A physicochemical, thermodynamical, structural and computational evaluation of kynurenic acid/cyclodextrin complexes.

Adrián Matencio, Fabrizio Caldera, Alberto Rubin Pedrazzo, Yousef Khazaei Monfared, Nilesh K Dhakar, Francesco Trotta

Food chemistry 2021 Sep 15

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In this work, the interaction between Kynurenic acid (KYNA) and several natural and modified cyclodextrins (CDs) is carried out. Among all the CD tested, HPβ-CD showed the strongest complexation constant (KF), with a value of 270.94 ± 29.80 M-1. Between natural (α- and β-) CDs, the complex of KYNA with β-CD was the most efficient. The inclusion complex of KYNA with CDs showed a strong influence of pH and temperature. The KF value decreased at high pH values, when the pKa was passed. Moreover, an increase of the temperature caused a decrease in the KF values. The thermodynamic parameters of the complexation (ΔH°, ΔS° and ΔG°) were studied with negative entropy, enthalpy and spontaneity of the process at 25 °C. Moreover, the inclusion complex was also characterized using FTIR and TGA. Finally, molecular docking calculations provided different interactions and their influence in the complexation constant. Copyright © 2021 Elsevier Ltd. All rights reserved.

Citation

Adrián Matencio, Fabrizio Caldera, Alberto Rubin Pedrazzo, Yousef Khazaei Monfared, Nilesh K Dhakar, Francesco Trotta. A physicochemical, thermodynamical, structural and computational evaluation of kynurenic acid/cyclodextrin complexes. Food chemistry. 2021 Sep 15;356:129639