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A water-soluble fluorescent probe for detecting nitric oxide in liver cells and its application

A fluorescent probe and nitric oxide technology, applied in the fields of analytical chemistry, life science and medicine, can solve the problems of inability to specifically identify cell tissue, poor water solubility, toxic side effects, etc., and achieve convenient post-processing, low cost input, and synthetic simple route effect

Active Publication Date: 2018-11-30
HUNAN UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] Aiming at the shortcomings of current small molecule fluorescent probes that cannot specifically recognize cell tissue, poor water solubility, and toxic side effects caused by organic solvents, the purpose of the present invention is to provide a water-soluble probe that specifically detects nitric oxide in liver cells. A fluorescent fluorescent probe and its application, the water-soluble fluorescent probe is based on 4-amino-3-nitrophenol, bromoacetylene, tetraacetyl-α-D-galactose bromide, sodium azide, rhodamine B A water-soluble fluorescent probe synthesized from sodium ascorbate

Method used

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  • A water-soluble fluorescent probe for detecting nitric oxide in liver cells and its application
  • A water-soluble fluorescent probe for detecting nitric oxide in liver cells and its application
  • A water-soluble fluorescent probe for detecting nitric oxide in liver cells and its application

Examples

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Embodiment 1

[0024] A preparation of a water-soluble fluorescent probe for detecting nitric oxide in liver cancer cells, comprising the following steps:

[0025] (1) Preparation of product 1.

[0026] Add 4-amino-3 nitrophenol (3.0 mmol) into 20 mL of acetone, then add propyne bromide (4.5 mmol), stir well and then add K 2 CO 3 (6.0 mmol). Heat to reflux for 14 hours. Stop after the reaction is finished, filter, wash with dichloromethane for 3-4 times, then concentrate and filter the filtrate with a rotary evaporator, and then pass through the column with silica gel chromatography to obtain the product 1.

[0027]Product 1 (1.2 mmol) was dissolved in 1,4-dioxane (15 mL), then stannous dichloride dihydrate (1.35 g, 6.0 mmol) and concentrated hydrochloric acid (3.0 mL )mixture. After the dropwise addition of the mixed solution was completed, the reaction was carried out at room temperature for 48 hours. After the reaction is complete, neutralize the reaction solution to neutrality wit...

Embodiment 2

[0033] Embodiment 2: detection experiment of nitric oxide.

[0034] Take 17 5mL sample bottles, respectively add 3 mL of the solution prepared by the fluorescent probe obtained in Example 1 (the concentration of the fluorescent probe is 5 μM, and it is prepared with an aqueous solution with a pH of 7), and then respectively add the solution with a concentration of [NO ] = 0(a), 5×10 -3 mol / L (b), 1×10 -2 mol / L (c), 1.5×10 -2 mol / L (d), 2×10 -2 mol / L(e), 2.5×10 -2 mol / L(f), 3×10 -2 mol / L (g), 3.5×10 -2 mol / L (h), 4×10 -2 mol / L(i), 4.5×10 -2 mol / L(j), 5×10 -2 mol / L (k), 5.5×10 -2 mol / L (l), 6×10 -2 mol / L (m), 7×10 -2 mol / L (n), 8×10 -2 mol / L(o), 9×10 -2 mol / L (p), 1×10 -1 mol / L (q) of 3 μL nitric oxide solution was added to 17 sample vials, stirred at room temperature for 10 min, and the fluorescence intensity of these samples was measured with 550 nm as the excitation wavelength, and the fluorescence emission of 17 samples was obtained. Spectral c...

Embodiment 3

[0035] Example 3: Selective detection experiment of other ions and peroxide influence.

[0036] Take 18 5 mL sample bottles and fill them with 3 mL of the fluorescent probe solution obtained in Example 1 (the concentration of the fluorescent probe is 5 μM, which is prepared with an aqueous solution with a pH of 7), and then respectively add the fluorescent probe solution with a concentration of 5.0× 10 -2 mol / L (H 2 o 2 , HClO, 1 o 2 , AA, NO, NO 3 - , NO 2 - , OH . , GSH, Cys, CNS - , Mn 2+ 、Na + 、K + , Zn 2+ , Fe 3+ , Ca 2+ ) and add 3µL each to the other first 18 sample vials, and sample No. 18 is the blank sample. Then measure the fluorescence emission intensity at 550 nm wavelength excitation and 580 nm wavelength emission of 18 samples respectively, the results are shown in image 3 . The measurement results show that, except nitric oxide, other above-mentioned ions and peroxides have no obvious influence on the fluorescence intensity of the prepared f...

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Abstract

The invention discloses a water-soluble fluorescent probe for detecting nitric oxide in hepatic cells and application thereof. Compared with the existing fluorescent detecting technology, the fluorescent probe can be quickly positioned in a hepatic cell and can be used for performing in-situ highly-selective real-time detection on nitric oxide in the hepatic cell. Furthermore, the probe has excellent water solubility, optical stability, biocompatibility and higher nitric oxide selectivity, and is not interfered by other common species in organisms, such as active oxygen and active nitrogen. The water-soluble fluorescent probe has huge application prospects in analytical chemistry, life science, medicine and other technical fields. Laser confocal imaging experiments indicate that the probe has relatively good cell permeability and does not have remarkable toxic or side effects on cells and organisms.

Description

technical field [0001] The invention relates to the technical fields of analytical chemistry, life science and medicine, and specifically relates to the application of a water-soluble fluorescent probe in detecting nitric oxide in liver cells. Background technique [0002] As a messenger molecule, nitric oxide (NO) plays a very important role in physiology and biology, and its content disorder is closely related to many diseases. Therefore, further understanding of the function of nitric oxide and the detection of nitric oxide are of great significance in biological research and medical diagnosis. In addition, changes in nitric oxide can reflect the health status of the human body. Liver tissue is one of the important components of living organisms. It prevents oxidation in living organisms, transforms some substances in living organisms, and has the function of secreting some proteins in living organisms. However, dysfunction of liver tissue may cause various diseases, su...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07H19/056C07H1/00C09K11/06G01N21/64
CPCC07H1/00C07H19/056C09K11/06C09K2211/1029C09K2211/1059C09K2211/1088G01N21/6486
Inventor 张培盛
Owner HUNAN UNIV OF SCI & TECH
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