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Bulletin of the Korean Chemical Society (BKCS)

ISSN 0253-2964(Print)
ISSN 1229-5949(Online)
Volume 29, Number 5
BKCSDE 29(5)
May 20, 2008 

Synthesis of a Novel Anthraquinone Diamino-Bridged Bis(β-cyclodextrin) and Its Cooperative Binding toward Guest Molecules
Yan Zhao*, Zi Ming Yang, Shao Ming Chi, Juan Gu, Yong Cun Yang, Rong Huang, Bang Jin Wang, Hong You Zhu
Bridged bis(β-cyclodextrin), Guest molecule, Molecular recognition, Cooperative binding mode, Inclusion complexation
A novel anthraquinone diamino-bridged bis(β-cyclodextrin) 2 was synthesized. The inclusion complexation behaviors of the native β-cyclodextrin 1 and the novel bis(β-cyclodextrin) 2 with guests, such as acridine red (AR), neutral red (NR), ammonium 8-anilino-1-naphthalenesulfonate (ANS), sodium 2-(p-toluidinyl) naphthalenesulfonate (TNS) and rhodamine B (RhB) were investigation by fluorescence, circular dichroism and 2D NMR spectroscopy. The spectral titrations were performed in phosphate buffer (pH 7.20) at 25 oC to give the complex stability constants (Ks) and Gibbs free energy changes (?ΔG0) for the stoichiometric 1:1 inclusion complexation of host 1 and 2 with guests. The results indicated that the novel bis(β-cyclodextrin) 2 greatly enhanced the original binding affinity of the native β-cyclodextrin 1. Typically, bis(β-cyclodextrin) 2 showed the highest binding constant towards ANS up to 34.8 times higher than that of 1. The 2D NMR spectra of bis(β-cyclodextrin) 2 with RhB and TNS were performed to confirm the binding mode. The increased binding affinity and molecular selectivity of guests by bis(β-cyclodextrin) 2 were discussed from the viewpoint of the size/shape-fit concept and multipoint recognition mechanism.
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