Cyclodextrin dimers as receptor molecules for steroid sensors


Jong, Menno R. de 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.
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Copyright:© 2000 Wiley
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