Complexation of calix[4]arene hydroxymethyl-phosphonic acid with tryptophan and N-acetyl-tryptophan amide

O. I. Kalchenko, S. O. Cherenok, R. V. Rodik, Y. Mely, A. S. Klymchenko, V. V. Gorbatchuk, V. I. Kalchenko

Abstract


The Host-Guest complexation of calixarene hydroxymethylphosphonic acid with tryptophan and N-acetyltryptophan amide has been investigated by the RP HPLC method in H2O/MeCN (99/1) solution (column support Hypersil CN, UV-detector, λ = 254 nm). Adsorption of calixarene hydroxymethylphosphonic acid on the Hypersil CN surface has been studied. It has been found that hydroxymethylphosphonic acid is characterized by reversible sorption on the Hypersil CN surface. The binding constants (KA = 23000 M-1 and 39000 M-1 for tryptophan and N-acetyltryptophan amide, respectively) of the supramolecular complexes have been calculated from the ratio between the capacity factors k’ of the Guest and the calixarene hydroxymethylphosphonic acid Host concentration in the mobile phase. The Gibbs free energies of the tryptophan and N-acetyltryptophan amide complexes are -24.84 and -26.15 kJ/mol, respectively. The molecular modelling of calixarene hydroxymethylphosphonic acid and its complexes with tryptophan and N-acetyltryptophan amide (Hyper Chem, version 8, force field PM3) has indicated that the complexes are stabilized by hydrogen bonds, electrostatic, π-π, and solvatophobic interactions. The geometric parameters of the energy minimized calixarene macrocycle and its complexes with tryptophan and N-acetyltryptophan amide have been calculated. According to the calculations it has been shown that the Host-Guest complexation does not change the flattened-cone conformation of calixarene. Finally, the inverse correlation has been found between the KA values of the complexes and the Log P values of the guest molecules.


Keywords


calixarene hydroxymethylphosphonic acid; tryptophan; N-acetyltryptophan amide; reversed-phase high performance liquid chromatography; supramolecular complexes; binding constants

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DOI: https://doi.org/10.24959/ophcj.14.796

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Abbreviated key title: Ž. org. farm. hìm.

ISSN 2518-1548 (Online), ISSN 2308-8303 (Print)