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Fluorescent probe, synthesis method and application of carbapenem-resistant bacteria

A technology of carbapenems and fluorescent probes, applied in the direction of fluorescence/phosphorescence, chemical instruments and methods, luminescent materials, etc., can solve the problems of insufficient sensitivity and selectivity, short wavelength, etc., and achieve low cost of use and high selectivity sexual effect

Active Publication Date: 2019-01-18
EAST CHINA UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the fluorescent probes have some shortcomings in fluorescence performance, such as short wavelength, insufficient sensitivity and selectivity, etc.

Method used

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  • Fluorescent probe, synthesis method and application of carbapenem-resistant bacteria
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  • Fluorescent probe, synthesis method and application of carbapenem-resistant bacteria

Examples

Experimental program
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Effect test

Embodiment 1

[0069] A method for synthesizing a fluorescent probe resistant to carbapenem antibiotics bacteria, the preparation method of its compound 2 is:

[0070] Under the protection of argon, add 20 ml of dry DMF solution of meropenem intermediate F9 into the reaction bottle (schlenk), and then add 3.62 g of tert-butyldimethylsilyl chloride TBDMSCl (2 mmol, 4 equivalent equiv) and 2.45 g of imidazole in sequence (36mmol, 6equiv); After reacting at 20°C for 5h, ethyl acetate was added, washed with water and saturated brine, dried over anhydrous sodium sulfate, concentrated and then purified by silica gel column chromatography to obtain a total of 2.95g of compound 2 as a white solid, The yield is 98%;

[0071] Its synthetic route and general structural formula are:

[0072] .

Embodiment 2

[0074] A method for synthesizing a fluorescent probe resistant to carbapenem antibiotics, wherein intermediates 3 and 4 are prepared by:

[0075] Get zinc dichloride 68mg (0.5mmol) and place reaction bottle bottle, add dichloromethane after drying, add compound 2 and rhodium tetraacetate (Rh 2 (OAc) 4 , under the protection of argon, the reaction system was heated to reflux for 90 minutes; the solution of intermediate 3 was obtained after the completion of the reaction was monitored by thin layer chromatography (TLC).

[0076] 7.6g (15mmol) diazo compound 2, 67mg (0.15mmol) Rh 2 (OAc) 4, 40mL of dry dichloromethane were added to the reaction flask in turn, under the protection of argon, the reaction system was heated to reflux for 90min, after the completion of the reaction was monitored by TLC, cooled to -55°C, 2,2,6,6- Tetramethylpiperidine 3.03mL (18mmol) and diisopropylethylenediamine 1.4mL (7.65mmol) were mixed and added dropwise for more than 15min; then, trifluoromet...

Embodiment 3

[0080] A method for synthesizing a fluorescent probe resistant to carbapenem antibiotics bacteria, the preparation method of its compound 5 is:

[0081] ZnCl 2 3.38g (24mmol, 1.8equiv) is placed in the reaction bottle, and the reaction tube is baked with an electric oven under vacuum; after cooling, add 20mL nitrogen methyl pyrrolidone (NMP), and after the system is cooled, degas under vacuum Substitute Ar three times; then add in turn the intermediate 4 prepared in Example 2 8.15g (13.5mmol), tris(2-furyl)phosphorus 275mg, Pd 2 dba 3 275mg (1.2mmol); Stir the resulting solution at room temperature at 25°C for 10min, then slowly add 4.8mL (16.8mmol) of tributylvinyltin; react the reaction system at 30°C for 10h, then use 150mL of ethyl acetate Diluted, washed twice with water and once with saturated brine, dried the organic phase with anhydrous sodium sulfate, and finally obtained 6.1 g of compound 5 as a white solid after column chromatography, with a yield of 93%;

[00...

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Abstract

The invention provides a structural general formula (shown in the description) of a fluorescent probe for carbapenem type antibiotic bacteria. In the structural general formula, X represents carbon atoms or sulfur atoms; when the X represents CH, R1 represents methyl and can be of the configuration S or R, or the X represents CH2 or S; Y represents oxygen atoms, sulfur atoms or linkers on a fluorophorearomatic nucleus and comprises 4-hydroxymethylbenzyl or 4-hydroxyl or sulfydrylbenzyl or carbamate linkers. The synthesis method of the fluorescent probe comprises the following steps that 1, a compound 2 is prepared; 2, intermediates 3 and 4 are prepared; 3, a compound 5 is prepared; 4, a compound 6 is prepared; 5, a compound 7 is prepared; 6, a compound 8 is prepared; 7, a compound 9 is prepared; 8, a compound 10 is prepared;9, a compound CPC-1, namely a fluorescent probe compound is prepared. The fluorescent probe can be applied to detection of carbapenemases and drug-resistant bacteria containing the carbapenemases and has the important significance on antibiotic abandoning or few antibiotics adopted in medical treatment.

Description

technical field [0001] The invention relates to the technical field of compound preparation, in particular, a fluorescent probe for bacteria resistant to carbapenem antibiotics and a synthesis method thereof and the ability of the fluorescent probe to detect carbapenem enzymes and carbapenem-containing bacteria. Application in resistant bacteria. Background technique [0002] β-lactam antibiotics are the most widely used class of antibiotics in the treatment of infectious diseases. However, these antibiotics are not omnipotent. Some pathogenic bacteria, such as tuberculosis (TB), have genes resistant to β-lactam antibiotics, so β-lactam antibiotics are often ineffective against them. What's more serious is that if people use a large number of antibiotics or even abuse them, some bacteria will quickly adapt to the environment where antibiotics exist and become drug-resistant, which will not be conducive to the treatment of certain diseases and endanger people's health. It h...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D487/04C09K11/06G01N21/64
CPCC07D487/04C09K11/06C09K2211/1029G01N21/6428
Inventor 谢贺新毛梧宇夏令英
Owner EAST CHINA UNIV OF SCI & TECH
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