Complexation and sensing behavior of dansyl-appended cyclodextrins and cyclodextrin dimers with bile salts

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Jong, Menno R. de and Berthault, Patrick and Hoek, Arie van and Visser, Antonie J.W.G. and Huskens, Jurriaan and Reinhoudt, David N. (2002) Complexation and sensing behavior of dansyl-appended cyclodextrins and cyclodextrin dimers with bile salts. Supramolecular Chemistry, 14 (2-3). pp. 143-151. ISSN 1061-0278

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Abstract:The dansyl-modified cyclodextrin derivatives 2 and 3 form complexes with the steroidal bile salts. The selectivity of the monomeric derivative 3 is similar to that of native β-cyclodextrin. All binding constants with 3 are lowered compared to β-cyclodextrin because of the competition for the cavity between the steroids and the dansyl moiety. Cholate ( 4a ) and deoxycholate ( 4b ) form weak complexes, the other bile salts ( 4c - e ) are complexed far more strongly. The difference is attributed to the absence of a 12-hydroxy group in the latter steroids. Data for dimer 2 reveal strongly enhanced binding of 4a and 4b and only slightly stronger complexes with the other steroids. Due to the low binding affinity of 3 for 4a and 4b , this receptor could not be used for their detection by fluorescence spectroscopy. Steroids 4c - e showed a decrease in fluorescence intensity. The detection of all steroids 4a - e was possible using 2 . The fluorescence intensity of the dimer increased or decreased, depending on which steroid was added.
Item Type:Article
Additional information:683
Copyright:© 2002 Taylor & Francis
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Science and Technology (TNW)
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Link to this item:http://purl.utwente.nl/publications/37946
Official URL:http://dx.doi.org/10.1080/10610270290026040
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Metis ID: 206205