Dicyano-stilbene type two-photon fluorescent solvent chromogenic water-soluble probe and its synthesis method and application

A dicyano-stilbene and two-photon fluorescence technology, which is applied in the fields of fluorescence/phosphorescence, chemical instruments and methods, and luminescent materials, can solve the problems of cell viscosity change monitoring that have not been reported, and achieve improved clarity and absorption Large cross-section, good chemical/light stability

Active Publication Date: 2020-10-13
ZUNYI NORMAL COLLEGE
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

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. , but the invention based on dicyano-stilbene for the monitoring of cell viscosity changes has not been reported

Method used

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  • Dicyano-stilbene type two-photon fluorescent solvent chromogenic water-soluble probe and its synthesis method and application
  • Dicyano-stilbene type two-photon fluorescent solvent chromogenic water-soluble probe and its synthesis method and application
  • Dicyano-stilbene type two-photon fluorescent solvent chromogenic water-soluble probe and its synthesis method and application

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Embodiment 1

[0037] Embodiment 1 Molecular structure and synthetic route

[0038] A dicyano-stilbene type two-photon fluorescent solvent chromogenic water-soluble probe VP has the following molecular structure:

[0039]

[0040] The synthetic route is:

[0041]

[0042] Wherein, intermediates 2, 3, 4, 5, 7, and 8 were all synthesized according to the following documents:

[0043] [1] H. Huang, Q. He, H. Lin, F. Bai, Z. Sun and Q. Li, Polym. Adv. Technol., 2004, 15 (): 84—88

[0044] [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

[0045] [3] Moon K.-J., Shim H.-K., Macromolecules, 1996, 29:861

Embodiment 2

[0046] The synthesis of embodiment 2 intermediate 9 and target compound VP

[0047] Synthetic method: (1) Put intermediate 8 (1.49g, 5.1mmol) in a 25mL round-bottom single-necked flask, then add 3mLTHF and NaH (130mg, 5.4mmol), vacuumize and fill with argon, and stir under an ice-water bath A solution of 1,4-dicyano-2-methyl-5-(diethylphosphorylmethyl)benzene (5) (1.46 g, 5.0 mmol) in THF (9 mL) was added dropwise. After the dropwise addition, react in an ice-water bath for 1 h, then remove the ice-water bath and react at room temperature for 12 h. And the reaction was continued overnight at room temperature. Spin dry with CH 2 Cl 2 (4×10mL) eluting with CH 2 Cl 2 eluent with H 2 O (2×10mL) was washed with anhydrous Na 2 SO 4 Dry, filter and spin-dry and dry in an oven for subsequent use;

[0048] (2) The crude product of intermediate 9 (400 mg) and Na 2 CO 3 (5mL, 10%) in ethanol (10mL) was stirred at 50°C for 2h, after the reaction was completed, 5mL of hydrochlor...

Embodiment 3

[0050] The water solubility research of embodiment 3 probe VP

[0051] In order to study the solubility of probe VP in water, the attached figure 1 Experiments shown. attached by figure 1 It can be seen that when the concentration of VP gradually increases from 0 to 6000 μmol L -1 , the single-photon fluorescence intensity of the solution also increases gradually, and is proportional to the concentration; when the concentration increases further, the single-photon fluorescence intensity increases very slowly, and the data points formed by the concentration of VP and the single-photon fluorescence intensity deviate from The original straight line falls below the original straight line. Since the fluorescence intensity of the fluorescent substance is directly proportional to its concentration, it can be concluded that when the concentration of VP is greater than 6000μmol L -1 When , the VP cannot be completely dissolved, otherwise the data points will not deviate from the or...

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Abstract

The invention belongs to the technical field of fine chemical engineering, and specifically relates to a dicyano-stilbene type two-photon fluorescent solvent chromogenic water soluble probe and a synthesis method and applications thereof. According to the preparation method, dicyano-stilbene (DCS) is taken as a two-photon fluorescent matrix. The volume of the probe is small; the water solubility of the probe is good, and the probe is suitable for detecting the polarity of a solvent. Furthermore, the fluorescent strength and two-photon absorption cross section of the probe changes obviously asthe viscosity is increased; the solvent chromogenic range is very wide, the two-photon absorption cross section is large, the Stokes shift is super large, the detection sensitivity, imaging definition, imaging sensitivity, vertical / horizontal resolution ratio, and detection accuracy are largely improved; and the results of cell microscopic imaging experiments show that the probe has a large chromogenic range and good absorption effect in cells or tissues, the probe can well detect and present the change of cell viscosity, and moreover, the probe does not have any side or toxic effect on cells.The probe has a great application value in fields such as biology, medicine, and the like.

Description

technical field [0001] The invention relates to the field of fine chemical industry, in particular to a dicyano-stilbene-type two-photon fluorescent solvent color-generating water-soluble probe and its synthesis method and application. Background technique [0002] The viscosity in the cell strongly affects the intracellular material transport and signal transmission, the interaction between biomacromolecules and the diffusion of active metabolites such as ROS (Reactive oxygen species) and RNS (reactive nitrogen species). Viscosity changes in cells are closely related to many diseases and pathologies. At present, the methods for measuring viscosity mainly use capillary viscometer, falling ball viscometer and rotational viscometer, but none of these methods can be used for the measurement of viscosity in cells, especially in living cells. In view of this, Luby-Phelps reported a single-photon fluorescent probe for intracellular viscosity measurement. [0003] Recently develo...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C255/58C07C253/30C09K11/06G01N21/64
CPCC07C255/58C09K11/06C09K2211/1007G01N21/6486
Inventor 黄池宝
Owner ZUNYI NORMAL COLLEGE
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