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Naphthalimide compound fluorescence probe for identifying Ag+ in HL-60 and its preparation method

A naphthalimide and fluorescent probe technology, applied in the field of metal ion fluorescent probes, can solve problems such as serious, easy to produce drug resistance, adverse reactions, etc., and achieve the effects of high response value, reliable detection method, and high sensitivity

Inactive Publication Date: 2018-04-17
FUJIAN MEDICAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Chemotherapy is an important method for the treatment of leukemia, but it has serious adverse reactions and is prone to drug resistance during clinical application.

Method used

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  • Naphthalimide compound fluorescence probe for identifying Ag+ in HL-60 and its preparation method
  • Naphthalimide compound fluorescence probe for identifying Ag+ in HL-60 and its preparation method
  • Naphthalimide compound fluorescence probe for identifying Ag+ in HL-60 and its preparation method

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] Embodiment 1: This embodiment is a specific embodiment prepared according to the reaction scheme of the compound of formula (I).

[0034] (2-pyridyl)-4-(2-thiazolyl)-1.8-naphthalimide: add 1 mmol of 4-bromo-1,8-naphthalene anhydride to a 100 ml round bottom flask equipped with a reflux condenser , 1 mmol 2-aminopyridine, 2 mmol sodium hydroxide and 2 mmol copper chloride were dissolved in 20 ml of toluene, and the reaction temperature was set at 115 °C. With Schlenk Line TechnologyN 2Reflux under protection, TLC monitors the reaction, after 17 h, the reaction is complete. After standing overnight and standing at room temperature, a solid precipitated, filtered, and recrystallized with 40 ml of toluene to obtain compound (II) with a yield of 82%. Weigh 1 mmol of N-(2-pyridyl)-4-bromo-1,8-naphthimide, 1 mmol of 2-aminothiazole, 2 mmol of cesium carbonate and excess iodide of compound (II) Copper in 20 ml of DMF. With Schlenk Line TechnologyN 2 Reflux under protection...

Embodiment 2

[0037] Embodiment 2: the ultraviolet absorption spectrogram of the N-(2-pyridyl)-4-(2-thiazolyl)-1.8-naphthalimide that embodiment 1 makes (see figure 1 ) and fluorescence spectra (see Picture 1-1 ).

[0038] Accurately weigh N-(2-pyridyl)-4-(2-thiazolyl)-1.8-naphthalimide, transfer it into a 10 mL volumetric flask, dissolve it with absolute ethanol, and keep to volume after the sample is completely dissolved , formulated to a concentration of 3.0×10 -5 mol•L -1 The solution was measured for its UV absorption spectrum and fluorescence excitation spectrum, respectively. Measurement results such as figure 1 , Picture 1-1 shown; figure 1 is the ultraviolet absorption spectrum of the silver ion fluorescent probe N-(2-pyridyl)-4-(2-thiazolyl)-1.8-naphthalimide; Picture 1-1 It is the fluorescence spectrum of the silver ion fluorescent probe N-(2-pyridyl)-4-(2-thiazolyl)-1.8-naphthalimide for the detection of aggregation-induced luminescent effect.

[0039] From figure 1...

Embodiment 3

[0040] Example 3: The N-(2-pyridyl)-4-(2-thiazolyl)-1.8-naphthoimide fluorescent probe prepared in Example 1 was measured at an excitation wavelength of 650 nm for Ag + selective.

[0041] Accurately weigh N-(2-pyridyl)-4-(2-thiazolyl)-1.8-naphthalimide, dissolve it in chromatographically pure absolute ethanol, and configure it to a concentration of 1.0×10 -4 mol•L -1 In the ligand solution, 10 different metal ions (Zn 2+ , Hg + 、Cu 2+ , Mg 2+ , Li + 、Al 3+ 、Ni + , K + , Ca 2+ 、Ag + ), with a ligand concentration of 3.0×10 -5 mol•L -1 , metal ion concentration 1.0×10 -4 mol•L -1 The mixed solution was measured to measure the change of the fluorescence spectrum of the solution. Measurement results such as figure 2 shown.

[0042] From figure 2 It can be seen that Ag + The fluorescence intensity of N-(2-pyridyl)-4-(2-thiazolyl)-1.8-naphthoimide fluorescent probe is significantly stronger than that of other ions. + There is a high degree of selectivity...

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Abstract

The invention discloses a naphthalimide compound fluorescence probe for identifying Ag+ in HL-60 and its preparation method. The naphthalimide compound with a structure of a formula (I) is applied tothe Ag+ detection in the HL-60 cell, and has high Ag+ sensitivity and response value; when it is used as the fluorescence probe, the fluorescence probe has obvious response for Ag+; when Ag+ with different concentrations is detected, the fluorescence probe shows good linear relationship; the fluorescence probe also has good selectivity of Ag+ in the HL-60 cell; the HL-60 suspending cell dyed withnaphthalimide compound is activated by blue light; through observation in a microscope, the cell emits green fluorescence, and the detection method is reliable.

Description

technical field [0001] The invention relates to a method capable of recognizing Ag in HL-60 cells + The invention discloses a naphthalimide compound fluorescent probe and a preparation method thereof, belonging to the field of metal ion fluorescent probes. Background technique [0002] Silver is one of the trace elements in human tissue. Trace amounts of silver not only help the body resist harmful invading germs, it also helps repair and rebuild human tissue that is vital to life, but Ag + Excessive amount will block the metabolic system of the organism, which is very harmful to the human body. The United Nations World Health Organization (WHO) clearly stipulates that the safe value of silver to the human body is below 0.05 mg / L, and the limit of silver ions in drinking water is 0.05 mg / L. If the silver content in drinking water exceeds 0.05 mg / L, it will produce obvious toxic and negative effects. Among them, leukemia is one of the more serious diseases. This method us...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D417/14C09K11/06G01N21/64
CPCC07D417/14C09K11/06C09K2211/1029C09K2211/1037G01N21/6428G01N21/6486
Inventor 柯方林珊珊徐书清许建华吴丽贤林晨
Owner FUJIAN MEDICAL UNIV
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