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Two-photon reversible type fluorescent probe FO-PSe for hypochlorous acid detection, and preparation method and application thereof

A fluorescent probe and two-photon technology, applied in preparations for in vivo experiments, fluorescence/phosphorescence, chemical instruments and methods, etc., to achieve high yield, reduced self-absorption, and short dyeing time

Inactive Publication Date: 2016-04-20
SHANDONG NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Therefore, the synthesis and development of new two-photon fluorescent probes is very necessary, especially the design and synthesis of reversible two-photon fluorescent probes is still very challenging.

Method used

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  • Two-photon reversible type fluorescent probe FO-PSe for hypochlorous acid detection, and preparation method and application thereof
  • Two-photon reversible type fluorescent probe FO-PSe for hypochlorous acid detection, and preparation method and application thereof
  • Two-photon reversible type fluorescent probe FO-PSe for hypochlorous acid detection, and preparation method and application thereof

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Experimental program
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Effect test

Embodiment 1

[0037] Embodiment 1: the synthesis of fluorescent probe

[0038] Under the protection of argon, compound 1 (0.374g, 1.2mmol) and dithiothreitol (0.308g, 2.0mmol) were dissolved in 10-15mL of N,N-dimethylformamide and reacted at 75-100°C Add compound 2 (0.135g, 0.4mmol) after 30min, continue stirring for 20min, add 1,8-diazabicyclo[5.4.0]undec-7-ene (0.75ml, 5.0mmol), 75-100°C Reaction 25-40h. After the reaction was complete, the mixture was extracted with dichloromethane and saturated sodium bicarbonate, and the organic phase was dried over anhydrous magnesium sulfate. Then it was redissolved and subjected to column separation to obtain an orange-red solid (40%-80%).

[0039] NMR and mass spectrometry characterization:

[0040] 1 HNMR (400MHz, CDCl 3 ): δ7.594(s, 2H; ArH), 7.528(d, 2H; ArH), 7.456(d, 2H; ArH), 7.180-7.248(m, 10H; ArH). 13 CNMR (100MHz, CDCl 3 )δ191.54, 141.72, 137.18, 132.77, 132.53, 130.59, 128.60, 127.17, 127.06, 126.69, 119.94. 77SeNMR (150MHz, CDCl...

Embodiment 2

[0048] Embodiment 2: the synthesis of fluorescent probe

[0049] Under the protection of argon, compound 1 (0.374g, 1.2mmol) and dithiothreitol (0.308g, 2.0mmol) were dissolved in 1mL of N,N-dimethylformamide, reacted at 75°C for 30min, and then added the compound 2 (0.135g, 0.4mmol), continue stirring for 20min, add 1,8-diazabicyclo[5.4.0]undec-7-ene (0.75ml, 5.0mmol), and react at 75°C for 25h. After the reaction was complete, the mixture was extracted with dichloromethane and saturated sodium bicarbonate, and the organic phase was dried over anhydrous magnesium sulfate. Then it was re-dissolved and separated by column to obtain an orange-red solid (40%).

[0050] NMR and mass spectrometry characterization:

[0051] 1 HNMR (400MHz, CDCl 3 ): δ7.594(s, 2H; ArH), 7.528(d, 2H; ArH), 7.456(d, 2H; ArH), 7.180-7.248(m, 10H; ArH). 13 CNMR (100MHz, CDCl 3 )δ191.54, 141.72, 137.18, 132.77, 132.53, 130.59, 128.60, 127.17, 127.06, 126.69, 119.94. 77 SeNMR (150MHz, CDCl 3 ):δ431...

Embodiment 3

[0059] Embodiment 3: the synthesis of fluorescent probe

[0060] Under the protection of argon, compound 1 (0.374g, 1.2mmol) and dithiothreitol (0.308g, 2.0mmol) were dissolved in 15mL of N,N-dimethylformamide, reacted at 100°C for 30min, and then added the compound 2 (0.135g, 0.4mmol), continue stirring for 20min, add 1,8-diazabicyclo[5.4.0]undec-7-ene (0.75ml, 5.0mmol), react at 100°C for 40h. After the reaction was complete, the mixture was extracted with dichloromethane and saturated sodium bicarbonate, and the organic phase was dried over anhydrous magnesium sulfate. Then it was redissolved and separated by column to obtain an orange-red solid (80%).

[0061] NMR and mass spectrometry characterization:

[0062] 1 HNMR (400MHz, CDCl 3 ): δ7.594(s, 2H; ArH), 7.528(d, 2H; ArH), 7.456(d, 2H; ArH), 7.180-7.248(m, 10H; ArH). 13 CNMR (100MHz, CDCl 3 )δ191.54, 141.72, 137.18, 132.77, 132.53, 130.59, 128.60, 127.17, 127.06, 126.69, 119.94. 77 SeNMR (150MHz, CDCl 3 ):δ431.4...

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Abstract

The invention designs and synthesizes a two-photon reversible type fluorescent probe FO-PSe for hypochlorous acid detection, and provides a preparation method and application of the two-photon reversible type fluorescent probe FO-PSe. Two kinds of easy-to-obtain synthesized compounds are used as initial raw materials to prepare the probe through one step of simple and efficient synthesis reaction; in addition, the post-treatment is easy; the purification is simple and convenient. The fluorescent probe has two-photon properties; the background fluorescence interference can be effectively reduced; in addition, the reversible performance is realized on hypochlorous acid; the concentration of the hypochlorous acid can be dynamically and reversibly detected. A good effect is achieved when the probe is used for live cell and living body imaging; in addition, the imaging analysis of the hypochlorous acid in the mouse abdominal cavity at different depth is realized. The probe has the advantages that the structure is novel, and the photophysical property is good. A good fluorescent tool is provided for studying the function and the biological significance of the hypochlorous acid in live cells and living bodies.

Description

Technical field: [0001] The invention belongs to the field of synthesis, and in particular relates to a two-photon reversible fluorescent probe FO-PSe for detecting hypochlorous acid and a preparation method and application thereof. Background technique: [0002] Hypochlorous acid is one of the important reactive oxygen species in the human body, and it plays a vital role in the physiology and pathology of organisms. In organisms, hydrogen peroxide and chloride ions can undergo a chemical reaction under the catalysis of myeloperoxidase, and the product hypochlorite and its protonated form, namely hypochlorous acid, exist in organisms under physiological conditions. Hypochlorous acid is an oxidizing substance with strong nucleophilic ability, which can react with various molecules in organisms such as RNA, DNA, fatty acids, cholesterol and various proteins. The most notable effect of hypochlorous acid is its strong antibacterial property, which achieves the purpose of steril...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09K11/06C07C391/02G01N21/64A61K49/00
CPCC09K11/06A61K49/0008A61K49/0041C07C391/02C09K2211/1007C09K2211/1011C09K2211/1014G01N21/6428
Inventor 张卫刘伟李平唐波
Owner SHANDONG NORMAL UNIV
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