A hypoxia-activated antibacterial prodrug

[Display omitted] A prodrug based on a known antibacterial compound is reported to target Staphylococcus aureus and Escherichia coli under reductive conditions. The prodrug was prepared by masking the N-terminus and side chain amines of a component lysine residue as 4-nitrobenzyl carbamates. Activat...

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Veröffentlicht in:	Bioorganic & medicinal chemistry letters 2020-06, Vol.30 (11), p.127140-127140, Article 127140
Hauptverfasser:	Yeoh, Yuan Qi, Horsley, John R., Polyak, Steven W., Abell, Andrew D.
Format:	Artikel
Sprache:	eng
Schlagworte:	Anti-Bacterial Agents - chemical synthesis Anti-Bacterial Agents - chemistry Anti-Bacterial Agents - pharmacology Antibacterial E. coli Escherichia coli - drug effects Hypoxia-activated Microbial Sensitivity Tests Prodrug Prodrugs - chemical synthesis Prodrugs - chemistry Prodrugs - pharmacology S. aureus Staphylococcus aureus - drug effects Tin Compounds - pharmacology
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Beschreibung
Zusammenfassung:	[Display omitted] A prodrug based on a known antibacterial compound is reported to target Staphylococcus aureus and Escherichia coli under reductive conditions. The prodrug was prepared by masking the N-terminus and side chain amines of a component lysine residue as 4-nitrobenzyl carbamates. Activation to liberate the antibacterial was demonstrated on treatment with a model reductant, tin(II) chloride. The bioactivity of 1 was confirmed in antibacterial susceptibility assays whereas prodrug 2 was inactive.
ISSN:	0960-894X 1464-3405
DOI:	10.1016/j.bmcl.2020.127140