title: Amphiphilic erythromycin-lipoamino acid ion pairs: characterization and in vitro microbiological evaluation.
abstract: A series of amphiphilic ion pairs of erythromycin (ERY) with lipoamino acids (LAAs) were produced. The ion pairs were prepared by evaporation of a water/ethanol co-solution of the drug and LAA bearing an alkyl side chain of 10-16 carbon atoms. For the sake of comparison, equimolar physical mixtures were prepared by triturating ERY and the LAA in the absence of any solvent. FTIR spectroscopy confirmed the structure of ion pairs, while differential scanning calorimetry and powder X-ray diffractometry were used to assess the formation of new saline species. The solubility pattern of the coevaporates in different aqueous and organic solvents confirmed their amphiphilic properties. ERY-LAA ion pairs were submitted to an in vitro microbiological assay against different bacterial strains, both susceptible and resistant to macrolides. The presence of the LAA moiety was shown not altering the antibacterial spectrum of activity of the drug. These results can be the basis for a further evaluation of ERY-LAA ion pairs as a mean to improve the penetration of the drug inside bacterial cells and to optimize the loading of ERY in lipid-based nanocarriers.
authors.affiliation: Dipartimento di Scienze del Farmaco, Università degli Studi di Catania, Città Universitaria, Italy. r.pignatello@unict.it
authors.forename: Rosario
authors.initials: R
authors.lastname: Pignatello
authors.forename: Annalisa
authors.initials: A
authors.lastname: Mangiafico
authors.forename: Barbara
authors.initials: B
authors.lastname: Ruozi
authors.forename: Giovanni
authors.initials: G
authors.lastname: Puglisi
authors.forename: Pio Maria
authors.initials: PM
authors.lastname: Furneri
mesh_terms: D000596:Amino Acids / Q000737:chemistry* / Q000494:pharmacology / Q000592:standards; D000900:Anti-Bacterial Agents / Q000737:chemistry* / Q000494:pharmacology / Q000592:standards; D004353:Drug Evaluation, Preclinical / Q000379:methods / Q000592:standards; D004917:Erythromycin / Q000737:chemistry* / Q000494:pharmacology / Q000592:standards; D008055:Lipids / Q000737:chemistry / Q000494:pharmacology / Q000592:standards; D008826:Microbial Sensitivity Tests / Q000379:methods / Q000592:standards; D013211:Staphylococcus aureus / Q000187:drug effects; D013501:Surface-Active Agents / Q000737:chemistry* / Q000494:pharmacology / Q000592:standards
chemical_list: D000596:Amino Acids; D000900:Anti-Bacterial Agents; D008055:Lipids; D013501:Surface-Active Agents; D004917:Erythromycin