AIE luminogens for visualization and treatment of cancer

A luminophore and fluorescence technology, applied in luminescent materials, chemical instruments and methods, preparations for in vivo experiments, etc., can solve the problems of non-selective staining of cancer cells and fluorescence quenching

Active Publication Date: 2018-03-27
THE HONG KONG UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, some fluorescent tracers are not selective when used to stain cancer cells, or even suffer from fluorescence quenching problems.

Method used

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  • AIE luminogens for visualization and treatment of cancer
  • AIE luminogens for visualization and treatment of cancer
  • AIE luminogens for visualization and treatment of cancer

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0168] Characterization: Steady-state fluorescence spectra were recorded on a Perkin Elmer LS 55 spectrometer. Fluorescence images were collected on an Olympus BX 41 fluorescence microscope.

[0169] Cell culture: at 37 °C in 5% CO 2 HeLa cells were cultured in MEM containing 10% FBS and 1% antibiotics (100 units / mL penicillin and 100 g / mL streptomycin) in a humidity incubator. 5% CO at 37°C 2 COS-7, MDA-MB-231, MCF-7 and MDCK-II cells were cultured in DMEM containing 10% FBS and antibiotics (100 units / mL penicillin and 100 g / mL streptomycin) in a humidity incubator.

[0170] Cell Imaging: Two different types of cells were grown overnight on 35mm Petri dishes fitted with coverslips. Live cells were incubated with 200 nM TPE-IQ-2O for 1, 5, 10 and 20 minutes. In a typical experiment, 2 μL of a 10 mM TPE-IQ-2O stock solution in DMSO is first diluted to 2 mL with cell culture medium and then further diluted to the desired concentration. Cells were then imaged under a fluores...

Embodiment 2

[0189] Preparation of Structure II (DPA-IQ): Briefly, [RhCp*Cl 2 ] 2 (2.0mol%), AgBF 4 (0.30mmol), Cu(OAc) 2 (0.30mmol), 4-(diphenylamino)benzaldehyde (0.36mmol), diphenylacetylene (0.30mmol), propylamine (0.45mmol) reaction mixture in 2.5ml tert-amyl alcohol was heated at 110°C Stir for 3 hours. After removal of solvent, the residue was purified by alumina column chromatography using dichloromethane / methanol (100:1 v / v) as eluent to give pure product as yellow solid in 60% yield.

[0190] 1 H-NMR (400MHz; d 6 -DMSO)δ H 9.77(s,1H),8.29(d,2H,J=9.6Hz),7.44-7.36(m,10H),7.30-7.24(m,6H),7.11-7.10(m,3H),7.04-7.02( m,2H),6.43(s,1H),4.18(t,2H,J=7.2Hz),1.75-1.69(m,2H),0.73(t,2H,J=7.2Hz)ppm. 13 C-NMR (400MHz; CDCl 3 )δ C 155.0,149.1,144.4,143.3,139.7,135.4,133.7,133.6,131.5,130.4,130.2,130.0,128.8,128.2,128.1,127.0,126.8,123.5,122.1,109.5,59.3,02 11 B-NMR-1.327ppm. 19 F-NMR-148.3ppm.MALDI-MS DPA-IQ cation (C 36 h 31 N 2 + ): The calculated value is 491.2482, and the me...

Embodiment 3

[0197] Preparation of Structure III (TPA-IQ): The synthesis method is similar to DPA-IQ.

[0198] 1 H-NMR (400MHz; d 6 -DMSO)δ H 10.29(s,1H),8.66(d,1H,J=8.8Hz),8.43(d,1H,J=8.4Hz),7.60-7.58(m,3H),7.49(s,2H),7.40-7.28 (m,12H),7.15-7.08(m,6H),7.00(d,2H,J=8.4Hz),4.36(t,2H,J=7.2Hz),1.85-1.80(m,2H),0.79( t,3H,J=7.2Hz)ppm. 13 C-NMR (400MHz; d 6 -DMSO)δ C 149.3,149.1,147.7,146.3,144.3,137.9,137.7,133.5,131.4,131.1,130.4,130.3,130.1,130.0,129.8,128.7,128.5,128.3,125.5,125.2,124.3,121.6,120.8,60.0,23.7, 10.5ppm. 11 B-NMR (128MHz; d 6 -DMSO)-1.32ppm. 19 F-NMR (376MHz; d 6 -DMSO)-148.3ppm. The cation of MALDI-MS TPA-IQ (C 42 h 35 N 2 + ): The calculated value is 567.2795, and the measured value is 567.2771.

[0199] TPA-IQ exhibits typical AIE features, as shown in Figure 10. The DMSO solution of TPA-IQ hardly emits light, while the aggregated state powder of the substance emits strong yellow-orange fluorescence when excited by UV. Figure 10 shows the UV absorption spec...

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Abstract

The present subject matter relates to AIE luminogens for visualization and treatment of cancer, particularly AIE luminogenic probes for cancer cell visualization and discrimination, lysosome-targetingAIEgens for imaging and autophagy visualization, highly fluorescent AIE-active theranostic agents for monitoring drug distribution and having anti-tumor activity to specific cancer cells, probes comprising AIE luminogens for cancer cell imaging and staining, AIE luminogens having clusteroluminogenic features and applications thereof, and methods of preparing thereof.

Description

[0001] related application [0002] This patent application claims Provisional U.S. Application Patent No. 62 / 231,069 filed June 24, 2015, Provisional U.S. Application Patent No. 62 / 231,932 filed July 20, 2015, Provisional U.S. Application Patent No. 62 / 231,932 filed September 22, 2015 Priority to Application Patent No. 62 / 284,162 and Provisional U.S. Application Patent No. 62 / 386,380, filed November 30, 2015, filed by the inventors and incorporated herein by reference in their entirety. technical field [0003] The subject of the present invention relates to aggregation-induced emission (AIE) luminophores for the visualization and therapy of cancer. In particular, the present invention relates to AIE fluorescent probes for visualization and differentiation of cancer cells, lysosome-targeted AIEgen for imaging and visualization of autophagy, high antitumor activity for monitoring drug distribution and specific cancer cells A reagent for diagnosis and treatment of AIE activity...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09K11/06C08G65/00A61K41/00A61K49/00A61K31/44A61K31/555A61P35/00
CPCC07D295/088C07D307/36C07D333/08C07D493/22C07D495/22C07D495/04C07C229/16C09K11/06A61P35/00G01N21/6486A61K49/0021C09K2211/1033C09K2211/1088C09K2211/1096C09K2211/1044C09K2211/1007C09K2211/1011C09K2211/1092C08G65/00A61K41/0057C09K2211/1014C09K2211/1029A61K31/47A61K31/4706A61K31/5375A61K31/695A61K33/22C09B23/04C09B26/02C09B57/00C09B57/008C09K2211/1018G01N33/582
Inventor 唐本忠赵恩贵归晨江美娟邓海琴梁玮彤王志明赵悦悦郭子健露西娅·维利安蒂谢你
Owner THE HONG KONG UNIV OF SCI & TECH
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