Molecular recognition thermodynamics and structural elucidation of interactions between steroids and bridged bis(beta-cyclodextrin)s

The Journal of Organic Chemistry
Yu LiuXu-Dong Guan

Abstract

A series of bridged bis(beta-cyclodextrin(CD))s (2-7) were synthesized, i.e., bridged bis(beta-CD)s 2 and 3 bearing binaphthyl or biquinoline tethers and bridged bis(beta-CD)s 4-7 possessing dithiobis(benzoyl) tether, and their complex stability constants (KS), enthalpy (DeltaH degrees), and entropy changes (DeltaS degrees) for the 1:2 inclusion complexation with representative steroids, deoxycholate, cholate, glycocholate, and taurocholate, have been determined in an aqueous phosphate buffer solution of pH 7.20 at 298.15 K by means of titration microcalorimetry. The original conformations of bridged bis(beta-cyclodextrin)s were investigated by circular dichroism and 1H ROESY spectroscopy. Structures of the inclusion complexes between steroids and bridged bis(beta-CD)s in solution were elucidated by 2D NMR experiments, indicating that anionic groups of two steroid molecules penetrate, respectively, into the two hydrophobic CD cavities in one 6,6'-bridged bis(beta-CD) molecule from the secondary rim to give a 1:2 binding mode upon inclusion complexation. The results obtained from titration microcalorimetry and 2D NMR experiments jointly demonstrate that bridged bis(beta-CD)s 2, 3 and 5-7 tethered by protonated amino group posses...Continue Reading

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Citations

Jun 28, 2011·Langmuir : the ACS Journal of Surfaces and Colloids·Juan M Casas-SolvasAntonio Vargas-Berenguel
May 2, 2013·Advanced Drug Delivery Reviews·Angel Concheiro, Carmen Alvarez-Lorenzo
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Jun 21, 2006·Bioorganic & Medicinal Chemistry·Yu LiuGuo-Song Chen
Mar 19, 2014·Accounts of Chemical Research·Ying-Wei YangNan Song

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