Fluorescent probe for detecting viscosity, preparation method and application thereof

A fluorescent probe and viscosity technology, applied in fluorescence/phosphorescence, chemical instruments and methods, luminescent materials, etc., can solve the problems of limited penetration depth, unfavorable biological imaging, etc., and achieve improved detection sensitivity and large Stokes shift changes , the effect of rapid detection

Active Publication Date: 2022-04-22
CENT SOUTH UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] At present, there have been more studies on fluorescent probes, but most viscous fluorescent probes have short-wavelength fluorescence emission signals (<600nm), which have interference from cell autofluorescence in the blue-green region, and the penetration depth Limited, not good for bioimaging

Method used

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  • Fluorescent probe for detecting viscosity, preparation method and application thereof
  • Fluorescent probe for detecting viscosity, preparation method and application thereof
  • Fluorescent probe for detecting viscosity, preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0046] Synthesis of 3-ethyl-1,1,2-trimethyl-1H-benzo(E)indole

[0047] Weigh 1g (4.8mmol) of 1,1,2-trimethyl-1H-benzo(E)indole, add 463μL (5.8mmol, 1.2equiv) of ethyl iodide in 10mL of anhydrous acetonitrile, 85 Reflux at °C for 12 hours, cool to room temperature after the reaction, filter with suction and wash with anhydrous ether to obtain compound 1, compound 1 is 0.95 g of lavender solid, yield 83.2%. Compound 1 is 3-ethyl-1,1,2-trimethyl-1H-benzo(E)indole.

[0048] see figure 1, is the H NMR spectrum of compound 1 in the preparation method of the fluorescent probe. The results of NMR test are as follows: 1H NMR (400MHz, CDCl3) δ8.24–7.57 (m, 6H), 4.84 (d, J = 6.2Hz, 2H), 3.22 (s, 3H), 1.86 (s, 7H), 1.68(s,3H).

Embodiment 2

[0050] Synthesis of fluorescent probes

[0051] Take 0.36g (1mmol) of N-[(3-(anilino methylene)-2-chloro-1-cyclohexen-1-yl) methylene] aniline hydrochloride, 0.24g (1mmol) 3-Ethyl-1,1,2-trimethyl-1H-benzo(E)indole, 81 mg (1 mmol) of anhydrous sodium acetate, dissolved in 15 mL of ultra-dry ethanol, set the oil bath temperature to 80°C, and reflux 8h, after the reaction was completed, cooled to room temperature, neutralized with phosphate buffer solution, extracted with dichloromethane several times to obtain an organic phase (purple), then dried with anhydrous magnesium sulfate, concentrated and separated by silica gel column chromatography, developed The solvent was methanol / dichloromethane (volume ratio 1:200) to obtain 61.8 mg of green solid compound 2 with a yield of 13%.

[0052] Please refer to figure 2 , is the H NMR spectrum of compound 2 in the preparation method of the fluorescent probe. The results of NMR test are as follows: 1H NMR (400MHz, DMSO) δ8.74(s, 1H), ...

Embodiment 3

[0060] In order to explore the response of fluorescent probe P-1 to different solvent polarities, at a concentration of 1×10 -5 Under the condition of mol / L, the fluorescent probe P-1 was tested in dichloromethane (CH 2 Cl 2 ), methanol (MeOH), ethanol (EtOH), acetonitrile (Acetonitrile), N,N-dimethylformamide (DMF), dimethyl sulfoxide (DMSO) in six different solvents UV-Vis absorption spectra and Changes in the fluorescence emission spectrum.

[0061] Please refer to Figure 4 , are the ultraviolet absorption spectra of the fluorescent probe P-1 in different solvents. Depend on Figure 4 It can be seen that the absorption peaks of ultraviolet in different solvents are between 640 and 670, so 650nm is selected as the excitation wavelength, and 10×10cm is used as the slit width. -5 mol / L The fluorescence emission of fluorescent probes in six different solvents was tested respectively. Please refer to Figure 5 , is the fluorescence emission spectrum of fluorescent probe ...

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Abstract

The invention discloses a fluorescent probe for detecting viscosity. Its structural formula is as follows: it has long-wave emission performance and large Stokes shift characteristics, so that the overlap between absorption and emission spectra is small, and the fluorescence efficiency caused by energy transfer can be avoided. Reduce and improve detection sensitivity; it can have a strong penetration depth in the process of imaging biological systems, and can effectively eliminate the interference of cell autofluorescence, low toxicity to cells, and has broad application prospects in the field of biomolecular detection . The invention also provides a preparation method and application of a fluorescent probe for detecting viscosity, and the fluorescent probe for detecting viscosity can be used for viscosity measurement in a solution system or a biological system.

Description

technical field [0001] The invention relates to the technical field of organic small molecule fluorescent probes, in particular to a fluorescent probe for detecting viscosity and its preparation method and application, in particular to a long-wave emission fluorescent probe for detecting viscosity and its preparation method and application. Background technique [0002] The flow characteristics of organisms make viscosity a very important microenvironmental parameter in biological systems. Viscosity plays a very important role in physiological processes such as material transport and signal transmission in organisms. Abnormal viscosity at the cellular level is associated with many diseases, such as Alzheimer's disease, atherosclerosis, tumors, etc. However, the traditional methods of measuring viscosity, such as rotational viscometer and capillary viscometer, can only test the biological environment under macroscopic conditions, but cannot measure the viscosity change in the...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C09K11/06C07D417/08G01N11/00G01N21/64
CPCC09K11/06C07D417/08G01N11/00G01N21/6428G01N21/643C09K2211/1029C09K2211/1007C09K2211/1037G01N2011/008
Inventor 唐瑞仁孔素娜
Owner CENT SOUTH UNIV
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