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Preparation and application of viscosity fluorescent probe based on isophorone-cinnamyl aldehyde

A technology of isophorone and fluorescent probe, applied in the field of fluorescent probe, can solve the problems of high background fluorescence and short emission wavelength, etc.

Active Publication Date: 2021-10-29
XIANGTAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, most fluorescent materials still have limitations such as short emission wavelength and high background fluorescence.

Method used

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  • Preparation and application of viscosity fluorescent probe based on isophorone-cinnamyl aldehyde
  • Preparation and application of viscosity fluorescent probe based on isophorone-cinnamyl aldehyde
  • Preparation and application of viscosity fluorescent probe based on isophorone-cinnamyl aldehyde

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] Synthesis of fluorescent probes

[0025] Synthetic route such as figure 1 . Synthesis of malononitrile-isophorone: Add 15mL of absolute ethanol to a 50mL round bottom flask, then add isophorone (0.95g, 6.9mmol) and malononitrile (0.45g, 6.9mmol) The round bottom flask was mixed, and finally 10 μL of piperidine was added, stirred and refluxed at 60 ° C for 12 h, and the reaction process was performed with N 2 Protect. After the reaction, cool to room temperature, then pour the mixture into a beaker with 80 g of ice water, and a brownish-yellow solid precipitates out. After standing for 1 hour, it is suction-filtered and dried to obtain a crude product, which is then recrystallized with n-heptane and dried by suction. , to obtain 0.77 g of yellow-brown compound (yield 60%).

[0026] Synthesis of fluorescent probe (IC-V): 15 mL of absolute ethanol was added to a 50 mL round-bottomed flask, and compound 1 (27.9 mg, 0.15 mmol) and 4-(dimethylamino) cinnamaldehyde (26.2 m...

Embodiment 2

[0028] Preparation of Fluorescent Probes and Different Viscosity Solutions

[0029] Preparation of probe solution: Weigh a certain amount of probe and dissolve it in dimethyl sulfoxide to make 1×10 -4 M probe solution. Preparation of solutions with different viscosities: Add 1mL of probe solution to a 10mL volumetric flask, and then add different percentages of glycerol (Gly) respectively, and then use buffer solution to constant volume to obtain a concentration of 1.0×10- 5 mol L -1 The fluorescent probes and glycerol of different viscosities were mixed with the solution to be tested.

Embodiment 3

[0031] Measurement of Fluorescence Spectra of Fluorescent Probes Interacting with Solutions of Different Viscosities

[0032] figure 2 Fluorescence spectra of fluorescent probes interacting with solutions of different viscosities, the concentration of fluorescent probes is 10 μM, and the concentrations of glycerol (Gly) are: 0, 10%, 20%, 30%, 40%, 50%, 60%, 70% , 80%, 90%, 99%, the corresponding viscosities are 1.05, 1.29, 1.71, 2.37, 3.44, 5.56, 9.02, 17.43, 40.13, 121.91, 545.03cp. The excitation wavelength is fixed at 530nm, and the emission wavelength range is 550-900nm. The slit width is 5.0 nm / 5.0 nm, and the fluorescence measurement instrument used is a Hitachi F4600 fluorescence spectrophotometer. From figure 2 It can be seen that the fluorescent probe itself has no obvious near-infrared emission peak at near-infrared (700nm); after adding glycerol solution, an obvious near-infrared emission peak appears at 700nm. This is because the probe follows the TICT mechan...

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Abstract

The invention relates to preparation and application of a viscosity fluorescent probe based on isophorone-cinnamyl aldehyde. The structural formula of the fluorescent probe is as shown in the specification. The invention provides a preparation method for synthesizing the fluorescent probe by taking isophorone, malononitrile, 4-(dimethylamino)cinnamal and the like as raw materials. The fluorescent probe is a near-infrared viscosity fluorescent probe. Firstly, the fluorescent probe shows very high sensitivity to viscosity, and as the viscosity is increased, fluorescence intensity is remarkably enhanced; secondly, the fluorescent probe shows very high selectivity on viscosity, and is not interfered by other active oxygen, active nitrogen, active sulfur and biological mercaptan; moreover, the fluorescent probe has better light stability, and the fluorescence intensity is not changed under continuous illumination for 120 minutes; and in addition, the fluorescent probe is applied to the detection of viscosity in living cells.

Description

technical field [0001] The invention belongs to the technical field of fluorescent probes, in particular to the preparation and application of isophorone-cinnamaldehyde-based viscosity fluorescent probes. Background technique [0002] Viscosity is an important microenvironmental parameter in biological systems, and plays an important role in signal transmission, electron transfer, and interactions between biomolecules (R.Kotani, H.Sotome, H.Okajima, S.Yokoyama, Y.Nakaike, A. Kashiwagi, J. Mater. Chem. C, 2017, 5, 5248-5256; E. Schenborn, D. Groskreutz, Mol. Biotechnol., 1999, 13, 29-44). Abnormal intracellular viscosity may disrupt cell function and lead to various diseases. Studies have shown that viscosity changes are closely related to hypertension, atherosclerosis, Alzheimer's disease, diabetes and other diseases (M.Kuimova, S.Botchway, A.Parker, M.Balaz, H.Colins, H. Anderson, Nature Chem, 2009, 1, 69-73; G.S. Zubenko, U. Kopp, T. Seto, L.L. Firestone, Psychopharmacol...

Claims

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Application Information

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IPC IPC(8): C07C255/30C07C253/30C09K11/06G01N21/64
CPCC07C255/30C09K11/06G01N21/6428C09K2211/1007Y02P20/55
Inventor 李春艳廖沁婷徐芬
Owner XIANGTAN UNIV
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