Morpholine-indanone-chalcone derivative fluorescent probe as well as preparation method and application thereof

A chalcone derivative, fluorescent probe technology, applied in fluorescence/phosphorescence, chemical instruments and methods, luminescent materials, etc., can solve the problems of low sensitivity, long response time, small Stokes shift, etc., to achieve synthesis And the effect of simple post-processing method, high fluorescence recognition performance, and wide application value

Active Publication Date: 2022-05-06
HENAN POLYTECHNIC UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, most of the existing CEs fluorescent probes have the problems of poor water solubility, long response time, low sensitivity and small Stokes shift, which are not conducive to the actual detection of CEs.
Moreover, currently only a few CEs probes provide lysosomal targeting function
Therefore, it is extremely challenging to study the imaging of CEs probes in the subcellular organelle lysosome domain.

Method used

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  • Morpholine-indanone-chalcone derivative fluorescent probe as well as preparation method and application thereof
  • Morpholine-indanone-chalcone derivative fluorescent probe as well as preparation method and application thereof
  • Morpholine-indanone-chalcone derivative fluorescent probe as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0037] The preparation method of the morpholine-indanone-chalcone derivative fluorescent probe of this embodiment is as follows:

[0038] To a solution of 5-hydroxy-1-indanone (2mmol, 0.296g) in absolute ethanol (10mL) was added 4-(4-morpholine)benzaldehyde (2mmol, 0.382g) and sodium hydroxide (3mmol, 0.12g ); The mixture was then stirred at 50° C. for 5 h. After the reaction was completed, the solution was cooled to room temperature, acidified with hydrochloric acid to pH = 6, and evaporated under reduced pressure. The resulting solid residue was recrystallized with ethanol, filtered under reduced pressure, and dried to obtain the intermediate 5-hydroxy-2-(4-mol (Phenylbenzyllidene)-2,3-dihydro-1H-indanone. Then 5-hydroxy-2-(4-morpholino benzyl subunit)-2,3-dihydro-1H-indanone (0.14mmol, 0.0458g), acetic anhydride (0.17mmol, 16μL,) and triethyl The amine (0.42 mmol, 58 μL) was dissolved in dichloromethane, and the resulting solution was stirred at room temperature for 5 h. ...

Embodiment 2

[0044] Determination of Optical Properties of Morpholine-Indanone-Chalcone Derivatives on CEs

[0045] The morpholine-indanone-chalcone derivative prepared in Example 1 above was used as a fluorescent probe in PBS / DMSO (95 / 5, v / v, 10 mM, pH=7.4) to prepare a molar concentration of 1× 10 -5 mol / L solution, add 2×10 -4 mol / L Enzyme analytes (CEs, acetylcholinesterase, cholesterol esterase, lactoproteinase, hyaluronidase, lipase, lysozyme and polyphenol oxidase), amino acids (Ala, Arg, Asp, Cys, Hcy, Leu and Ser), redox active species (C 6 h 12 o 6 , GSH, HClO, H 2 o 2 and V c ) and other ions (Al 3+ , Ca 2+ , Fe 3+ , Mg 2+ , CO 3 2- 、HCO 3 - 、OAc - and SO 4 2- ), using a UV-Vis spectrophotometer or a fluorescence spectrometer to analyze (excitation wavelength is 400nm), the resulting fluorescence spectrum is shown in Figure 4 and Figure 5 . pass Figure 4 and Figure 5 It can be seen that the morpholine-indanone-chalcone derivatives prepared by the prese...

Embodiment 3

[0048] Detection experiment of morpholine-indanone-chalcone derivative fluorescent probe in intracellular CEs

[0049] 1 x 10 for C6 cells -5 The morpholine-indanone-chalcone derivative fluorescent probe prepared in the above-mentioned Example 1 of mol / L was incubated at 37° C. for 30 min, or with 1×10 -4 mol / L CEs inhibitor bis(4-nitrophenyl) phosphate (BNPP) was incubated for 30 min and then 1 × 10 -5 The mol / L morpholine-indanone-chalcone derivative fluorescent probe prepared in Example 1 above was incubated at 37° C. for 30 min to obtain the fluorescence imaging image of C6 cells. Specific as Figure 7 As shown, where: a is the fluorescence imaging image of the green channel of the fluorescent probe; b is the bright field image of the fluorescent probe; c is the superimposed image of the green channel and the bright field of the fluorescent probe; d is the green channel of the fluorescent probe + BNPP Fluorescence imaging image; e is the bright field image after fluores...

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Abstract

The invention provides a morpholine-indanone-chalcone derivative fluorescent probe as well as a preparation method and application thereof. The chemical structural formula of a morpholine-indanone-chalcone derivative is shown in the specification. The preparation method comprises the following steps: dissolving 5-hydroxy-1-indanone, 4-(4-morpholine) benzaldehyde and sodium hydroxide in an organic solvent, carrying out reflux stirring reaction, acidizing with hydrochloric acid until the pH is equal to 6, and treating to obtain an intermediate 5-hydroxy-2-(4-morpholine benzyl subunit)-2, 3-dihydro-1H-indanone; dissolving the chitosan, acetic anhydride and triethylamine in an organic solvent; stirring and reacting at room temperature to obtain the morpholine-indanone-chalcone derivative fluorescent probe. The morpholine-indanone-chalcone derivative fluorescent probe can selectively act with carboxylesterase (CEs) under the condition of 95% of water phase (containing 5% of dimethyl sulfoxide, v/v), green fluorescence is remarkably enhanced, and the morpholine-indanone-chalcone derivative fluorescent probe is particularly applied to cell lysosome fluorescence imaging as a CEs fluorescent probe.

Description

technical field [0001] The invention belongs to the field of organic synthesis, and specifically relates to morpholine-indanone-chalcone derivatives and their preparation methods and applications. Background technique [0002] Carboxylesterases (CEs), one of serine hydrolases, are widely distributed in nature, especially in mammalian liver. It is a type of enzyme that catalyzes the hydrolysis of ester compounds to generate alcohols and carboxylic acids, and can also catalyze the hydrolysis and metabolism of amides, carbamates and thioesters. Therefore, it plays a very important role in the metabolic activation and clearance of some exogenous drugs and the metabolic hydrolysis of endogenous lipids. Moreover, abnormal regulation or deficiency of CEs is closely related to human diseases, such as obesity, atherosclerosis, hepatic steatosis, Wolman's disease, hyperlipidemia, hypoinsulinism sensitivity and even hepatocellular carcinoma. Lysosomes are known as the digestive organ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D295/116C09K11/06G01N21/64
CPCC07D295/116C09K11/06G01N21/6428C09K2211/1011C09K2211/1033
Inventor 赵晓雷吴伟娜王元张玲
Owner HENAN POLYTECHNIC UNIV
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