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Hypochlorous acid detection fluorescent probes and preparation method and application thereof

A fluorescent probe, hypochlorous acid technology, applied in the field of analytical chemistry

Active Publication Date: 2017-10-17
FUDAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, no hypochlorous acid fluorescent probes that can observe obvious color changes after responding to hypochlorous acid at the living level have been reported, so the development of such probes is of great significance

Method used

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  • Hypochlorous acid detection fluorescent probes and preparation method and application thereof
  • Hypochlorous acid detection fluorescent probes and preparation method and application thereof
  • Hypochlorous acid detection fluorescent probes and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0048] Preparation of compound FDOCl-1 (R11 is hydrogen) with formula I structure and research on its response performance with hypochlorous acid:

[0049]

[0050] (1) Preparation of Vilsmeyer-Haack Reagent

[0051] Dimethylformamide (4.6g, 62.52mmol) was dissolved in 20ml of dichloromethane, and thionyl chloride (7.44g, 62.52mmol) diluted with 10ml of dichloromethane was added dropwise at room temperature. The reaction was stirred for 15 minutes. After the reaction was completed, the solvent was directly evaporated to dryness, and the obtained Wilsmeyer-Hacker formylating reagent was directly used in the next step reaction.

[0052] (2) Preparation of FDOCl-1

[0053] Add methylene blue (5.0 g, 15.63 mmol) into a three-necked flask and dissolve it with 30 mL of dichloromethane and 40 mL of water. Sodium carbonate (6.63g, 62.52mmol) was added to the system and the system was stirred at 40°C. After nitrogen protection, sodium dithionite (8.16g, 46.89mmol) dissolved in 20mL ...

Embodiment 2

[0064] Preparation of compound FDOCl-2 (R11 is a substituted amino group) with the structure of formula I and research on its response performance with hypochlorous acid

[0065]

[0066] (1) Preparation of compounds

[0067] Add methylene blue (2.0 g, 6.25 mmol) into a three-necked flask and dissolve it with 15 mL of dichloromethane and 40 mL of water. Sodium carbonate (2.65g, 25.00mmol) was added to the system and the system was stirred at 40°C. After nitrogen protection, sodium dithionite (3.26g, 18.75mmol) dissolved in 20mL of water was added dropwise to the system. After the addition was completed, the reaction was carried out for 20 minutes. At this time, the system was clearly separated, and the lower layer was a yellow solution. The system was left to stand, and then 10 mL of triphosgene (0.93 g, 3.13 mmol) dissolved in dichloromethane was added dropwise to the system, and then transferred to room temperature and stirred for 1 h. The system was left to stand, and ...

Embodiment 3

[0072] Preparation of compound FDOCl-3 (R11 is an alkyl group) with the structure of formula I and research on its response performance with hypochlorous acid

[0073]

[0074] (1) Preparation of target compound

[0075] Add methylene blue (2.0 g, 6.25 mmol) into a three-necked flask and dissolve it with 15 mL of dichloromethane and 40 mL of water. Sodium carbonate (2.65g, 25.00mmol) was added to the system and the system was stirred at 40°C. After nitrogen protection, sodium dithionite (3.26g, 18.75mmol) dissolved in 20mL of water was added dropwise to the system. After the addition was completed, the reaction was carried out for 20 minutes. At this time, the system was clearly separated, and the lower layer was a yellow solution. Let the system stand still, after the layers were separated, suck out the lower layer of clear night with a syringe, add 4-dimethylaminopyridine (0.76g, 6.25mmol), sodium carbonate (1.99g, 18.75mmol) and 20mL of dichloromethane mixed system, ice...

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Abstract

The invention belongs to the technical field of analytical chemistry and particularly relates to a type of hypochlorous acid detection fluorescent probes and a preparation method and application thereof. The compounds have excellent selectivity of hypochlorous acid and are unresponsive to other common active oxygen / active nitrogen. The hypochlorous acid detection fluorescent probes are high in hypochlorous acid selectivity and sensitivity, and recognition with naked eyes instead of complicated instruments can be realized after response to hypochlorous acid; hypochlorous acid recognition in in-vivo level can be realized, and obvious color changes can be observed. The compounds can serve as the fluorescent probes to be applied to fields of hypochlorous acid detection, fluorescence imaging and the like.

Description

technical field [0001] The invention belongs to the technical field of analytical chemistry, and in particular relates to a fluorescent probe which can be used for hypochlorous acid detection and its preparation method and application. Background technique [0002] Hypochlorous acid (HOCl) is a kind of reactive oxygen species with strong oxidizing properties, which is generated in living organisms from chloride ions and hydrogen peroxide under the action of myeloperoxidase (MPO). Hypochlorous acid is the strongest oxidative bactericidal substance produced by neutrophils, and can participate in the removal process of various types of harmful bacteria. However, excessive hypochlorous acid can be harmful to the body and can cause oxidative stress, leading to many diseases such as atherosclerosis and cardiovascular diseases. Therefore, it is of great significance to monitor the change and distribution of hypochlorous acid concentration in living systems, especially living organ...

Claims

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Application Information

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IPC IPC(8): C07D279/30C09K11/06G01N21/64
CPCC07D279/30C09K11/06C09K2211/1037G01N21/6428G01N21/643
Inventor 易涛魏鹏薛峰峰李若涵吕光磊钟亚平曹春艳
Owner FUDAN UNIV
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