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Building Block Approach to the Synthesis of a Cucurbit[7]uril Derivative Bearing Sulfonate Functional Groups

dc.contributor.advisorIsaacs, Lyleen_US
dc.contributor.authorBrownlow, Lorene Elizabethen_US
dc.description.abstractLow 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[7] will enhance the aqueous solubility of the CB[7] derivative as compared to CB[7] itself. The building-block approach to obtain a difunctionalized CB[7] derivative by the condensation of glycoluril hexamer (21) and ((¬CH2)4SO3Na)2 glycoluril bis(cyclic ether) (30) is described. The new CB[7] derivative had surprisingly low aqueous solubility (20.2 mM), but very similar molecular recognition properties to those of CB[7]. The CB[7] derivative was investigated for its use as an excipient for drug solubilization and found to have no enhancement compared to CB[7].en_US
dc.titleBuilding Block Approach to the Synthesis of a Cucurbit[7]uril Derivative Bearing Sulfonate Functional Groupsen_US
dc.contributor.publisherDigital Repository at the University of Marylanden_US
dc.contributor.publisherUniversity of Maryland (College Park, Md.)en_US
dc.subject.pquncontrolleddrug deliveryen_US

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