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Stilbene two-photon fluorescence probe for detecting zinc ion in cell

A technology of stilbene and two-photon fluorescence, which is applied in the direction of fluorescence/phosphorescence, luminescent materials, chemical instruments and methods, etc., can solve the problems of large interference in cell detection, achieve good cell permeability, no toxic side effects, chemical -Good photostability effect

Inactive Publication Date: 2011-08-17
SHAOGUAN COLLEGE
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Single-photon fluorescent zinc ion probes are derivatives such as quinoline and fluorescein[(1) Hendrickson, K. M.; Geue, J. P.; Wyness, O.; Lincoln, S. F.; Ward, A. D. J. Am. Chem. Soc .2003, 125 (13), 3889–3895; (2) omatsu, K.; Kikuchi, K.; Kojima, H.; Urano Y.; Nagano, T. J. Am. Chem. Soc. 2005, 127: 10197-10204], because the excitation wavelength is 350-560 nm, it is easy to produce adverse effects such as phototoxicity and fluorescent bleaching , causing greater interference to cell detection

Method used

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  • Stilbene two-photon fluorescence probe for detecting zinc ion in cell
  • Stilbene two-photon fluorescence probe for detecting zinc ion in cell
  • Stilbene two-photon fluorescence probe for detecting zinc ion in cell

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0037]

[0038] (1) Synthesis of Intermediate 2

[0039] Measure dichloromethane (50 mL) with a graduated cylinder, place it in a 150 mL double-necked round-bottom flask, accurately measure p-xylene (16.96 g, 0.16 mol, 19.8 mL) with a pipette and drop it into dichloromethane , Weighed elemental iodine (0.1 g, 0.8 mmol) and added it to the mixture, installed an air condenser on one of the openings of the flask and connected it to a tail gas recovery device, installed a constant pressure feeder on the other opening of the flask, and used a pipette Accurately measure the liquid bromine (18 mL) in the liquid pipe and transfer it to the constant pressure feeder, and add a layer of water (about 0.3 ~ 0.5 cm) on the top surface of the liquid bromine to prevent the liquid bromine from volatilizing, and then pour it on the top of the constant pressure feeder. Mouth capped. The temperature of the reaction system was controlled at 12 °C, and liquid bromine was added dropwise to the m...

Embodiment 2

[0054] The selectivity to zinc ions was evaluated using Compound I-1 synthesized above. Add 1 mM compound I-1 to 20-fold excess of various metal ions in MOPS buffer at pH 7.2 (100 mM KCl, 10 mM EGTA, pH 7.2. EGTA = ethylene glycol bis(2-aminoethyl ether) N ,N,N',N'-tetraacetic acid, and MOPS = 3-(morpholino)propanesulfonic acid) (divided into two cases with 1 mM zinc ions and without zinc ions), the single-photon excitation wavelength of the probe is 403 nm , the emission wavelength is 610 nm, and the test results are shown in Figure 5 middle. It can be seen from the figure that the probe I-1 has a high selectivity for zinc ions, and the addition of zinc ions produces a large fluorescence quenching. In addition, metal ions such as sodium, potassium, calcium, magnesium, and manganese have no effect on the detection. interference.

[0055] Example 3

Embodiment 3

[0057] Use the compound I-1 synthesized above to evaluate the response to pH. For compound I-1, adjust the pH value to about 1.0 in an aqueous solution with an ionic strength of 0.1. After measuring the fluorescence intensity, add lye to slowly increase the pH value. Record the corresponding changes in fluorescence intensity, and the test results are displayed in Figure 6 middle. It can be seen from the figure that the probe I-1 is within the physiological pH range, and the pH change basically has no effect on the fluorescence emission. Therefore, probe I-1 can be used for the detection of intracellular zinc ions in a large pH range.

[0058] Example 4

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Abstract

The invention relates to a stilbene two-photon fluorescence probe for detecting a zinc ion in a cell. Single-photon excitation and two-photon excitation of a probe molecule are respectively carried out in a range from 390 to 420 nm and in a range from 790 to 820 nm, and chemical-optic stability is good; the fluorescence quantum yield is high before the probe molecule is complexed with the zinc ion, and single-photon detection and two-photon detection on the zinc ion can be carried out; the probe molecule has a good selectivity on the zinc ion; in a physiological pH range, the probe molecule is insensitive to the variation of the pH; in a range of pH5-pH8, pH variation dose not basically influence fluorescence-emission of a complex; dissociation constant between the probe molecule and the zinc ion is in a micromole grade range, the cell zinc ion with micromole concentration can be detected; the probe molecule has a good cell permeability, is suitable for the detection of zinc ion concentration variation in the cell; and distribution fluorescence images or false color proportion fluorescence images of the zinc ion in various active cells or tissues are obtained by a laser confocal fluorescence microscope.

Description

technical field [0001] The invention belongs to the field of fine chemical industry and relates to a stilbene two-photon fluorescent probe for detecting intracellular zinc ions. Background technique [0002] Zinc is an important component involved in cell physiological activities. Although traditional zinc ion bioinorganic chemistry studies focus on the structure, function and catalytic function of zinc in proteins, more and more attention has been paid to the neurobiological research of zinc ions. Through chemical studies of mammalian tissues, including the prostate, the islet-secreting pancreas, and microneurons in the hippocampus, it has been found that diseases such as prostate cancer, diabetes, and neural tissue aging can lead to disturbances in the distribution of zinc. Most of zinc ions in organisms are combined with proteins, and the content of zinc ions in cells ranges from subnanomolar to 300 μM. Zinc ions can regulate the function of ion channels. Zinc ions not ...

Claims

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Application Information

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IPC IPC(8): C09K11/06C07D401/04G01N21/64
Inventor 黄池宝任安祥冯承浩李海渤
Owner SHAOGUAN COLLEGE
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