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A kind of pyrrole-rhodamine acylhydrazone derivative and its preparation method and application

A technology of cyanohydrazone and derivatives, which is applied in the field of pyrrole-rhodamine acylhydrazone derivatives and its preparation, can solve the problem of few fluorescent probes, achieve high selectivity ratio fluorescence recognition performance, wide potential application value, The effect of easy access to raw materials

Active Publication Date: 2020-01-07
XUCHANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, there are few copper ion ratiometric fluorescent probes that can target lysosomes

Method used

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  • A kind of pyrrole-rhodamine acylhydrazone derivative and its preparation method and application
  • A kind of pyrrole-rhodamine acylhydrazone derivative and its preparation method and application
  • A kind of pyrrole-rhodamine acylhydrazone derivative and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0035] Synthesis of pyrrole-rhodamine acylhydrazone derivatives:

[0036]

[0037] N-(2-morpholine-4-ethyl)-5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxamide (279 mg, 1 mmol) was added to rhodamine 6G hydrazide ( 428mg, 1mmol) of absolute ethanol (30mL), heated to reflux for 3 hours, then cooled to room temperature, after cooling to room temperature, vacuum filtration under reduced pressure, washed filter cake with absolute ethanol, and then dried in air to obtain The white solid is the target product, and the yield is 72%.

[0038] The crystal structure of the pyrrole-rhodamine acylhydrazone derivative ethanolate was determined by single crystal diffraction, seefigure 1 .

[0039] Carry out nuclear magnetic resonance analysis to the obtained pyrrole-rhodamine acylhydrazone derivatives, see the specific nuclear magnetic spectrum figure 2 , figure 2 The analysis results are as follows:

[0040] 1 H NMR (400MHz, DMSO-d 6 ), δ (ppm): 11.09 (s, 1H, NH-pyrrole), 8.00 (s, 1H...

Embodiment 2

[0043] Determination of Optical Properties of Pyrrole-Rhodamine Hydrazone Derivatives to Divalent Copper Ions

[0044] The pyrrole-rhodamine acylhydrazone derivatives prepared in the above example 1 were used as fluorescent probes in CH 3 CN / HEPES (volume ratio 8︰2) medium to prepare a molar concentration of 1×10 -5 mol / L solution, respectively, at a molar concentration of 3×10 -5 mol / L Ag + , Al 3+ , Ca 2+ , Cd 2+ ,Co 2+ , Cr 3+ , Cu 2+ , Fe 3+ , Hg 2+ , K + , Mg 2+ , Mn 2+ , Na + , Ni 2+ , Pb 2 and Zn 2+ Add an equal volume of the above-mentioned fluorescent probe solution to the aqueous solution of metal ions, and use a fluorescence spectrometer to perform fluorescence spectrum analysis (excitation wavelength is 360 nm, real-time detection), and the obtained fluorescence spectrum diagram is shown in Figure 4 . pass Figure 4 It can be seen that after the pyrrole-rhodamine acylhydrazone derivative prepared in Example 1 of the present invention acts as a ...

Embodiment 3

[0047] Detection experiment of pyrrole-rhodamine acylhydrazone derivatives in intracellular copper ions

[0048] 1 x 10 for Hela cells -5 The pyrrole-rhodamine acylhydrazone derivative fluorescent probe prepared in the above-mentioned Example 2 of mol / L was incubated with commercial lysosome localization dye LysoTracker Red for 30 minutes and then added 2×10 -5 mol / L Cu 2+ solution (solvent is water) such that Cu 2+ The final concentration was 50 μmol / L, and after continuing to incubate for 30 minutes, use the Olympus FV500-IX70 laser confocal microscope to perform fluorescence imaging to obtain the fluorescence imaging map of Hela cells, specifically as follows Figure 6 shown. Fluorescent probe + LysoTracker Red co-staining: a is the fluorescence imaging image of the blue channel; b is the fluorescence imaging image of the green channel; c is the fluorescence imaging image of the red channel of LysoTracker Red; d is the overlay image of the blue channel, green channel a...

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Abstract

The invention relates to a pyrrole-rhodamine acylhydrazone derivative as well as a preparation method and application of the derivative, belonging to the organic synthesis field. The preparation method of the pyrrole-rhodamine acylhydrazone derivative comprises the following steps: (S1) adding N-(2-morpholin-4-ethyl)-5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxamide into an organic solvent, and adding rhodamine 6G hydrazide, so as to obtain a mixture; (S2) carrying out reflux stirring reaction on the mixture obtained in the step (S1) at a normal pressure; (S3) after the reaction is finished, cooling to the room temperature so as to separate solids, carrying out reduced pressure filtration, and extracting filter residue; and (S4) washing the filter residue obtained in the step (S3), so as to obtain the pyrrole-rhodamine acylhydrazone derivative. The pyrrole-rhodamine acylhydrazone derivative is capable of selectively acting with bivalent copper ions, blue fluorescence is changed into greenfluorescence, a ratio fluorescence effect is realized, the naked eye distinguishing detection can be realized, and particularly, the pyrrole-rhodamine acylhydrazone derivative can be taken as a fluorescence probe to be applied to the convenient detection of bivalent copper ions in cell lyase.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and specifically relates to a pyrrole-rhodamine acylhydrazone derivative and a preparation method and application thereof. Background technique [0002] Fluorescent sensors are powerful tools for monitoring cations, anions, and small molecules, mainly due to their advantages of high sensitivity, facile operation, and real-time and on-line detection. Copper is an essential micronutrient for all living organisms to maintain normal survival and is the third most abundant transition metal in the human body. Excess divalent copper ions are mainly excreted into bile through the lysosome-biliary pathway, causing human neurodegenerative diseases such as Wilson's disease, Menkes' disease and Alzheimer's disease. In addition, some copper transporters localize in lysosomes to facilitate cellular copper uptake. In view of the role of divalent copper ions in the human body, it is very important to...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D491/107G01N21/64
CPCC07D491/107G01N21/643G01N21/6486
Inventor 许志红王阳王元罗文峰雷萌萌周起航
Owner XUCHANG UNIV
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