Next Article in Journal
Total Syntheses of Telisatin A, Telisatin B and Lettowianthine
Next Article in Special Issue
Laser Photolysis and Thermolysis of Organic Selenides and Tellurides for Chemical Gas-phase Deposition of Nanostructured Materials
Previous Article in Journal
Synthesis of 1α,25-Dihydroxyvitamin D Analogues Featuring a S2-symmetric CD-ring Core
Previous Article in Special Issue
The X-Ray Crystal Structures of Primary Aryl Substituted Selenoamides
Article Menu

Export Article

Open AccessArticle
Molecules 2009, 14(3), 904-916; https://doi.org/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)
Full-Text   |   PDF [283 KB, uploaded 18 June 2014]   |  

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. View Full-Text
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
Figures

Figure 1

This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).
SciFeed

Share & Cite This Article

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.

Show more citation formats Show less citations formats

Related Articles

Article Metrics

Article Access Statistics

1

Comments

[Return to top]
Molecules EISSN 1420-3049 Published by MDPI AG, Basel, Switzerland RSS E-Mail Table of Contents Alert
Back to Top