Lysosome-targeted hypochlorous acid near-infrared fluorescent probe as well as preparation method and application thereof

A fluorescent probe, hypochlorous acid technology, applied in the field of analytical chemistry, to achieve high lysosome targeting ability, accurate and stable optical signal and imaging effect, and the effect of reducing background interference

Inactive Publication Date: 2018-12-21
HENAN NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] In view of the current situation that there is no lysosome-targeted near-infrared hypochlorous acid fluorescent probe report and the problems faced by the detection of hypochlorous acid in lysosomes, the present invention provides a lysosome-targeted hypochlorous acid near-infrared probe Fluorescent probe, which has the characteristics of near-infrared emission, high sensitivity, good selectivity and rapid response

Method used

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  • Lysosome-targeted hypochlorous acid near-infrared fluorescent probe as well as preparation method and application thereof
  • Lysosome-targeted hypochlorous acid near-infrared fluorescent probe as well as preparation method and application thereof
  • Lysosome-targeted hypochlorous acid near-infrared fluorescent probe as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] Synthesis of Fluorescent Probe Compound Lyso-NIR-HClO

[0030] (1) Synthesis of compound 1

[0031] Add 6 g of 3-bromo-N,N-dimethylaniline and 60 ml of anhydrous diethyl ether into a dry 250 ml round bottom flask at -78°C under the protection of argon, and stir magnetically for 5 minutes to dissolve , and then 13.1 milliliters of n-butyllithium n-hexane solution with a molar concentration of 2.4mol / L was slowly added dropwise to the reaction solution, and after the dropwise addition was completed, it was reacted at 0°C for 2 hours, and then 2.2 milliliters of dichlorodimethylsilane Dissolve in 10 ml of anhydrous ether, and then slowly add it dropwise to the above reaction solution. After the dropwise addition, react to room temperature and stir overnight, add 50 ml of water to quench the reaction, and extract the reaction solution with ether, and separate it with a separatory funnel. The organic phase was washed with water (50 ml × 2), washed with saturated NaCl aqueou...

Embodiment 2

[0043] Determination of Fluorescence Spectrum of Fluorescent Probe Compound Lyso-NIR-HClO with Different Concentrations of Hypochlorous Acid

[0044] Dissolve the fluorescent probe compound Lyso-NIR-HClO prepared in Example 1 in N,N-dimethylformamide (DMF) to make a 10 μM stock solution, take 2 ml from the stock solution and add it to a 5 ml centrifuge In the tube, add hypochlorous acid standard solutions of different equivalents (0-8), dilute to 4 ml with a solution of PBS buffer solution (10mM, pH=7.4) (DMF / PBS volume ratio is 1:1), and use 620nm as the Excitation light, the slit width is set to 5nm / 5nm, and the fluorescence spectrum is measured. Fluorescence spectra such as figure 1 As shown, with the addition of hypochlorous acid, the fluorescence at 680nm is gradually enhanced, and the relationship between the fluorescence intensity and the concentration of hypochlorous acid is as follows image 3 shown at 5.0 x 10 -8 -1.0×10 -5 There is a linear relationship within t...

Embodiment 3

[0046] Determination of UV-Vis Absorption Spectrum of Fluorescent Probe Compound Lyso-NIR-HClO with Different Concentrations of Hypochlorous Acid

[0047] figure 2 It is an ultraviolet-visible absorption spectrum diagram of the fluorescent probe compound Lyso-NIR-HClO prepared in Example 1 reacted with different concentrations of hypochlorous acid, and the amount of hypochlorous acid added is 0-40 μM. As can be seen from Figure 2, an absorption peak can be observed at 660nm, and as the concentration of hypochlorous acid increases, the absorbance at 660nm increases gradually. The instrument used for the determination of the ultraviolet-visible absorption spectrum is a TU-1900 ultraviolet-visible spectrophotometer (Beijing Purkinje General Instrument Co., Ltd.).

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Abstract

The invention discloses a lysosome-targeted hypochlorous acid near-infrared fluorescent probe as well as a preparation method and application thereof, which belongs to the technical field of analysischemistry. The lysosome-targeted hypochlorous acid near-infrared fluorescent probe is characterized in that a structural formula of the lysosome-targeted hypochlorous acid near-infrared fluorescent probe is as follows: (shown in the description). The invention also discloses a preparation method of the lysosome-targeted hypochlorous acid near-infrared fluorescent probe as well as application in water environment or biological cell system detection. The fluorescent probe of the invention has the characteristics of near-infrared transmission, high sensitivity, good selectivity, rapidness in response and the like.

Description

technical field [0001] The invention belongs to the technical field of analytical chemistry, and in particular relates to a lysosome-targeted hypochlorous acid near-infrared fluorescent probe and a preparation method and application thereof. Background technique [0002] Reactive oxygen species (ROS) are associated with various physiological and pathological processes, such as pathogen response processes, body aging processes, and anti-inflammatory processes. Hypochlorous acid (HClO), a highly efficient oxidant among reactive oxygen species, is usually produced during phagocytosis and inflammatory reactions, and plays an important role in the innate immune system. Hypochlorous acid is mainly distributed in acidic lysosomes of phagocytic cells, and is usually produced by the peroxidation of chloride ions catalyzed by myeloperoxidase (MPO) in phagosomes. Evidence has shown that misplaced or excessive HClO concentration expression in vivo is associated with various diseases, s...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F7/08C09K11/06G01N21/64
CPCC07F7/0816C07F7/083C09K11/06C09K2211/1029C09K2211/1033C09K2211/104G01N21/6428G01N21/643
Inventor 毛国江梁珍珍吴呈珂高广琦王盈盈
Owner HENAN NORMAL UNIV
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