title: Helical peptide-polyamine and -polyether conjugates as synthetic ionophores.
abstract: Two new synthetic ionophores in which the hydrophobic portion is represented by a short helical Aib-peptide (Aib=α-amino-isobutyric acid) and the hydrophilic one is a poly-amino (1a) or a polyether (1b) chain have been prepared. The two conjugates show a high ionophoric activity in phospholipid membranes being able to efficiently dissipate a pH gradient and, in the case of 1b, to transport Na(+) across the membrane. Bioactivity evaluation of the two conjugates shows that 1a has a moderate antimicrobial activity against a broad spectrum of microorganisms and it is able to permeabilize the inner and the outer membrane of Escherichia coli cells.
authors.affiliation: University of Trieste, Department of Life Sciences, via Giorgieri 5, I-34127 Trieste, Italy.
authors.forename: Monica
authors.initials: M
authors.lastname: Benincasa
authors.affiliation: University of Trieste, Department of Chemical and Pharmaceutical Sciences, via Giorgieri 1, I-34127 Trieste, Italy.
authors.forename: Marco
authors.initials: M
authors.lastname: Francescon
authors.affiliation: University of Trieste, Department of Chemical and Pharmaceutical Sciences, via Giorgieri 1, I-34127 Trieste, Italy.
authors.forename: Massimo
authors.initials: M
authors.lastname: Fregonese
authors.affiliation: University of Trieste, Department of Life Sciences, via Giorgieri 5, I-34127 Trieste, Italy. Electronic address: rgennaro@units.t.
authors.forename: Renato
authors.initials: R
authors.lastname: Gennaro
authors.affiliation: University of Trieste, Department of Chemical and Pharmaceutical Sciences, via Giorgieri 1, I-34127 Trieste, Italy.
authors.forename: Paolo
authors.initials: P
authors.lastname: Pengo
authors.affiliation: University of Trieste, Department of Chemical and Pharmaceutical Sciences, via Giorgieri 1, I-34127 Trieste, Italy.
authors.forename: Paola
authors.initials: P
authors.lastname: Rossi
authors.affiliation: University of Padova, Department of Chemical Sciences, via Marzolo 1, I-35131 Padova, Italy. Electronic address: paolo.scrimin@unipd.it.
authors.forename: Paolo
authors.initials: P
authors.lastname: Scrimin
authors.affiliation: University of Trieste, Department of Chemical and Pharmaceutical Sciences, via Giorgieri 1, I-34127 Trieste, Italy. Electronic address: ptecilla@units.it.
authors.forename: Paolo
authors.initials: P
authors.lastname: Tecilla
mesh_terms: D000900:Anti-Bacterial Agents / Q000138:chemical synthesis / Q000494:pharmacology*; D002176:Candida albicans / Q000187:drug effects; D002463:Cell Membrane Permeability / Q000187:drug effects; D003455:Cryptococcus neoformans / Q000187:drug effects; D004926:Escherichia coli / Q000187:drug effects; D007700:Kinetics; D009842:Oligopeptides / Q000138:chemical synthesis / Q000494:pharmacology*; D010755:Organophosphates / Q000138:chemical synthesis / Q000494:pharmacology*; D061209:Proton Ionophores / Q000138:chemical synthesis / Q000494:pharmacology*; D018892:Proton-Motive Force; D011550:Pseudomonas aeruginosa / Q000187:drug effects; D061210:Sodium Ionophores / Q000138:chemical synthesis / Q000494:pharmacology*; D013211:Staphylococcus aureus / Q000187:drug effects; D053835:Unilamellar Liposomes
chemical_list: D000900:Anti-Bacterial Agents; C000610531:N1-(4'-(phosphinyl)oxy)benzoyl-Aib(8)-1,17-diamine-3,6,9,12,15-pentaoxaheptadecane; C000610530:N1-(4'-(phosphinyloxy)benzoyl-Aib(8)-1,12-diamino-4,9-diazadodecane; D009842:Oligopeptides; D010755:Organophosphates; D061209:Proton Ionophores; D061210:Sodium Ionophores; D053835:Unilamellar Liposomes
keywords: Antimicrobial activity; Helical peptide; Liposome; Membrane permeability; Synthetic ionophores