title: Preparation and Microbiological Evaluation of Amphiphilic Kanamycin-Lipoamino Acid Ion-Pairs.
abstract: Amphiphilic ion-pairs of kanamycin (KAN) were prepared by evaporation of a water-ethanol co-solution of KAN base and a lipoamino acid bearing a 12-carbon atoms alkyl side chain (LAA12), at different molar ratios. Infrared spectroscopy confirmed the structure of ion-pairs, while differential scanning calorimetry (DSC) and powder X-ray diffractometry (PXRD) studies supported the formation of new saline species with a different crystalline structure than the starting components. The solubility pattern shown in a range of both aqueous and organic solvents confirmed that the ion-pairs possess an amphiphilic character. The LAA12 counter-ion showed not to improve the antibacterial activity of KAN, suggesting that such chemical strategy is not able to favor the penetration of this drug inside the bacteria cells. Nevertheless, a slight improving, i.e., a one-fold dilution, was observed in E. coli. The present study can also serve as the basis for a further evaluation of LAA ion-pairing of antibiotics, as a means to improve the loading of hydrophilic drugs into lipid-based nanocarriers.
authors.affiliation: Department of Drug Sciences, University of Catania, Città Universitaria, viale A. Doria 6, I-95125 Catania, Italy. r.pignatello@unict.it.|NANO-i, Research Centre for Ocular Nanotechnology, Department of Drug Sciences, University of Catania, viale A. Doria 6, I-95125 Catania, Italy. r.pignatello@unict.it.
authors.forename: Rosario
authors.initials: R
authors.lastname: Pignatello
authors.affiliation: Department of Drug Sciences, University of Catania, Città Universitaria, viale A. Doria 6, I-95125 Catania, Italy. antonio.leonardi@gmail.com.
authors.forename: Antonio
authors.initials: A
authors.lastname: Leonardi
authors.affiliation: Department of Biomedical Sciences, University of Catania, via Androne 83, I-95124 Catania, Italy. gpetroniopetronio@gmail.com.|IRCCS San Raffaele Pisana, Via della Pisana 235, I-00163 Roma, Italy. gpetroniopetronio@gmail.com.
authors.forename: Giulio Petronio
authors.initials: GP
authors.lastname: Petronio
authors.affiliation: Pharmaceutical Technology, Te.Far.T.I. group, Department of Life Sciences, University of Modena and Reggio Emilia, via Campi 183, I-41100 Modena, Italy. barbara.ruozi@unimore.it.
authors.forename: Barbara
authors.initials: B
authors.lastname: Ruozi
authors.affiliation: Department of Drug Sciences, University of Catania, Città Universitaria, viale A. Doria 6, I-95125 Catania, Italy. puglisig@unict.it.|NANO-i, Research Centre for Ocular Nanotechnology, Department of Drug Sciences, University of Catania, viale A. Doria 6, I-95125 Catania, Italy. puglisig@unict.it.
authors.forename: Giovanni
authors.initials: G
authors.lastname: Puglisi
authors.affiliation: Department of Biomedical Sciences, University of Catania, via Androne 83, I-95124 Catania, Italy. furneri@unict.it.
authors.forename: Pio Maria
authors.initials: PM
authors.lastname: Furneri
keywords: DSC; E. coli; MIC; PXDR; amphiphilicity; antibacterial activity; coevaporates; ion-pairs; lipoamino acids; physical mixtures