Cyclodextrin dimers as receptor molecules for steroid sensors

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Jong de, Menno R. and Engbersen, Johan F.J. and Huskens, Jurriaan and Reinhoudt, David N. (2000) Cyclodextrin dimers as receptor molecules for steroid sensors. Chemistry: a European journal, 6 (21). pp. 4034-4040. ISSN 0947-6539

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Abstract:The dansyl-modified dimer 9 complexes strongly with the steroidal bile salts. Relative to native -cyclodextrin, the binding of cholate (1 a) and deoxycholate (1 b) salts is especially enhanced. These steroids bind exclusively in a 1:1 fashion. For other bile salts (1 c-1 e) both 1:1 and 1:2 complexes were observed with stabilities similar to those of native -cyclodextrin. This indicates that only one cavity is used, with a small contribution from the second. The difference is attributed to the absence of a 12-hydroxy group in the second group of steroids. Comparison with a dimer that lacks the dansyl moiety (6) shows that this group especially hinders the cooperative binding of 1 a and 1 b. The smaller interference in the binding of the other steroids indicates that self-inclusion of the dansyl moiety hardly occurs. This weak self-inclusion is supported by fluorescence studies. The dansyl fluorescence of dimer 9 is less blue-shifted than that of other known dansyl-appended cyclodextrin derivatives; this is indicative of a more polar micro-environment. Addition of guests causes a change in fluorescence intensity.
Item Type:Article
Copyright:© 2000 Wiley
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Science and Technology (TNW)
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Link to this item:http://purl.utwente.nl/publications/11678
Official URL:http://dx.doi.org/10.1002/1521-3765(20001103)6:21<4034::AID-CHEM4034>3.0.CO;2-3
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