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Two-photon viscosity fluorescence probe as well as preparation method and application thereof

A fluorescent probe and two-photon technology, applied in the direction of fluorescence/phosphorescence, chemical instruments and methods, luminescent materials, etc., can solve the problems of high cell phototoxicity, small excitation wavelength, fluorescence self-quenching, etc., and achieve high sensitivity and operation Simple and highly selective effect

Active Publication Date: 2016-07-27
ANHUI UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] At present, most of the fluorescent probes for detecting cell viscosity are still single-photon fluorescent probes. However, single-photon fluorescent probes have many disadvantages, such as: large autofluorescence interference, and small excitation wavelengths lead to high phototoxicity to cells. , prone to self-quenching of fluorescence, etc.

Method used

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  • Two-photon viscosity fluorescence probe as well as preparation method and application thereof
  • Two-photon viscosity fluorescence probe as well as preparation method and application thereof
  • Two-photon viscosity fluorescence probe as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] Embodiment 1: the synthesis of fluorescent probe molecule MCN

[0028] Dissolve 3.6g of compound 1, 1.24g of malononitrile and 0.38g of basic alumina in 40mL of dichloromethane, stir and react at room temperature for 4h, filter the mixture, spin the filtrate to remove the solvent to obtain a crude product, and then use column layer Chromatographic column separation (ethyl acetate / petroleum ether = 1 / 4 as eluent, v / v) gave 3.36 g (10.04 mmol, yield 80%) of the target product.

[0029] The structural formula of the compound 1 is:

[0030]

[0031] 1 HNMR (400MHz, DMSO): δ8.72(s, 1H), 8.59(d, J=8.5Hz, 1H), 8.29(s, 1H), 8.05(d, J=8.9Hz, 1H), 7.96(d ,J=8.8Hz,1H),7.88(d,J=8.5Hz,1H),7.59(d,J=8.6Hz,2H),7.04(d,J=8.6Hz,2H),3.82(s,3H ). 13 CNMR (100MHz, CDCl 3 ): δ160.38, 156.99, 148.44, 147.31, 136.87, 133.82, 133.44, 130.40, 130.07, 128.97, 125.50, 122.81, 114.59, 114.29, 113.69, 112.15, 93.67, 87.602

Embodiment 2

[0032] Example 2: Two-photon testing of fluorescent probe molecules

[0033] Dissolve the fluorescent probe of the present invention in DMSO to prepare a 1mM mother solution, take 150 μL of the mother solution in a 10mL volumetric flask, and then use glycerol / water mixed solutions of different volume ratios (the volume ratio of glycerol and water is 50:50 respectively) , 60:40, 70:30, 80:20, 90:10, 95:5, 99:1) to constant volume, and prepared to 15μM. The excitation wavelengths of the single-photon and two-photon fluorescent probes are 400nm and 800nm ​​respectively, and the fluorescence spectrum changes in the wavelength range of 420-780nm are detected.

[0034] Using two-photon testing technology, the two-photon absorption cross section of the fluorescent probe (MCN) was tested in different viscosity systems, from image 3 It can be seen that the maximum two-photon absorption cross section of the fluorescent probe molecule in glycerol is 400 GM, and the two-photon excitatio...

Embodiment 3

[0035] Example 3: Cytotoxicity Test

[0036] The MTT (3-(4,5-dimethylthiazole-2)-2,5-diphenyltetrazolium bromide) experiment was based on the reported articles to do some cytotoxicity tests. Add 0, 5, 10, 15, 20, 25 μM fluorescent probes to the same batch of cells respectively, the condition is at 37°C, containing 5% CO 2 According to the formula of cell viability: cell viability %=OD570 (sample) / OD570 (control group) × 100, the cell viability can be calculated ( Figure 4 ). from Figure 4 We can see that when the concentration is 15 μM, the survival rate of the cells is about 92%, which shows that the fluorescent probe of the present invention has no toxic effect on the cells, so it can be used to detect the viscosity in the cells.

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Abstract

The invention discloses a two-photon viscosity fluorescence probe as well as a preparation method and application thereof. With quinoline as parent, the two-photon viscosity fluorescence probe has a structure shown in the specification. The two-photon viscosity fluorescence probe disclosed by the invention realizes specific fluorescence signal response to viscosity. Cell toxicity tests indicate that the two-photon viscosity fluorescence probe rarely causes toxic and side effects on cells; and two-photon confocal fluorescence microscopy imaging experiments show that the two-photon viscosity fluorescence probe has good cell permeability to HeLa cells and can be adapted to intracellular viscosity detection.

Description

1. Technical field [0001] The invention relates to a two-photon viscosity fluorescent probe and its preparation method and application. 2. Background technology [0002] Viscosity is an important property in the microenvironment of the biological system. The change of the viscosity value in the cell can reflect the healthy state of the cell, or the viscosity is closely related to various diseases or physiological processes in the biological system, especially the change of the viscosity of the cytoplasm It is closely related to apoptosis. How to detect the viscosity in cells is of great significance to biological systems, and research in this area has aroused the interest of many scientists. [0003] Fluorescent probes have many advantages as a detection tool, such as: high sensitivity, easy operation, cheap and easy to obtain, and so on. The interaction between the detection object and the fluorescent probe can cause a change in the response of the fluorescent signal, the...

Claims

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Application Information

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IPC IPC(8): C07D215/14C09K11/06G01N21/64
CPCC07D215/14C09K11/06C09K2211/1029G01N21/6428
Inventor 孟祥明宁鹏余升龙岳平冯燕朱满洲
Owner ANHUI UNIVERSITY
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