Fluorescent probe for detecting hypochlorite ion, preparation method and application thereof

A hypochlorite and fluorescent probe technology, applied in the field of fluorescent probes, can solve the problems of affecting the sensitivity and selectivity of the sensing method, unable to monitor the fluctuation of hypochlorous acid in real time, unstable basic level, etc. High rate, low biotoxicity effect

Active Publication Date: 2022-04-08
GUANGDONG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

It is worth noting that some reactive oxygen species and reactive nitrogen species, including hypochlorous acid, have similar strong oxidizing abilities, which seriously affect the sensitivity and selectivity of the sensing method.
On the other hand, like most reactive nitrogen and reactive oxygen species, hypochlorous acid is relatively short-lived and its basal levels in biological systems are often unstable
Most of the reported hypochlorous acid probes have a delayed response time, so the fluctuation of hypochlorous acid at its site of action cannot be monitored in real time

Method used

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  • Fluorescent probe for detecting hypochlorite ion, preparation method and application thereof
  • Fluorescent probe for detecting hypochlorite ion, preparation method and application thereof
  • Fluorescent probe for detecting hypochlorite ion, preparation method and application thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0035] Embodiment 1 detects the preparation of the fluorescent probe of hypochlorite ion

[0036] Under argon protection, 172.18 mg (1 mmol) of 6-hydroxy-2-naphthaldehyde was dissolved in 10 ml of dichloromethane, and 104 μl (1.5 mmol) of dimercaptoethanol and 18 μl (0.1 mmol) of TMSOTf (trifluoromethanesulfonate methyl silicon ester) at room temperature 25°C for 30min; after the reaction was completed, the reaction solution was washed with saturated brine and dried over anhydrous sodium sulfate; after drying, the solvent was spin-dried, and purified by silica gel column chromatography (eluent was ethyl acetate Esters: petroleum ether = 1:4 (V: V)), to obtain 135 mg of compound 6-(1,3-oxathiolan-2-yl)naphthalene-2-ol (60% yield), namely A fluorescent probe for detecting hypochlorite ions has a synthetic route as follows:

[0037]

[0038] The H NMR spectrum data of the probe molecules are as follows:

[0039] probe- 1 H NMR (400MHz, DMSO): δ9.77(s, 1H), 7.80(s, 1H), 7.76...

Embodiment 2

[0040] Embodiment 2 detects the preparation of the fluorescent probe of hypochlorite ion

[0041] Under argon protection, 344.36 mg (2 mmol) of 6-hydroxy-2-naphthaldehyde was dissolved in 10 ml of dichloromethane, and 208 μl (3 mmol) of dimercaptoethanol and 36 μl (0.2 mmol) of TMSOTf (trimethyl trifluoromethanesulfonate) were added base silicon ester) at 20°C for 20 minutes; after the reaction was completed, the reaction solution was washed with saturated brine and dried over anhydrous sodium sulfate; after drying, the solvent was spin-dried, and purified by silica gel column chromatography (eluent: ethyl acetate: Petroleum ether=1:4 (V:V)), to obtain 261 mg of compound 6-(1,3-oxathiolan-2-yl)naphthalene-2-ol (58% yield), that is, the detection times Fluorescent probe for chlorate ion.

Embodiment 3

[0042] Embodiment 3 detects the preparation of the fluorescent probe of hypochlorite ion

[0043] Under argon protection, 258.57 mg (1.5 mmol) of 6-hydroxy-2-naphthaldehyde was dissolved in 10 ml of dichloromethane, and 156 μl (2.25 mmol) of dimercaptoethanol and 27 μl (0.15 mmol) of TMSOTf (trifluoromethanesulfonic acid Trimethylsilyl ester) was reacted at 40°C for 10 min; after the reaction was completed, the reaction solution was washed successively with saturated brine, and dried over anhydrous sodium sulfate; after drying, the solvent was spin-dried, and then purified by silica gel column chromatography (eluent was ethyl acetate Esters: Petroleum ether = 1:4 (V:V)), to obtain 205.9 mg of compound 6-(1,3-oxathiolan-2-yl)naphthalene-2-ol (61% yield), namely A fluorescent probe for the detection of hypochlorite ions.

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Abstract

The invention belongs to the field of fluorescent probes, and in particular relates to a fluorescent probe for detecting hypochlorite ions, a preparation method and an application thereof. The fluorescent probe of described detection hypochlorite ion, name is 6-(1,3-oxathiolan-2-yl) naphthalene-2-alcohol, molecular formula is C 13 h 12 o 2 S, the structure of which is shown in formula I; the probe reacts with hypochlorite ions in pure PBS buffer solution, and the concentration of hypochlorite ions can be detected by using the change of fluorescence intensity before and after the reaction. The preparation method of the probe is simple, the yield is high, and it has the advantages of fast response, high sensitivity and high selectivity.

Description

technical field [0001] The invention belongs to the field of fluorescent probes, and in particular relates to a fluorescent probe for detecting hypochlorite ions, a preparation method and application thereof. Background technique [0002] The important role of reactive oxygen species in various physiological and pathological processes, such as anti-inflammatory regulation, pathogen response, cell signaling, and aging, has received increasing attention in recent years. Among them, hypochlorous acid produced by myeloperoxidase catalyzing the peroxidation reaction of chloride ions is an antibacterial agent that plays a major role in the human immune defense system. Recently, however, increasing evidence has shown that excess hypochlorous acid in living systems is associated with neurodegenerative diseases such as ischemic stroke, Alzheimer's disease, and Parkinson's disease. Therefore, it is urgent to develop a rapid and efficient method for the detection of hypochlorous acid....

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C09K11/06C07D327/04G01N21/64
CPCC09K11/06C07D327/04G01N21/643C09K2211/1011C09K2211/1025
Inventor 段琴雅张华堂李泽君郑观生蒋银何军成晓玲
Owner GUANGDONG UNIV OF TECH
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