Pyrrole-naphthalimide derivative fluorescent probe as well as preparation method and application thereof

A fluorescent probe and naphthalimide technology, applied in fluorescence/phosphorescence, chemical instruments and methods, luminescent materials, etc., can solve the problems of complex purification process, long synthesis route, high cost of raw materials, etc., and achieve synthesis and post-processing methods Simple, easy to obtain raw materials, wide application value effect

Active Publication Date: 2020-04-10
HENAN POLYTECHNIC UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, there are not many reports on lysosome-targeted Cu2+ fluorescent probes, and the existing lysosome-targeted Cu2+ fluorescent probes Usual

Method used

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  • Pyrrole-naphthalimide derivative fluorescent probe as well as preparation method and application thereof
  • Pyrrole-naphthalimide derivative fluorescent probe as well as preparation method and application thereof
  • Pyrrole-naphthalimide derivative fluorescent probe as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] The preparation method of the pyrrole-naphthalimide derivative fluorescent probe in this embodiment is as follows:

[0032] 2.79 g (10 mmol) N-morpholinoethyl-2,4-dimethyl-5-formylpyrrole-3-carboxamide and 2.71 g (10 mmol) 4-hydrazino-N-hydroxyethylnaphthoylidene Dissolve the amine in 0.05L ethanol, add dropwise 0.012g acetic acid (0.2 mmol) as a catalyst, reflux and stir at 80°C for 3-4h, cool and stand to room temperature, filter under reduced pressure, and wash the obtained solid with ethanol to obtain the pyrrole- Fluorescent probes of naphthalimide derivatives. The yield of the target product was 86%.

[0033] Adopt nuclear magnetic resonance instrument to carry out nuclear magnetic resonance analysis to the prepared pyrrole-containing merocyanine derivatives, the results are as follows:

[0034] 1 H NMR (400 MHz, DMSO- d 6 ), δ (ppm): 11.30 (s, 1H, NH-pyrrole), 11.22 (s,1H, NH), 8.73-8.76 (d, 1H, Aryl-H), 8.47-8.49 (d, 1H, Aryl- H), 8.36 (s, 1H, CH=N), 8.32-...

Embodiment 2

[0037] Determination of Optical Properties of Copper Ions Containing Pyrrole-Naphthimide Derivatives

[0038] The pyrrole-naphthalimide derivatives prepared in the above example 1 were used as fluorescent probes in acetonitrile / HEPES buffer solution (v:v, 3:7, 0.02 mol / L, pH=5) to prepare a molar concentration of 1×10 -5 mol / L solution, respectively, at a molar concentration of 2×10 -5 mol / L metal ion (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+ ) solution, adding an equal amount of the above-mentioned fluorescent probe solution, and using a UV-Vis spectrophotometer or a fluorescence spectrometer for analysis (excitation wavelength is 440 nm), the resulting UV and fluorescence spectra are shown in image 3 . pass image 3 It can be seen that the pyrrole-naphthoimide derivative prepared in the present invention is used as a probe to only have a significant response to copper io...

Embodiment 3

[0041] Detection experiment of pyrrole-naphthalimide derivative fluorescent probe in intracellular copper ion

[0042] 1 x 10 for HeLa cells -5 mol / L pyrrole-naphthalimide derivative fluorescent probe prepared in Example 1 above was incubated at 37°C for 30 minutes, and Cu 2+ (2×10 -5 mol / L) and then incubated for 30 minutes to obtain the fluorescence imaging image of HeLa cells, as shown in Figure 5 As shown, wherein: a is the fluorescence imaging image of the green channel of the above-mentioned fluorescent probe; b is the bright-field image of the above-mentioned fluorescent probe; c is the superimposed picture of the bright-field image and the fluorescence image of the above-mentioned fluorescent probe; d is the image of the above-mentioned fluorescent probe Needle + Cu 2+ Green channel fluorescence imaging; e is the above fluorescent probe + Cu 2+ Imaging image under bright field; f is the above-mentioned fluorescent probe Cu 2+ Superimposed images of brightfield ...

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Abstract

The invention provides a pyrrole-naphthalimide derivative fluorescent probe as well as a preparation method and application thereof. The chemical structural formula of the pyrrole-naphthalimide derivative is shown in the specification; the method comprises the following steps of: dissolving N-morpholineethyl-2, 4-dimethyl-5-formyl pyrrole-3-formamide and 4-hydrazino-N-hydroxyethyl naphthalimide inan organic solvent; dropwise adding acetic acid into the obtained solution to serve as a catalyst, and then carrying out reflux stirring reaction at 80 DEG C for 3-4 hours; and cooling to room temperature, carrying out reduced pressure suction filtration, and washing the obtained solid residue with ethanol to obtain the pyrrole-naphthalimide derivative fluorescent probe. The pyrrole-naphthalimidederivative fluorescent probe disclosed by the invention can selectively react with copper ions under physiological conditions, a red solution is faded, green fluorescence is remarkably enhanced, andthe pyrrole-naphthalimide derivative fluorescent probe as a fluorescent probe is particularly applied to convenient detection of the copper ions in a cytolysosome.

Description

technical field [0001] The invention belongs to the field of organic synthesis, and specifically relates to pyrrole-naphthalimide derivatives and their preparation methods and applications. Background technique [0002] Copper ions, as the third most abundant transition metal ions, play an important role in the biological systems of plants and humans. However, Cu 2+ When the concentration is too high, it can cause oxidative stress and neurodegenerative diseases related diseases, such as Alzheimer's disease, Wilson's disease and Meck's disease. It has been reported in the literature that Cu 2+ Accumulates in lysosomes of patients with advanced Wilson's disease and is found as Cu 2+ Transporter and amyloid precursor protein accumulated in Alzheimer's disease is degraded in lysosomes. Apparently, lysosomes target Cu 2+ The design and synthesis of probes is of great significance to the study of their biological behavior. [0003] In recent years, fluorescent molecular prob...

Claims

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Application Information

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IPC IPC(8): C07D401/12C09K11/06G01N21/64
CPCC07D401/12C09K11/06G01N21/6428C09K2211/1029C09K2211/1033
Inventor 吴伟娜王元赵晓雷刘盼郭芳芳李晓红
Owner HENAN POLYTECHNIC UNIV
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