Optimization of 1,2,4-Triazole-3-thiones toward Broad-Spectrum Metallo-β-lactamase Inhibitors Showing Potent Synergistic Activity on VIM- and NDM-1-Producing Clinical Isolates.


Journal

Journal of medicinal chemistry
ISSN: 1520-4804
Titre abrégé: J Med Chem
Pays: United States
ID NLM: 9716531

Informations de publication

Date de publication:
22 12 2022
Historique:
pubmed: 1 12 2022
medline: 24 12 2022
entrez: 30 11 2022
Statut: ppublish

Résumé

Metallo-β-lactamases (MBLs) contribute to the resistance of Gram-negative bacteria to carbapenems, last-resort antibiotics at hospital, and MBL inhibitors are urgently needed to preserve these important antibacterial drugs. Here, we describe a series of 1,2,4-triazole-3-thione-based inhibitors displaying an α-amino acid substituent, which amine was mono- or disubstituted by (hetero)aryl groups. Compounds disubstituted by certain nitrogen-containing heterocycles showed submicromolar activities against VIM-type enzymes and strong NDM-1 inhibition (

Identifiants

pubmed: 36450011
doi: 10.1021/acs.jmedchem.2c01257
doi:

Substances chimiques

beta-Lactamase Inhibitors 0
beta-lactamase NDM-1 EC 3.5.2.6
Thiones 0
1,2,4-triazole 288-88-0
Anti-Bacterial Agents 0
beta-Lactamases EC 3.5.2.6

Types de publication

Journal Article Research Support, Non-U.S. Gov't

Langues

eng

Sous-ensembles de citation

IM

Pagination

16392-16419

Auteurs

Alice Legru (A)

IBMM, CNRS, Univ Montpellier, ENSCM, 34000 Montpellier, France.

Federica Verdirosa (F)

Dipartimento di Biotecnologie Mediche, Università di Siena, 53100 Siena, Italy.

Yen Vo-Hoang (Y)

IBMM, CNRS, Univ Montpellier, ENSCM, 34000 Montpellier, France.

Giusy Tassone (G)

Dipartimento di Biotecnologie, Chimica e Farmacia, Università di Siena, 53100 Siena, Italy.

Filippo Vascon (F)

Laboratory of Structural Biology, Department of Biology, University of Padua, 35121 Padova, Italy.

Caitlyn A Thomas (CA)

Department of Chemistry and Biochemistry, Miami University, Oxford, Ohio 45056, United States.

Filomena Sannio (F)

Dipartimento di Biotecnologie Mediche, Università di Siena, 53100 Siena, Italy.

Giuseppina Corsica (G)

Dipartimento di Biotecnologie Mediche, Università di Siena, 53100 Siena, Italy.

Manuela Benvenuti (M)

Dipartimento di Biotecnologie, Chimica e Farmacia, Università di Siena, 53100 Siena, Italy.

Georges Feller (G)

Laboratoire de Biochimie, Centre d'Ingénierie des Protéines-InBioS, Université de Liège, Allée du 6 août B6, Sart-Tilman, B-4000 Liège, Belgium.

Rémi Coulon (R)

IBMM, CNRS, Univ Montpellier, ENSCM, 34000 Montpellier, France.

Francesca Marcoccia (F)

Dipartimento di Biotecnologie Mediche, Università di Siena, 53100 Siena, Italy.

Savannah Rowane Devente (SR)

Dipartimento di Biotecnologie Mediche, Università di Siena, 53100 Siena, Italy.

Ezeddine Bouajila (E)

IBMM, CNRS, Univ Montpellier, ENSCM, 34000 Montpellier, France.

Catherine Piveteau (C)

Drugs and Molecules for Living System, U1177, Inserm, Université de Lille, Faculté de Pharmacie, 59006 Lille, France.

Florence Leroux (F)

Drugs and Molecules for Living System, U1177, Inserm, Université de Lille, Faculté de Pharmacie, 59006 Lille, France.

Rebecca Deprez-Poulain (R)

Drugs and Molecules for Living System, U1177, Inserm, Université de Lille, Faculté de Pharmacie, 59006 Lille, France.

Benoît Deprez (B)

Drugs and Molecules for Living System, U1177, Inserm, Université de Lille, Faculté de Pharmacie, 59006 Lille, France.

Patricia Licznar-Fajardo (P)

HydroSciences Montpellier, UMR5151, Univ Montpellier, CNRS, IRD, CHU Montpellier, 34000 Montpellier, France.

Michael W Crowder (MW)

Department of Chemistry and Biochemistry, Miami University, Oxford, Ohio 45056, United States.

Laura Cendron (L)

Laboratory of Structural Biology, Department of Biology, University of Padua, 35121 Padova, Italy.

Cecilia Pozzi (C)

Dipartimento di Biotecnologie, Chimica e Farmacia, Università di Siena, 53100 Siena, Italy.

Stefano Mangani (S)

Dipartimento di Biotecnologie, Chimica e Farmacia, Università di Siena, 53100 Siena, Italy.

Jean-Denis Docquier (JD)

Dipartimento di Biotecnologie Mediche, Università di Siena, 53100 Siena, Italy.
Centre d'Ingénierie des Protéines-InBioS, Université de Liège, B-4000 Liège, Belgium.

Jean-François Hernandez (JF)

IBMM, CNRS, Univ Montpellier, ENSCM, 34000 Montpellier, France.

Laurent Gavara (L)

IBMM, CNRS, Univ Montpellier, ENSCM, 34000 Montpellier, France.

Articles similaires

[Redispensing of expensive oral anticancer medicines: a practical application].

Lisanne N van Merendonk, Kübra Akgöl, Bastiaan Nuijen
1.00
Humans Antineoplastic Agents Administration, Oral Drug Costs Counterfeit Drugs

Smoking Cessation and Incident Cardiovascular Disease.

Jun Hwan Cho, Seung Yong Shin, Hoseob Kim et al.
1.00
Humans Male Smoking Cessation Cardiovascular Diseases Female
Humans United States Aged Cross-Sectional Studies Medicare Part C
1.00
Humans Yoga Low Back Pain Female Male

Classifications MeSH