2004
DOI: 10.1021/jo049143k
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Molecular Recognition Thermodynamics and Structural Elucidation of Interactions between Steroids and Bridged Bis(β-cyclodextrin)s

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.… Show more

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Cited by 43 publications
(38 citation statements)
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References 53 publications
(38 reference statements)
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“…However, the metallobridged -CDs 71 and 72 may adopt intramolecular 2:4 stoichiometry upon inclusion complexation with bile salts. Thermodynamically, the binding constants for the inclusion complexation of CA and DCA with bridged -CDs 65-68 are higher than the KS values reported for the inclusion complexation of these bile salts with native or mono-modified -CDs [33,38]. These enhanced binding abilities highlight the inherent advantage of the cooperative "hostlinker-guest" binding mode of bridged -CDs 65-68.…”
Section: Metallobridged -Cds With Oxamidobisbenzoyl Linkersmentioning
confidence: 79%
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“…However, the metallobridged -CDs 71 and 72 may adopt intramolecular 2:4 stoichiometry upon inclusion complexation with bile salts. Thermodynamically, the binding constants for the inclusion complexation of CA and DCA with bridged -CDs 65-68 are higher than the KS values reported for the inclusion complexation of these bile salts with native or mono-modified -CDs [33,38]. These enhanced binding abilities highlight the inherent advantage of the cooperative "hostlinker-guest" binding mode of bridged -CDs 65-68.…”
Section: Metallobridged -Cds With Oxamidobisbenzoyl Linkersmentioning
confidence: 79%
“…All the complexation of aminated bridged -CDs (50, 51, and 53-55) toward DCA and CA give more negative enthalpy changes as compared with that of neutral bridged -CD 52, validating the contribution of the attractive electrostatic interactions between positively charged protonated amino group of -CD tethers and negatively charged carboxylate group of DCA and CA [33]. Accompanied with the more exothermic reaction enthalpies, the inclusion complexation of DCA and CA by aminated bridged -CDs (50, 51, and 53-55) exhibits more unfavorable entropy changes compared to that for neutral bridged bis( -CD) 52, which possibly originates from the conformation fixation of host and guest and the rigid complex formation upon complexation.…”
Section: Binaphthyl- Biquinoline-and Dithio-bridged -Cdsmentioning
confidence: 83%
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