A Method for Selective Imaging of Capsulated Bacteria Using Tetraphenylene Derivatives

A tetraphenylethylene, selective technology, applied in biochemical equipment and methods, microbial measurement/inspection, fluorescence/phosphorescence, etc., can solve problems such as difficult to stain thick capsular bacteria, achieve excellent water solubility, strong penetrating Effect of film ability, good photostability

Active Publication Date: 2021-10-01
BEIJING UNIV OF CHEM TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Solve the problem that fluorescent dyes are difficult to stain with thick capsulated bacteria and fluorescent imaging in the prior art, and provide a new method for detecting capsulated bacteria

Method used

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  • A Method for Selective Imaging of Capsulated Bacteria Using Tetraphenylene Derivatives
  • A Method for Selective Imaging of Capsulated Bacteria Using Tetraphenylene Derivatives
  • A Method for Selective Imaging of Capsulated Bacteria Using Tetraphenylene Derivatives

Examples

Experimental program
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Embodiment

[0032] Example: Synthesized tetrastyryl compounds with aggregation-induced luminescent properties

[0033] Structural formula:

[0034]

[0035] Synthesis process see figure 1 The synthetic route shown.

[0036] (1) Synthesis of TPE-Py +: First, the reactants 1,2-lutidine-1-iodide (55.95mg, 0.24mmol) and TPE-CHO (50mg, 0.12mmol) were dissolved in absolute ethanol (30mL) and a few drops of triethyl amine. Then the reaction mixture was heated under N 2 Reflux for 48 hours under protection. After the reaction mixture was cooled to room temperature, the mixture was dissolved in water and CH 2 Cl 2 Extract three times. Then add Na 2 SO 4 dry. The crude product was purified by silica gel column using CH 2 Cl 2 / MeOH mixture (10:1 v / v) as eluent to give a yellow powder (23.50 mg, yield: 31%). 1 H NMR (500MHz, Chloroform-d) δ9.32(d, J=6.2Hz, 1H), 8.34(t, J=8.0Hz, 1H), 8.25(d, J=8.4Hz, 1H), 7.80(t ,J=6.9Hz,1H),7.59(d,J=15.7Hz,1H),7.49(d,J=7.9Hz,2H),7.34(s,1H),7.14(q,J...

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Abstract

The invention relates to a method for selectively imaging capsulated bacteria with tetraphenylethylene derivatives. The method involved in the present invention includes the design and synthesis of a positively charged compound with aggregation-induced luminescent properties with tetraphenylethenyl as the skeleton, wherein the probe with two positive charges has better membrane penetration ability and can Efficiently stains thick-capsulated bacteria, whereas single-charge probes only stain common bacteria. At the same time, by connecting different electron-donating and accepting groups, the emission spectrum of the probe molecule can be adjusted. This method utilizes the charge number of the compound, the difference in the fluorescence signal and the difference in the ability to penetrate the membrane, and the combination of single and double charges to selectively image the pod. Membrane bacteria, which solves the problem that capsule bacteria are difficult to stain. The compounds involved in the method have good photostability and fluorescence imaging ability; they can be used for bacterial fluorescence imaging and dynamic visual tracking; they can selectively recognize capsulated bacteria, and have potential application value in realizing rapid imaging diagnosis of pathogens.

Description

technical field [0001] The invention relates to a method for selective imaging of capsulated bacteria with tetraphenylethylene derivatives, comprising a series of tetraphenylethylene compounds with aggregation-induced luminescent properties capable of staining capsulated bacteria and the number of charges of the compounds, the difference of fluorescence signals and Different combinations of membrane penetrating abilities to selectively image encapsulated bacteria. Background technique [0002] In recent years, fluorescence techniques have attracted extensive attention due to their high sensitivity and simplicity. However, most traditional fluorescent probes suffer from aggregation-induced quenching (ACQ) effects. Furthermore, the photobleaching of the probes during dynamic visualization and long-term monitoring greatly limits their application in microbial detection. Materials with aggregation-induced luminescence can effectively solve this problem. At present, the main ag...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): G01N21/64C12Q1/04C07D213/30C07C217/18
CPCC07C217/18C07D213/30C12Q1/04G01N21/6428
Inventor 王卓艾文婷
Owner BEIJING UNIV OF CHEM TECH
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