention in DMSO to prepare a 2mM mother solution, each take 15 μL of the mother solution in 3mL of different polar solvents, and obtain the ultraviolet absorption spectra of the probe Mito-PV in different solvents ( figure 1 left). Under the excitation of 360nm wavelength, its fluorescence intensity at 410nm decreases gradually with the increase of the polarity of the test system. The probe Mito-PV only has a strong fluorescence peak at 580nm in the glycerol solvent with higher viscosity. This shows that Mito-PV can be used to detect the polarity and viscosity of common solutions ( figure 1 right). In order to further demonstrate the dual response characteristics of the polarity and viscosity of the probe Mito-PV, the absorption and fluorescence spectra of Mito-PV were measured at 25 °C in mixed solvents with different proportions of ...

Embodiment 3

[0031] Example 3: Two-photon performance test of fluorescent probe molecules

[0032] Firstly, the effective two-photon absorption cross sections of Mito-PV in different polar mixed solvents of water and 1,4-dioxane (water content of 10%, 40% and 70%) were tested. The effective two-photon absorption cross section appears maximum at 720nm and gradually decreases from 88GM to 29GM with the increase of water content ( image 3 left). In Mito-PF in different mixed solvents of methanol and glycerin (glycerol content is 99%, 80% and 60% respectively), the effective two-photon absorption cross section appears maximum at 840nm and gradually decreases from 96GM to 48GM with the decrease of glycerol content ( image 3 right). The above demonstrates that Mito-PV is capable of two-photon bioimaging of intracellular polarity and viscosity.

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Abstract

The invention discloses a two-photon fluorescent probe for detecting polarity and viscosity through two channels as well as a preparation method and application thereof. The two-photon fluorescent probe can monitor the real-time change of polarity and viscosity in cell mitochondria in two different channels at the same time, and the structural formula of the two-photon fluorescent probe is shown in the specification. The two-photon fluorescent probe molecule can perform fluorescence response on polarity (short wave with the wave length of 410 nm) and viscosity (long wave with the wave length of 580 nm) at the same time by utilizing two different fluorescence bands. Furthermore, a cytotoxicity test shows that the probe has almost no toxic or side effect on cells; a two-photon confocal fluorescence microimaging experiment shows that the probe has good permeability to HeLa cells, can effectively locate mitochondria (the locating coefficient is 0.97) in the cells, and is suitable for two-channel two-photon fluorescence imaging and detection of polarity and viscosity in the cell mitochondria.

Description

technical field [0001] The invention relates to a two-photon fluorescent probe for dual-channel detection of polarity and viscosity and its preparation method and application, so as to realize dual-channel two-photon imaging and simultaneously detect changes in polarity and viscosity in cell mitochondria. It has the advantages of excellent two-photon absorption performance, high membrane permeability, low cytotoxicity, high photostability and biocompatibility. Background technique [0002] Cellular and subcellular organelle viscosity is an important microenvironmental parameter that exerts biological functions by affecting the interaction and transmission of biomolecular and chemical signals in living cells. Abnormal changes in cell viscosity are closely related to diseases such as diabetes, infarction, and hypertension. Cell polarity is the feedback of a complex set of mechanisms that establish and maintain specific domain function. Many cellular processes involving spati...

Claims

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Application Information

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IPC IPC(8): C09K11/06C07D417/06G01N21/64
CPCC09K11/06C07D417/06G01N21/6428C09K2211/1007C09K2211/1029C09K2211/1037
Inventor 冯燕孙川孟祥明汪旭东董坤
Owner ANHUI UNIVERSITY
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