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Rhodamine acylhydrazone derivative, preparation method and application thereof, and fluorescent probe

A fluorescent probe and acylhydrazone-like technology, which is applied in the field of organic synthesis, can solve problems such as limited application, high cost, and complex synthesis, and achieve the effect of fluorescent discrimination

Active Publication Date: 2019-02-22
XUCHANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] However, the synthesis of existing lysosome-targeted tumor cell-labeled fluorescent probes is complex and costly, and a large amount of organic solvents need to be added to aid in dissolution. dissolved, limiting its further application

Method used

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  • Rhodamine acylhydrazone derivative, preparation method and application thereof, and fluorescent probe
  • Rhodamine acylhydrazone derivative, preparation method and application thereof, and fluorescent probe
  • Rhodamine acylhydrazone derivative, preparation method and application thereof, and fluorescent probe

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preparation example Construction

[0032] The present invention provides the preparation method of rhodamine acylhydrazone derivative described in the scheme, comprising the following steps:

[0033] Rhodamine 6G hydrazide, 4-morpholino benzaldehyde and an alcohol solvent are mixed for condensation reaction to obtain rhodamine acylhydrazone derivatives with the structure shown in formula I.

[0034] In the present invention, the molar ratio of the rhodamine 6G hydrazide and 4-morpholino benzaldehyde is preferably 1:1~1.1, more preferably 1:1; the alcohol solvent is preferably ethanol; the rhodamine The volume ratio of the amount of Ming 6G hydrazide to the alcohol solvent is preferably 0.01-0.02 mol: 0.3-0.6 L, more preferably 0.01 mol: 0.3-0.5 L.

[0035] In the present invention, the rhodamine 6G hydrazide is preferably dissolved in an alcohol solvent, and then 4-morpholinobenzaldehyde is added into the solution. In a specific embodiment of the present invention, it is preferable to add 2 to 3 drops of aceti...

Embodiment 1

[0047] Dissolve 428mg of rhodamine 6G hydrazide in 30mL of ethanol, then add 191mg of 4-morpholinobenzaldehyde, add 2 drops of acetic acid under normal pressure to catalyze reflux and stir for 3h, cool to room temperature, precipitate a solid, and filter under reduced pressure. The filter residue was washed with ethanol to obtain a white solid which was the target product, and the yield of the target product was 89%.

[0048] The resulting product is recrystallized with acetonitrile, and the resulting recrystallized product is subjected to single crystal diffraction analysis to determine the crystal structure of the resulting product. The obtained results are as follows figure 1 Shown; The crystal structure shows that the obtained rhodamine acylhydrazone derivative exists in the form of acetonitrile.

[0049] The obtained rhodamine class acylhydrazone derivatives are carried out nuclear magnetic resonance analysis, and the results are as follows:

[0050] 1 H NMR (400MHz, DM...

Embodiment 2

[0053] The rhodamine-like acylhydrazone derivatives prepared in Example 1 were tested for fluorescence properties in buffer solutions with different pH values, the steps are as follows:

[0054] (1) The rhodamine acylhydrazone derivatives prepared in Example 1 are formulated into molar concentrations in different pH values ​​(1.0~6.0) disodium hydrogen phosphate-citric acid buffer solution (containing 0.5% DMSO by volume ratio) 1×10 -5 mol / L solution, adopt fluorescence spectrometer to carry out fluorescence spectrum analysis respectively (excitation wavelength is 480nm), the fluorescence spectrum figure of gained is shown in Figure 4 . pass Figure 4 It can be seen that the rhodamine-like acylhydrazone derivatives prepared in Example 1 of the present invention have no obvious fluorescence emission as fluorescent probes at 4.0<pH<6.0, whereas they emit obvious green fluorescence at pH<4.0, and at pH3. A jump occurs in the range of 0-4.0, indicating that it can be used as a...

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Abstract

The invention provides a rhodamine acylhydrazone derivative, a preparation method and application thereof, and a fluorescent probe, and belongs to the field of organic synthesis. The rhodamine acylhydrazone derivative can be obtained through a condensation reaction by taking 4-Morpholinobenzaldehyde and rhodamine 6G hydrazine as reactants through a condensation reaction. The rhodamine acylhydrazone derivative has the structure shown in the formula I and is very sensitive to the pH, no obvious fluorescence is emitted when the pH is larger than 4.0, obvious green fluorescence is emitted when thepH is smaller than 4.0, and sudden change is generated when the pH is within the range of 3.0-4.0; and the rhodamine acylhydrazone derivative provided by the invention can target cell lysosomes and can be used for fluorescence differentiation of normal cells and tumor cells.

Description

technical field [0001] The invention relates to the technical field of organic synthesis, in particular to a rhodamine-like acylhydrazone derivative, a preparation method and application thereof, and a fluorescent probe. Background technique [0002] Fluorescent sensors are powerful tools for monitoring cations, anions, and small molecules, with the advantages of high sensitivity, easy operation, and real-time and online detection. The detection and labeling of tumor cells is of great significance, which is helpful for elucidating cancer-related processes and facilitating clinical diagnosis. A lower pH value is an important feature of tumor cells compared to normal cells. Using the difference in lysosomal pH between tumor cells (pH<4.0) and normal cells (4.0<pH<6.0) to achieve tumor cell labeling is one of the effective strategies for the design of pH fluorescent probes. [0003] However, the synthesis of existing lysosome-targeted tumor cell-labeled fluorescent p...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D491/107C09K11/06G01N21/64
CPCC07D491/107C09K11/06C09K2211/1007C09K2211/1029C09K2211/1033C09K2211/1088G01N21/6428
Inventor 许志红罗文峰王阳雷萌萌周起航
Owner XUCHANG UNIV
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