Experimental Characterization of the Association of Nine Novel Cyclodextrin Derivatives with Two Guest Compounds

17 July 2020, Version 1
This content is a preprint and has not undergone peer review at the time of posting.

Abstract

We investigate the binding of native β-cyclodextrin (β-CD) and eight novel β-CD derivatives with two different guest compounds, using isothermal calorimetry (ITC) and 2D NOESY NMR. In all cases, the stoichiometry is 1:1 and binding is exothermic. Overall, modifications at the 3’ position of β-CD, which is at the secondary face, weaken binding by several kJ/mol relative to native β-CD, while modifications at the 6’ position (primary face) maintain or somewhat reduce the binding affinity. The variations in binding enthalpy are larger than the variations in binding free energy, so entropy-enthalpy compensation is observed. Characterization of the bound conformations with NOESY NMR shows that the polar groups of the guests may be situated at either face, depending on the host molecule, and, in some cases, both orientations are populated. The present results were used in the SAMPL7 blinded prediction challenge whose results are detailed in the same special issue of JCAMD.

Keywords

cyclodextrin
host-guest
SAMPL
ITC
NMR experiments

Supplementary materials

Title
Description
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Title
SAMPL7 Kellett Gilson NMR-trans-methyl-cyclohexanol
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SAMPL7 Kellett Gilson ITC complexes
Description
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SAMPL7 Kellett Gilson Hosts SMILES
Description
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Title
SAMPL7 Kellett Gilson NMR-R-Rimantidine
Description
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SAMPL7 Kellett Gilson enthalpograms
Description
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