Hypochlorous acid fluorescent probe, as well as preparation method and application thereof

A fluorescent probe, hypochlorous acid technology, applied in the field of analytical chemistry, can solve the problems of long reaction time and poor specificity, and achieve the effects of simple post-processing process, rapid detection and simple synthesis

Inactive Publication Date: 2017-08-18
UNIV OF JINAN
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the existing hypochlorous acid probes have poor selection specificity and long reaction time in vivo.

Method used

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  • Hypochlorous acid fluorescent probe, as well as preparation method and application thereof
  • Hypochlorous acid fluorescent probe, as well as preparation method and application thereof
  • Hypochlorous acid fluorescent probe, as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036] Example 1 Synthesis of fluorescent probe PZ-HClO.

[0037] (1) Dissolve o-hydroxyacetophenone (10.0 g, 13.5 mmol) in 200 mL of ethyl acetate, and slowly add sodium (8.0 g, 340 mmol) while stirring. React at room temperature for 4 hours. Use a TCL plate to detect the reaction. After the reaction is complete, filter under reduced pressure. The obtained solid is dissolved in 100 mL of water and neutralized with hydrochloric acid until the pH is neutral. Extract with ethyl acetate, dry over anhydrous sodium sulfate, and spin dry the solvent under reduced pressure to obtain a crude product, which is separated with a silica gel column, the silica gel particle size is 200-300 mesh, and the eluent ratio is ethyl acetate / petroleum ether=1: 6. The yield is 80%.

[0038] (2) Compound 1 (6.95 g, 38.9 mmol) was dissolved in 70 mL of acetic acid, sulfuric acid (4.6 mL) was slowly added to the above solution, and heated at 120 °C for 1 h. The reaction was detected with a TCL plate. ...

Embodiment 2

[0043] Example 2 Fluorescence intensity of fluorescent probe PZ-HClO changes with HClO concentration.

[0044] The PZ-HClO hypochlorous acid fluorescent probe prepared in Example 1 was dissolved in N,N-dimethylformamide (DMF) to prepare a 1 mmol / L stock solution. Take 30uL from the stock solution and add it to a 5mL centrifuge tube, dilute to 3 mL with 0.1mol / L, pH=7.5 phosphate buffered saline (PBS) and ethanol at a volume ratio of 1:1, add different concentrations (0 -25 μM) NaClO standard solution (NaClO will spontaneously produce acid-base balance shift in aqueous solution under neutral conditions to produce HClO, the same below), and use 450 nm as the excitation wavelength to measure its fluorescence spectrum. The fluorescence spectrum is as follows: figure 2 shown. Taking the concentration of NaClO as the abscissa and the fluorescence intensity as the ordinate, we can get image 3 , the fluorescence intensity increased significantly with the increase of NaClO concent...

Embodiment 3

[0045] Example 3 Selectivity of fluorescent probe PZ-HClO to different molecules or ions.

[0046] Take 30 μL from the fluorescent probe stock solution in Example 2 and add it to a 5 mL centrifuge tube, add equimolar amounts of sulfhydryl ions (HS - ), sulfide ion (S 2- ), sulfite ion (SO 3 2- ), dibutyl butyl phosphate (DBBP), tert-butyl hydroperoxide (TBHP), nitric oxide (NO), hydrogen peroxide (H 2 o 2 ), nitrite ion (NO 2 - ), nitrate ion (NO 3 2- ), hydroxyl radical (OH . ) and other standard solutions of competing or interfering molecules / ions, another two test tubes were added with an equimolar amount of sodium hypochlorite standard solution and an equal amount of water (blank control), and after 30 minutes, 450 nm was used as the excitation light to detect the fluorescence emission of the solution Spectral changes, results such as Figure 4 shown. Plotting the fluorescence intensities of different competing molecules or ions, such as Figure 5 shown. Depen...

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Abstract

The invention provides a hypochlorous acid fluorescent probe with quick response and high selectivity and sensitivity by molecular structure design, as well as a preparation method thereof and application of the hypochlorous acid fluorescent probe to detection of hypochlorous acid in an aqueous solution and a cell. The fluorescent probe can be applied to detection of the hypochlorous acid in the aqueous solution or a biological system, and detection comprises fluorescence detection, cell imaging and visual colorimetry. The fluorescence intensity forms linear positive correlation with the concentration of the hypochlorous acid within a certain concentration range, and the concentration of the hypochlorous acid can be quantitatively measured. The hypochlorous acid fluorescent probe is easy to synthesize, and a posttreatment process is relatively simple; selective and rapid detection of the hypochlorous acid molecular probe is realized, the selectivity is good, and the hypochlorite fluorescent probe is high in resistance to interference of other molecules, is a simple, rapid and sensitive hypochlorous acid molecular specific detection reagent, and has broad application prospect in the field of biomolecular detection.

Description

technical field [0001] The invention relates to a fluorescent probe for rapidly detecting hypochlorous acid, its preparation and application in detecting hypochlorous acid in cells, belonging to the technical field of analytical chemistry. Background technique [0002] Hypochlorous acid (HClO) is a kind of active oxygen, as a highly effective bactericide, it plays an important role in the immune system of life. Endogenous hypochlorous acid in cells is mainly produced by the myeloperoxidase system in leukocytes (such as monocytes, eosinophils, neutrophils, etc.). Cellular immune response can produce hypochlorous acid, but once the concentration of hypochlorous acid in cells is abnormal, it will cause various diseases including rheumatoid arthritis, cardiovascular disease and cancer. As a relatively important organelle in intracellular lysosomes, hypochlorous acid can maintain the balance of oxidation-reduction of lysosomes, which plays a very important role in the stability ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D417/06C09K11/06G01N21/64
CPCC07D417/06C09K11/06C09K2211/1037C09K2211/1088G01N21/64
Inventor 林伟英任明光邓贝贝
Owner UNIV OF JINAN
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