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High-selectivity and ultra-sensitive liver cancer specific peroxynitrite probe and application thereof

The technology of a compound and naphthalimide is applied in the field of highly selective and ultrasensitive liver cancer-specific peroxynitrite probe and its application field, which can solve the problems of inability to specifically detect liver cell peroxynitrite and achieve a reaction Sensitive, simple synthesis, good stability

Inactive Publication Date: 2019-06-18
UNIV OF JINAN
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

General detection methods cannot specifically detect peroxynitrite in liver cells. Therefore, the development of highly selective and sensitive fluorescent probes has become an urgent problem to be solved.

Method used

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  • High-selectivity and ultra-sensitive liver cancer specific peroxynitrite probe and application thereof
  • High-selectivity and ultra-sensitive liver cancer specific peroxynitrite probe and application thereof
  • High-selectivity and ultra-sensitive liver cancer specific peroxynitrite probe and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034]

[0035] (Scheme 1) Dissolve 500mg (1.46mmol) of naphthalimide compounds in 10mL of water and dichloromethane (1:1), then add 450mg (1.21mmol) of galactose compounds to reflux for 12h, extract under reduced pressure The solvent was evaporated to dryness. Dissolve the product and triethylamine (5ml) in a mixed system of 9ml methanol and water (8:1), stir at room temperature for 12h, spin the solvent under reduced pressure, if you want to get a purer product, you can use the crude product The mixed system of dichloromethane and methanol (for example, v / v, 10:1) was separated by column chromatography to obtain the pure product, and 430 mg of the pure yellow product was obtained with a yield of 54%.

[0036] (Scheme 2) Dissolve 500mg (1.46mmol) of naphthalimide compounds in 10mL of water and dichloromethane (1:1), then add 708mg (1.9mmol) of galactose compounds to reflux for 12h, extract under reduced pressure The solvent was evaporated to dryness. Dissolve the product...

Embodiment 2

[0041] Figure 1a is the fluorescence spectrum of the probe (5 μM) before and after adding peroxynitrite (0-50 μM). Figure 1b It is a linear relationship diagram of different concentrations of peroxynitrite (0-15 μM) to probe (5 μM).

[0042] Configure multiple parallel samples with a probe concentration of 5 μM in a 10mL colorimetric tube, then add different concentrations of peroxynitrite into the test system, shake it evenly and let it stand. The above determinations were carried out in a pure water (20mM PBS, pH 7.4) system, the probe used was the probe prepared in Example 1, and all spectral tests were measured at 25°C.

[0043] Fluorescence intensity changes were measured with a fluorescence spectrometer, from Figure 1a It can be clearly seen that as the concentration of peroxynitrite increases, the fluorescence intensity at 550 nm increases gradually. and, by Figure 1b It can be seen that after the fluorescent probe (5μM) is added to peroxynitrite (0-15μM), there i...

Embodiment 3

[0045] figure 2 is the response time of the probe (5 μM) after addition of peroxynitrite (10 μM). Take 50 μL of the probe mother solution and place it in 10 mL of the test system, then add 10 μM peroxynitrite into the test system, shake it evenly, and immediately measure the change of its fluorescence intensity with a fluorescence spectrometer. The above determinations were carried out in a pure water (20mM PBS, pH 7.4) system, the probe used was the probe prepared in Example 1, and all spectral tests were measured at 25°C.

[0046] It can be clearly seen from the figure that after the addition of peroxynitrite, the fluorescence intensity reaches the maximum value and remains unchanged after detection for about 3s, which indicates that the probe reacts rapidly with peroxynitrite and can be used for peroxynitrite. The determination of nitrate provides a rapid analytical method.

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Abstract

The invention relates to a high-selectivity and ultra-sensitive liver cancer cell specific peroxynitrite probe. Specifically, the probe is a naphthalimide compound and can be taken as a peroxynitritefluorescence probe to be used for detecting peroxynitrite in liver cancer cells. The probe can realize at least one of the following technical effects: peroxynitrite can be recognized with high selectivity; response to peroxynitrite can be rapidly realized; ultra-sensitive analysis for peroxynitrite can be realized; quantitative analysis for peroxynitrite can be realized; peroxynitrite in the liver cancer cells can be specifically detected; the property is stable, and the probe can be stored for a long time for use.

Description

technical field [0001] The present invention relates to naphthalimide compounds as fluorescent probes for peroxynitrite, capable of highly selective and ultrasensitive analysis of peroxynitrite, or it can measure the concentration of peroxynitrite in a sample, and specifically target to liver cancer cells. Background technique [0002] Reactive oxygen and reactive nitrogen species are involved in a variety of physiological processes in living systems, including signal transduction, inflammation, and resistance to oxidative damage. As a strong oxidizing substance in active oxygen and active nitrogen, peroxynitrite is produced by the reaction of nitric oxide and superoxide radicals, and has high reactivity and instability. It is used in living systems It plays an important role in signal transduction and antibacterial effect. However, due to its nitration damage to proteins, nucleic acids, lipids, etc., peroxynitrite is also considered harmful, and abnormal accumulation of p...

Claims

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Application Information

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IPC IPC(8): C07H19/056C07H1/00C09K11/06G01N21/64
Inventor 张雪柳彩云段庆霞陈亚男虞亚敏朱宝存
Owner UNIV OF JINAN
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