title: Captopril analogues as metallo-β-lactamase inhibitors.
abstract: A number of captopril analogues were synthesised and tested as inhibitors of the metallo-β-lactamase IMP-1. Structure-activity studies showed that the methyl group was unimportant for activity, and that the potencies of these inhibitors could be best improved by shortening the length of the mercaptoalkanoyl side-chain. Replacing the thiol group with a carboxylic acid led to complete loss of activity, and extending the length of the carboxylate group led to decreased potency. Good activity could be maintained by substituting the proline ring with pipecolic acid.
authors.affiliation: School of Chemistry and Molecular Biosciences, The University of Queensland, Queensland 4072, Australia.
authors.forename: Yusralina
authors.initials: Y
authors.lastname: Yusof
authors.affiliation: School of Chemistry and Molecular Biosciences, The University of Queensland, Queensland 4072, Australia.
authors.forename: Daniel T C
authors.initials: DTC
authors.lastname: Tan
authors.affiliation: School of Chemistry and Molecular Biosciences, The University of Queensland, Queensland 4072, Australia.
authors.forename: Omid Khalili
authors.initials: OK
authors.lastname: Arjomandi
authors.affiliation: School of Chemistry and Molecular Biosciences, The University of Queensland, Queensland 4072, Australia.
authors.forename: Gerhard
authors.initials: G
authors.lastname: Schenk
authors.affiliation: School of Chemistry and Molecular Biosciences, The University of Queensland, Queensland 4072, Australia. Electronic address: r.mcgeary@uq.edu.au.
authors.forename: Ross P
authors.initials: RP
authors.lastname: McGeary
mesh_terms: D002216:Captopril / Q000031:analogs & derivatives* / Q000737:chemistry / Q000494:pharmacology*; D004305:Dose-Response Relationship, Drug; D062105:Molecular Docking Simulation; D015394:Molecular Structure; D013329:Structure-Activity Relationship; D065093:beta-Lactamase Inhibitors / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D001618:beta-Lactamases / Q000378:metabolism*
chemical_list: D065093:beta-Lactamase Inhibitors; D002216:Captopril; C409201:beta-lactamase IMP-1; D001618:beta-Lactamases
keywords: Antibiotic resistance; Captopril; IMP-1 inhibitor; Metallo-β-lactamase