Building Block Approach to the Synthesis of a Cucurbituril Derivative Bearing Sulfonate Functional Groups
Brownlow, Lorene Elizabeth
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Low aqueous solubility prevents 40-70% of new pharmaceutical agents from reaching their full potential. The use of molecular containers as solubilizing agents is one solution currently under development. Chapter 1 introduces molecular containers under investigation as drug delivery excipients. Synthetic approaches, properties and important derivatives of cyclodextrins and cucurbiturils are briefly reviewed. Chapter 2 describes the tested hypothesis that the addition of sulfonate functional groups to CB will enhance the aqueous solubility of the CB derivative as compared to CB itself. The building-block approach to obtain a difunctionalized CB derivative by the condensation of glycoluril hexamer (21) and ((¬CH2)4SO3Na)2 glycoluril bis(cyclic ether) (30) is described. The new CB derivative had surprisingly low aqueous solubility (20.2 mM), but very similar molecular recognition properties to those of CB. The CB derivative was investigated for its use as an excipient for drug solubilization and found to have no enhancement compared to CB.