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Two-photon fluorescent sodium ion probe and its synthesis method and application

A technology of two-photon fluorescence and synthesis method, which is applied in the field of two-photon fluorescence sodium ion probe and its synthesis, can solve the problems of inability to identify and detect specific ions, poor water solubility of the probe, and not reaching the ideal, so as to improve the clarity, cell Good permeability and short response time

Active Publication Date: 2020-08-14
ZUNYI NORMAL COLLEGE
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Therefore, it cannot be used for the identification and detection of specific ions
[0005] Marketed products such as sodium ion fluorescent probes (Na + indicator)-SBFI AM, commonly used to predict purified mitochondrial Na + Gradient, detection of intracellular Na + Level, determination of cellular Na + efflux, and in combination with other fluorescent indicators to analyze Na + with Ca 2+ and Mg 2+ The correlation of concentration, intracellular pH and membrane potential changes, but the effect of SBFI on Na + The selection ability of Ca is weaker than that of Ca 2+ Indicators such as Fura-2 can only be said to detect Na + Physiological concentration, but the ideal effect has not yet been achieved, and the probes in the form of AM esters are relatively poor in water solubility
[0006] In the research process of the two-photon fluorescent probe, the researchers of the present invention have conducted research on the detection of mercury ions, zinc ions, and silver ions in cells, the activity detection of intracellular sugar chain antigens, and temperature sensing detection. However, the invention based on dicyano-stilbene for the detection and imaging of intracellular sodium ions has not been reported

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  • Two-photon fluorescent sodium ion probe and its synthesis method and application
  • Two-photon fluorescent sodium ion probe and its synthesis method and application
  • Two-photon fluorescent sodium ion probe and its synthesis method and application

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Embodiment 1

[0042] Embodiment 1 Molecular structure and synthetic route

[0043] A two-photon fluorescent sodium ion probe PNa has the following molecular structure:

[0044]

[0045] The synthetic route is:

[0046]

[0047] Among them, intermediates 2 and 3 were synthesized according to the following document 1, and intermediates 4 and 5 were synthesized according to the following document 2: 6, namely 4'-formylbenzo-15-crown-5, was purchased from Shanghai Lanjun Biotechnology Co., Ltd.

[0048] [1] H. Huang, Q. He, H. Lin, F. Bai, Z. Sun and Q. Li, Polym. Adv. Technol., 2004, 15 (): 84—88

[0049] [2] Huang C., Fan J., Peng X., Lin Z., Guo B., Ren A., Cui J., Sun S., J. Photochem. Photobio. A: Chem., 2008, 199 (2) –3):144—149

Embodiment 2

[0050] The synthesis of embodiment 2 target compound PNa

[0051] Synthetic method: Accurately weigh 6 (296mg, 1mmol) and sodium hydride (30mg, 1.25mmol) in a 25mL dry single-necked flask, accurately weigh 5 (292mg, 1mmol) and dissolve in 10mL tetrahydrofuran, and place in a constant pressure feeder , Install the constant pressure feeder on the single-necked flask, and evacuate it with argon protection. The flask was placed in an ice-water bath, and the tetrahydrofuran solution of 5 was added dropwise to the mixed solution under the conditions of strong stirring and light protection (dropping time 40-50 min). After the dropwise addition was completed, the reaction was stirred at room temperature for 24 h. After the reaction, THF was removed in vacuo, extracted with dichloromethane (3×15 mL), washed with water (3×10 mL), and dried by adding anhydrous calcium chloride. Filter and remove solvent in vacuo. The crude product was separated by silica gel column chromatography [elu...

Embodiment 3

[0053] The photophysical property research in the water of embodiment 3 probe PNa

[0054] In order to study the fluorescence intensity of the probe PNa in water, the attached Figure 1-4 Experiments shown. at 1 μmol L - 1 In the aqueous solution of PNa, the single-photon absorption maximum wavelength was measured respectively single photon emission maximum wavelength fluorescence quantum yield Two-photon absorption cross-sections at different two-photon excitation wavelengths, and the Stokes shift (Δλ ST ), the maximum two-photon excitation wavelength and the maximum two-photon absorption cross section (δ max ).

[0055] Table 1 Photophysical properties of PNa

[0056]

[0057] Note: a) maximum wavelength of single photon absorption (nm); b) maximum wavelength of single photon emission (nm);

[0058] c) fluorescence quantum yield; d) maximum two-photon excitation wavelength (nm);

[0059] e) Stokes shift (nm); f) maximum two-photon absorption cross section (...

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Abstract

The invention belongs to the technical field of fine chemical engineering, particularly relates to a dual-photon fluorescence sodium ion probe and a synthesis method and application thereof. The probeis prepared by using distyrene dicyanide as the parent of the dual-photon fluorescence. The probe has small molecule volume and good selectivity to sodium ions. Oher ions other than sodium ions suchas zinc, potassium, calcium, magnesium, manganese, mercury and the like have no interference to the detection. The sodium ions of micro-molar concentration can be detected. The fluorescence intensityof the probe molecular is reduced after complexation with sodium ions, and the sodium ion content can be detected by double-photon fluorescence. The double-photon fluorescence microscopic imaging experiment shows that the probe has good permeability to cells or tissues such as fibroblast, has no toxic and side effect on the cells, is particularly suitable for detecting the concentration change ofsodium ions in the cell and the detection of the distribution of the mercury ions, and has great application value in the field of biology and medicine.

Description

technical field [0001] The invention relates to the field of fine chemical industry, in particular to a two-photon fluorescent sodium ion probe and its synthesis method and application. Background technique [0002] The development of the global economy has brought about the improvement of people's material living standards. But it also brings a lot of environmental problems, such as: pollution of metal ions. The detection and monitoring of metal ions is a hot issue in the field of biology and medicine. Previous detection methods for metal ions damaged cells to a certain extent and were not accurate enough. The development of metal ion fluorescent probes can realize the specific detection of metal ions, real-time detection under the fluorescence microscope, avoiding the damage to cells due to the injection of a large number of chemical reagents. Therefore, it is necessary to develop two-photon metal ion fluorescent probes with biocompatibility, specific structure and site...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D323/00C09K11/06G01N21/64
CPCC07D323/00C09K11/06C09K2211/1007C09K2211/1088G01N21/6486
Inventor 黄池宝
Owner ZUNYI NORMAL COLLEGE
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