title: Spectroscopic studies of the equilibrium between complexes of lasalocid acid with propargylamine and metal cations.
abstract: 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, (1)H NMR, (13)C 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.
authors.affiliation: Faculty of Chemistry, Adam Mickiewicz University, Grunwaldzka 6, 60-780 Poznań, Poland. Electronic address: jacekr@amu.edu.pl.
authors.forename: Jacek
authors.initials: J
authors.lastname: Rutkowski
authors.affiliation: Faculty of Chemistry, Adam Mickiewicz University, Grunwaldzka 6, 60-780 Poznań, Poland.
authors.forename: Adam
authors.initials: A
authors.lastname: Huczyński
authors.affiliation: Faculty of Chemistry, Adam Mickiewicz University, Grunwaldzka 6, 60-780 Poznań, Poland.
authors.forename: Małgorzata
authors.initials: M
authors.lastname: Ratajczak-Sitarz
authors.affiliation: Faculty of Chemistry, Adam Mickiewicz University, Grunwaldzka 6, 60-780 Poznań, Poland.
authors.forename: Andrzej
authors.initials: A
authors.lastname: Katrusiak
authors.affiliation: Faculty of Chemistry, Adam Mickiewicz University, Grunwaldzka 6, 60-780 Poznań, Poland.
authors.forename: Bogumil
authors.initials: B
authors.lastname: Brzezinski
authors.affiliation: Institute of Medical Physics and Biophysics, Charité, Universitätsmedizin Berlin, Charitéplatz 1, 10117 Berlin, Germany.
authors.forename: Franz
authors.initials: F
authors.lastname: Bartl
mesh_terms: D002412:Cations / Q000737:chemistry; D056831:Coordination Complexes / Q000737:chemistry*; D018360:Crystallography, X-Ray; D006860:Hydrogen Bonding; D007476:Ionophores / Q000737:chemistry*; D007832:Lasalocid / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D008670:Metals / Q000737:chemistry*; D008958:Models, Molecular; D010293:Pargyline / Q000031:analogs & derivatives* / Q000737:chemistry; D011437:Propylamines / Q000737:chemistry*; D021241:Spectrometry, Mass, Electrospray Ionization; D017550:Spectroscopy, Fourier Transform Infrared
chemical_list: D002412:Cations; D056831:Coordination Complexes; D007476:Ionophores; D008670:Metals; D011437:Propylamines; C009054:propargylamine; D010293:Pargyline; D007832:Lasalocid
keywords: Complexes; Crystal structure; FT-IR; Hydrogen bonds; Ionophores