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Preparation and application of viscosity near-infrared fluorescent probe

A fluorescent probe and near-infrared technology, applied in the field of fluorescent probes, can solve problems such as viscosity detection

Pending Publication Date: 2022-06-10
XIANGTAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, until now, there has been no detection of viscosity based on quinoline-xanthene dyes as fluorescent probes.

Method used

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  • Preparation and application of viscosity near-infrared fluorescent probe
  • Preparation and application of viscosity near-infrared fluorescent probe
  • Preparation and application of viscosity near-infrared fluorescent probe

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] Synthesis of Fluorescent Probes

[0028] Synthetic routes such as figure 1 . In a 25 mL round-bottom flask, 2-methyl-N-ethylquinoline (204 mg, 1.2 mmol) and diethylaminoxanthene (285 mg, 1 mmol) were dissolved in 10 mL of EtOH, purged with nitrogen, and evacuated . Under stirring conditions, 0.3 mL of piperidine was added, and the mixture was refluxed in an oil bath at 80 °C for 16 h. After completion of the reaction, the solvent was evaporated under reduced pressure. The obtained crude product was purified by column chromatography (dichloromethane:methanol=100:3) to obtain a blue solid QX-V, which was the fluorescent probe. (263 mg, 60% yield). 1 H NMR (400MHz, CDCl 3 ):δ8.63(d,J=9.4Hz,1H),8.56(d,J=9.3Hz,1H),8.52(d,J=14.2Hz,1H),7.81(d,J=8.0Hz,1H) ),7.78(d,J=8.9Hz,1H),7.67(t,J=8.8,Hz,1H),7.39(t,J=7.5Hz,1H),7.08(d,J=6.5Hz,1H) ,7.06(s,1H)6.83(s,1H),6.52(d,J=8.8,Hz,1H),6.22(d,J=14.2Hz,1H),4.76(q,J=7.3Hz,2H) ,3.58(q,J=7.1Hz,4H),2.53(t,J=7.5Hz,4H),1.83-1.75(m,2H),1....

Embodiment 2

[0030] Preparation and Viscosity Determination of Fluorescent Probes and Different Proportions of Glycerol Solutions

[0031] Preparation of probe solution: Weigh a certain amount of probe and dissolve it in dimethyl sulfoxide to make 1×10 -4 Stock solution for M. Add 1.0 mL of the probe's stock solution to a 10 mL volumetric flask, and make up to the volume with Tris-HCl buffer solution to obtain a concentration of 1.0 × 10 -5 mol / L of fluorescent probe solution. Prepare solutions with different proportions of glycerol in water (0, 30%, 40%, 50%, 60%, 70%, 80%, 85%, 90%, 95%), and rotate with the NDJ-1 pointer digital display The viscosity was measured by a viscometer, and the corresponding viscosities were obtained as 1cp, 2.5cp, 3.7cp, 5.4cp, 10.8cp, 30.5cp, 60.1cp, 109cp, 219cp, and 523cp, respectively.

Embodiment 3

[0033] Determination of Fluorescence Spectra of Fluorescent Probes in Solutions of Different Viscosity

[0034] figure 2 is the fluorescence spectrum of the fluorescent probe in different viscosity solutions, the concentration of the fluorescent probe is 10 μM, and the proportion of glycerol in the solution is 0, 30%, 40%, 50%, 60%, 70%, 80%, 85 %, 90%, 95%. The excitation wavelength used in the experiment was 710 nm, and the emission wavelength ranged from 700 to 900 nm. The slit width is 5.0 nm / 5.0 nm, and the fluorescence measuring instrument used is Hitachi F4600 fluorescence spectrophotometer. It can be seen from the figure that when the probe is in an aqueous solution, there is almost no emission peak; as the proportion of glycerol increases, that is, the viscosity of the solution increases, the fluorescence gradually increases. image 3 is the linear response plot of the probe to different logarithms of viscosity. The logarithmic value of fluorescence intensity and...

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Abstract

The invention relates to preparation and application of a near-infrared fluorescent probe for detecting cell viscosity. The structural formula of the probe is shown in the specification. The invention provides a preparation method for synthesizing the fluorescent probe by taking diethylaminoxanthene and quinoline as raw materials. The fluorescent probe is a viscosity type fluorescent probe with good water solubility and near infrared emission; firstly, the fluorescent probe shows better sensitivity to solutions with different viscosities, and the linear range is 2.5 cP to 523cP; secondly, the fluorescent probe shows very high selectivity on viscosity, and is not influenced by various other ions, active oxygen, biological mercaptan and amino acid; moreover, the fluorescence intensity of the fluorescent probe remains unchanged after 2 hours in a high-viscosity solution, which shows that the fluorescent probe has excellent optical stability; in addition, the fluorescent probe can also be applied to detection of viscosity of living cells.

Description

technical field [0001] The invention belongs to the technical field of fluorescent probes, in particular to the preparation and application of a viscosity near-infrared fluorescent probe. Background technique [0002] Viscosity controls the diffusion rate and biological activity of substances by affecting metabolic processes in the cellular microenvironment. Processes such as protein folding, enzymatic catalysis, and signaling are all dependent on viscosity. Abnormal viscosity can affect the activity of membrane-bound proteins, inhibit insulin synthesis, and cause mitochondrial swelling (Sun M, Wang T, Yang X, Yu H, Huang D. Facilemitochondria localized fluorescent probe for viscosity detection in living cells[J]. Talanta, 2021 , 225:121996.). At the same time, the increase in viscosity is related to the occurrence and development of diseases such as cellular malignancies, atherosclerosis, diabetes and Alzheimer's disease (Ren M, Kai Z, Li W, Liu K, Lin W. Construction of ...

Claims

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Application Information

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IPC IPC(8): C07D405/06C09K11/06G01N21/64G01N11/00
CPCC07D405/06C09K11/06G01N21/6428G01N11/00C09K2211/1029C09K2211/1088G01N2011/008
Inventor 李春艳钞静静徐芬
Owner XIANGTAN UNIV
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