Date of Award

Summer 2022

Document Type

Open Access Thesis


Chemistry and Biochemistry

First Advisor

Linda Shimizu


Assembled pyridyl bis-urea macrocycles have been utilized as 1D supramolecular synthons to construct hierarchical assemblies. These macrocycles have both urea and pyridyl functional groups and can form non-covalent interactions with hydrogen or halogen bond donors through symmetric, ditopic acceptor motifs. Bis-urea macrocycles offer interesting capabilities as synthons to organize donors into well-defined crystal structures. In part, this is due to the urea motifs’ propensity to assemble through hydrogen bonding. New, asymmetric pyridyl macrocycles were synthesized, crystallized, and experimentally probed to determine how symmetry affects their assembly and utility as supramolecular synthons.

The Uphadhyay group identified small molecules, including NSC11150, from the National Cancer Institute’s (NCI) library to bind lymphocyte antigen 6K (LY6K) protein by the. The LY6K protein has been implicated in the progression of several types of cancer. Docking simulations were performed on NSC11150, as well as several derivatives, to determine the binding mechanism to LY6K. NSC11150 was synthesized on a large scale and purified. Additionally, several derivatives of NSC11150 were synthesized in order to attach functional tags, such as D-biotin and BODIPY, for streptavidin binding assays or fluorescence microscopy, respectively.

Available for download on Thursday, October 05, 2023

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