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Antibiotics 2014, 3(2), 216-232; https://doi.org/10.3390/antibiotics3020216

Preparation and Microbiological Evaluation of Amphiphilic Kanamycin-Lipoamino Acid Ion-Pairs

1
Department of Drug Sciences, University of Catania, Città Universitaria, viale A. Doria 6, I-95125 Catania, Italy
2
NANO-i, Research Centre for Ocular Nanotechnology, Department of Drug Sciences, University of Catania, viale A. Doria 6, I-95125 Catania, Italy
3
Department of Biomedical Sciences, University of Catania, via Androne 83, I-95124 Catania, Italy
4
IRCCS San Raffaele Pisana, Via della Pisana 235, I-00163 Roma, Italy
5
Pharmaceutical Technology, Te.Far.T.I. group, Department of Life Sciences, University of Modena and Reggio Emilia, via Campi 183, I-41100 Modena, Italy
*
Author to whom correspondence should be addressed.
Received: 18 February 2014 / Revised: 29 April 2014 / Accepted: 14 May 2014 / Published: 26 May 2014
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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. View Full-Text
Keywords: coevaporates; physical mixtures; ion-pairs; lipoamino acids; amphiphilicity; DSC; PXDR; antibacterial activity; MIC; E. coli coevaporates; physical mixtures; ion-pairs; lipoamino acids; amphiphilicity; DSC; PXDR; antibacterial activity; MIC; E. coli
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Pignatello, R.; Leonardi, A.; Petronio, G.P.; Ruozi, B.; Puglisi, G.; Furneri, P.M. Preparation and Microbiological Evaluation of Amphiphilic Kanamycin-Lipoamino Acid Ion-Pairs. Antibiotics 2014, 3, 216-232.

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