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Diphenylethene group dual cyano benzene two-photon fluorescence probe for detecting and displaying intracellular Hg ion

A two-photon fluorescence, biscyanobenzene technology, applied in fluorescence/phosphorescence, luminescent materials, thioether preparation, etc., can solve the problems of unsatisfactory detection sensitivity and unusable probes.

Active Publication Date: 2015-11-25
ZUNYI NORMAL COLLEGE
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

A representative report is azathia crown ether or open-chain crown ether two-photon fluorescent mercury ion probe , 3285-3289; (2) C.S.Lim, D.W.Kang, Y.S.Tian, ​​J.H.Han, H.L.Hwang, B.R.Cho. J. Fan, X. Peng, Z. Lin, B. Guo, A. Ren, J. Cui, S. Sun, Highly selective and sensitive twin–cyano–stilbene–based two–photon fluorescent probe former cury (ii) inaqueous solution with large two–photonabsorption cross–section, J. Photochem. Photobio.A:Chem.,2008,199(2–3):144–149], the probe reported in literature (1) cannot be used for cell imaging, and literature (2) can achieve imaging, but the detection sensitivity is not very ideal , document (3) is exactly the same kind of probe developed by the patent applicant, but unfortunately it has never been used in cell imaging experiments

Method used

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  • Diphenylethene group dual cyano benzene two-photon fluorescence probe for detecting and displaying intracellular Hg ion
  • Diphenylethene group dual cyano benzene two-photon fluorescence probe for detecting and displaying intracellular Hg ion
  • Diphenylethene group dual cyano benzene two-photon fluorescence probe for detecting and displaying intracellular Hg ion

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] Synthesis of Probe I:

[0033]

[0034] (a) POCl 3 / DMF, 90℃, 2h (95%); (b) Br 2 / CH 2 Cl 2 , nolight, 20℃, 24h (90%); (c) CuCN / DMF, 150℃, 48h (78%); (d) NBS / CCl 4 ,6h(15%); (e)P(OEt) 3 / toluene,120℃,5h(96%); (f)NaH(2equiv) / THF,12h(65%);(g)K 2 CO 3 / MeCN,HS(CH 2 ) 2 OH, 40℃, 12h(86%).)

[0035] (1) Synthesis of intermediate 2

[0036] Dehydrated DMF (30.0g, 411mmol) was added to a 100mL single-necked round-bottomed flask with a drying tube, stirred in an ice-water bath and cooled to 0°C, the drying tube was removed, and a constant pressure feeder containing POCl3 (27.6g, 181.5mmol) was inserted Add POCl3 dropwise with stirring at 0°C, continue the reaction at 0°C for 45 min after the dropwise addition, and then add N,N-dihydroxyethylaniline (10.0 g, 55 mmol) in DMF ( 10.0g, 137mmol) solution, then slowly raised to 110°C and continued to react for 2h, cooled and poured into 0.5L ice water, stirred and added dropwise 1M NaOH solution to adjust the pH to arou...

Embodiment 2

[0050] Probe I selectivity for mercury ions:

[0051] The selectivity to mercury ions was evaluated using compound I synthesized above. Probe molecule I (probe concentration is ) were added to the buffer solution of different metal ions (the ion concentration is 20mmol / L), the ratio of the difference between the single-photon fluorescence intensity of the probe molecule solution without metal ions and the single-photon fluorescence intensity of different ion solutions to the former That is, the percentage quenching rate of the ion-to-probe molecule fluorescence intensity, which is used to judge the selectivity of the probe molecule to the ion. The single- and two-photon excitation wavelengths of the probe are 467nm and 810nm, respectively, and the emission wavelength is 588nm. The test results are shown in Figure 6 middle. It can be seen from the figure that the probe I has a high selectivity to mercury ions, and the addition of mercury ions produces a large fluorescenc...

Embodiment 3

[0053] Insensitivity of Probe I to pH:

[0054] The compound I synthesized above was used to evaluate the response to pH, and the probe molecule (probe concentration of ) respectively add ions with an ion concentration of In the aqueous solution of 20mmol / L and 0, adjust the pH to about 2.0. After measuring the fluorescence intensity, add lye, slowly increase the pH, record the corresponding fluorescence intensity change, and plot the pH change with the fluorescence intensity change. The test results are shown in Figure 7 middle. It can be seen from the figure that within the range of pH 4.5-13, the pH change basically has no effect on the fluorescence emission. Therefore, probe I can be used for the detection of intracellular mercury ions in a large pH range.

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Abstract

The invention relates to a diphenylethene group dual cyano benzene two-photon fluorescence probe for detecting and displaying intracellular Hg ions, and the probe is prepared by performing nucleophilic substitution on mercaptoethanol and 2,5-di(4-[di(2-chloroethyl)amino]styryl)para-phthalonitrile. Laser excitation of 810nm can avoid photoinduced toxicity of cells. In a range of pH being 4.5-13, the probe has good selectivity on the Hg ions, and Na, K, Ca, Mg and Mn ions have no interference with detection, and the Hg ions of micro molarity can be detected. Fluorescence intensity is reduced after complexing of probe molecules and the Hg ions, and the content of the Hg ions can be subjected to two-photon fluorescence detection. A two-photon fluorescence microimaging experiment shows that the probe has good permeability on fibroblasts and other cells, has no toxic or side effects on the cells and is particularly suitable for the detection of intracellular Hg ion concentration change and Hg ion distribution.

Description

Technical field: [0001] The invention belongs to the field of fine chemical industry and relates to a distyryl dicyanobenzene two-photon fluorescent probe for detection and imaging of mercury ions in cells. Background technique: [0002] Mercury is a highly toxic heavy metal element that is harmful to the human body, and it is also an important metal that has many uses in industry. The toxicity and mechanism of action of mercury in different forms (chemicalspecies) are very different. Metallic mercury has high diffusivity and fat solubility. Because mercury has a low vapor pressure, it can easily enter the organism through respiration, and enter the brain tissue through the blood-brain barrier, where it is oxidized into mercury ions. Because mercury ions are difficult to pass through the blood barrier, they are accumulated in the brain tissue, causing serious damage to the central nervous system; and because mercury binds to the cell membrane, it will inhibit the active tra...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C323/25C07C319/14C09K11/06G01N21/64
Inventor 黄池宝曾伯平刘其斌张道海
Owner ZUNYI NORMAL COLLEGE
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