Dynamically chiral phosphonic acid-type metallo-β-lactamase inhibitors

Abstract Antibiotic resistance is a growing global health threat that risks the lives of millions. Among the resistance mechanisms, that mediated by metallo-β-lactamases is of particular concern as these bacterial enzymes dismantle most β-lactam antibiotics, which are our widest applied and cheapest...

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Main Authors: Kinga Virág Gulyás, Liping Zhou, Daniel Salamonsen, Andreas Prester, Kim Bartels, Robert Bosman, Paul Haffke, Jintian Li, Viola Tamási, Fritz Deufel, Johannes Thoma, Anna Andersson Rasmussen, Miklós Csala, Hanna-Kirsti Schroder Leiros, Zhijian Xu, Mikael Widersten, Holger Rohde, Eike C. Schulz, Weiliang Zhu, Máté Erdélyi
Format: Article
Language:English
Published: Nature Portfolio 2025-04-01
Series:Communications Chemistry
Online Access:https://doi.org/10.1038/s42004-025-01510-5
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Summary:Abstract Antibiotic resistance is a growing global health threat that risks the lives of millions. Among the resistance mechanisms, that mediated by metallo-β-lactamases is of particular concern as these bacterial enzymes dismantle most β-lactam antibiotics, which are our widest applied and cheapest to produce antibiotic agents. So far, no clinically applicable metallo-β-lactamase inhibitors are available. Aiming to adapt to structural variations, we introduce the inhibitor concept: dynamically chiral phosphonic acids. We demonstrate that they are straightforward to synthesize, penetrate bacterial membranes, inhibit the metallo-β-lactamase enzymes NDM-1, VIM-2 and GIM-1, and are non-toxic to human cells. Mimicking the transition state of β-lactam hydrolysis, they target the Zn ions of the metallo-β-lactamase active site. As a unique feature, both of their stereoisomers bind metallo-β-lactamases, which provides them unparalleled adaptability to the structural diversity of these enzymes, and may allow them to hamper bacteria’s ability for resistance development.
ISSN:2399-3669