Lysosome-targeted hypochlorite ion fluorescent probe and application thereof

A fluorescent probe and hypochlorite technology, applied in the field of analytical chemistry, can solve the problems of inability to detect hypochlorite, low sensitivity, complex synthesis, etc., and achieve novel probe structure, strong anti-interference ability, and simple post-processing. Effect

Active Publication Date: 2017-08-18
ZHENGZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] There are many defects in the reported hypochlorous acid fluorescent probes, such as low sensitivity, poor selectivity, slow response speed and complex synthesis, etc. The more important defect is poor targeting, and the applied patents [CN103173213A], [CN104910070A] s

Method used

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  • Lysosome-targeted hypochlorite ion fluorescent probe and application thereof
  • Lysosome-targeted hypochlorite ion fluorescent probe and application thereof
  • Lysosome-targeted hypochlorite ion fluorescent probe and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0021] Example 1. Preparation of target probe compound N16: 1) Synthesis of compound N16-1: Dissolve 1g (3.6mmol) of 4-bromo-1,8-naphthalimide in ethanol, add 1g (7.2mmol) of morpholine, reflow. After the reaction was completed, the reaction solution was cooled at room temperature, the solid was filtered off, and purified by column chromatography, which was the target product N16-1 with a yield of 85%; 2) Synthesis of compound N16: 388 mg (1 mmol) N16-1 and 276 mg (2 mmol) ) Potassium carbonate was dissolved in 5 mL of DMF, 140 mg (2 mmol) of sodium methyl mercaptide was added, and reacted at a constant temperature of 80° C. for 2 h under the protection of nitrogen. After the reaction, the reaction solution was cooled to room temperature and poured into 40mL of water. A solid was produced, which was filtered and purified by chromatography to obtain N16 with a yield of 88%.

Embodiment 2

[0022] Example 2. N16 to ClO - Fluorescence selectivity experiment of 1: Take the N16 hypochlorite fluorescent probe prepared in Example 1 and dissolve it in DMF to make a 1mmol / L stock solution. Take 30 μL of the stock solution and add it to 3 mL of PB buffer solution (pH=7.4), and then add 30 μL of different anions and cations at a concentration of 100 μM, ClO - The addition of ions completely quenched the fluorescence. The excitation wavelength is 405nm, and the emission wavelength is 506nm. The ordinate indicates the fluorescence intensity, and the abscissa indicates the wavelength; N16 is to ClO - UV selectivity experiment: take 30 μL of the fluorescent probe stock solution in Example 2 and add it to 3 mL of PB buffer solution (pH=7.4), and add 30 μL of different anions and cations with a concentration of 100 μM respectively. The visible absorption spectrum. ClO - The absorbance at 405nm decreased significantly, and the absorbance at 350nm increased significantly. T...

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Abstract

The invention relates to a fluorescent probe which can directly detect hypochlorite in lysosome on the basis of 1,8-naphthalimide and a preparation method and application of the fluorescent probe. The fluorescent probe has the molecular structure as shown in (I), is simple to synthesize, can selectively detect hypochlorite ions in a pure PB buffer solution and can resist interference from other active oxygen small molecules. Besides, by use of the fluorescent probe, color changes of the solution can be observed with naked eyes and also can be observed under an ultraviolet lamp. The fluorescent probe can also be used for detecting hypochlorite ions in the cytolysosome, is short in response time and low in limit of detection and has a potential application value.

Description

technical field [0001] The invention relates to a preparation method and application of a fluorescent probe for rapidly detecting hypochlorite ions in lysosomes of cells, and belongs to the technical field of analytical chemistry. Background technique [0002] In recent years, the detection of inorganic anions in the environment, in biological systems and even in medicine has attracted much attention. Active oxygen compounds in inorganic anions play an important role in physiological and pathological processes. Among them, hypochlorous acid is mainly generated in the living body by the reaction of hydrogen peroxide and chloride ions under the catalysis of myeloperoxidase (MPO). Under physiological conditions, about half of hypochlorous acid is understood as hypochlorite, which is also one of the strongest oxidants in nature. Hypochlorite is also a strong oxidizing agent widely used in daily life. Hypochlorous acid is related to the immune function of the body and can kill...

Claims

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Application Information

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IPC IPC(8): C07D221/14C09K11/06G01N21/64C12Q1/02
CPCC07D221/14C09K11/06C09K2211/1033G01N21/6428
Inventor 叶勇刘瑶赵玉芬
Owner ZHENGZHOU UNIV
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