ArticleNature chemistry2014
Rhodanine hydrolysis leads to potent thioenolate mediated metallo-β-lactamase inhibition.
Article in Nature chemistry, 2014. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 51 papers.
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Who cites it
51 citing papers in PubMed, 116 citations in OpenAlex.
- Article
- Structure-activity relationship of captopril derivatives as New Delhi metallo beta-lactamase 1 inhibitors.ADMET & DMPK · 2026Review
- Thiazolidinones: novel insights from microwave synthesis, computational studies, and potentially bioactive hybrids.Beilstein journal of organic chemistry · 2025Article
- Approachable Synthetic Methodologies for Second-GenerationPharmaceuticals (Basel, Switzerland) · 2024Review
- Rhodanine derived enethiols react to give 1,3-dithiolanes and mixed disulfides.RSC medicinal chemistry · 2024Article
- Cell-active small molecule inhibitors validate the SNM1A DNA repair nuclease as a cancer target.Chemical science · 2024Article
- Evaluation of Rhodanine Indolinones as AANAT Inhibitors.ChemMedChem · 2024Article
- Evaluation of Anticancer and Antibacterial Activity of Four 4-Thiazolidinone-Based Derivatives.Molecules (Basel, Switzerland) · 2022Article
- Imitation of β-lactam binding enables broad-spectrum metallo-β-lactamase inhibitors.Nature chemistry · 2022Article
- Drug development concerning metallo-β-lactamases in gram-negative bacteria.Frontiers in microbiology · 2022Review
- Enzyme Inhibitors: The Best Strategy to Tackle Superbug NDM-1 and Its Variants.International journal of molecular sciences · 2021Review
- Article
- Design and enantioselective synthesis of 3-(α-acrylic acid) benzoxaboroles to combat carbapenemase resistance.Chemical communications (Cambridge, England) · 2021Article
- Metallo-β-lactamases in the Age of Multidrug Resistance: From Structure and Mechanism to Evolution, Dissemination, and Inhibitor Design.Chemical reviews · 2021Review
- Discovery and characterization of New Delhi metallo-β-lactamase-1 inhibitor peptides that potentiate meropenem-dependent killing of carbapenemase-producing Enterobacteriaceae.The Journal of antimicrobial chemotherapy · 2020Article
- DeSiphering receptor core-induced and ligand-dependent conformational changes in arrestin via genetic encoded trimethylsilylNature communications · 2020Article
- Recent advances in the development of β-lactamase inhibitors.Journal of microbiology (Seoul, Korea) · 2020Review
- Metallo-β-Lactamase Inhibitors Inspired on Snapshots from the Catalytic Mechanism.Biomolecules · 2020Review
- Article
- Article
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Authors and funding
12 authors at 2 institutions in 1 country.
Funding
Abstract
The use of β-lactam antibiotics is compromised by resistance, which is provided by β-lactamases belonging to both metallo (MBL)- and serine (SBL)-β-lactamase subfamilies. The rhodanines are one of very few compound classes that inhibit penicillin-binding proteins (PBPs), SBLs and, as recently reported, MBLs. Here, we describe crystallographic analyses of the mechanism of inhibition of the clinically relevant VIM-2 MBL by a rhodanine, which reveal that the rhodanine ring undergoes hydrolysis to give a thioenolate. The thioenolate is found to bind via di-zinc chelation, mimicking the binding of intermediates in β-lactam hydrolysis. Crystallization of VIM-2 in the presence of the intact rhodanine led to observation of a ternary complex of MBL, a thioenolate fragment and rhodanine. The crystallographic observations are supported by kinetic and biophysical studies, including (19)F NMR analyses, which reveal the rhodanine-derived thioenolate to be a potent broad-spectrum MBL inhibitor and a lead structure for the development of new types of clinically useful MBL inhibitors.
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Registered trials
Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.