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Liu Y, Kang S Z, Li L. Supramol. Chem., 2002,14:329~337

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supramolecular Chemistry

2005 Impact Factor: 1.715 (Thomson ISI Journal Citation Reports 2006)
Published By: Taylor & Francis
Volume Number: 19
Frequency: 8 issues per year
Print ISSN: 1061-0278
Online ISSN: 1029-0478
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Synthesis of Novel b.beta-cyclodextrin Derivatives Bearing a 1-naphthyloxamino-oligo(ethyleneamino) Moiety and their Inclusion Complexation with some Fluorescent Dyes
Authors: Yu Liu a;  Shi-Zhao Kang a; Li Li a
Affiliation:           a Department of Chemistry, Nankai University, Tianjin 300071, People's Republic of China.
DOI: 10.1080/10610270290029371
Publication Frequency: 8 issues per year
Published in: journal Supramolecular Chemistry, Volume 14, Issue 4 2002 , pages 329 - 337
Subject: Organic Chemistry;
Number of References: 31
Formats available: PDF (English)

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Abstract
Two novel b.beta-cyclodextrin derivatives bearing a (1-naphthyloxamino)-ethyleneamino ( 4 ) or (1-naphthyloxamino)-diethylenediamino ( 5 ) moiety have been synthesized by a convenient method in 34% and 30% yields, respectively. Examinations of the circular dichroism (CD) spectra and fluorescence lifetime revealed that the naphthyloxamino-oligo (ethyleneamino) moiety tethered to b.beta-cyclodextrin is not deeply embedded in the hydrophobic cavity of b.beta-cyclodextrin itself even in the absence of a guest. The inclusion complexation behavior of 4 and 5 with some fluorescent dyes, i.e. ammonium 8-anilino-1-naphthalenesulfonate (ANS), sodium 2-( p -toluidinyl)naphthalenesulfonate (TNS), Acridine Red (AR) and Rhodamine B (RhB), was assessed in aqueous phosphate buffer solution (pH 7.2) at 25¡ãC by fluorometric titration to give the complex stability constants ( K S ) and Gibbs free energy changes ( b.DeltaG 0 ) for the stoichiometric 1:1 inclusion complexation with the fluorescent dyes. The results obtained indicate that the naphthyloxamino-oligo(ethyleneamino) moiety attached to the b.beta-cyclodextrin ( 1 ) can alter not only the original molecular binding-ability of the parent b.beta-cyclodextrin, but also the molecular selectivity through the micro-environment changes of cyclodextrin cavity, which are discussed from the viewpoints of the size/shape-fit concept and the stereochemical complementary relationship between host cyclodextrin and model substrate.
Keywords: Modified Cyclodextrins; Dyes; Inclusion Complexation; Molecular Recognition
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