Bacterial siderophores: synthesis and biological activities of novel pyochelin analogues

• Published in: Bioorganic & medicinal chemistry letters 2003-03, Vol.13 (6), p.1147-1150
• Main Authors: Zamri, A, Schalk, I.J, Pattus, F, Abdallah, M.A
• Format: Article
• Language: English
• Subjects: Bacteriology; Biochemistry, Molecular Biology; Biological and medical sciences; Fundamental and applied biological sciences. Psychology; Indicators and Reagents; Iron; Iron - metabolism; Iron Chelating Agents; Iron Chelating Agents - chemical synthesis; Iron Chelating Agents - pharmacology; Life Sciences; Magnetic Resonance Spectroscopy; Microbiology; Permeability, membrane transport, intracellular transport; Phenols; Phenols - chemical synthesis; Phenols - pharmacology; Pseudomonas aeruginosa; Pseudomonas aeruginosa - chemistry; Pseudomonas aeruginosa - drug effects; Pseudomonas aeruginosa - metabolism; Siderophores; Siderophores - chemical synthesis; Siderophores - pharmacology; Thiazoles
• ISSN: 0960-894X; 1464-3405
• DOI: 10.1016/S0960-894X(03)00010-6

The synthesis and biological activities of four pyochelin analogues substituted in different parts of the molecule are reported: 5- NHBoc-pyochelin, 3″ N-Boc-pyochelin, 3″-nor- NH-pyochelin and neopyochelin II, the enantiomer of natural pyochelin. All these compounds complex iron(III) and transport it at different rates into the cells of Pseudomonas aeruginosa. The synthesis and biological activities of four pyochelin analogues substituted in different parts of the molecule are reported: 5-NHBoc-pyochelin, 3″ N-Boc-pyochelin, 3″-nor- NH-pyochelin and neopyochelin II, the enantiomer of natural pyochelin. All these compounds complex iron(III) and transport it at different rates into the cells of Pseudomonas aeruginosa.