Nanomolar Binding of Steroids to Cucurbit[n]urils: Selectivity and Applications

Alexandra I. Lazar, Frank Biedermann, Kamila R. Mustafina, Khaleel I. Assaf, Andreas Hennig & Werner M. Nau
Cucurbit[n]urils (CBn, n = 7, 8) serve as artificial receptors for steroids (21 tested), including the hormones testosterone and estradiol as well as steroidal drugs. Fluorescence displacement titrations and isothermal titration calorimetry (ITC) provided up to nanomolar binding affinities in aqueous solution for these hydrophobic target molecules, exceeding the values of known synthetic receptors. Remarkable binding selectivities, even for homologous steroid pairs, were investigated in detail by NMR, X-ray crystal diffraction, ITC, and quantum chemical...
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