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Alkaline phosphatase response type molecular probe and application thereof

A technology of molecular probes and phosphatases, which is applied to the analysis of materials, fluorescence/phosphorescence, and material excitation analysis, etc., to achieve the effects of low energy, strong tissue penetration ability, and small damage

Active Publication Date: 2019-08-09
SUZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, a variety of technical means have been successfully used in the detection of alkaline phosphatase, including: fluorescence, isotope labeling, electrochemistry, chromatography and surface-enhanced Raman scattering, etc. However, the detailed description of alkaline phosphatase in the body Physiological and pathological functions are still a huge challenge

Method used

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  • Alkaline phosphatase response type molecular probe and application thereof
  • Alkaline phosphatase response type molecular probe and application thereof
  • Alkaline phosphatase response type molecular probe and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0039] Example 1: Synthesis and characterization of alkaline phosphatase-responsive aggregation-induced luminescent molecular probes

[0040](1) Under nitrogen protection, add 2-methylquinoline (7.15 g, 50.0 mmol), methyl iodide (21.30 g, 150.0 mmol) and 50 mL of acetonitrile into a 100 mL round bottom flask as a solvent, and stir the mixture magnetically and reflux 12 h. After the reaction was completed, it was cooled to room temperature, and the solvent was removed by rotary evaporation to obtain compound 1 (8.84 g, yield: 62 %) as a light yellow solid product, which was directly used as the next step raw material without further treatment.

[0041] (2) Add compound 1 (5.24 g, 18.4 mmol), malononitrile (3.04 g, 46.0 mmol) and 35.0 mL of absolute ethanol into a 100 mL round-bottomed flask under ice-bath conditions. Add sodium ethoxide solution (0.97 g sodium metal dissolved in 20 mL absolute ethanol) and react for 4 h. After the reaction was completed, the mixed solution wa...

Embodiment 2

[0050] Example 2: Photophysical properties and aggregation-induced luminescent properties of the target probe QMP

[0051] Such as figure 2 As shown in (a), the target probe QMP and compound 4 prepared in Example 1 were diluted with Tris-HCl buffer to a concentration of 5 μM, and their UV-visible spectra and fluorescence spectra. The excitation wavelength is 476 nm. The results showed that the ultraviolet-visible absorption of the two did not change much, and the best absorption was around 476 nm; while the fluorescence spectra were significantly different, and the fluorescence intensity of the target probe QMP was weak, while compound 4 had significant fluorescence emission under the same conditions. The aggregation-induced luminescent properties of target probes in water are as follows: figure 2 (b), in DMSO / H 2 In the mixed solvent of O, as the water content increased, the fluorescence intensity of QMP was significantly enhanced, and when the water content reached 70%...

Embodiment 3

[0052] Embodiment 3: Responsiveness and selectivity of target probe QMP to alkaline phosphatase

[0053] Such as image 3 As shown in (a), the target probe QMP prepared in Example 1 was diluted with Tris-HCl buffer to a concentration of 5 μM, and different concentrations of alkaline phosphatase (0-2000 U / L) were added to test the system changes in the fluorescence spectrum. The results showed that the fluorescence intensity of simple probe QMP was low, and the fluorescence intensity increased with the increase of alkaline phosphatase, and the fluorescence intensity reached the peak when the concentration of alkaline phosphatase reached 1800 U / L. At the same time, compound 4 was used to replace QMP as a comparison, and the fluorescence signals before and after adding alkaline phosphatase were equivalent. image 3 (b) is the linear relationship fitted in 3(a) within the concentration range of alkaline phosphatase from 0 to 1200 U / L. image 3 (c) Kinetic properties of the prob...

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Abstract

The invention discloses an alkaline phosphatase response type molecular probe and application thereof. The activated micromolecular fluorescent probe is synthesized so that the in-vivo and in-vivo alkaline phosphatase level can be specifically detected, and interference of other biomolecules, enzymes and the like is avoided. Meanwhile, after being sheared by alkaline phosphatase, the target probehas an obvious aggregation-induced luminescence behavior, the emission wavelength is located in the red light waveband, the energy is lower, the damage is small, and the tissue penetration capabilityis high. According to a preparation method, the alkaline phosphatase response type probe can be obtained, the spatial distribution of alkaline phosphatase in HeLa cells and the alkaline phosphatase level of liver injury zebra fish larvae can be qualitatively displayed, and the probe has important scientific research and economic value for researching physiological and pathological processes related to the alkaline phosphatase.

Description

technical field [0001] The invention belongs to the technical field of functional modification of responsive molecular probes, and in particular relates to a preparation method of an alkaline phosphatase-responsive aggregation-induced luminescence molecular probe, and the application of the probe in developing living cells and zebrafish larvae. Background technique [0002] As we all know, activating small molecule fluorescent probes have the advantages of non-invasiveness, fast metabolism, and low toxicity, and have been widely used in clinical imaging. So far, many activated small-molecule fluorescent probes targeting enzymes, biothiols, reactive oxygen species (ROS), ions, and pH have been widely reported for early diagnosis of diseases. Among them, enzymes, as one of the most important biomarkers, are involved in the regulation of various disease processes and have great clinical research value. Therefore, it is of great significance to rationally design enzyme-activati...

Claims

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Application Information

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IPC IPC(8): C07F9/6558C09K11/06G01N21/64A61K49/00
CPCA61K49/0021C07F9/65586C09K11/06C09K2211/1007C09K2211/1029C09K2211/1092G01N21/6428
Inventor 史海斌赵梦周如鸿
Owner SUZHOU UNIV
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