Cyclodextrin dimers as receptor molecules for steroid sensors

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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.
Original languageUndefined
Pages (from-to)4034-4040
JournalChemistry: a European journal
Issue number21
Publication statusPublished - 2000


  • METIS-106283
  • Calorimetry
  • IR-11678
  • Steroids
  • Sensors
  • Fluorescence spectroscopy
  • Cyclodextrins

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