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Aggregation-induced emission principle-based fluorescent probe, its preparation method and use and endotoxin detection method

A technology of aggregation-induced luminescence and fluorescent probes, applied in the field of fluorescent probes based on the principle of aggregation-induced luminescence and their preparation, detection of endotoxin, can solve the problems of insufficient detection technology of endotoxin, shorten the time required for detection, and reduce the operation time Simple, highly specific results

Active Publication Date: 2016-06-01
HKUST SHENZHEN RES INST +1
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  • Claims
  • Application Information

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Problems solved by technology

[0005] The purpose of the present invention is to provide a fluorescent probe based on the principle of aggregation-induced luminescence and its preparation method, application and use of the aggregation-induced luminescence characteristics of the fluorescent probe and the deiodide ion fluorescence quenching effect to quickly and intuitively detect internal substances qualitatively or quantitatively. Toxin method to solve the problem of insufficient endotoxin detection technology in the prior art

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  • Aggregation-induced emission principle-based fluorescent probe, its preparation method and use and endotoxin detection method
  • Aggregation-induced emission principle-based fluorescent probe, its preparation method and use and endotoxin detection method
  • Aggregation-induced emission principle-based fluorescent probe, its preparation method and use and endotoxin detection method

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preparation example Construction

[0045] The preparation method of fluorescent probe is as follows: figure 1 shown, including the following steps:

[0046] 1) Dissolve TPE-Br in tetrahydrofuran solvent, place it at -88°C ~ -68°C, slowly add butyl lithium dropwise to the reaction bottle; after the dropwise addition, keep the reaction solution at -88°C ~ -68°C After reacting at ℃ for 2 hours to 4 hours, slowly add piperidine to the above reaction solution to form a mixture; then return to room temperature and continue the reaction for 1 hour to 3 hours; after the reaction is completed, the mixture is poured into water, extracted with dichloromethane, combined with organic phase, washed with saturated brine, dried over anhydrous magnesium sulfate, and finally the organic solvent was evaporated to dryness; the product 4-(1,2,2-triphenyl Ethylene)-benzaldehyde (abbreviated as TPE-CHO). The above-mentioned number of times of extraction with dichloromethane can be determined according to needs, can be extracted onc...

Embodiment 1

[0062] The preparation of fluorescent probe TPE-Be-I, the steps are as follows:

[0063] 1) Synthesis of TPE-CHO: Dissolve 5 mmol of TPE-Br in 50 ml of tetrahydrofuran solvent, place it at -78°C, slowly add 6 mmol of butyllithium (1.6 mol / L, 3.8 ml ); after the dropwise addition, keep the reaction solution at -78°C for 3 hours, slowly add 10 mmol of piperidine to the above reaction solution to form a mixture; then return to room temperature and continue the reaction for 2 hours, after the reaction is completed, pour the mixture into Extract in water three times with dichloromethane, combine the organic phases, wash with saturated brine, dry over anhydrous magnesium sulfate, and finally evaporate the organic solvent to dryness; use n-hexane and dichloromethane as eluents, and separate the product by column chromatography TPE-CHO, its nuclear magnetic resonance spectrum is as follows: 1 HNMR (400MHz, CDCl 3 ), δ (ppm): 9.90 (s, 1H), 7.61 (d, J = 8.2Hz, 2H), 7.19 (d, J = 8.2Hz,...

Embodiment 2

[0068] The preparation of fluorescent probe TPE-Be-I, the steps are as follows:

[0069] 1) Synthesis of TPE-CHO: Dissolve 2.5mmol of TPE-Br in 50ml of tetrahydrofuran solvent, place it at -68°C, slowly add 3mmol of butyllithium (1.6mol / L, 1.9 milliliters); after the dropwise addition, keep the reaction solution at -68°C for 2 hours, then slowly add 5 mmol of piperidine to the above reaction solution to form a mixture; then return to room temperature and continue the reaction for 1 hour. After the reaction is completed, the mixture is poured into water, extracted once with dichloromethane, combined organic phases, washed with saturated brine, dried over anhydrous magnesium sulfate, and finally evaporated the organic solvent to dryness; using n-hexane and dichloromethane as eluents, separated by column chromatography to obtain Product TPE-CHO;

[0070] 2) Synthesis of Be-I: Dissolve 5 mmol of benzothiazole and 10 mmol of ethyl iodide in 20 ml of acetonitrile, and reflux it for...

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Abstract

The invention relates to an aggregation-induced emission principle-based fluorescent probe, its preparation method and use and an endotoxin detection method utilizing fluorescent probe aggregation-induced emission characteristics and iodine ion fluorescence quenching removal characteristics to realize fast, visual and qualitative or quantitative detection of endotoxin.

Description

technical field [0001] The invention relates to the field of fluorescence technology, in particular to a fluorescent probe based on the principle of aggregation-induced luminescence, its preparation method, application and endotoxin detection method. Background technique [0002] Endotoxin is a component of the cell wall of Gram-negative bacteria, also known as lipopolysaccharide (LPS). The clinical injection contaminated by it can cause fever, microcirculation disturbance, endotoxin shock and disseminated disease after entering the human body. Toxic reactions such as intravascular coagulation. [0003] At present, the main method for detecting endotoxin is the limulus test. According to different limulus reagent products, the specific test methods can be divided into gel method, dynamic turbidity method, endpoint turbidity method, dynamic chromogenic method and terminal chromogenic method. The gel method is a semi-quantitative detection method for endotoxin, which is only ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09K11/06C07D277/64G01N21/64
Inventor 唐本忠郑启昌李民赵娜杨霄
Owner HKUST SHENZHEN RES INST
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