The influence of linkages between 1-hydroxy-2(1H)-pyridinone coordinating groups and a tris(2-aminoethyl)amine core in a novel series of synthetic hexadentate iron(III) chelators on antimicrobial activity.
Acinetobacter baumannii
/ drug effects
Amines
/ chemistry
Anti-Bacterial Agents
/ chemical synthesis
Antifungal Agents
/ chemical synthesis
Bacillus subtilis
/ drug effects
Candida albicans
/ drug effects
Dose-Response Relationship, Drug
Iron Chelating Agents
/ chemical synthesis
Klebsiella pneumoniae
/ drug effects
Microbial Sensitivity Tests
Molecular Structure
Pseudomonas aeruginosa
/ drug effects
Pyridones
/ chemistry
Staphylococcus aureus
/ drug effects
Structure-Activity Relationship
1-hydroxy-2(1H)-pyridinone
Bacterial growth
Biostatic agent
Chelator
Siderophore
Journal
Bioorganic chemistry
ISSN: 1090-2120
Titre abrégé: Bioorg Chem
Pays: United States
ID NLM: 1303703
Informations de publication
Date de publication:
01 2020
01 2020
Historique:
received:
19
06
2019
revised:
30
09
2019
accepted:
21
11
2019
pubmed:
20
12
2019
medline:
2
3
2021
entrez:
20
12
2019
Statut:
ppublish
Résumé
Resistance of pathogens to antimicrobials is a major current healthcare concern. In a series of linked studies, we have investigated synthetic iron chelators based on hydroxy-pyridinone ligands as novel bacteriostatic agents. Herein we describe our synthesis of several useful building blocks based on the 1-hydroxy-2(1H)-pyridinone moiety, including a novel formyl derivative, which were combined with a tris(2-aminoethyl)amine core to obtain a series of new high-affinity hexadentate Fe(III) chelators. The design principle examined by this series is the size and flexibility of the linker between the core and the metal ligands. Measurement of the pKa and stability constants (Fe
Identifiants
pubmed: 31855824
pii: S0045-2068(19)30983-6
doi: 10.1016/j.bioorg.2019.103465
pii:
doi:
Substances chimiques
Amines
0
Anti-Bacterial Agents
0
Antifungal Agents
0
Iron Chelating Agents
0
Pyridones
0
1-hydroxy-2(1H)-pyridinone
YO3915897S
Types de publication
Journal Article
Research Support, Non-U.S. Gov't
Langues
eng
Sous-ensembles de citation
IM
Pagination
103465Informations de copyright
Copyright © 2019 Elsevier Inc. All rights reserved.
Déclaration de conflit d'intérêts
Declaration of Competing Interest The authors declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper.