Spectroscopic studies of the equilibrium between complexes of lasalocid acid with propargylamine and metal cations

• The crystal structure of the lasalocid complexes with propargylamine is studied.
• Lasalocid forms concurrent complexes with metal cations and amines existing in equilibrium.
• Lasalocid is a useful ligand for complexation of amines and metal cations.

The molecular structure of 1:1 complex formed between the naturally occurring polyether ionophore, called lasalocid acid (LAS) and propargylamine (PROP) is studied by X-ray, FT-IR, 1H NMR, 13C NMR and ESI-MS methods. The complex formed between deprotonated LAS acid and protonated PROP molecule is stabilized by intra- and inter-molecular hydrogen bonds. The protons of the protonated amine group are hydrogen bonded to etheric and hydroxyl oxygen atoms of the LAS anion. The similarity of the FT-IR spectra of the LAS–PROP complex in solid state and in solution demonstrated that the molecular structures of the complex in both states are comparable. It is shown that LAS in solution can form concurrent complexes with metal cations (M = Li+, Na+, K+) and amine existing in equilibrium. Analysis of the structures of lasalocid complexes is important for a better understanding of the antibacterial and anticancer properties of lasalocid acid.

The polyether ionophore antibiotic – lasalocid acid forms concurrent complexes with metal cations and amines existing in equilibrium.Figure optionsDownload as PowerPoint slide