Probe with functions of successive imaging and killing of bacteria and cancer cells and application thereof

Active Publication Date: 2020-07-28
SOUTH CHINA UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In terms of fluorescence imaging, traditional fluorescent probes with aggregation-induced quenching (ACQ) effect have the following disadvantages: 1) local high-concentration aggregation is prone to self-quenching of fluorescence; 2) poor photostability, easy to Quenching occurs under light; 3) There is strong background noise in fluorescence imaging, which requires cumbersome washing steps to remove background interference; 4) The Stokes shift is small (less than 40nm), and the interference generated by excitation light in fluorescence imaging Need to be removed by a filter, but can greatly affect the intensity of emitted light
Recently, a series of photodynamically active AIE molecules have been used to kill bacteria and cancer cells, but they are not resistant to bacterial infections caused by anaerobic bacteria and solid tumors in hypoxic environments

Method used

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  • Probe with functions of successive imaging and killing of bacteria and cancer cells and application thereof
  • Probe with functions of successive imaging and killing of bacteria and cancer cells and application thereof
  • Probe with functions of successive imaging and killing of bacteria and cancer cells and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0053] Example 1 Preparation of AIE-Mito-TPP probes with sequential imaging and killing functions for bacteria and cancer cells

[0054] (1) Add 2,4-dihydroxybenzaldehyde (690mg, 5.0mmol) and 1,6-dibromohexane (1.22g, 5.0mmol) into 20mL of acetonitrile, then add potassium carbonate (690mg, 5.0mmol) in N 2 Under reflux, the reaction was stirred for 6 h, the solvent was spin-dried, and the compound IX was obtained by separation through a silica gel column (PE:EA=80:1).

[0055] (2) Compound IX (300mg, 1.0mmol) and triphenylphosphine (262mg, 1.0mmol) were dissolved in 5mL of acetonitrile, under N 2 Under reflux, stir the reaction for 5h, rotary evaporate under reduced pressure, remove the solvent, and recrystallize to obtain compound X.

[0056] (3) Compound X (250mg, 0.44mmol) was dissolved in ethanol, then hydrazine hydrate (11mg, 0.22mmol) was added, and the 2 Under reflux, stir the reaction for 4h, filter, wash with absolute ethanol three times, and dry in vacuum to obtain...

Embodiment 2

[0059] Example 2 Fluorescence imaging of bacteria

[0060] (1) Culture and dilution of bacteria

[0061] A single clone of Staphylococcus aureus (Gram-positive bacteria) on the agar plate was added to 5 mL of NB liquid medium, and placed on a shaker with a temperature of 37° C. and a rotation speed of 180 rpm for 12 hours. Then the bacterial suspension was centrifuged at 7100g for 3 minutes, washed 3 times with PBS, the supernatant was discarded, and the remaining bacteria were resuspended in PBS. Then the bacterial suspension was diluted to an absorbance value of 1.0 (OD 600 = 1.0). For the cultivation of Escherichia coli (Gram-negative bacteria), except that LB liquid medium is used as the culture medium, other experimental conditions and operations are the same as those of Staphylococcus aureus.

[0062] (2) Fluorescence imaging experiment of bacteria

[0063] 100 μL of bacterial suspension (OD 600 =1.0) into the PBS (400 μL) solution containing AIE-Mito-TPP, so that t...

Embodiment 3

[0072] Embodiment 3 antibacterial activity experiment

[0073] Bacterial (Staphylococcus aureus and Escherichia coli) suspension (10 6 CFU mL -1 ) were mixed evenly with different concentrations of AIE-Mito-TPP, placed on a shaker with a temperature of 37°C and a rotation speed of 180rpm, and incubated for 30 minutes; 4 CFU mL -1 ; Then take 10 μ L and drop it on the agar plate, and smear it gently on the agarose gel plate with a bacterial coating stick, in order to disperse the bacterial solution evenly on the agar plate; When the friction force increased, stop smearing; finally, these agar plates were incubated at 37°C for 18 hours, and the number of bacterial colonies was recorded. The antibacterial experimental operation of methicillin-resistant Staphylococcus aureus is the same as the above operation.

[0074] Figure 7 Bacterial survival graphs and agarose plate photos of Staphylococcus aureus and Escherichia coli treated with AIE-Mito-TPP at different concentration...

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Abstract

The invention belongs to the technical field of molecular probes, and discloses a probe with functions of successive imaging and killing of bacteria and cancer cells and application of the probe. Thestructure of the probe is shown as a formula I, wherein X is preferably hydrogen; Y is preferably a linking bond; Z is preferably O; R is preferably hydrogen; W is preferably absent; L is preferably aC1-C16 alkylene ether group; T<+> is one of tricyclohexylphosphine salt cations, triphenylphosphine salt cations and pyridine cations; and Q<-> is a monovalent anion. The probe disclosed by the invention is applied to preparation of antibacterial and / or anticancer drugs and preparation of a fluorescence imaging agent. The probe provided by the invention realizes dual effects of antibiosis and anticancer by increasing permeability of bacterial cell membranes and destroying the structure of mitochondria in cancer cells, and has successive imaging and killing functions of bacteria and cancer cells.

Description

technical field [0001] The invention belongs to the technical field of molecular probes, and relates to a probe capable of sequentially imaging and killing bacteria and cancer cells and its application. Sequential fluorescence imaging and molecular probes with antibacterial and anticancer functions and their applications. Background technique [0002] Bacterial infection is closely related to the occurrence and development of cancer, and the effective killing of bacteria can significantly improve the therapeutic effect of cancer. For example, Fusobacterium infection is closely related to colorectal cancer, and killing Fusobacteria with antibiotics can greatly improve the therapeutic effect of colorectal cancer. In addition, immunocompromised cancer patients are more susceptible to bacterial infections. For example, lung cancer patients often suffer from pneumonia caused by bacterial infection. Therefore, clinically, antibiotics and anticancer drugs need to be used in comb...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F9/54A61K31/66A61P35/00A61P31/04G01N21/64A61K49/00
CPCA61K49/0021A61P31/04A61P35/00C07F9/5407G01N21/6402G01N21/6428G01N21/6458G01N21/6486
Inventor 唐本忠任力高蒙陈晓辉
Owner SOUTH CHINA UNIV OF TECH
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