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Hypochlorite ion fluorescent probe, preparation method and application thereof

A hypochlorite and fluorescent probe technology, applied in organic chemistry and other directions, can solve the problems of low sensitivity, poor water solubility of the probe, poor cell membrane permeability, and achieve good selectivity and specificity, and the preparation process is simple and feasible. Ease of mass production

Active Publication Date: 2017-03-29
NANJING TECH UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, many of these probes have poor water solubility, low sensitivity, great influence of pH on their detection results, and some probes have high biological toxicity and poor cell membrane penetration ability. These defects greatly affect the application of probes.

Method used

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  • Hypochlorite ion fluorescent probe, preparation method and application thereof
  • Hypochlorite ion fluorescent probe, preparation method and application thereof
  • Hypochlorite ion fluorescent probe, preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] Embodiment 1 prepares hypochlorite fluorescent probe

[0032] 1. Preparation of fluorescein monoaldehyde

[0033] Put 4g of fluorescein, 10mL of chloroform, 6mL of methanol, and 0.06g of 15-crown-5 into the flask for reaction, then add 20g of 50% sodium hydroxide solution, stir at 55°C for 5 hours, after cooling, use a concentration of 10mol / L Acidify with sulfuric acid to produce a precipitate, filter, collect the precipitate, and dry it in vacuum. The product is separated by silica gel chromatography using dichloromethane / methanol (200:3) as the eluent to obtain a pale yellow fluorescein monoaldehyde solid.

[0034] 2. Preparation of probes

[0035] Within 30 min, slowly dropwise add 5 mL of methanol solution in which 59 mg of hydrazinopyridine was dissolved in 200 mg of fluorescein monoaldehyde in 40 mL of ethanol. The reaction was carried out at room temperature for 12 hours, and the product was precipitated out after the reaction was completed. The product was c...

Embodiment 2

[0038] Spectral properties of hypochlorite fluorescent probes reacted with various reactive oxygen species prepared in embodiment 2

[0039] Weigh 4.5 mg of the hypochlorite fluorescent probe prepared in Example 1, and prepare a 10 mL acetonitrile solution with a concentration of 1 mM as the mother solution.

[0040] Fluorescence spectrum test: 30 μL of the above mother solution was added to a certain amount of 10 mM PBS buffer solution (pH 7.4), and then various ionic reactive oxygen species (ROS) were added respectively. (H 2 o 2 :200μM; NO · : 200 μM NOC-12; · o 2 - :0.1unitxanthine oxidase and 200μM xanthine; ONOOˉ:1mM KNO 2 +1mM H 2 o 2 ;ROO · : 200μM 2,2-azobis(2-methylpropylimidium) dihydrochloride; 1 o 2 : 1mM ammonium ferrous sulfate+1mM tert-butyl hydroperoxide; · OH: 1mM ammonium ferrous sulfate + 200μM H 2 o 2 ; NaClO: 100 μM) The final concentration of the fluorescent probe was 10 μM. The fluorescence emission spectrum was tested immediately under t...

Embodiment 3

[0044] Spectral properties of hypochlorite fluorescent probe and hypochlorite reaction product prepared in embodiment 3

[0045] Add 30 μL of the mother solution in Example 2 to a certain amount of 10 mM PBS buffer solution (pH 7.4), and then add different equivalents of sodium hypochlorite solution, so that the final concentration of the fluorescent probe is 10 μM, and the final concentration of hypochlorite ions is 0 μM respectively , 5 μM, 10 μM, 20 μM, 30 μM, 40 μM, 50 μM. Immediately after the addition of ions, their fluorescence emission spectra were measured. The fluorescence emission spectrum is excited at 494nm; the slit width of excitation and emission is 1.5 / 1.5nm. The resulting fluorescence increment graph is shown in figure 2 .

[0046] The experimental results show that the fluorescence intensity after the reaction increases with the concentration of sodium hypochlorite; the fluorescence intensity after the reaction has a linear relationship with the concentr...

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Abstract

The invention discloses a hypochlorite ion fluorescent probe, a preparation method and its application, which can be used for detection of hypochlorite ion content in the environment and fluorescence development and content detection of hypochlorite distribution in biological samples. The fluorescent probe of the present invention only has a fluorescence response to hypochlorite, and has no reaction to various other reactive oxygen species (ROS) including H2O2, NO·,·O2‑, ONOOˉ, ROO·, 1O2,·OH, and has good Selectivity and specificity; the probe preparation process is simple and easy to produce on a large scale. The structure of the probe of the present invention is shown in Formula I; its preparation method is as follows: reacting fluorescein monoaldehyde and hydrazinopyridine in an ethanol solution to generate a hypochlorite ion fluorescent probe.

Description

technical field [0001] The invention relates to a hypochlorite ion fluorescent probe, a preparation method and an application thereof. Background technique [0002] As a kind of reactive oxygen species, hypochlorite plays an extremely important role in the process of immunity against microbial infection and inflammation. In living organisms, H 2 o 2 Under the catalysis of myeloperoxidase and chloride ions, hypochlorite is produced, which is the main source of endogenous hypochlorite. Maintaining an appropriate hypochlorite concentration is critical to many cellular functions, however studies have shown that once intracellular hypochlorite levels cannot be maintained within the normal physiological range, it may lead to a variety of diseases such as atherosclerosis sclerosis, arthritis, rheumatoid arthritis and even tumors. Compared with other types of probes, fluorescent probes have many inherent advantages, such as high sensitivity, good specificity, easy operation and ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D493/10
CPCC09B11/08C09B26/02
Inventor 陈小强王碧慧王苏鲁
Owner NANJING TECH UNIV
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