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.

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

Matencio, Adrián
First
;
Caldera, Fabrizio;Rubin Pedrazzo, Alberto;Khazaei Monfared, Yousef;Trotta, Francesco
2021

Abstract

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.
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https://www.sciencedirect.com/science/article/pii/S0308814621006452
Kynurenic acid, Cyclodextrin, Inclusion complex, Physicochemical, Stability
Matencio, Adrián; Caldera, Fabrizio; Rubin Pedrazzo, Alberto; Khazaei Monfared, Yousef; K. Dhakar, Nilesh; Trotta, Francesco
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Utilizza questo identificativo per citare o creare un link a questo documento: http://hdl.handle.net/2318/1807561
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