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Double-organelle-targeted nano probe as well as preparation and application thereof

A nanoprobe and organelle technology, applied in the field of nanoprobes, can solve the problems of reducing the intensity of emitted light, poor photostability, high background noise, etc., and achieve the effects of reducing membrane potential, improving stability, and increasing accumulation.

Active Publication Date: 2018-12-21
SOUTH CHINA UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] In terms of organelle imaging, the traditional fluorescent probes with aggregation-quenching (ACQ) effect have the following disadvantages: 1) After the fluorescent probe with ACQ effect enters the organelle, it leads to local high-concentration aggregation, which easily leads to self-quenching of fluorescence. 2) Fluorescent probes with ACQ effect can only be used at very low concentrations, usually have the disadvantage of poor photostability, and are prone to fluorescence quenching under continuous light; 3) Fluorescent probes with ACQ effect , there is a high background noise in the cell culture medium, and it is necessary to go through tedious washing steps to remove the background interference; 4) Fluorescent probes with ACQ effects usually have a small Stokes shift (less than 40nm), which requires a filter to eliminate the excitation light interference, but also greatly reduce the intensity of emitted light
Therefore, fluorescent probes with ACQ effects limit their application in organelle imaging

Method used

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  • Double-organelle-targeted nano probe as well as preparation and application thereof
  • Double-organelle-targeted nano probe as well as preparation and application thereof
  • Double-organelle-targeted nano probe as well as preparation and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0056] Example 1 Mitochondria and lysosomes—preparation of dual organelle-targeted nanoprobes (1) Preparation of mitochondria-targeted AIE molecule I-1

[0057]

[0058] (1-1) Add 2,4-dihydroxybenzaldehyde V-1 (690mg, 5.0mmol) and 1,6-dibromohexane (1.22g, 5.0mmol) into 20mL of acetonitrile, and then add potassium carbonate ( 690mg, 5.0mmol) in N 2 Under reflux, stir the reaction for 6h, spin to dry the solvent, and separate through a silica gel column (PE:EA=80:1) to obtain compound II-1;

[0059] (1-2) Compound IV-1 (300mg, 1.0mmol) and triphenylphosphine (262mg, 1.0mmol) were dissolved in 5mL of chloroform (or acetonitrile), under N 2 Under reflux, stir the reaction for 5h, rotary evaporate under reduced pressure, remove the solvent, and recrystallize to obtain compound III-1;

[0060] (1-3) Compound III-1 (250mg, 0.44mmol) was dissolved in ethanol, then hydrazine hydrate (11mg, 0.22mmol) was added, and the 2 Under reflux, stirred and reacted for 4 hours, filtered, wa...

Embodiment 2

[0067] Example 2: Characterization of photophysical properties of nanoprobes

[0068] Aqueous solutions of I-1 (2.5 μM), II-1 (1.25 μM) and I-1 / II-1 nanoprobes (2.5 μM of I-1 and 1.25 μM of II-1) were subjected to UV-Vis absorption spectroscopy , fluorescence spectrum detection and fluorescence photo collection under ultraviolet light irradiation.

[0069] figure 2 A is the UV-Vis absorption spectrum, I-1 / II-1 nanoprobes (NPs) have two tailing peaks at 400-460nm and 700-800nm, which is due to the π– of I-1 and II-1 Caused by π interaction; figure 2 B is the emission spectrum of I-1 and the absorption spectrum of II-1. Since the emission spectrum of I-1 overlaps with the absorption spectrum of II-1, the fluorescence resonance energy transfer (FRET) process can occur, and at the same time due to the π-plane II-1 has the effect of aggregation quenching luminescence, and the nanoparticles themselves do not emit fluorescence; figure 2 C is the fluorescence spectrogram of I-1...

Embodiment 3

[0070] Embodiment 3: Hydrophobic force test of I-1 and II-1

[0071] When the nanoprobe obtained in Example 1 was in 0.2% SDS solution, the fluorescence signals of I-1 and II-1 recovered ( image 3 ), indicating that SDS can disturb the hydrophobic interaction of nanoprobes, thereby promoting the release of free I-1 and II-1 from nanoprobes. This result confirms the existence of hydrophobic interactions between the molecules that make up nanoprobes. image 3 It is the fluorescence spectrum of I-1 / II-1 nanoprobes (NPs) in solutions containing 0.2% SDS and not containing 0.2% SDS.

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Abstract

The invention belongs to the technical field of nano probes, and discloses a double-organelle-targeted nano probe as well as a preparation method and application thereof. The double-organelle-targetednano probe is mainly prepared from a compound of formula I and a photo-sensitive agent II; and the photo-sensitive agent II is phthalocyanines or porphyrins photo-sensitive agent with negative charges. The compound of formula I is a mitochondria-targeted chemotherapy reagent with an aggregation-induced luminescent effect. The nano probe of the invention not only can monitor the release process ina cell in real time by virtue of a double-fluorescent illumination way, but also can effectively improve the killing efficiency for cancer cells by virtue of the synergism of the mitochondria-targeted chemotherapy and lysosome-targeted photodynamics therapy. The invention also relates to application of nano probe in preparing an antitumor drug and / or fluorescent imaging. (The formulas are shown in the description).

Description

technical field [0001] The invention belongs to the technical field of nanoprobes, and relates to a nanoprobe targeting dual organelles and its preparation method and application, in particular to a dual organelle targeting of cancer cell mitochondria and lysosomes, which integrates fluorescence imaging and has Nanoprobes with therapeutic functions and their preparation and application. Background technique [0002] Cancer is one of the diseases that seriously threaten human health, and organelles are closely related to the diagnosis and treatment of cancer. For example, mitochondrial dysfunction will lead to decreased ATP synthesis and trigger cell apoptosis; lysosomes contain a large number of hydrolytic enzymes, which can effectively kill cancer cells by destroying lysosomes and releasing hydrolytic enzymes. Therefore, chemotherapeutic drugs targeting mitochondria can induce apoptosis of cancer cells by inhibiting the synthesis of ATP; while photodynamic therapy targetin...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09K11/06G01N21/64B82Y30/00B82Y40/00A61K49/00A61K41/00A61P35/00
CPCA61K41/0076A61K49/0021A61P35/00B82Y30/00B82Y40/00C09K11/06C09K2211/1029C09K2211/186C09K2211/187C09K2211/188G01N21/6428G01N21/6486G01N2021/6432
Inventor 唐本忠任力高蒙陈晓辉
Owner SOUTH CHINA UNIV OF TECH
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