Thermodynamics of Molecular Recognition of Bile Salts by 3,6- (Oligoethylenediamino-Bridged) β-Cyclodextrin Dimers

Author(s): Yu Liu, Shu Kang, Yong Chen, Rui Cao, Jun Shi

Journal Name: Combinatorial Chemistry & High Throughput Screening
Accelerated Technologies for Biotechnology, Bioassays, Medicinal Chemistry and Natural Products Research

Volume 10 , Issue 5 , 2007

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The molecular recognition behaviors of some representative bile salts by three 3,6-bridged β-cyclodextrin dimers with oligo(ethylenediamino) linkers in different lengths, i.e. 3,6-(ethylenediamino-bridged) β-cyclodextrin dimer (1), 3,6-(diethylenetriamino-bridged) β-cyclodextrin dimer (2), and 3,6-(triethylenetetraamino-bridged) β-cyclodextrin dimer (3), were investigated in aqueous phosphate buffer solution (pH 7.20) at 25°C by means of 2D NMR spectroscopy and isothermal titration microcalorimetry. Owing to the cooperative host-linker-guest binding mode between host and guest, these 3,6-bridged β-cyclodextrin dimers showed significantly enhanced binding abilities and molecular selectivities as compared with native β-cyclodextrin through the simultaneous contributions of hydrophobic, hydrogen bond, and electrostatic interactions. Thermodynamically, the inclusion complexations of these β-cyclodextrin dimers with bile salts were mainly driven by large enthalpic gain, accompanied by slight to moderate entropic loss. An enthalpy-entropy compensation analysis demonstrated that these β-cyclodextrin dimers experienced large conformational changes and extensive desolvation effect upon inclusion complexation with guest molecules.

Keywords: Cyclodextrin, bile salt, calorimetry, inclusion phenomena, synthetic receptors, host-guest modeling systems, molecular recognition, thermodynamics

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Article Details

Year: 2007
Page: [350 - 357]
Pages: 8
DOI: 10.2174/138620707781662844
Price: $65

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