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Development of carbapenem-based fluorogenic probes for the clinical screening of carbapenemase-producing bacteria

Authors
Kim, JuhyeonKim, YihoonAbdelazem, Ahmed Z.Kim, Hak JoongChoo, HyunahKim, Hoon SeokKim, Jung OkPark, Yeon-JoonMin, Sun-Joon
Issue Date
1월-2020
Publisher
ACADEMIC PRESS INC ELSEVIER SCIENCE
Keywords
Carbapenems; Carbapenemase-producing bacteria; Linker; Fluorescence; Probes
Citation
BIOORGANIC CHEMISTRY, v.94
Indexed
SCIE
SCOPUS
Journal Title
BIOORGANIC CHEMISTRY
Volume
94
URI
https://scholar.korea.ac.kr/handle/2021.sw.korea/58516
DOI
10.1016/j.bioorg.2019.103405
ISSN
0045-2068
Abstract
This report describes the synthesis of a library of fluorogenic carbapenemase substrates consisting of carbapenem derivatives, fluorescence dyes, and active cleavable linkers and their evaluation for specifically detecting carbapenemase-producing organisms (CPOs). We synthesized a series of compounds having three different types of linkers such as benzyl ether, carbamate, and amine using hydroxymethyl carbapenem 7a and hydroxyallyl carbapenem 7b as key intermediates. Probe 1b exhibited high stability and a prompt turn-on fluorescence signal upon hydrolysis by carbapenemases. In particular, the screening of clinical samples indicated that the probe 1b exhibited excellent selectivity to the CPOs over other beta-lactamases or non-carbapenemase producing bacteria, which may be of clinical use for the rapid and accurate detection of CPOs for timely diagnosis and treatment.
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