Interaction of water-soluble calix[4]arene with L-tryptophan studied by fluorescence spectroscopy

The complexing ability of water-soluble calix[4]arene for L-tryptophan (L-try) was investigated by a variety of techniques. The spectrofluorometry titrations were performed at different temperatures to determine stability constants, as well as to evaluate the thermodynamic parameters of the obtained complex. The effect of pH on the complexation process was quantitatively assessed. Moreover, to obtain information about the binding mechanism of the interaction, H-1 NMR studies were carried out. Molecular modeling showed that water-soluble calix[4]arene accommodated part of L-amino acid in its cavity meanwhile the aliphatic chain of L-tryptophan stuck out of the cavity. Based on the experiment data, the association process of complexes was established. The water-soluble calix[4]arene was found to be able to adjust its conformation to fit the size of aromatic L-tryptophan, and the benzene ring of amino acid penetrated into the hydrophobic cavity of calix[4]arene. (C) 2008 Elsevier B.V. All rights reserved.