A fluorescent probe for detecting viscosity and hydrogen peroxide, its synthesis method and application

A fluorescent molecular probe and structural formula technology, applied in the field of chemical analysis and detection, can solve the problems of unfavorable biological sample detection, weak photobiological penetration ability, biological damage, unfavorable and other problems, and achieve good stability and optical properties, high sensitivity, fast response effect

Active Publication Date: 2021-11-02
SHANGQIU NORMAL UNIVERSITY
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, fluorescent probes that can be used for viscosity and hydrogen peroxide detection at the same time are rarely reported.
However, most of the reported fluorescent probe molecules do not have emission wavelengths in the near-infrared region or the Stokes shift value of the probe is small (Ren M, Analytical Chemistry, 2017, 89, 552; Chan J, Nature Chemistry, 2012, 4, 973. ), due to the weak bio-penetration ability and biological damage of shorter wavelength bands, and the small Stokes shift value will bring interference to the excitation light, so this type of probe molecule is not conducive to the elimination of complex sample background interference , which is not conducive to the detection of complex environmental samples and biological samples

Method used

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  • A fluorescent probe for detecting viscosity and hydrogen peroxide, its synthesis method and application
  • A fluorescent probe for detecting viscosity and hydrogen peroxide, its synthesis method and application
  • A fluorescent probe for detecting viscosity and hydrogen peroxide, its synthesis method and application

Examples

Experimental program
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Effect test

Embodiment 1

[0038] Example 1: Synthesis of Fluorescent Molecular Probes

[0039]Dissolve the benzothiazole (0.1746g, 0.6490mmol) of compound 2 and the 4-methylpyridinium salt (0.200g, 0.6493mmol) substituted by compound 3 methylene benzene boronic acid in 30mL ethanol, add 0.5mL piper Pyridine, reflux at 80°C for 12h. After the reaction, the solvent was distilled off under reduced pressure, then dissolved in dichloromethane and methanol, purified by column chromatography, and finally 0.304 g of near-red solid powder was obtained (yield: 83.74%). The product structural formula is as follows:

[0040]

[0041] 1 H NMR(400MHz,DMSO):δ8.66(s,2H),8.54–8.39(m,2H),8.13–8.03(m,2H),7.94(s,4H),7.82(s,2H),7.44 (s,4H),7.23(s,3H),5.58(s,2H),2.22(s,3H).MS:m / z,Theoretical value:[M-Br] - 479.16; Calculated: 478.95.

Embodiment 2

[0042] Example 2: Fluorescent detection of probes for viscosity

[0043] The molecular probe prepared above was dissolved in a mixed solution of glycerol and dimethyl sulfoxide in different proportions to prepare a 10 μmol L -1 probe solution. Test its fluorescence spectrum, the results are as follows figure 2 shown. The logarithm of the logarithm of the fluorescence emission intensity of the solution at 680nm is plotted against the logarithm of the viscosity, and when the viscosity is in the range of 96.58cp to 568.88cp, there is a good linear relationship between the two ( image 3 ), can realize the quantitative detection of the viscosity in this range.

Embodiment 3

[0044] Embodiment 3: Fluorescent detection of probes to hydrogen peroxide

[0045] The molecular probe prepared above was dissolved in a phosphate buffered solution of water and dimethyl sulfoxide (H 2 O / DMSO=1 / 1, v / v, 10mM, pH 7.4), prepared to 10μmol L -1 probe solution. Add 2 mL of prepared 10 μmol L to a 3 mL cuvette -1 Probe solution of the present invention, and then add different concentrations of hydrogen peroxide to mix uniformly, test its fluorescence spectrum, the results are as follows Figure 5 shown. The fluorescence emission intensity of the solution at 590nm is plotted against the concentration of hydrogen peroxide, and the concentration of hydrogen peroxide is 0–25 μmol L -1 In the range, there is a good linear relationship between the two ( Figure 6 ), the quantitative detection of hydrogen peroxide in this concentration range can be realized, and the solution changes from red to yellow, which is also suitable for naked eye detection. And this probe is...

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Abstract

The invention discloses a fluorescent probe for detecting viscosity and hydrogen peroxide, a synthesis method and an application thereof, and belongs to the technical field of chemical analysis and detection. The probe of the present invention is obtained by the coupling reaction of aldylated benzothiazole and 4-picoline salt substituted by methylene phenylboronic acid, and has the following structure: due to the quenching effect of distorted intramolecular charge transfer (TICT), The probe molecule has almost no fluorescence emission characteristics; however, as the viscosity of the environment system increases, the TICT effect is suppressed, and the probe molecule presents a strong fluorescence emission with an emission peak at 680 nm. In addition, the probe can also detect H 2 o 2 Produces a sensitive fluorescence response, and the position of the emission peak is at 590 nm after the reaction. The concentration range for detection of hydrogen peroxide is 0–25 μmol L ‑1 , with a detection limit of 0.34 μmol L ‑1 . The probe can be used in water and intracellular H 2 o 2 detection.

Description

technical field [0001] The invention belongs to the technical field of chemical analysis and detection, and in particular relates to a long-wavelength turn-on fluorescent probe for detecting viscosity and hydrogen peroxide and its combination method and application. Background technique [0002] Hydrogen peroxide (H 2 o 2 ) is an important physiologically active oxygen molecule, and studies have shown that abnormal levels of hydrogen peroxide are associated with various diseases, such as inflammatory diseases, cardiovascular diseases, neurodegenerative diseases and cancer. On the other hand, viscosity is an important index parameter for the normal operation of cells, which can reflect the signal transduction of biomolecules in cells, the transportation of nutrients and metabolic waste. Changes in cell viscosity and abnormal levels of hydrogen peroxide have also been linked to a number of diseases. Therefore, the development of a simple and reliable method to realize the s...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F5/02C09K11/06G01N21/64
CPCC07F5/025C09K11/06C09K2211/1007C09K2211/1029C09K2211/1037G01N21/6428G01N21/643
Inventor 郝远强朱单单瞿鹏徐茂田
Owner SHANGQIU NORMAL UNIVERSITY
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