Steroid-based receptors and transporters for inorganic anions

INOR 404

Anthony P. Davis, Anthony.Davis@bristol.ac.uk, School of Chemistry, University of Bristol, Cantock's Close, Bristol, BS8 1TS, United Kingdom
The steroidal nucleus provides a useful framework for anion receptors, especially for use in non-polar media. The rigid hydrocarbon scaffold confers lipophilicity while allowing precise positioning of binding units. We have focussed on the “cholapod” architecture 1, derived from inexpensive cholic acid 2. These receptors retain solubility in chloroform even when they possess highly polar binding sites. The combination allows the measurement of very high binding constants, up to ~ 1011 M-1 for chloride anion. Selectivities can be tuned by modifying the array of H-bond donors and, especially, by restricting conformational freedom through cyclisation. The cholapods also dissolve in bilayer membranes, and thus have potential as anion transporters. Studies in liposomes have indeed shown transport activity, with high rates at low loadings, and good selectivities. The lecture will expand on these points, and will discuss the latest work on transport mechanisms and structure-activity relationships.