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Preparation and application of fluorescence probes used for real-time sensitive hypochlorous acid detection

A preparation, sulfonic acid group technology, applied in the field of hypochlorous acid fluorescent probes, can solve the problems of complex synthesis, poor selectivity, low sensitivity and the like, and achieve the effects of simple synthesis, good stability and low cost

Pending Publication Date: 2018-11-09
姜懿珊
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, there are still some problems with the fluorescent probes reported so far, including low sensitivity, poor selectivity, and complex synthesis.

Method used

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  • Preparation and application of fluorescence probes used for real-time sensitive hypochlorous acid detection
  • Preparation and application of fluorescence probes used for real-time sensitive hypochlorous acid detection
  • Preparation and application of fluorescence probes used for real-time sensitive hypochlorous acid detection

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034]

[0035] (Scheme 1) Dissolve 345mg (1mmol) of 4-chloro-1,8-naphthalimide and 122mg (2mmol) of monoethanolamine in 15mL of ethylene glycol methyl ether and heat to reflux for 10h, and use a dichloromethane / methanol system for column After chromatographic separation, 269 mg of a yellow solid was obtained with a yield of 73%.

[0036] (Scheme 2) Dissolve 345mg (1mmol) of 4-chloro-1,8-naphthalimide and 183mg (3mmol) of monoethanolamine in 15mL of ethylene glycol methyl ether and heat to reflux for 10h, and use a dichloromethane / methanol system for column After chromatographic separation, 299 mg of a yellow solid was obtained with a yield of 81%.

[0037] (Scheme 3) Dissolve 345mg (1mmol) of 4-chloro-1,8-naphthoimide and 305mg (5mmol) of monoethanolamine in 15mL of ethylene glycol methyl ether and heat to reflux for 10h, using a dichloromethane / methanol system for column After chromatographic separation, 339 mg of a yellow solid was obtained with a yield of 92%.

[0038...

Embodiment 2

[0041] Test results of probe (5 μM) response time to HClO (5 μM). The above determinations were carried out in 5 mM PBS, pH 7.4 aqueous solution, the probe used was the probe prepared in Example 1, and all spectral tests were measured at 25°C. See results figure 1 .

[0042] from figure 1 It can be seen that after adding 5 μM hypochlorous acid, the fluorescence intensity drops suddenly, and the response can be completed within 3s.

Embodiment 3

[0044] Effects of different concentrations of hypochlorous acid (0-10 μM) on the fluorescence spectrum of the probe (5 μM). The above determinations were carried out in 5mM PBS, pH 7.4 aqueous solution, the probe used was the probe prepared in Example 1, and all spectral tests were measured after acting at 25°C for 1 min. See results figure 2 a.

[0045] from figure 2b It can be seen that with the increase of the concentration of hypochlorous acid in the probe solution, the fluorescence spectrum gradually weakens, and within the concentration range of 0-1 μM hypochlorous acid, the concentration of hypochlorous acid and the fluorescence intensity show a linear relationship, and the detection The output limit is as low as 2.3nM. Therefore, the probe of the present invention can more accurately determine the content of hypochlorous acid in the sample to be tested.

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PUM

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Abstract

The invention relates to fluorescence probes used for real-time sensitive high-selectivity recognition of hypochlorous acid. The probes are a type of 4-amino-1,8-naphthalimide compounds, and the compounds can be adopted as hypochlorous acid fluorescence probes for hypochlorous acid detection. The probes can achieve at least one of: high-sensitivity high-selectivity recognition of hypochlorous acidand accurate detection; capability of rapid response to the hypochlorous acid; capability of real-time detection of hypochlorous acid; stable properties and capability of long-term storage and use; and capability of facilitating detection of (in-vivo / in-vitro) hypochlorous acid in actual samples.

Description

technical field [0001] The present invention relates to 4-amino-1,8-naphthoimide compounds as hypochlorous acid fluorescent probes, which can perform real-time ultrasensitive and highly selective detection of endogenous hypochlorous acid in cells in a pure water system, or It determines the concentration of hypochlorous acid in real water samples. Background technique [0002] In humans, hypochlorous acid (HClO) can be produced in a regulated manner from the myeloperoxidase (MPO)-catalyzed reaction of hydrogen peroxide and chloride ions, which is important for innate host defense and for killing various pathogens. In vitro, swimming pool poisoning incidents due to high concentrations of hypochlorous acid in swimming pool water still occur frequently. Excessive production or accumulation of hypochlorous acid in organisms can cause a variety of diseases, including cardiovascular disease, atherosclerosis, osteoarthritis, rheumatoid arthritis and lung damage, and even cancer. ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D221/14C09K11/06G01N21/64
CPCC07D221/14C09K11/06C09K2211/1029C09K2211/1033G01N21/6428
Inventor 姜懿珊
Owner 姜懿珊
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