Rapid high-selectivity hypochloric acid fluorescence probe and application thereof

A technology of hypochlorous acid and hypochlorite, applied in fluorescence/phosphorescence, luminescent materials, organic chemistry, etc., can solve problems such as slow response speed, poor selectivity, complex synthesis, etc., and achieve good stability, good water solubility, and synthetic simple effect

Inactive Publication Date: 2015-09-16
UNIV OF JINAN
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the reported fluorescent probes still have some defects, such as poor selectivity, slow response, low sensitivity, and complex synthesis.

Method used

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  • Rapid high-selectivity hypochloric acid fluorescence probe and application thereof
  • Rapid high-selectivity hypochloric acid fluorescence probe and application thereof
  • Rapid high-selectivity hypochloric acid fluorescence probe and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0035]

[0036] (Scheme 1) Dissolve 285.5mg (1.0mmol) of N-butyl 4-chloro-1,8-naphthalimide, 220mg (2.0mmol) of hydroquinone and 552mg (4.0mmol) of potassium carbonate in 10mL of dimethyl base sulfoxide (DMSO), and then reacted at a constant temperature of 80°C for 10h. The reaction solution was poured into 100 mL of water, extracted with dichloromethane to obtain a dichloromethane phase, and then rotary evaporated to obtain a crude product, which was separated by column chromatography using a dichloromethane system to obtain 256 mg of a yellow pure product with a yield of 71%.

[0037] (Scheme 2) Dissolve 285.5 mg (1.0 mmol) of 4-chloro-1,8-naphthalimide, 330 mg (3.0 mmol) of hydroquinone and 828 mg (6.0 mmol) of potassium carbonate in 10 mL of dimethylsulfoxide ( DMSO), then reacted at a constant temperature of 80 °C for 10 h, poured the reaction solution into 100 mL of water, extracted with dichloromethane to obtain a dichloromethane phase, and then rotary evaporated to ...

Embodiment 2

[0043] The inventor of the present invention has carried out following test: (a) the influence of different concentration NaClO (0~500 μ M) on probe (5 μ M) fluorescence spectrum; linear relationship between. The above determination is carried out in a mixed system of absolute ethanol and water (5:5, v / v), 5mM PBS, pH 7.4, the probe used is the probe prepared in Example 1, and all spectra The tests are all measured after adding NaClO for 10 minutes at 25°C. See Figure 1 for the results.

[0044] It can be seen from Figure 1 that with the increase of NaClO concentration in the probe solution, the fluorescence spectrum gradually increases, and within the concentration range of 0-250 μM NaClO, the concentration of NaClO and the fluorescence intensity have a linear relationship. Therefore, the NaClO in the sample can be quantitatively analyzed by means of the probe of the present invention.

Embodiment 3

[0046] Effect of different analytes (40 μM) on the fluorescence spectra of probes (5 μM). Analytes include: Hydrogen peroxide H 2 o 2 , tert-butanol peroxide TBHP, potassium superoxide KO 2 , hydroxyl radical · OH, peroxide tert-butanol radical · TBHP, peroxynitrite ONOO - , sodium hypochlorite NaClO, and their concentrations are all 40 μM. All test conditions are carried out in the mixed system (5:5, v / v) of absolute ethanol and water, 5mM PBS, pH 7.4, the probe used is the probe prepared in embodiment 1, and all Spectral tests were all measured after adding NaClO for 10 min at 25°C. Specifically, pipette 50 μL of the probe stock solution (1 mM) into a 10 mL colorimetric tube, then add 5 mL of absolute ethanol, then pipette 20 μL of the above analyte stock solution (10 mM) into the colorimetric tube, and then pipette 0.5 mL of PBS solution (pH7.4, 100mM), and finally dilute to 10mL with ultrapure water. Shake well, let it stand for 10min, then measure. The result is as...

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Abstract

The invention relates to a rapid high-selectivity hypochloric acid fluorescence probe and an application thereof. The probe is 4-hydroquinone based naphthalimide compounds, and the compounds can be used to detect hypochloric acid as a hypochloric acid fluorescence probe. The probe has at least one of the following technical effects: highly-selectively identification of hypochloric acid/hypochlorite ions; rapid response to hypochloric acid/hypochlorite ions; instant detection of hypochloric acid/hypochlorite ions; stable properties and long-term preservation and use; facilitation of detection of hypochloric acid under physiologic level conditions; and strong anti-interference ability.

Description

technical field [0001] The present invention relates to 4-hydroquinone naphthalimide compounds as hypochlorous acid fluorescent probes, which can be used for fast and highly selective recognition of hypochlorous acid under physiological level conditions, or can be used to determine hypochlorous acid in samples. Chloric acid / hypochlorite concentration. Background technique [0002] Hypochlorite is widely used in household bleach, drinking water disinfection, cyanide treatment, etc., and its concentration range is 10-10 4 μM. However, studies have shown that high concentrations of hypochlorous acid solutions are potentially harmful to human and animal health. Reactive oxygen species (ROS) and reactive nitrogen species (RNS) are ubiquitous in cellular metabolism and are essential for several biological functions. As an important ROS, hypochlorous acid plays a vital role in living systems and participates in many physiological processes. Hypochlorous acid in living organisms...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D221/14C09K11/06G01N21/64
CPCC07D221/14C09K11/06C09K2211/1088G01N21/64
Inventor 朱宝存舒伟闫良国于海琴柳彩云杜斌
Owner UNIV OF JINAN
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