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Probe for bacteria resistant to extended-spectrum beta-lactam and cephalosporin antibiotics as well as synthesis method and application of probe

A technology of cephalosporins and lactams, which is applied in the field of compounds, can solve the problems of indistinguishable decomposition, etc., and achieve the effect of simple and cheap operation, rapid detection and imaging

Active Publication Date: 2022-01-11
京黔山科技(北京)有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Cephalosporin-based probes with a 6,7R,R configuration are readily cleaved by β-lactamases but cannot differentiate between cleavage by metallo-β-lactamases and other β-lactamases

Method used

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  • Probe for bacteria resistant to extended-spectrum beta-lactam and cephalosporin antibiotics as well as synthesis method and application of probe
  • Probe for bacteria resistant to extended-spectrum beta-lactam and cephalosporin antibiotics as well as synthesis method and application of probe
  • Probe for bacteria resistant to extended-spectrum beta-lactam and cephalosporin antibiotics as well as synthesis method and application of probe

Examples

Experimental program
Comparison scheme
Effect test

preparation example Construction

[0062] The preparation method of the above-mentioned probe compound, the steps are as follows:

[0063]

[0064] Under the protection of argon, add 1eq Pd(OAc) to the eggplant type reaction flask in sequence 2 , and 1eq P(o-Tol) 3 After repeated freezing and thawing for 3 times, stir at room temperature for 1 h to activate the catalyst; then add 2.5 eq cefdinir, 10 eq charge-absorbing halogenated compound, DMF and triethylamine (10:1) in sequence, perform 3 freezing and degassing operations, and finally The temperature of the reaction was raised to 80°C for 12 hours; to terminate the reaction, add 100 mL of ethyl acetate to dilute, then use 100 mL of 0.2 mol / L HCl solution, 100 mL of NaHCO 3 Saturated aqueous solution and 100mL saturated brine, anhydrous MgSO 4 Drying; concentrating the organic phase and purifying through a silica gel column, wherein the volume ratio of dichloromethane:methanol in the silica gel column is 5:1 to obtain the probe compound.

[0065] The ap...

Embodiment 1

[0076]

[0077] The above reaction formula is the structural change of the probe before and after enzymatic hydrolysis.

[0078] The result is as figure 1 and figure 2 shown, from figure 1 , figure 2 It can be seen that the probe amide ring can be hydrolyzed by extended-spectrum β-lactamase (ESBL) and cephalosporinase (AmpC) enzymes.

[0079]

[0080] Under argon protection, 4-bromo-N,N-dimethylaniline (1g, 5mmol) and methyl bromide (1.5g, 15mmol) were added to a single-necked flask containing 20mL ETOH, stirred at room temperature for 12h, and then heated to reflux 1h, until a large amount of light yellow solid is produced. Part of ETOH was rotary evaporated, recrystallized after refrigeration at -20°C, and the obtained precipitate was washed with pure water and ether in turn to obtain white solid compound 1 (1.02 g, yield 95%). Characterization data of the compound: 1H NMR (400MHz, MeOD) δ7.97 (d, J = 8Hz, 2H), 7.88 (d, J = 16Hz, 2H), 3.65 (s, 9H).13C NMR (101MH...

Embodiment 2

[0084]

[0085] Under the protection of argon, add Pd(OAc) to the eggplant-type reaction flask in sequence 2 (446.66mg, 2mmol) and P(o-Tol) 3 (608.89mg, 2mmol), repeated freezing and thawing three times, then stirred at room temperature for 1 hour to activate the catalyst. Then add cefdinir (1.98g, 5mmol), 2,4-dinitroiodobenzene (5.88g, 20mmol), 30mL DMF and 3mL triethylamine in sequence, perform 3 freezing and degassing operations, and finally raise the temperature of the reaction to 80°C Reaction 12h. Terminate the reaction, add 100mL ethyl acetate to dilute, and then use 100mL0.2mol / L HCl solution, 100mL NaHCO 3 Saturated aqueous solution and 100mL saturated brine, anhydrous MgSO 4 dry. The organic phase was concentrated and purified by a silica gel column (dichloromethane:methanol=5:1) to obtain compound 3 (0.87 g, 31%) as a brown-yellow solid.

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Abstract

The invention discloses a probe compound for bacteria resistant to extended-spectrum beta-lactam and cephalosporin antibiotics. The probe compound is a compound with the following structure shown in the specification. A resonance Raman probe with an off-on switching effect is developed by taking the important national demand of rapid detection of drug resistance of bacteria as a research target; the specific detection on the drug resistance of the extended-spectrum beta-lactam and cephalosporin antibiotics is realized at a single bacterium level.

Description

technical field [0001] The invention belongs to the technical field of compounds, in particular to a probe compound for highly sensitive extended-spectrum β-lactam and cephalosporin antibiotic bacteria, a synthesis method and application thereof. Background technique [0002] Since Fleming discovered penicillin in 1929, antibiotics have saved countless lives and become the guardians of human health. However, due to the large-scale use or even abuse of antibiotics, bacterial gene mutations have been exacerbated, leading to the emergence of a large number of drug-resistant strains. Especially in recent years, more and more superbugs (superbugs) have been discovered, which have caused great harm to human life and health. Drug-resistant bacterial infections currently kill 700,000 people worldwide each year, mostly in developing countries, and are expected to reach 10 million by 2050. my country promulgated the "2016-2020 National Action Plan to Contain Bacterial Resistance", w...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D501/24C07D501/22C07D501/04G01N21/65C12Q1/06C12Q1/10C12Q1/34C12R1/19
CPCC07D501/24C07D501/22C07D501/04G01N21/65C12Q1/34C12Q1/10C12Q1/06C07B2200/07G01N2333/986G01N2333/245Y02A50/30
Inventor 刘定斌李文帅
Owner 京黔山科技(北京)有限公司
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