Exploring 3D structural influences of aliphatic and aromatic chemicals on α-cyclodextrin binding

Journal of Colloid and Interface Science
Lukas LindenSatoshi Endo

Abstract

Binding of solutes to macromolecules is often influenced by steric effects caused by the 3D structures of both binding partners. In this study, the 1:1 α-cyclodextrin (αCD) binding constants (Ka1) for 70 organic chemicals were determined to explore the solute-structural effects on the αCD binding. Ka1 was measured using a three-part partitioning system with either a headspace or a passive sampler serving as the reference phase. The Ka1 values ranged from 1.08 to 4.97 log units. The results show that longer linear aliphatic chemicals form more stable complexes than shorter ones, and that the position of the functional group has a strong influence on Ka1, even stronger than the type of the functional group. Comparison of linear and variously branched aliphatic chemicals indicates that having a sterically unhindered alkyl chain is favorable for binding. These results suggest that only one alkyl chain can enter the binding cavity. Relatively small aromatic chemicals such as 1,3-dichlorobenzene bind to αCD well, while larger ones like tetrachlorobenzene and 3-ring aromatic chemicals show only a weak interaction with αCD, which can be explained by cavity exclusion. The findings of this study help interpret cyclodextrin binding data a...Continue Reading

References

Sep 2, 1999·Journal of Colloid and Interface Science·S TanadaS Kitayama
Aug 5, 1997·Chemical Reviews·Kenneth A. Connors
May 6, 2009·Angewandte Chemie·Hans-Jörg Schneider
Aug 6, 2009·Analytical Chemistry·Adam KloskowskiJacek Namieśnik
Jun 21, 2011·Environment International·Anett GeislerKai-Uwe Goss
Aug 11, 2011·The Journal of Pharmacy and Pharmacology·Thorsteinn Loftsson, Marcus E Brewster
Nov 11, 2011·Chemical Research in Toxicology·Satoshi Endo, Kai-Uwe Goss
Feb 16, 2012·Journal of Pharmaceutical Sciences·Thorsteinn Loftsson, Marcus E Brewster
Sep 10, 2013·Advances in Colloid and Interface Science·Artur J M Valente, Olle Söderman
Oct 4, 2014·Environmental Science & Technology·Satoshi Endo, Kai-Uwe Goss

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Citations

Apr 18, 2018·Environmental Science and Pollution Research International·Mengbi WeiHuihui Liu
Dec 30, 2017·The Journal of Physical Chemistry. B·Julia GebhardtNiels Hansen

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