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Water-soluble compounds with aggregation-induced emission characteristics

A technique for aggregation-induced luminescence and fluorescent compounds, applied in the field of fluorescent compounds

Active Publication Date: 2020-06-09
THE HONG KONG UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, almost all previously reported plasma membrane-staining fluorophores can only be used as imaging probes rather than having dual applications in simultaneous imaging and therapy

Method used

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  • Water-soluble compounds with aggregation-induced emission characteristics
  • Water-soluble compounds with aggregation-induced emission characteristics
  • Water-soluble compounds with aggregation-induced emission characteristics

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0100] Synthesis of TTVP

[0101] 5-(4-(diphenylamino)phenyl)thiophene-2-carbaldehyde (71mg, 0.2mmol) and 1-(3-trimethylaminopropyl)-4-methylpyridinium dibromide (71mg, A solution of 0.2 mmol) was refluxed under nitrogen atmosphere in dry ethanol catalyzed by adding a few drops of piperidine overnight. After cooling to room temperature, the solvent was removed by distillation under reduced pressure. Separation by neutral alumina column and purification of the residue using DCM and methanol (98:2 v / v) as eluents afforded TTVP (98 mg, yield 71%) as a reddish-brown powder. 1 H NMR (400MHz, CD 3 OD), δ(ppm): 8.78(d, J=6.8Hz, 2H), 8.13-8.17(m, 3H), 7.58-7.60(m, 2H), 7.48(d, J=4.0Hz, 1H), 7.40(d, J=4.0Hz, 1H), 7.30-7.34(m, 4H), 7.02-7.12(m, 9H), 4.60(t, J=7.8Hz, 2H), 3.52-3.56(m, 2H) ,3.20(s,9H),2.51-2.59(m,2H). 13 C NMR (100MHz, CDCl 3 ),δ(ppm):155.99,150.81,150.19,148.72,145.26,140.33,136.72,135.83,130.81,128.12,126.40,125.16,125.04,124.90,123.80,121.71,64.04,58.04,54.13,2...

Embodiment 2

[0103] photophysical properties

[0104] TTVP has good water solubility. TTVP benefits from the hydrophilic nature of its positively charged amine and pyridinium salt, and the small size of the hydrophobic part. The aqueous solution of TTVP exhibits the maximum absorption band peak at 515nm, and the molar extinction coefficient is 33517M -1 cm -1 ( figure 2 ). The relatively long absorption wavelength can be attributed to its small HOMO-LOMO energy gap, which is caused by the strong electron donating-accepting interaction of the luminescent center ( Figures 3A to 3C ).

[0105] For different THF fractions (f T ) The study of the AIE characteristics of TTVP in the water / THF mixture shows that TTVP is a typical AIE active molecule ( Figure 1A ). The unimolecular state of TTVP in aqueous solution hardly emits light, and when the fraction of THF increases, the photoluminescence (PL) intensity gradually increases due to the formation of aggregates ( Figure 1C ). In t...

Embodiment 3

[0112] cell imaging

[0113] As a water-soluble NIR-luminescent AIE emitter, TTVP maintains an "off" state in an aqueous environment. Thus, TTVP can be used as a "light-up" probe for biological imaging with minimal background interference from both free dye and biological substrate autofluorescence. In preliminary bioimaging experiments, HeLa cells were used as cell models and incubated in 500 nM TTVP for 10 minutes for cell imaging studies. It was observed that regardless of whether the cells were washed after staining, the plasma membrane of the cells could be clearly visualized with excellent image contrast with the cell background ( Figures 6A to 6B ). The effect on the incubation period was then studied by using a no-wash program with different staining times. The results showed that the staining time was shortened from 10 minutes to 30 seconds without significant changes in fluorescence imaging quality in terms of both fluorescence intensity and specificity ( Fig...

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Abstract

The present subject matter relates to water-soluble, fluorescent compounds that have aggregation-induced emission (AIE) characteristics and exhibit near infrared (NIR) absorption. The compounds can beutilized as plasma-membrane specific bio-probes in cell imaging through a wash-free and fast staining procedure. In addition, the compounds can efficiently generate reactive oxygen species (ROS) in vivo when irradiated with visible light. As such, the compounds can be effective in killing cancer cells through image-guided, photodynamic therapy (PDT) processes.

Description

[0001] cross reference [0002] This application claims priority to U.S. Provisional Patent Application No. 62 / 707,135, filed October 24, 2017, by the inventors of this application, and the entire contents of which application are incorporated herein by reference. technical field [0003] This topic generally concerns a series of fluorescent compounds with aggregation-induced luminescent properties and near-infrared absorption, and their applications in bioimaging and optical therapy. Background technique [0004] Fluorescence bioimaging is a powerful non-invasive method because it visualizes biological species, provides fast response, excellent temporal resolution, high sensitivity, in situ operability, ease of operation, and good reproducibility. gender analysis tool. As the main branch of fluorescent materials, small-molecule organic fluorophores, especially those with near-infrared (NIR) emission (>700nm), have obvious advantages, such as high penetration depth, low ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D213/38C07D249/06C09K11/06C08G65/333A61K41/00A61P35/00
CPCC07D213/38A61P35/00C09K11/07C09K2211/1007C09K2211/1014C09K2211/1029C09K2211/1092A61K41/0057C07D215/12C07D409/06A61B90/20A61N5/062A61N2005/0662C09K2211/1018G01N21/6458G01N21/76G02B21/0076G02B21/16
Inventor 唐本忠王东
Owner THE HONG KONG UNIV OF SCI & TECH
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