PMID: 11322555Apr 27, 2001Paper

Synthesis and molecular recognition of novel oligo(ethylenediamino) bridged bis(beta-cyclodextrin)s and their copper(II) complexes: enhanced molecular binding ability and selectivity by multiple recognition

Chemistry : a European Journal
Y LiuB Li

Abstract

Four bridged bis(beta-cyclodextrin)s tethered by different lengths of oligo(ethylenediamine)s have been synthesized and their inclusion complexation behavior with selected substrates elucidated by circular dichroism spectroscopy and fluorescence decay. In order to study their binding ability quantitatively, inclusion complexation stability constants with four dye guests, that is, brilliant green (BG), methyl orange (MO), ammonium 8-anilino-1-naphthalenesulfonic acid (ANS), and sodium 6-(p-toluidino)-2-naphthalenesulfonate (TNS), have been determined in aqueous solution at 25 degrees C with spectrophotometric, spectropolarimetric, or spectrofluorometric titrations. The results obtained indicate that the two tethered cyclodextrin units might cooperatively bind to a guest, and the molecular binding ability toward model substrates, especially linear guests such as TNS and MO, could be extended. The tether length plays a crucial role in the molecular recognition, the binding constants for ANS and TNS decrease linearly with an increase in the tether length of dimeric cyclodextrin. The Gibbs free energy changes (-deltaGo) for the unit increment per ethylene are 0.99 kJ mol(-1) for ANS and 0.44 kJmol(-1) for TNS, respectively. On the o...Continue Reading

References

Aug 1, 1992·Proceedings of the National Academy of Sciences of the United States of America·R Breslow, S Halfon
Feb 19, 2002·Chemical Reviews·József Szejtli
Feb 19, 2002·Chemical Reviews·Ronald Breslow, Steven D. Dong

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Citations

Jan 11, 2003·Biotechnology & Genetic Engineering Reviews·T Ashton CroppKevin A Reynolds
Jan 4, 2003·Chemical Communications : Chem Comm·Alart MulderDavid N Reinhoudt
Jun 10, 2004·Organic & Biomolecular Chemistry·Alart MulderDavid N Reinhoudt
Sep 9, 2006·Journal of Biomedical Materials Research. Part a·Hui GaoJian-Biao Ma
Jul 7, 2009·Chemistry, an Asian Journal·Si-Ping TangLiang-Nian Ji
Sep 27, 2005·Bioorganic & Medicinal Chemistry·Hui GaoJian-Biao Ma
Mar 7, 2014·Langmuir : the ACS Journal of Surfaces and Colloids·O Fernando SilvaMariana A Fernández
Mar 21, 2002·Journal of the American Chemical Society·Victor V BorovkovYoshihisa Inoue
Sep 14, 2006·Chemical Reviews·Michael Kruppa, Burkhard König

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