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A ratiometric fluorescent probe responsive to membrane charge and its application in bacterial detection

A ratiometric fluorescent probe and fluorescent probe technology, applied in the field of biological analysis and detection, can solve the problems of small application range, poor repeatability, cumbersome operation, etc.

Active Publication Date: 2022-07-15
DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the fluorescent probes reported so far are all based on the array method to detect bacteria, which requires the simultaneous use of multiple compounds to distinguish the small differences of different species. This method has the problems of cumbersome operation, poor repeatability, and small scope of application. , and can only distinguish between different types of bacteria, and does not have the ability to identify bacteria, such as identifying Gram-negative or positive bacteria

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  • A ratiometric fluorescent probe responsive to membrane charge and its application in bacterial detection
  • A ratiometric fluorescent probe responsive to membrane charge and its application in bacterial detection
  • A ratiometric fluorescent probe responsive to membrane charge and its application in bacterial detection

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Embodiment 1

[0034] The preparation of ratiometric fluorescent probes for bacterial detection, the basic synthesis method is as follows:

[0035] Under nitrogen conditions, pyrene (4g, 19.77mmol) and bromoacetyl bromide (3.33g, 16.48mmol) were added to a 50mL double-necked flask and dissolved in 40mL of dichloromethane, keeping the temperature at 0°C, and slowly adding aluminum chloride powder (2.64g, 19.77mmol) in the reaction solution, stirred for 2 hours to obtain a dark solution; after the temperature was raised to room temperature and stirred for 8 hours, 20 mL of ice water was added to quench the excess aluminum chloride, followed by extraction with 100 mL of dichloromethane The crude product was obtained by separation, and by silica gel column chromatography, 2-bromo-1-pyrenyl ethanone was obtained by separation under the condition of petroleum ether:dichloromethane=7:3;

[0036]Under nitrogen, a 50 mL double-necked flask was added with lithium aluminum tetrahydrogen (0.295 g, 7.78 ...

Embodiment 2

[0041] The preparation of ratiometric fluorescent probes for bacterial detection, the basic synthesis method is as follows:

[0042] Under nitrogen conditions, pyrene (4g, 19.77mmol) and bromoacetyl bromide (4.5g, 22.27mmol) were added to a 50mL double-necked flask and dissolved in 40mL of dichloromethane, keeping the temperature at 0°C, and slowly adding aluminum chloride powder (4 g, 29.95 mmol) in the reaction solution, stirred for 2 hours to obtain a dark solution; after the temperature was raised to room temperature and stirred for 8 hours, 20 mL of ice water was added to quench excess aluminum chloride, followed by extraction and separation with 100 mL of dichloromethane The crude product was obtained, and by silica gel column chromatography, 2-bromo-1-pyrenyl ethanone was obtained by separation under the condition of petroleum ether:dichloromethane=7:3;

[0043] Under nitrogen conditions, lithium aluminum tetrahydrogen (0.38 g, 10 mmol) and aluminum chloride (1.07 g, 8 ...

Embodiment 3

[0046] The preparation of ratiometric fluorescent probes for bacterial detection, the basic synthesis method is as follows:

[0047] Under nitrogen conditions, pyrene (3g, 14.83mmol) and bromoacetyl bromide (8.1g, 40mmol) were added to a 50mL double-necked flask and dissolved in 40mL of dichloromethane, keeping the temperature at 0°C, and slowly adding aluminum chloride powder ( 5.33g, 40mmol) in the reaction solution, stirred for 2 hours to obtain a dark solution; after the temperature was raised to room temperature and stirred for 8 hours, 20mL of ice water was added to quench excess aluminum chloride, followed by extraction and separation with 100mL of dichloromethane to obtain The crude product was separated by silica gel column chromatography under the condition of petroleum ether:dichloromethane=7:3 to obtain 2-bromo-1-pyrenyl ethanone;

[0048] Under nitrogen conditions, lithium aluminum tetrahydrogen (0.3 g, 7.91 mmol) and aluminum chloride (2.14 g, 16 mmol) were added...

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Abstract

The present invention provides a ratio fluorescent probe responsive to membrane charge and its application in bacterial detection. Fluorescence, at 375nm and 482nm, respectively, and their structures are shown in (1). This compound has 2 positive charges, which leads to fluorescence quenching in aqueous solution due to the formation of nano-aggregates due to hydrophobic interactions. The surface of bacteria has a large amount of charges, and the interaction with the probe nano-aggregates will depolymerize them and cause a large increase in fluorescence. Due to the different charge distribution on the bacterial surface, the probes form different degrees of monomer and dimer, resulting in a change in the ratio of pyrene monomer and exciplex fluorescence (I 482 / I 375 ). Using the fluorescence enhancement generated by the binding of the probe polymer to the bacteria and the change in the fluorescence ratio of the monomer to the exciplex as the fluorescence signal, the Gram-negative or positive bacteria can be identified, and different types of bacteria can be distinguished.

Description

technical field [0001] The invention belongs to the field of biological analysis and detection, in particular to a ratio fluorescent probe responsive to membrane charge and its application in bacterial detection. Background technique [0002] Bacteria, whether pathogenic or non-pathogenic, are ubiquitous in the biological world. The growth of bacteria is closely related to our life. There are about 500-1000 different types of bacteria in each person's body, accounting for 90% of all living cells in the human body. But at the same time, food-borne diseases caused by bacterial contamination are also the most prominent problems in food safety. Bacterial food poisoning incidents in my country account for 30%-90% of the total number of food poisoning incidents, and the number of people accounts for 60%-90% of the total number of food poisoning cases. Therefore, the identification and detection of bacteria is very important in many fields such as medical diagnosis, biology and f...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D233/58C09K11/06G01N21/64
CPCC07D233/58C09K11/06G01N21/6428G01N2021/6432C09K2211/1044C09K2211/1011
Inventor 徐兆超苗露龙双双
Owner DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI