Application method of aggregation-induced emission-based photosensitizer in cell imaging and photodynamic therapy

An aggregation-induced luminescent, multi-purpose technology, applied in the field of medical materials, can solve the problems that cannot be applied in the biological field, fluorescent dyes are easy to leak, and do not have water solubility, etc., and achieve good water solubility, high fluorescence intensity, and prevent leakage.

Active Publication Date: 2021-06-08
SHANGHAI UNIV OF ENG SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005]Through the above analysis, the problems and defects of the existing technology are: the existing fluorescent molecular materials are pr

Method used

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  • Application method of aggregation-induced emission-based photosensitizer in cell imaging and photodynamic therapy
  • Application method of aggregation-induced emission-based photosensitizer in cell imaging and photodynamic therapy
  • Application method of aggregation-induced emission-based photosensitizer in cell imaging and photodynamic therapy

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preparation example Construction

[0044] The preparation method of the supramolecular polymerized fluorescent nanomaterial provided by the embodiment of the present invention includes:

[0045] The aggregation-induced luminescent compound is introduced into the polydiacetylene supramolecular system through covalent or non-covalent, and the nanoparticles are spontaneously assembled and polymerized by the intermolecular hydrophilic-hydrophobic interaction.

[0046]The chemical structural formula of the aggregation-induced luminescence compound provided by the embodiment of the present invention is:

[0047]

[0048] Such as figure 1 As shown, the preparation method of the supramolecular polymerized fluorescent nanomaterial provided in the embodiment of the present invention includes the following steps:

[0049] S101, the compound NT-DA is obtained by covalently combining the fluorescent small molecule NapTpa with aggregation-induced luminescent properties and the diacetylenic monomer PCDA;

[0050] S102, c...

Embodiment 1

[0061] Step 1. Synthesis of compound NT-DA: Accurately weigh NapTpa-OH (151 mg), DMAP (47.14 mg), and DCC (100 mg) on ​​a balance and add them to a 25 ml reaction tube, add 5 ml of tetrahydrofuran, and stir to dissolve them; Then accurately weigh (106mg) PCDA in a small beaker, add 5ml of tetrahydrofuran to dissolve it, then slowly add the dissolved PCDA solution dropwise to the above reaction tube; Stir on a stirrer at room temperature for 72 hours, point the plate to confirm the progress of the reaction; after the reaction is over, transfer the solution in the reaction tube to a round bottom flask, remove THF (35°C) by rotary evaporation under reduced pressure, and spin dry with an appropriate amount of Dichloromethane was dissolved; the resulting solution was washed with supersaturated NaHCO 3 Extraction, the purpose is to remove DCC; Add an appropriate amount of anhydrous sodium sulfate to remove water to obtain a crude product; Finally, add a small amount of silica gel to...

Embodiment 2

[0064] Embodiment 2: the test of NT-DA optical performance

[0065] Steps: At 25°C, the UV absorption and fluorescence emission spectra of NT-DA were measured, and the changes in the fluorescence emission spectra of 10uL NT-DA (1mM) in different volume ratios of DMSO / H2O mixed solvents (total volume 2mL) were investigated.

[0066] Result: if figure 2 The UV-Vis absorption spectrum of NT-DA shows that there are two maximum absorption peaks at 306nm and 418nm, image 3 The emission spectrum is arranged at 500-800nm, and the peak is around 590nm. It can be seen that the compound has a large Stokes shift (167nm), which avoids the light pollution of the excitation light and the self-absorption of the emission in the process of biomedical imaging. Such as Figure 4 , NT-DA has typical AIE effect characteristics, and it is almost weakly emitted in DMSO. When 0%-90% deionized water is gradually added, as the proportion of water increases, due to the limitation of intramolecular m...

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Abstract

The invention belongs to the technical field of medical materials, and discloses an application of a photosensitizer based on aggregation-induced emission in cell imaging and photodynamic therapy. The applicaiton is characterized in that an aggregation-induced emission compound is covalently or non-covalently introduced into a polydiacetylene supramolecular system, and is spontaneously assembled and polymerized under the hydrophilic and hydrophobic action among molecules to obtain nanoparticles. According to the invention, AIE micromolecules are covalently/non-covalently introduced into a polydiacetylene supramolecular system by utilizing the excellent performance of diacetylene in the aspect of self-assembly, and the aggregation-induced emission supramolecular polymer is spontaneously assembled under the hydrophilic and hydrophobic action among molecules. The problem of aggregation fluorescence quenching is solved, and good water solubility is achieved. In addition, polymerization of diacetylene enables the aggregate structure to be rigidified, and leakage of the fluorescent dye can be prevented, so that a novel nanostructure with a clear structure is developed. The invention discusses the application of the supramolecular luminescent nano material in cell imaging and photodynamic therapy for the first time, and realizes integration of diagnosis and treatment.

Description

technical field [0001] The invention belongs to the technical field of medical materials, and in particular relates to a preparation method of supramolecular polymerized fluorescent nanometer material and its application in biology. Background technique [0002] Currently, theranostic nanolights refer to luminescent nanoparticles that have both imaging and therapeutic functions. Among them, photodynamic therapy (PDT) has emerged as a noninvasive and reliable cancer therapy with high spatiotemporal precision. Different from traditional nanomedicine, it can control the imaging and therapeutic functions of nanolight through localized photons to cause minimal damage to surrounding tissues. Various luminescent materials have been developed and studied as biological probes. [0003] Supramolecular chemistry is a science that studies the formation of ordered aggregates of multiple simple small molecules through intermolecular interactions. Usually, supramolecular luminescent mat...

Claims

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Application Information

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IPC IPC(8): C07D221/14C09K11/06G01N21/64A61K41/00A61P35/00
CPCC07D221/14C09K11/06G01N21/6428G01N21/6486G01N21/6456A61K41/0057A61P35/00C09K2211/1029
Inventor 尹小英曹梦慧刘庆山
Owner SHANGHAI UNIV OF ENG SCI
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