Lasalocid acid as a lipophilic carrier ionophore for allylamine: Spectroscopic, crystallographic and microbiological investigation

A new complex of lasalocid acid with allylamine (LAS–AM) is synthesised and studied by X-ray, FT-IR, 1H NMR and 13C NMR, ESI MS methods. In the solid state allylamine is protonated and all protons of NH3+ are hydrogen bonded. We show that in the gas, liquid and solid states lasalocid forms 1:1 complexes with allylamine and that its structures of all states are comparable, which indicates that the complex LAS–AM is very stable. The stability of the LAS–AM complex is achieved by some intra-molecular hydrogen bonds. Due to these interactions the outside of the complex is hydrophobic enabling its transport across the biological membranes. This property of the complex is reflected in its anti-microbial activity, which is discussed.