Synthesis of Gentamicins C1, C2, and C2a and Antiribosomal and Antibacterial Activity of Gentamicins B1, C1, C1a, C2, C2a, C2b, and X2.
antibacterial resistance
gentamicins
mitochondrial and cytoplasmic ribosomes
ototoxicity
Journal
ACS infectious diseases
ISSN: 2373-8227
Titre abrégé: ACS Infect Dis
Pays: United States
ID NLM: 101654580
Informations de publication
Date de publication:
11 08 2023
11 08 2023
Historique:
medline:
14
8
2023
pubmed:
23
7
2023
entrez:
23
7
2023
Statut:
ppublish
Résumé
Complementing our earlier syntheses of the gentamicins B1, C1a, C2b, and X2, we describe the synthesis of gentamicins C1, C2, and C2a characterized by methyl substitution at the 6'-position, and so present an alternative access to previous chromatographic methods for accessing these sought-after compounds. We describe the antiribosomal activity of our full set of synthetic gentamicin congeners against bacterial ribosomes and hybrid ribosomes carrying the decoding A site of the human mitochondrial, A1555G mutant mitochondrial, and cytoplasmic ribosomes and establish structure-activity relationships with the substitution pattern around ring I to antiribosomal activity, antibacterial resistance due to the presence of aminoglycoside acetyl transferases acting on the 6'-position in ring I, and literature cochlear toxicity data.
Identifiants
pubmed: 37481733
doi: 10.1021/acsinfecdis.3c00233
pmc: PMC10425985
doi:
Substances chimiques
Gentamicins
0
Anti-Bacterial Agents
0
Aminoglycosides
0
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
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