Date of Award

Winter 2022

Project Type

Thesis

Program or Major

Chemistry

Degree Name

Master of Science

First Advisor

Roy P Planalp

Second Advisor

Erik B Berda

Third Advisor

Nathan J Oldenhuis

Abstract

The design and synthesis of novel zirconium and scandium complexes, ZrIV(p-NO2-sal-DFO) and ScIII(p-NO2-Bn-NOTPi) respectively, and their potential for use in immuno-positron emission tomography (immuno-PET) are discussed. The design for a linear octadentate ligand for Zr was hypothesized and derived from deferoxamine B (DFO), a well-known hexadentate siderophore for Fe complexation. A p-NO2-salicyclic acid derivative was prepared to provide a bifunctional handle for antibody conjugation. Deferoxamine B chelates with hydroxamate moieties, which have proven useful for chelation of hard acids. While difficulties in purification led to no complexation studies being performed, this chelator was confirmed via 1H NMR , 13C NMR, and time-of-flight electron ionization mass spectrometry (TOF ESI-MS). A cyclic hexadentate ligand for Sc derived from 1,4,7-triazacyclononane (TACN) was chosen because it can be readily derived. The design and viability for this ligand has been worked on computationally using a model cyclic, octadentate chelator derived from 1,4,7,10-tetraazacyclododecane (cyclen). This work led to design and undertaking of a multistep synthesis to the novel complex, ScIII(p-NO2-Bn-NOTPi), which incorporates phosphinate pendant arms and a para-nitrobenzyl group for bioconjugation. While the synthesis of p-NO2-Bn-NOTPi has not been completed, intermediates have been analyzed via 1H NMR, 13C NMR.

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