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Two-photon fluorescent probe for detecting Cu (II) and preparation method and application of two-photon fluorescent probe

A two-photon fluorescence and probe technology, applied in fluorescence/phosphorescence, chemical instruments and methods, luminescent materials, etc., can solve problems such as gastrointestinal dysfunction and human toxicity

Inactive Publication Date: 2018-02-02
SHAANXI UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The existence of appropriate amount of Cu(Ⅱ) in the body is beneficial to maintain the normal work of the body, but excessive Cu(Ⅱ) will be toxic to the human body, causing gastrointestinal dysfunction and neurological diseases, such as Wilson's and Alzheimer's syndrome

Method used

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  • Two-photon fluorescent probe for detecting Cu (II) and preparation method and application of two-photon fluorescent probe
  • Two-photon fluorescent probe for detecting Cu (II) and preparation method and application of two-photon fluorescent probe
  • Two-photon fluorescent probe for detecting Cu (II) and preparation method and application of two-photon fluorescent probe

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Experimental program
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preparation example Construction

[0030] A method for preparing a two-photon fluorescent probe for detecting Cu(II), specifically comprising the following steps:

[0031] Step 1, 4-bromo-1,8-naphthalene anhydride and N-(2-aminoethyl)morpholine are added to the round bottom flask A with a material ratio of 1:1, and then added to the round bottom Add ethanol to flask A, place round bottom flask A in an 80°C oil bath, stir and reflux the solution in round bottom flask A with a magnetic stirrer for 2 hours, and suction filter the reaction system while it is hot to obtain compound A, compound A The structural formula is as follows:

[0032]

[0033] Step 2, the compound A obtained in step 1 and hydroxyethylpiperazine are added in the round-bottomed flask B in the ratio of 1:1 in the ratio of substance, and then ethylene glycol methyl ether is added in the round-bottomed flask B until the compound A is completely dissolved, and the round bottom flask B is placed in an oil bath at 125°C, and the solution in the r...

Embodiment 1

[0035] Embodiment 1: the synthesis of fluorescent probe Probe 1:

[0036] To 100 mL round bottom flask A was added glacial acetic acid, 4-bromo-1,8-naphthalene anhydride (2.77 g, 0.01 mol), n-butylamine (4.93 mL, 0.05 mol). In an oil bath at 80°C, the magnetic stirrer was stirred and refluxed for 2 hours, and the reaction system was filtered while hot to obtain Compound A; (1.0132g, 3.06mmol) Compound A, (0.39mL, 3.06mmol ) hydroxyethylpiperazine and ethylene glycol methyl ether, stirred and refluxed at 125°C for 24 hours, cooled the reaction system to room temperature, and distilled under reduced pressure to remove ethylene glycol methyl ether to obtain solution A, using dichloromethane and methanol volume ratio Probe 1 (yellow powder), 0.71 g, was obtained by column separation with an eluent of 100-10:1, yield: 61.11%. 1 H NMR (CDCl 3 , 400MHz, ppm), δ8.58(dt, J=10.5,5.2Hz, 1H), 8.52(dd, J=8.2,0.9Hz, 1H), 8.40(d, J=8.6Hz, 1H), 7.69( t,J=8.5Hz,1H),7.23(d,J=9.0Hz,1H),4.34–4...

Embodiment 2

[0038] Embodiment 2: Fluorescence spectrum test of fluorescent probe:

[0039] Dissolve the fluorescent probe of the present invention in CH 3 CN-H 2 In the solution of O (4:1, v / v), the concentration is 10 μM, and its excitation and emission spectra are detected by a fluorescence spectrometer, as shown in Figure 1 (Figure 1(a) is the excitation spectrum of Probe 1, and Figure 1( b) is the emission spectrum of Probe1): the maximum excitation wavelength of the fluorescent probe of the present invention is at 385nm, and the maximum emission wavelength is at 530nm.

[0040] in CH 3 CN-H 2O (4:1, v / v) solution, add Probe 1 (10μM), and then add 40μM Li + 、Na + 、K + , Ca 2+ , Mg 2+ 、Ba 2+ 、Ni 2+ , Mn 2+ 、Co 2+ 、Ag + and Cu(Ⅱ) metal salt solution, and then put the fluorescence cuvette in the FS5 fluorescence spectrometer for testing to study the selective recognition of Probe1 for metal ions. The test results are as follows figure 2 : Only when 40μM Cu(II) is added, the...

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Abstract

The invention discloses a two-photon fluorescent probe for detecting Cu (II) and a preparation method and application of the two-photon fluorescent probe. The preparation method includes the steps offirstly, adding 4-bromine-1, 8-anhydride naphthalene and N-(2-amino ethyl) morpholine into a round-bottom flask A, adding ethanol into the round-bottom flask A, placing the round-bottom A in oil bath,stirring the solution in the round-bottom flask A with a magnetic stirrer, and performing suction filtration on the reaction system while the reaction system is hot to obtain a compound A; secondly,adding the compound A obtained in the first step and hydroxyethyl piperazine into a round-bottom flask B, adding ethylene glycol monomethyl ether until the compound A is completely dissolved, placingthe round-bottom flask B in oil bath, stirring the solution in the round-bottom flask B with a magnetic stirrer to obtain a solution A; thirdly, using an eluting agent comprising dichloromethane and methanol to perform column chromatography separation to obtain the two-photon fluorescent probe. The two-photon fluorescent probe is applied to the targeting two-photon fluorescent imaging detection ofthe Cu (II) in cell lysosome.

Description

technical field [0001] The invention belongs to the technical field of fluorescent probes for metal ion detection, in particular to a two-photon fluorescent probe for detecting Cu(II), and also relates to a preparation method and application of the fluorescent probe. Background technique [0002] Copper is one of the basic trace elements in living organisms. As the third transition metal ion in the human body, it plays an important role in biological processes. It plays an important role as a catalytic cofactor in different physiological processes such as mitochondrial respiration, iron absorption, and redox processes of a large number of enzymes (including superoxide dismutase and tyrosinase, etc.). The presence of appropriate amount of Cu(Ⅱ) in the body is beneficial to maintain the normal work of the body, but excessive Cu(Ⅱ) will cause toxicity to the human body, causing gastrointestinal dysfunction and neurological diseases, such as Wilson's and Alzheimer's syndrome. T...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D221/14C09K11/06G01N21/64
CPCC07D221/14C09K11/06C09K2211/1029C09K2211/1033C09K2211/1044G01N21/643
Inventor 姜慧娥杨林杰李俊炜刘汉斌李志健杜飞孟卿君杨保宏
Owner SHAANXI UNIV OF SCI & TECH
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