Theoretical Study of the Complexation of Lidocaine by α- and β-Cyclodextrins. | [Journal of Chemical Society of Pakistan • 2021]

Author(s):

1. Nourredine Meddah-Araibi,: Laboratory of Physical Chemistry of Macromolecular and Biological Interfaces (LCPMIB), Faculty of Sciences, University of Mascara Mustapha Stambouli, BP 305, road of Mamounia Mascara, Algeria.

2. Teffaha Fergoug: Laboratory of Physical Chemistry of Macromolecular and Biological Interfaces (LCPMIB), Faculty of Sciences, University of Mascara Mustapha Stambouli, BP 305, road of Mamounia Mascara, 29000 Algeria

3. Mansour Azayez: Laboratory of Physical Chemistry of Macromolecular and Biological Interfaces (LCPMIB), Faculty of Sciences, University of Mascara Mustapha Stambouli, BP 305, road of Mamounia Mascara, 29000 Algeria

4. Cherifa Zelmat: Laboratory of Physical Chemistry of Macromolecular and Biological Interfaces (LCPMIB), Faculty of Sciences, University of Mascara Mustapha Stambouli, BP 305, road of Mamounia Mascara, 29000 Algeria.

5. Jendara Ali Cherif: Laboratory of Physical Chemistry of Macromolecular and Biological Interfaces (LCPMIB), Faculty of Sciences, University of Mascara Mustapha Stambouli, BP 305, road of Mamounia Mascara, 29000 Algeria.

6. Youcef Bouhadda: Laboratory of Physical Chemistry of Macromolecular and Biological Interfaces (LCPMIB), Faculty of Sciences, University of Mascara Mustapha Stambouli, BP 305, road of Mamounia Mascara, 29000 Algeria.

Abstract:

Summary: Structure and stability of an eventual inclusion complex formed by Lidocaine and two cyclodextrins (a- and ß-CD) were investigated using molecular mechanics and quantum-chemical methods in the gas phase and in water. The molecular docking and quantum chemical calculations results show that no inclusion complex is formed between a-CD and Lidocaine molecule, while the conformational research allowed observing two minimum-energy structures between this molecule and ß-CD. From a potential energy scan, a partial inclusion of the two ends of Lidocaine by the secondary face of the cavity of ß-CD is observed with a better stability for the complex including the ((-N(C2H5)2) group in it. The minimum energy conformers, obtained by semi empirical method (PM3), have been exposed to fully geometry optimization employing ONIOM2 calculations by combining PM3 method with B3LYP, M06-HF and WB97XD functionals at 6-311G (d,p) basis set. The results show that complexation reactions are thermodynamically favored (DG° ? 0) and the inclusion complexes are energetically stables and well structured (DS° ? 0). According to the analysis of natural bond orbitals, the Van der Waals interactions are the sole driving forces that ensure the stability of the formed complexes.

Page(s): 429-435

DOI: DOI not available

Published: Journal: Journal of Chemical Society of Pakistan, Volume: 43, Issue: 4, Year: 2021

Keywords:

Lidocaine , molecular docking , inclusion complex , Cyclodextrins

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