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Fluorescent probe for double-organelle imaging, cell viability evaluation and photodynamic cancer cell ablation as well as preparation and application of fluorescent probe

A technology for fluorescent probes and cancer cells, which is applied in the field of fluorescent probes and organic fluorescent probes, can solve problems that are rarely studied, and achieve the effects of high yield, simple synthesis route, and simple operation

Pending Publication Date: 2022-02-11
JILIN INST OF CHEM TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although the existing biological probes based on the AIE principle have superior performance, an AIE fluorescent probe capable of dual imaging of mitochondria / lipid droplets (LDs), detection of cell viability, and simultaneous use in PDT of cancer cells has rarely been investigated.

Method used

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  • Fluorescent probe for double-organelle imaging, cell viability evaluation and photodynamic cancer cell ablation as well as preparation and application of fluorescent probe
  • Fluorescent probe for double-organelle imaging, cell viability evaluation and photodynamic cancer cell ablation as well as preparation and application of fluorescent probe
  • Fluorescent probe for double-organelle imaging, cell viability evaluation and photodynamic cancer cell ablation as well as preparation and application of fluorescent probe

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0042] Example 1 A fluorescent probe for dual cell organelle imaging, cell viability assessment and photodynamic cancer cell ablation A fluorescent probe for dual cell organelle imaging, cell viability assessment and photodynamic cancer cell ablation, the chemical structural formula is as follows figure 1 In a), the photophysical properties of the compound are shown in Table 1.

[0043] Table 1 Photophysical properties of Mito-TTPE

[0044]

[0045] λ in Table 1 abs is the maximum absorption value; λ em is the emission maximum; ε is the molar absorptivity of the maximum absorption wavelength; Φ is the fluorescence quantum yield, using XDS 307 as a standard reference, the quantum yield in ethanol is 0.56.

Embodiment 2

[0046] Example 2 Preparation of a fluorescent probe for dual organelle imaging, cell viability assessment and photodynamic cancer cell ablation

[0047] A method for preparing a fluorescent probe for dual organelle imaging, cell viability assessment and photodynamic cancer cell ablation, the synthesis route is as follows Figure 9 As shown, the specific synthesis steps are: LD-TTP (50mg, 0.12mol) and 4-(bromomethyl)phenyl acetate (55mg, 0.24mol) were refluxed overnight under argon in anhydrous toluene (2.5mL); cooling to room temperature, the solvent was removed under reduced pressure, and CH 2 Cl 2 / MeOH=30:1 (v / v) The residue was purified by silica gel chromatography to obtain Mito-TTPE (72 mg, 78%) as a purple solid.

[0048] 1 H NMR (600MHz, DMSO-d 6 )δ9.03(s, J=6.0Hz, 2H), 8.24-8.21(m, 3H), 7.62-7.63(d, 2H), 7.59-7.58(d, 2H), 7.51(s, 2H), 7.35 -7.34(m,4H),7.23-7.21(d,J=8.4Hz,2H),7.15-7.08(m,7H),6.98-6.97(d,J=8.4Hz,2H),5.72(s,2H ),2.27(s,3H). See Figure 14 .

[00...

Embodiment 3

[0050] Example 3 AIE characteristic of Mito-TTPE in ethanol / hexane mixed solvent with increasing hexane component.

[0051] Mito-TTPE was dissolved in dimethyl sulfoxide to prepare a stock solution (1.0mM); the AIE performance of Mito-TTPE (5μM) in ethanol / hexane mixed solvents with different hexane components was studied. like figure 2 As shown in a, Mito-TTPE exhibited weak luminescence in 100% ethanol. When the hexane component was higher than 60%, the fluorescence intensity increased rapidly and moved slowly from 712nm to 646nm; the hexane component was 60% to 90 %, the fluorescence intensity increases rapidly, and when the hexane component reaches 95%, the fluorescence intensity is the strongest, and αAIE (1 / 10) is about 28 ( figure 2b); Mito-TTPE in component (f H ) is the dynamic light scattering data in 95% ethanol / hexane mixed solvent as Figure 10 a, the solid-state fluorescence spectrum of Mito-TTPE is shown in Figure 10 As shown in b, the experimental result...

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Abstract

The invention relates to a fluorescent probe for double-organelle imaging, cell viability evaluation and photodynamic cancer cell ablation as well as preparation and application of the fluorescent probe, the chemical structure of the fluorescent probe is a compound as shown in a formula (I): the fluorescent probe Mito-TTPE contains a pyridine cation part, and mitochondria is targeted through electrostatic interaction with an electronegative mitochondrial membrane; besides, the fluorescent probe Mito-TTPE selects acetoxyl as an esterase activatable site, after being hydrolyzed by mitochondrial esterase in living cells, part of the fluorescent probe Mito-TTPE is converted into blue radioactive LD-TTP and can be specifically accumulated in LDs, and due to the fact that the unique bicolor radiation and double-organelle targeted change of Mito-TTPE is controlled by esterase hydrolysis, Mito-TTPE can be used for evaluating cell activity; besides, the fluorescent probe Mito-TTPE has a stronger D-pi-A effect, and the ROS generation capability is obviously higher than that of LD-TTP, so that the fluorescent probe Mito-TTPE has a strong effect on photodynamic cancer cell ablation.

Description

technical field [0001] The invention belongs to the field of organic fluorescent probes, and in particular relates to a fluorescent probe for dual organelle imaging, cell viability assessment and photodynamic cancer cell ablation, preparation and application. Background technique [0002] Fluorescent probe-assisted fluorescence imaging has emerged as a powerful tool due to its non-invasiveness, high sensitivity, and in situ and real-time visualization of biological species at the subcellular level. Currently, many probes have been developed for the imaging of intracellular active substances and / or single / double organelles. However, due to π-π stacking and other non-radiative pathways, traditional fluorophores often suffer from aggregation-caused quenching (ACQ) effects, which may lead to weaker fluorescence emission in the aggregated state and prone to photobleaching. A new class of aggregation-induced emission (AIE) luminescent agents first proposed by Tang Benzhong's team...

Claims

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Application Information

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IPC IPC(8): C07D409/06C09K11/06G01N21/64
CPCC07D409/06C09K11/06G01N21/6428G01N21/6456G01N21/6486C09K2211/1029C09K2211/1092C09K2211/1007Y02B20/00
Inventor 张跃伟于雪樊丽朱守俊王硕航王晓东王丹黄雨浓田金金
Owner JILIN INST OF CHEM TECH
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