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((S)-3-Mercapto-2-methylpropanamido)acetic acid derivatives as metallo-β-lactamase inhibitors: Synthesis, kinetic and crystallographic studies.

Abstract：

:The emergence and global spread of metallo-β-lactamase (MBL) mediated resistance to almost all β-lactam antibacterials poses a serious threat to public health. Since no clinically useful MBL inhibitors have been reported, there is an urgent need to develop new potent broad-spectrum MBL inhibitors effective against antibacterial resistance. Herein, we synthesized a set of 2-substituted ((S)-3-mercapto-2-methylpropanamido) acetic acid derivatives, some of which displayed potent inhibition with high ligand efficiency to the clinically relevant MBL subtypes, Verona Integron-encoded MBL (VIM)-2 and New Delhi MBL (NDM)-1. Kinetic studies revealed that the inhibitors are not strong zinc chelators in solution, and they bind reversibly to VIM-2 but dissociate very slowly. Crystallographic analyses revealed that they inhibit VIM-2 via chelating the active site zinc ions and interacting with catalytically important residues. Further cell- and zebrafish-based assays revealed that the inhibitors slightly increase susceptibility of E. coli cells expressing VIM-2 to meropenem, and they have no apparent toxicity to the viability of HEK293T cells and the zebrafish embryogenesis.

journal_name

Eur J Med Chem

journal_title

European journal of medicinal chemistry

authors

Liu S,Jing L,Yu ZJ,Wu C,Zheng Y,Zhang E,Chen Q,Yu Y,Guo L,Wu Y,Li GB

doi

10.1016/j.ejmech.2018.01.032

subject

Has Abstract

pub_date

2018-02-10 00:00:00

pages

649-660

eissn

0223-5234

issn

1768-3254

pii

S0223-5234(18)30045-X

journal_volume

145

pub_type

杂志文章

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