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

Jong de, Menno R. and Berthault, Patrick and Hoek van, Arie 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
Copyright:	© 2002 Taylor & Francis
Faculty:	Science and Technology (TNW)
Research Group:	Molecular Nanofabrication (MNF)
Link to this item:	http://purl.utwente.nl/publications/37946
Official URL:	http://dx.doi.org/10.1080/10610270290026040
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