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.

Preparation and Microbiological Evaluation of Amphiphilic Kanamycin-Lipoamino Acid Ion-Pairs / Pignatello, Rosario; Leonardi, Antonio; Petronio, Giulio; Ruozi, Barbara; Puglisi, Giovanni; Furneri, Pio Maria. - In: ANTIBIOTICS. - ISSN 2079-6382. - STAMPA. - 3:(2014), pp. 216-232. [10.3390/antibiotics3020216]

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

RUOZI, Barbara;
2014

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.
2014
3
216
232
Preparation and Microbiological Evaluation of Amphiphilic Kanamycin-Lipoamino Acid Ion-Pairs / Pignatello, Rosario; Leonardi, Antonio; Petronio, Giulio; Ruozi, Barbara; Puglisi, Giovanni; Furneri, Pio Maria. - In: ANTIBIOTICS. - ISSN 2079-6382. - STAMPA. - 3:(2014), pp. 216-232. [10.3390/antibiotics3020216]
Pignatello, Rosario; Leonardi, Antonio; Petronio, Giulio; Ruozi, Barbara; Puglisi, Giovanni; Furneri, Pio Maria
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11380/1077165
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