Aggregation-induced luminescence molecular probe capable of realizing selective identification on lead ions and aluminium ions, and preparation method and applications thereof

A technology of aggregation-induced luminescence and molecular probes, applied in chemical instruments and methods, preparation of organic compounds, preparation of ethers, etc., can solve the problems affecting the sensitivity and accuracy of tracking Al3+, no molecular probes, poor probe solubility, etc. , to avoid self-precipitation, increase water solubility, and achieve the effect of good solubility

Active Publication Date: 2019-08-23
ZHEJIANG NORMAL UNIVERSITY
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, due to the poor solubility of the probe in water, Al 3+ Concomitant addition of DMSO is required for quantification and imaging
The low solubility of AIE probes in aqueous solution may generate false signals of self-precipitation in living cells during imaging, which will greatly affect the tracking of Al in biological systems. 3+ sensitivity and accuracy
[0004] Application No. 2018101055194 Invention Patent Application Document discloses a dual-channel fluorescein-based fluorescent probe for aluminum ions and zinc ions and its preparation method and application. A fluorescent probe with selectivity for both aluminum ions and zinc ions is developed. needles, but there is no molecular probe with good selectivity and qualitative and quantitative analysis functions for aluminum ions and lead ions at the same time.

Method used

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  • Aggregation-induced luminescence molecular probe capable of realizing selective identification on lead ions and aluminium ions, and preparation method and applications thereof
  • Aggregation-induced luminescence molecular probe capable of realizing selective identification on lead ions and aluminium ions, and preparation method and applications thereof
  • Aggregation-induced luminescence molecular probe capable of realizing selective identification on lead ions and aluminium ions, and preparation method and applications thereof

Examples

Experimental program
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Effect test

preparation example Construction

[0049] This embodiment discloses the molecular probe TPE-4CO that first discloses 2 The preparation method of Na comprises the following steps:

[0050] Step 1, preparing 1,1,2,2-tetrakis(4-methoxyphenyl)ethylene;

[0051] The synthesis method is as follows:

[0052] Zinc powder (1.84g, 28mmol) and TiCl 4 (1.58ml, 14mmol) in 50ml dry THF, refluxed under nitrogen atmosphere for 2h. A solution of 4,4-dihydroxybenzophenone (1.50 g, 7.0 mmol) in dry THF (20 ml) was added to the above suspension, followed by reflux at 80° C. for 12 h. After cooling the reaction mixture to room temperature, add 10% K 2 CO 3 (50 mL) in water. The resulting product was extracted with ethyl acetate. The solvent was evaporated under vacuum and the crude product was purified on a silica gel column using ethyl n-hexane: ethyl acetate (1:1, V / V) as eluent. The yield of 1,1,2,2-tetrakis(4-methoxyphenyl)ethylene was 70% (1.01 g).

[0053] Step 2, synthesizing 1,1,2,2-tetrakis(4-hydroxyphenyl)ethylen...

Embodiment 2

[0068] This embodiment uses the probe TPE-4CO that embodiment 1 makes 2 Na for the identification and detection of aluminum ions and lead ions: for the quantitative detection of Al 3+ , first prepare a fixed concentration (20.0μM) of TPE-4CO in HEPES buffer (pH7.0) 2 Na solution, and then different amounts of Al in the range of 0.0–650.0 μM 3+ respectively added to the above TPE-4CO 2 in Na solution. The PL spectrum of the resulting mixture was recorded using a xenon arc lamp under excitation at 355 nm. will Pb 2+instead of Al 3+ , with the same method for Pb 2+ Quantitative detection of Pb 2+ The dosage is in the range of 0.0–500.0μM, such as Figure 4 (C) and (D) shown.

[0069] to Al 3+ and Pb 2+ The selectivity test is as follows;

[0070] TPE-4CO in HEPES buffer 2 Add quantitative amounts of different kinds of metal cations (100.0 μM) to Na solution (20.0 μM), including K + ,Mg 2+ , Ca 2+ , Ba 2+ ,Al 3+ ,Pb 2+ ,Cd 2+ ,Co 2+ , Fe 2+ , Ag + ,Zn 2+ ,H...

Embodiment 3

[0075] This embodiment uses the TPE-4CO that embodiment makes 2 Na in live cell imaging of aluminum ions in Arabidopsis root cells, the specific steps are as follows:

[0076] There is a large amount of glutathione in Arabidopsis root cells, and glutathione has a masking effect on lead ions, so based on TPE-4CO 2 Discriminative detection strategy for Al versus Pb ions of Na, enabling specific imaging of Al in living cells 3+ .

[0077] The specific operation steps are as follows:

[0078] Step 1. Disinfect the surface of Arabidopsis wild-type seeds, soak them in the dark at 4°C for 3 days, and then sow them on 0.5× medium 1.5% (w / v) plates;

[0079] Step 2, placing the flat plate sown with Arabidopsis wild-type seeds in a climate-controlled growth chamber to vertically grow the seedlings on the flat plate;

[0080] Cultivation conditions in a climate-controlled growth chamber were as follows:

[0081] Day / night temperature: 22 / 20°C;

[0082] Photoperiod: 16 / 8h;

[0083]...

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Abstract

The invention discloses an aggregation-induced luminescence molecular probe capable of realizing selective identification on lead ions and aluminium ions. The synthesis route comprises following steps: 4, 4'-dimethoxy benzophenone is taken as an initial raw material, McMurry coupling reaction is adopted to synthesize 1, 1, 2, 2 -tetra(4-methoxyphenyl)ethane; the obtained product is subjected to treatment of methoxy groups with BBr3 for conversion into hydroxy groups, and nucleophilic substitution between 1, 1, 2, 2-tetra(4-hydroxy phenyl)ethane and ethyl chloroacetate is carried out for further introduction of four kinds of carboxylic esters so as to obtain 2, 2', 2'', 2''-((ethane, 1, 1, 2, 2-tetra(benzene-4, 1-diyl))tetra(oxo) tetraethyl acetate; and then sodium hydroxide is adopted forhydrolysis so as to obtain the probe TPE-4CO2Na. The invention also discloses applications of the probe in Arabidopis thaliana root cell aluminium ion living cell imaging. The aggregation-induced luminescence molecular probe can be used for qualitative quantificative distinguish determination of aluminium ions and lead ions, the water solubility is excellent, and imaging performance in biologicalcells is achieved.

Description

technical field [0001] The invention relates to the technical field of molecular probes, in particular to an aggregation-induced luminescent molecular probe for selectively recognizing lead ions and aluminum ions, a preparation method and application thereof. Background technique [0002] With the intensification of industrialization, some metal ions that play an indispensable role in different biological processes are more and more exposed to heavy metals and toxic metal ions, so the high selectivity of metal ions is accurate Determination has also become a huge challenge for chemists. Aluminum, as the third most abundant element in the earth's crust, continuously enters the ecosphere and biosphere with the increase of acid rain. Available evidence indicates that ingestion of aluminum ions causes serious toxicity to organisms including plants and humans. In addition, lead ions are another important pollutant that widely exists in the environment and are highly toxic to or...

Claims

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Application Information

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IPC IPC(8): C09K11/06C07C51/41C07C59/13G01N21/64
CPCC09K11/06C07C51/412C07C59/13G01N21/6428C07C67/31C07C37/055C07C41/01C09K2211/1007C07C69/712C07C39/215C07C43/215
Inventor 丰慧钱兆生徐鹏飞
Owner ZHEJIANG NORMAL UNIVERSITY
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