Date of Award

5-2014

Degree Type

Honors College Thesis

Department

Polymers and High Performance Materials

First Advisor

Charles L. McCormick, Ph.D.

Advisor Department

Polymers and High Performance Materials

Abstract

Targeted delivery of cancer therapeutics offers an exciting new opportunity for utilization of controlled polymerization techniques. However, a major obstacle in achieving the desired therapeutic effect is facilitating endosomal release of active agents following endocytosis. Peptides and pH-responsive polymers have been utilized as a means of triggering endosomal release via phase transition-induced membrane disruption. Unfortunately, the fidelity by which the pKa of these polymers/peptides can be varied is limited, such that it reduces their versatility in altering the phase transition point to best match the endosomal pH of a particular cell-type. Herein, we report the controlled polymerization of library of methacryloylsulfonamide derivatives via reversible addition-fragmentation chain transfer (RAFT) polymerization that exhibit a range of physiologically relevant pKa’s. Polymerization control was observed by noting the low polydispersity indices of the polymers along with the linear progression of Mn with time during the polymerizations for methacryloylsulfacetamide, methacryloylsulfabenzamide, and methacryloylsulfamethazine. RAFT chain transfer agent degradation and a loss of polymerization control were observed for methacryloylsulfamerazine, methacryloylsulfadiazine, methacryloylsulfadimethoxine, methacryloylsulfadoxin, and methacryloylsulfamethizole.

Comments

Honors College Award: Top Thesis

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