Method for selectively imaging capsular bacteria by using tetraphenyl ethylene 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, good light The effect of stability and strong membrane penetration ability

Active Publication Date: 2020-08-28
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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  • Method for selectively imaging capsular bacteria by using tetraphenyl ethylene derivatives
  • Method for selectively imaging capsular bacteria by using tetraphenyl ethylene derivatives
  • Method for selectively imaging capsular bacteria by using tetraphenyl ethylene derivatives

Examples

Experimental program
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Effect test

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...

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Abstract

The invention relates to a method for selectively imaging capsular bacteria by using tetraphenyl ethylene derivatives. The method comprises design and synthesis of a positively charged compound whichtakes tetraphenyl ethylene as a skeleton and has an aggregation-induced emission property, a probe with two positive charges has better membrane penetration capability, bacteria with thick capsules can be effectively dyed, and a single-charge probe can only dye common bacteria. Meanwhile, the molecular emission spectrum of the probe is adjusted by connecting different electron donating and accepting groups, and the method selectively images the capsular bacteria by utilizing the charge number of a compound, the difference of fluorescence signals and the difference of transmembrane capability and the combination of single charges and double charges, so that the problem that the capsular bacteria are difficult to dye is solved. The compound involved in the method has good light stability andfluorescence imaging ability; the method can be used for bacterial fluorescence imaging and dynamic visual tracking; and capsule bacteria can be selectively recognized, and the method has potential application value in 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 Applications(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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