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Molecules 2009, 14(3), 904-916; doi:10.3390/molecules14030904

Association Mechanism of S-Dinitrophenyl Glutathione with Two Glutathione Peroxidase Mimics: 2, 2¢-Ditelluro- and 2, 2¢-Diseleno-bridged b-cyclodextrins

State Key Laboratory for Supramolecular Structure and Materials, Jilin University, Changchun, 130012, P. R. China
* Author to whom correspondence should be addressed.
Received: 1 November 2008 / Revised: 17 December 2008 / Accepted: 23 December 2008 / Published: 25 February 2009
(This article belongs to the Special Issue Selenium and Tellurium Chemistry)
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Complex formation of the glutathione peroxidase mimics 2,2¢-ditelluro-bridged b-cyclodextrin (1) and 2,2¢-diseleno-bridged b-cyclodextrin (2), with S-substituted dinitrophenyl glutathione (3) were determined by ultraviolet-visible (UV-Vis) absorption spectroscopy in phosphate buffer (pH 7.4) and 1H-NMR spectroscopy. Molecular mechanics (MM2) modeling calculations were used to deduce a three-dimensional model for each complex. The dinitrophenyl (DNP) group of 3 appears to penetrate the cavity of b-cyclodextrin (b-CD) or 1, but it is located between the two secondary rims of 2. The complexes’ stability constants (Ks) from 19 to 37 °C, Gibbs free energy changes (DG° ), DH° and TDS° for 1:1 complexes of b-CD, 1 and 2 with ligand 3 as obtained from UV-Vis spectra were compared. The binding of 3 by the three cyclodextrin hosts generally decreased in the order of 1>2>b-CD. The binding ability of 3 by b-CD, 1 and 2 was discussed with regard to the size/shape-fit concept, the induced-fit interaction, and the cooperative interaction of the dual hydrophobic cavities. The binding ability of 1>2indicated that the length of linkage between two cyclodextrin units plays a crucial role in the interaction with 3.
Keywords: 2;2’-Ditelluro-bridged ß-cyclodextrins; 2;2’-Diseleno-bridged ß-cyclodextrins; Association mechanism; MM2 modeling; NMR spectroscopy 2; 2’-Ditelluro-bridged ß-cyclodextrins; 2; 2’-Diseleno-bridged ß-cyclodextrins; Association mechanism; MM2 modeling; NMR spectroscopy
This is an open access article distributed under the Creative Commons Attribution License (CC BY) which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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Hao, Y.-Q.; Liu, X.-C.; Liu, J.-Q.; Wu, Y.-Q. Association Mechanism of S-Dinitrophenyl Glutathione with Two Glutathione Peroxidase Mimics: 2, 2¢-Ditelluro- and 2, 2¢-Diseleno-bridged b-cyclodextrins. Molecules 2009, 14, 904-916.

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