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Fluorescence probe for detecting hypochlorous acid in biological system and application of fluorescence probe

A technology of fluorescent probe and hypochlorous acid, which is applied in the field of fluorescence analysis, can solve the problems of incomparable fluorescence imaging technology, etc., and achieve the effects of good fluorescence emission spectrum characteristics, low preparation cost, and cheap and easy-to-obtain raw materials

Inactive Publication Date: 2017-03-29
UNIV OF JINAN
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Traditional hypochlorous acid detection mainly uses titration method, but this technology is not comparable to fluorescence imaging technology in terms of accuracy and applicability

Method used

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  • Fluorescence probe for detecting hypochlorous acid in biological system and application of fluorescence probe
  • Fluorescence probe for detecting hypochlorous acid in biological system and application of fluorescence probe
  • Fluorescence probe for detecting hypochlorous acid in biological system and application of fluorescence probe

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] Embodiment 1: Preparation of fluorescent probe 1a for detecting hypochlorous acid in biological systems according to the present invention

[0030] 3-acetyl-7-hydroxycoumarin (204mg, 10mmol), 4-(diethylamino) salicylaldehyde (193mg, 10mmol) and methanesulfonic acid (5mL) were added to a 50mL single-necked flask, refluxed for 6 hours, cooled, poured into 10g of ice, filtered, and dried.

[0031] The resulting solid was purified by column chromatography (dichloromethane:methanol=10:1) to obtain 371 mg of a dark blue product, which is the fluorescent probe 1a for detecting hypochlorous acid in biological systems according to the present invention, with a yield of 67%.

[0032] The above-mentioned fluorescent probe 1a for detecting hypochlorous acid in biological systems 1 H NMR spectrum see figure 1 .

Embodiment 2

[0033] Embodiment 2: The selectivity of fluorescent probe 1a for detecting hypochlorous acid in biological systems according to the present invention to different substances

[0034] Prepare 8 parts of 5 mL of 5 μM probe PBS solution (containing 5% methanol, pH=7.4), and then add 50 μL of 10 mM NaClO, Na 2 S, Na 2 SO 3 , NO, H 2 o 2 、CH 3 COOOH, HClO 4 , cys, GSH, NaNO 2 , VC, etc. in PBS solution. Fluorescence detection was then performed (λ Ex =410nm,λ Em =452nm); Calculate the fluorescence intensity in each system; Evaluate the selectivity of the probe to hypochlorous acid (see image 3 ).

[0035] Similar method analyzes the fluorescent spectrum of the fluorescent probe 1a of detecting hypochlorous acid in the biological system of the present invention under different pH conditions, the results are shown in figure 2 .

Embodiment 3

[0036] Embodiment 3: Absorption and fluorescence change analysis of fluorescent probe 1a for detecting hypochlorous acid in a biological system reacted with different concentrations of hypochlorous acid according to the present invention

[0037] Prepare 1 mL of acetonitrile solution with a concentration of 0-1 mM hypochlorous acid, and then add 9 mL of a probe PBS solution (containing 5% methanol, pH=7.4) with a concentration of 5 μM. After reacting 10min, carry out absorption spectrum test (see Figure 4 ); for fluorescence detection (λ Ex =410nm,λ Em =452nm), calculate the fluorescence intensity in each system, establish the standard curve of fluorescence intensity and hypochlorous acid concentration (see Figure 5 ) to determine the lower limit of the probe for hypochlorous acid detection.

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Abstract

The invention discloses a fluorescence probe for detecting hypochlorous acid in a biological system. The fluorescence probe is a benzopyran derivative containing different substituent groups, and the chemical construction general formula of the fluorescence probe is shown as the formula (I). The fluorescence probe is easy to manufacture and low in cost, has the high specificity, can make a chemical reaction with the hypochlorous acid to generate a corresponding oxidative product, cannot be disturbed by other components when the corresponding hypochlorous acid content detecting process is executed, can be used for quantitative and qualitative determination on the content of the hypochlorous acid in living cells and has the wide application prospect.

Description

technical field [0001] The invention relates to a fluorescent probe for detecting hypochlorous acid in a biological system and an application thereof, belonging to the technical field of fluorescence analysis. Background technique [0002] Hypochlorous acid (HClO) is a very important reactive oxygen species, which participates in many physiological and pathological processes in biological systems. The hypochlorous acid in the biological system mainly comes from the reaction of hydrogen peroxide and chloride ions in the body under the catalysis of myeloperoxidase. Hypochlorous acid can oxidize and modify various biological macromolecules in the body, such as proteins, lipids, DNA and RNA. As a strong nucleophilic non-free radical oxidizing agent, hypochlorous acid can prevent the invasion of microorganisms by promoting the fusion of lysosomes and phagosomes in cells, and also plays a role in resisting exogenous substances and neutralizing toxins. important role. The chlora...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09K11/06C07D311/58G01N21/64
Inventor 林伟英董宝利宋学真王超唐永和
Owner UNIV OF JINAN
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