Date of Award
Spring 2026
Document Type
Open Access Dissertation
Department
Chemistry and Biochemistry
First Advisor
John J. Lavigne
Abstract
Breast cancer is one of the most prolific diseases in the world. It is well understood that early and accurate detection of cancer leads to improved prognosis. Herein, we describe the need for a method of cancer detection which utilizes an array of synthetic lectins to probe for cancer-associated glycans. We demonstrate the utility of an internal standard fluorescent bead to improve the precision of our measurements. Next, we describe the process of adaptation from analysis via fluorescent microscopy to flow cytometry. Finally, a thorough examination was conducted using an array of synthetic lectins to detect cancer in cell lines, mouse models, and human blood, including the discovery of new synthetic lectin sequences which show selective binding towards triple-negative breast cancer blood samples.
Phenylboronic esters are planar, conjugated molecules that display Lewis acidity at the boron center. This Lewis acidity is tunable by placing substituents on either side of the PBE. PBEs are commonly applied in sensors, separatory materials, batteries, and are effective catalysts in the fields of polymer synthesis and carbon capture. As the effectiveness of PBEs in these applications is dependent on the Lewis acidity of the boron center, a greater understanding of how substituents modulate the electronics of the ester and acidity of this center can inform many fields of material science. Using the Guttman-Beckett method, we have assessed the acidity of 27 PBEs and generated a model of acid tunability. Herein, we develop this model through the comparison of experimental acidity to substituent effects using Hammett plots, Isothermal Titration Calorimetry, Fluoride Ion Affinity, and an analysis of field, resonance, and steric effects. Furthermore, we explore the opto-electronic properties of these compounds.
Rights
© 2026, James Boyt
Recommended Citation
Boyt, J.(2026). Gearing Synthetic Lectin Arrays Towards Clinical Applications and the Electronic Analysis of Substituted Catechol Phenylboronic Esters. (Doctoral dissertation). Retrieved from https://scholarcommons.sc.edu/etd/8931