Abstract
Molecular dynamics simulations on β-cyclodextrin in vacuo, with water and complexed with spironolactone (SP) were performed at a temperature of 300 K over a period of 1 ns. Two different orientations of SP in the cavity were considered. Along with conformational parameters, the formation of hydrogen bonds has been monitored during the whole simulation time. Cyclodextrins have the capability to form hydrogen bonds with the surrounding water molecules or intramolecular ones. The incorporation of ligands into the hydrophobic interior of β-cyclodextrin changes the preference of hydrogen bonds significantly and results in a contribution to the decrease of flexibility. Quantum chemical calculations on SP β-CD inclusion complex were performed to determine the interaction energy and to prove the applicability of various methods. Although all applied methods describe reasonable geometries for the association complex, higher level methods (e.g., B3LYP/6-31G(d,p)) seem to be necessary to determine reliable interaction energies.
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This investigation was supported by the Hochschuljubiläumsstiftung der Stadt Wien (Project P H-778/2005). Technical assistance of Ms. Martina Ziehengraser is gratefully acknowledged.
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Weinzinger, P., Weiss-Greiler, P., Snor, W. et al. Molecular dynamics simulations and quantum chemical calculations on β-cyclodextrin spironolactone complex. J Incl Phenom Macrocycl Chem 57, 29–33 (2007). https://doi.org/10.1007/s10847-006-9165-3
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DOI: https://doi.org/10.1007/s10847-006-9165-3