Probe for dual-mode bio-imaging

A biological imaging, dual-modal technology, applied in the direction of using spectral diagnosis, using fluorescence emission for analysis, instruments, etc., can solve the problems of increasing Raman signal background, incompatibility of fluorescence and Raman microscopic imaging, etc.

Active Publication Date: 2019-09-13
THE HONG KONG UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] Traditionally, fluorescence has not been compatible with Raman microscopy because fluorescence can greatly increase the background of the Raman signal

Method used

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  • Probe for dual-mode bio-imaging
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  • Probe for dual-mode bio-imaging

Examples

Experimental program
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Effect test

preparation example Construction

[0107] The method shown here is similar to the synthesis above using ASCP, except that the 4-(dimethylamino)benzaldehyde is replaced by commercially available 4-(phenylethynyl)benzaldehyde. As shown in the Alternative Reaction Schemes, the preparation of the compounds of the present invention may comprise the following sequential steps: Knoevenagel condensation, Suzuki coupling and alkylation. The structures of AIE-SRS-Mito and its synthetic precursors (AIE-SRS-1 and AIE-SRS-2) were confirmed by 1HNMR, 13C NMR and high-resolution mass spectrometry with satisfactory results.

[0108] Identify target of interest

[0109] According to one embodiment, one or more compounds of the invention may be contacted with a target cell to identify the target of interest in the target cell, eg, to detect the presence or absence of the target of interest. Targets of interest can be identified by imaging methods such as fluorescence microscopy and / or Raman microscopy. Targets of interest ma...

Embodiment 1

[0120] Synthesis of AIE-SRS-1

[0121] In a 100 mL round bottom flask, 4-(phenylethynyl)benzaldehyde (206 mg, 1 mmol) and 4-bromophenylacetonitrile (196 mg, 1 mmol) were dissolved in 40 mL of ethanol solution to form a mixture. Sodium hydroxide (100 mg) was added to the mixture. After stirring at 50° C. for 5 hours, the resulting pale yellow precipitate was filtered and washed with cold ethanol. The product was dried and weighed. Yield: 95%. 1 H-NMR (400MHz, d 6 -DMSO)δ(ppm)8.13(s,1H),8.00(d,2H,J=8.0Hz),7.74-7.71(m,6H),7.60-7.58(m,2H),7.46-7.45(m, 3H). 13 C NMR (100MHz, d 6 -DMSO) δ (ppm) 142.4, 133.6, 133.0, 132.1, 131.9, 131.5, 129.5, 129.2, 128.8, 127.9, 124.4, 122.8, 121.9, 117.5, 109.8, 91.8, 89.0. MS (MALDI-TOF): AIE-SRS-1 (C 23 h 14 Calculated for BrN: 383.0310, found: 383.0309.

Embodiment 2

[0123] Synthesis of AIE-SRS-2

[0124] Compound 1 (192 mg, 0.5 mmol), 4-pyridylboronic acid (74 mg, 0.6 mmol), potassium carbonate (172 mg, 1.25 mmol) and Pd(PPh 3 ) 4 (10 mg, 0.01 mmol) in total of 10 mL of aqueous solution and 3 mL of water were added to a 100 mL two-neck round bottom flask equipped with a condenser to form a mixture. The mixture was stirred and heated to reflux overnight. After cooling to room temperature and evaporating THF, the mixture was extracted three times with dichloromethane (DCM). The organic phase was collected, washed with water and dried over anhydrous magnesium sulfate. After solvent evaporation, the crude product was purified by silica gel column chromatography using DCM / MeOH as eluent. Yield: 99%. 1 H NMR (400MHz, CDCl 3 )δ (ppm) 8.71 (d, 2H, J = 4.4Hz), 7.93 (d, 2H, J = 8.4Hz), 7.82 (d, 2H, J = 8.4Hz), 7.74 (d, 2H, J = 8.4 Hz), 7.63 (d, 2H, J=8.4Hz), 7.60-7.54 (m, 5H), 7.39-7.36 (m, 3H). 13 C NMR (100MHz; CDCl 3 )δ (ppm) 150.7, 1...

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Abstract

The present subject matter relates to compounds that have aggregation-induced emission (AIE) characteristics and are capable of generating Raman signals in the Ramancell-silent region (1800 cm -1-2800cm -1). The compounds can be used in dual-mode cell imaging by fluorescence and Raman microscopes.

Description

technical field [0001] This topic generally concerns the Raman cells in the silent region (i.e., 1800cm -1 to 2800cm -1 ) of compounds with aggregation-induced luminescent features and Raman signals and their application in dual-modal bioimaging using fluorescence and Raman microscopy. Background technique [0002] To elucidate the biological properties of fluorescent probes or drugs, it is extremely important to obtain detailed images of their intracellular distribution (local concentration) and their evolution over time. Fluorescence methods are suitable for this purpose due to their high sensitivity, specificity, and spatial and temporal resolution. Fluorescent probes such as Rhodamine 123 and JC-1 are typically used to label one or more cellular targets of interest (eg, molecules or organelles of interest). However, due to the heterogeneity of cells, the accumulated dye concentration in organelles (especially mitochondria) can be very high. For example, based on elec...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09K11/06C07C211/63C07C211/54
CPCC09K11/06C07D213/57G01N33/54366C09K2211/1018G01N21/6428G01N21/6458A61B5/0071A61B5/0075G01N33/533
Inventor 唐本忠江美娟李雪松瞿佳男
Owner THE HONG KONG UNIV OF SCI & TECH
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