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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
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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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Abstract

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 3.0).

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MDPI and ACS Style

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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