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Fluorescent probe for detecting active oxygen molecules , preparation method and application thereof

Pending Publication Date: 2021-10-22
THE HONG KONG POLYTECHNIC UNIV SHENZHEN RES INST
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] In view of the above deficiencies in the prior art, the purpose of the present invention is to provide a fluorescent probe for detecting active oxygen molecules and its preparation method and application, aiming at solving the lack of fluorescent probes for detecting active small molecules at the subcellular level in the prior art. needle problem

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  • Fluorescent probe for detecting active oxygen molecules , preparation method and application thereof
  • Fluorescent probe for detecting active oxygen molecules , preparation method and application thereof
  • Fluorescent probe for detecting active oxygen molecules , preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0047] Embodiment 1: the synthesis of fluorescent probe I

[0048] The synthetic route of fluorescent probe I is as follows:

[0049]

[0050] The preparation method of fluorescent probe I comprises the steps:

[0051] (1) Under nitrogen protection, add 4-iodophenylboronic acid (1.2g, 5.0mmol), pinacol (0.59g, 5.0mmol) and magnesium sulfate (10g) in ether (25mL), and react after stirring for 2 hours , the resulting mixture was filtered through celite, and the volatiles were removed under reduced pressure. 4-iodophenylboronic acid pinacid (1.5 g, 89%) was obtained by silica gel column chromatography (n-hexane: ether=10:1, volume ratio);

[0052] (2) Pd(PPh 3 ) 2 Cl 2 (28 mg, 0.040mmol) and cuprous iodide (15mg, 0.080mmol). The flask was evacuated and backfilled with nitrogen. Tetrahydrofuran (6 mL) was added to the flask. The flask was cooled to 0 °C by an ice-water bath. Triethylamine (0.30 g, 3.0 mmol), 4-iodophenylboronic acid pinacid (0.70 g, 2.1 mmol) and silic...

Embodiment 2

[0058] Embodiment 2: the optical property of fluorescent probe I

[0059] The fluorescent probe I synthesized according to the above experimental steps was excited in the violet-visible light band and emitted blue fluorescence. Quantum yield Φ is calculated as follows:

[0060]

[0061] Fluorescein is used as the standard (Φ=0.95in 0.1N NaOH solution).

[0062] Specific optical parameters, including maximum absorption wavelength, maximum emission wavelength, Stokes shift and quantum yield are shown in Table 1 below.

[0063] Table 1. Optical properties of fluorescent probe I

[0064]

Embodiment 3

[0065] Example 3: Fluorescent probes I and H 2 o 2 ESI-MS analysis before and after action

[0066] Blank experiment: In a 1.5mL centrifuge tube, add 20μL of fluorescent probe I solution (5mmol / L, the solvent is methanol), and 20μL of Milli-Q ultrapure water, and perform positive ion ESI on the reaction solution after ten minutes -MS test analysis, the test results see figure 1 Middle A.

[0067] In a 1.5 mL centrifuge tube, add 20 μL of fluorescent probe I solution (5 mmol / L, solvent is methanol), and 20 μL of commercially available 30% H 2 o 2 Solution, after ten minutes, carry out positive ion ESI-MS test analysis to reaction solution, its test result sees figure 1 Middle B.

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Abstract

The invention discloses a fluorescent probe for detecting active oxygen molecules, a preparation method and application thereof. The fluorescent probe comprises a quinolinium ion skeleton, trimethylsilyl bonded with the quinolinium ion skeleton structure through a carbon-silicon single bond, p-boronic acid pinacol ester phenyl connected with the quinolinium ion skeleton structure through a carbon-carbon single bond, and counter ions. According to the invention, the boronic acid pinacol ester group on the molecule reacts with active oxygen to realize high-selectivity detection of the active oxygen molecule.

Description

technical field [0001] The invention relates to the technical field of fluorescent probes, in particular to a fluorescent probe for detecting active oxygen molecules and its preparation method and application. Background technique [0002] Fluorescent molecular imaging is a fast-growing interdisciplinary subject involving molecular biology, chemistry, and pharmacy. It can realize non-invasive and real-time visualization, detect physiological or pathological processes in organisms at the cellular or molecular level, and is of great value to the study of life processes and the process and metabolism of drugs in the human body. The detection and tracking of small molecules in vitro, at the cellular level or in vivo by designing small molecule fluorescent probes is one of the important areas of chemical biology research. One of the popular directions is to extend the detection from the cellular level to the subcellular level, that is, to selectively track the action process of ...

Claims

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Application Information

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IPC IPC(8): C07F7/08C09K11/06G01N21/64
CPCC07F7/0814C09K11/06G01N21/6428G01N2021/6432C09K2211/1029C09K2211/1096
Inventor 黄文健俞琼艾查拉潘·坦蒂潘查彭龚嘉恩
Owner THE HONG KONG POLYTECHNIC UNIV SHENZHEN RES INST
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