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Naphthalene-indandione donor-acceptor compound, preparation method thereof and application of naphthalene-indandione donor-acceptor compound in lipid droplet washing-free fluorescent probe

A fluorescent probe and indenedione technology, applied in the field of biomedicine, can solve the problems of unsuitable fatty liver disease diagnosis, unstable chemical structure, low selectivity and sensitivity, and achieve excellent photostability and biocompatibility Effect

Active Publication Date: 2022-04-01
SHANDONG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, this method has disadvantages such as unstable chemical structure, low selectivity and sensitivity, complex and time-consuming steps, etc.
Fluorescent probes can be used for lipid droplet imaging and dynamic tracking. However, the inventors found that most of the current lipid droplet probes are not suitable for the diagnosis of fatty liver disease. Staining differences between samples
At the same time, some key imaging parameters of current diagnostic probes, such as photostability and imaging contrast, still need to be further improved and perfected.

Method used

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  • Naphthalene-indandione donor-acceptor compound, preparation method thereof and application of naphthalene-indandione donor-acceptor compound in lipid droplet washing-free fluorescent probe
  • Naphthalene-indandione donor-acceptor compound, preparation method thereof and application of naphthalene-indandione donor-acceptor compound in lipid droplet washing-free fluorescent probe
  • Naphthalene-indandione donor-acceptor compound, preparation method thereof and application of naphthalene-indandione donor-acceptor compound in lipid droplet washing-free fluorescent probe

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Embodiment approach

[0054] The third embodiment of the present invention provides a composition containing the above-mentioned naphthalene-indanedione donor-receptor compound or a pharmaceutically acceptable salt thereof.

[0055] The fourth embodiment of the present invention provides a preparation comprising the above-mentioned naphthalene-indanedione donor-receptor compound or a pharmaceutically acceptable salt or composition thereof and a pharmaceutically acceptable carrier.

[0056] The carrier of the present invention can be water, buffer solution (phosphate, etc.) and the like.

[0057] The fifth embodiment of the present invention provides an application of the above-mentioned naphthalene-indanedione donor-receptor compound, composition and / or preparation in a lipid droplet wash-free fluorescent probe.

[0058] The sixth embodiment of the present invention provides an application of the above-mentioned naphthalene-indanedione donor-receptor compound, composition and / or preparation in diag...

Embodiment 1

[0063] Embodiment 1: the synthesis of probe ANI

[0064] Compound 1 and compound 2 undergo a nucleophilic reaction to obtain the probe ANI( figure 1 A). Compound 1 (115mg, 0.5mmol), compound 2 (88mg, 0.6mmol) and a few drops of piperidine were refluxed at 90°C for 8h in absolute ethanol (10mL), cooled to room temperature, and the solvent was removed under reduced pressure. AcOEt (10:1, 6:1, to 1:1 by volume ratio) was used as the eluent, and the residue was purified by silica gel chromatography to obtain a green solid (mass 133 mg, yield 74%). 1 H NMR spectrum, 13 C NMR spectrum and high-resolution mass spectrometry were as Figure 9 , Figure 10 and Figure 11 shown. And X-ray single crystal diffraction proved the structure of ANI ( figure 1 B), the corresponding unit cell parameters and refined data are shown in Table 1.

[0065] The detailed characterization data are as follows: 1 H NMR (400MHz, CDCl 3 ),δ(ppm):9.02(d,J=9.0Hz,1H),8.52(s,1H),8.07(d,J=9.3Hz,1H),8.02...

Embodiment 2

[0068] Example 2: Basic photophysical properties

[0069] First, the HOMO and LUMO electron cloud distributions of the probe ANI were calculated by density functional theory ( figure 1 C), the electron cloud of HOMO is basically delocalized in the substituted naphthalene ring part, while the electron cloud of LUMO is mainly distributed in the 1,3-indanedione part. This apparent electron separation reveals a strong charge transfer effect and a narrow energy gap. Next, the detailed photophysical properties of ANI were tested. A test solution containing 5 μM of different polar solvents (toluene, ether, tetrahydrofuran, acetone, dimethyl sulfoxide, PBS) was prepared, and the above solution was tested with a UV-visible spectrophotometer and a fluorescence spectrometer for its absorption spectrum and fluorescence emission spectrum ( figure 2 and image 3 ). Maximum absorption peak (λ abs ) in the small range of 492-523nm, with increasing polarity from toluene to DMSO, λ abs ...

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Abstract

The invention belongs to the technical field of biological medicine, and relates to a naphthalene-indandione donor-acceptor compound, a preparation method thereof and application of the naphthalene-indandione donor-acceptor compound in a lipid droplet no-wash fluorescent probe. The chemical structure is shown as a formula I, wherein R1 and R2 are respectively and independently hydrogen, lower alkyl, ether group, substituted alkyl or acyl; r3, R4, R5 and R6 are respectively and independently hydrogen, methyl, fluorine, chlorine, bromine, iodine, cyano, trihalomethyl, nitryl, phenyl or pyridyl. When the naphthalene-indandione donor-acceptor compound provided by the invention is used as a lipid droplet fluorescent probe, very weak fluorescence is shown in a high-polarity solvent, but fluorescence emission is remarkably increased in a low-polarity environment, so that lipid droplets can be lighted in a washing-free manner with high selectivity and high contrast; meanwhile, selective distinguishing of fatty liver tissues can be successfully realized. Compared with the existing oil red O staining, the fluorescent probe has the advantages of high sensitivity, good selectivity, time saving, simplicity in operation, low incubation concentration and the like.

Description

technical field [0001] The invention belongs to the technical field of biomedicine, and relates to a naphthalene-indanedione donor-receptor compound and a preparation method thereof and its application in a lipid droplet-free fluorescent probe. Background technique [0002] The information disclosed in this background section is only intended to increase the understanding of the general background of the present invention, and is not necessarily taken as an acknowledgment or any form of suggestion that the information constitutes the prior art already known to those skilled in the art. [0003] According to the research of the inventors, at present, oil red O staining is a widely used method for the diagnosis of fatty liver disease, by performing histological staining on lipid droplets. However, this method has disadvantages such as unstable chemical structure, low selectivity and sensitivity, complicated steps and time-consuming steps. Fluorescent probes can be used for li...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C225/22C07C221/00C09K11/06G01N21/64
Inventor 牛广乐冯璐朱婷赵梦莹
Owner SHANDONG UNIV
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