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Fluorescence probe for double-channel detection of viscosity and hydrogen peroxide as well as preparation and application of fluorescence probe

A hydrogen peroxide and fluorescent probe technology, applied in the field of fluorescent probes, can solve problems such as limitations, and achieve the effects of improving sensitivity, avoiding spectral interference, and simple detection methods

Active Publication Date: 2021-03-19
SHANXI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, limited disease models limit our understanding of viscosity and H 2 o 2 In-depth understanding of the internal relationship between blood levels and related diseases

Method used

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  • Fluorescence probe for double-channel detection of viscosity and hydrogen peroxide as well as preparation and application of fluorescence probe
  • Fluorescence probe for double-channel detection of viscosity and hydrogen peroxide as well as preparation and application of fluorescence probe
  • Fluorescence probe for double-channel detection of viscosity and hydrogen peroxide as well as preparation and application of fluorescence probe

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0052] Preparation and characterization of a fluorescent probe for dual-channel detection of viscosity and hydrogen peroxide:

[0053]

[0054] (1) 4-bromo-N, N-diphenylaniline (810mg, 2.5mmol) and Pd(dppf)Cl 2 (183mg, 0.25mmol) was dissolved in anhydrous THF (35mL), then added K 2 CO 3 / H 2 O (2.07g, 15mmol / 25mL). The reaction mixture was stirred at reflux under argon for 1 hour. Then (5-formylthiophen-2-yl)boronic acid (780 mg, 5.0 mmol) dissolved in anhydrous tetrahydrofuran (15 mL) was slowly added to the reaction solution, and the reaction mixture was stirred at 80° C. for 12 h. Cool to room temperature, concentrate the solvent in vacuo, and purify by silica gel column chromatography (petroleum ether / ethyl acetate, 50:1, v / v) to obtain a yellow solid, compound 2 (899 mg, yield 79%). 1 H NMR (400MHz, CDCl 3 ):δ9.85(s,1H),7.69(d,J=4.0Hz,1H),7.51(d,J=8.8Hz,2H),7.30–7.20(m,5H),7.17–7.11(m, 4H), 7.11–7.03 (m, 4H).

[0055] (2) t-BuOK (138mg, 1.23mmol) and mono(4-(((...

Embodiment 2

[0058] Aggregation-induced fluorescence emission characteristics of fluorescent probe Mito-TPB in ethanol / n-hexane mixed solvent

[0059] The fluorescence probe in embodiment 1 is diluted to final concentration with ethanol / n-hexane mixed solvent to be 5 μ mol / L, and fixed excitation wavelength is 480nm, and the fluorescence emission spectrum ( Figure 4 ), and draw the curve of the fluorescence intensity of the probe changing with the volume content of n-hexane in the ethanol / n-hexane mixed system ( Figure 5 ). As the volume content of n-hexane increased from 0% to 95%, the fluorescence intensity at 695nm gradually increased and blue-shifted to 655nm, and reached the maximum when the volume content of n-hexane was 90%, indicating that the probe had typical aggregation-induced luminescence characteristics .

Embodiment 3

[0061] Fluorescent Response Characteristics of Fluorescent Probe Mito-TPB to Viscosity in Methanol / Glycerol Mixed Solvent

[0062] Dilute the probe in Example 1 to a final concentration of 5 μmol / L with methanol / glycerin mixed solvent, and the fixed excitation wavelength is 488nm, and record the fluorescence emission spectrum ( Figure 6 ), and plot the fluorescence intensity value of the probe at 666nm (log I 666 ), a linear relationship diagram ( Figure 7 ). As the volume ratio of glycerol increases from 0% (0.59cP) to 99% (950cP), the near-infrared fluorescence emission at 666nm increases sequentially, indicating that the probe can achieve highly sensitive detection of environmental viscosity.

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Abstract

The invention discloses a fluorescent probe Mito-TPB for double-channel detection of viscosity and hydrogen peroxide, as well as preparation and application of the fluorescent probe Mito-TPB, and belongs to the technical field of fluorescent probes. The fluorescent probe Mito-TPB for double-channel detection of viscosity and hydrogen peroxide provided by the invention has aggregation-induced emission characteristics, can be used as a detection reagent for simultaneous detection of viscosity and H2O2 change in an inflammatory cell model or a tumor tissue model, and realizes a simple and sensitive detection means.

Description

technical field [0001] The invention belongs to the technical field of fluorescent probes, and in particular relates to a dual-channel fluorescent probe for detecting viscosity and hydrogen peroxide, as well as its preparation and application. Background technique [0002] Cell viscosity, as an important microenvironmental parameter, plays a crucial role in many diffusion-mediated biological processes, such as signal transport and electron transport, etc. Mitochondria are considered to be the energy factories of cells and are closely related to cell vitality and physiological activities. Abnormal changes in viscosity can lead to mutations in the mitochondrial network organization, which in turn affects the diffusion of mitochondrial metabolites, eventually leading to inflammation, diabetes, neurodegenerative diseases, and even cancer. [0003] Hydrogen peroxide (H 2 o 2 ) is a physiologically active oxygen molecule mainly produced in mitochondria, which plays a regulatory...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F5/02C09K11/06G01N21/64
CPCC07F5/025C09K11/06C09K2211/1014C09K2211/1029C09K2211/1092G01N21/6428G01N21/643G01N2021/6432
Inventor 樊丽暂琪张跃伟
Owner SHANXI UNIV
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