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A coumarin-based wash-free fluorescent probe for detecting Gram-positive bacteria and its application

A technology of gram-positive bacteria and fluorescent probes, which is applied in the field of wash-free fluorescent probes and applications, can solve the problems of heavy workload, complicated operation, complex instruments, etc., and achieve low cytotoxicity, good photostability, quantum The effect of high yield

Active Publication Date: 2021-07-02
ZHENGZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] Gram staining is a commonly used traditional method to distinguish Gram-positive from Gram-negative bacteria, but this strategy requires tedious work and lacks the ability to achieve in situ detection of viable bacteria
Other routine bacterial identification methods, reported in the literature including polymerase chain reaction (PCR), DNA microarrays, immunotechniques, mass spectrometry, surface-enhanced Raman spectroscopy (SERS) and biosensing techniques are often time, cost and energy consuming Expendable and require complex instruments, these disadvantages greatly limit their clinical application
[0004] At present, the conventional detection method adopts the traditional culture method, and each kind of bacteria needs to be cultured and tested separately, and the workload is heavy; while using a single fluorescent quantitative detection method to operate one by one, configuring a large number of reaction systems, consumes a lot of reagents, manpower, and material resources and time; immunological detection needs to find highly sensitive and specific antigens, and the reagents are expensive and the operation is complicated
Mammalian cells are also prone to staining, although probes are now available to distinguish between Gram-positive and Gram-negative bacteria

Method used

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  • A coumarin-based wash-free fluorescent probe for detecting Gram-positive bacteria and its application
  • A coumarin-based wash-free fluorescent probe for detecting Gram-positive bacteria and its application
  • A coumarin-based wash-free fluorescent probe for detecting Gram-positive bacteria and its application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] The structural formula of probe 1 is as follows:

[0033]

[0034]Probe 1 was prepared as follows: a mixture of diethyl oxalooxalate (1.818 g, 10 mM) and 3-(dimethylamino)phenol (1.3718 g, 10 mM) was stirred at 120° C. for 3 hours. After cooling, the reaction mixture was washed with CH 2 Cl 2 diluted and purified by silica gel column chromatography (CH 2 Cl 2 ), an orange solid (1.07 g, 45% yield) was obtained.

[0035] A solution of the orange solid (0.37g, mmol) in ethanol (7.5ml) was treated with 2N sodium hydroxide (0.75ml). The mixture was refluxed for 3 hours, and after cooling to room temperature, 20 ml of water was added to the mixture, and then the pH of the resulting solution was adjusted to 2-3 with hydrochloric acid until 7-ethylaminocoumarin-4-carboxylic acid was precipitated. The bulky brown precipitate was filtered and the precipitate was washed with CH 2 Cl 2 Washing afforded the desired product as a brown solid (0.24 g, 73% yield).

[0036] ...

Embodiment 2

[0038] The structural formula of probe 2 is as follows:

[0039]

[0040] Probe 2 was prepared as follows: a mixture of diethyl oxalate (1.818 g, 10 mM) and 3-(diethylamino)phenol (1.3718 g, 10 mM) was stirred at 120° C. for 3 hours. After cooling, the reaction mixture was washed with CH 2 Cl 2 diluted and purified by silica gel column chromatography (CH 2 Cl 2 ) to give a orange solid (1.07 g, 45% yield).

[0041] A solution of a (0.37 g, mmol) in ethanol (7.5 ml) was treated with 2N sodium hydroxide (0.75 ml). The mixture was refluxed for 3 hours, and after cooling to room temperature, 20 ml of water was added to the mixture, and then the pH of the resulting solution was adjusted to 2-3 with hydrochloric acid until 7-ethylaminocoumarin-4-carboxylic acid was precipitated. The bulky brown precipitate was filtered and the precipitate was washed with CH 2 Cl 2 Washing afforded the desired product as a brown solid (0.24 g, 73% yield).

[0042]

[0043] Application o...

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Abstract

The invention provides a coumarin-based wash-free fluorescent probe for detecting Gram-positive bacteria and its application, and its chemical structural formula is as follows. The fluorescent probe designed in the invention has sensitive fluorescent response to the polarity of the microenvironment. The probe shows very weak fluorescence in highly polar solutions and strong fluorescence in less polar solutions. The probe has no obvious fluorescence change in the aqueous solution of anionic surfactant, amphoteric surfactant and neutral surfactant, but shows very strong fluorescence in the solution of cationic surfactant. The probe specifically binds to Gram-positive bacteria and displays very strong fluorescence, while Gram-negative bacteria, fungi, and mammalian cells cannot cause significant fluorescence changes. This type of probe is an effective tool for the specific no-wash detection of Gram-positive bacteria, and can be used for the detection of Gram-positive bacteria in various fields such as medical care, production and life.

Description

technical field [0001] The invention relates to the field of preparation of surfactants and fluorescent probes for detecting Gram-positive bacteria, in particular to a coumarin-based disposable fluorescent probe for detecting Gram-positive bacteria and its application. Background technique [0002] In the past few decades, bacterial infectious diseases have posed serious challenges to human health and have increasingly attracted the attention of the medical community and the public. Millions of people are infected every year around the world. Furthermore, surgical site infections (SSIs), which account for 25% of nosocomial infections, are mainly caused by Gram-positive bacteria. At the same time, certain Gram-positive bacteria in tumors can significantly enhance chemoresistance and reduce the efficacy of chemotherapy drugs, and promote tumor growth and metastasis. Given the enormous threat posed by Gram-positive bacteria, rapid differentiation of Gram-positive bacteria has...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D311/16C09K11/06C12Q1/04G01N21/64G01N21/33
CPCC07D311/16C09K11/06C09K2211/1088C12Q1/04G01N21/33G01N21/6428G01N21/6486
Inventor 孙远强魏星李朝辉杨冉王霞
Owner ZHENGZHOU UNIV