Date of Award

Spring 5-1-2018

Degree Type

Dissertation

Degree Name

Doctor of Philosophy (PhD)

Department

Polymers and High Performance Materials

Committee Chair

Derek L. Patton

Committee Chair Department

Polymers and High Performance Materials

Committee Member 2

Robson F. Storey

Committee Member 2 Department

Polymers and High Performance Materials

Committee Member 3

Sarah E. Morgan

Committee Member 3 Department

Polymers and High Performance Materials

Committee Member 4

Sergei I. Nazarenko

Committee Member 4 Department

Polymers and High Performance Materials

Committee Member 5

Dmitri V. Mavrodi

Committee Member 5 Department

Biological Sciences

Abstract

With the increasing prevalence of antimicrobial resistance, the escalation of opportunistic/pathogenic infections is a looming global crisis. To avoid the pitfalls of conventional antibiotics, this dissertation focuses on developing macromolecular solutions to develop novel antimicrobial materials based on essential oils (thymol, carvacrol, and aldehydes). It is well established that essential oil derivatives exhibit high potency towards a wide range of pathogenic microbes. The rapid photopolymerization kinetics, limited by-products, and homogeneous network formation afforded by thiol-ene photopolymerization are utilized to either encapsulate essential oil derivatives or convert them into monomers which can subsequently be incorporated into new antimicrobial materials with new structure-function relationships.

The first chapter of this dissertation outlines the need for alternatives to traditional antibiotics and the motivation for developing essential oil-based therapies. In the second chapter, the utilization of thiol-ene chemistry in the design of drug delivery and encapsulation are reviewed. The third chapter of this dissertation focus on the development of one-pot/solvent-free thiol-ene miniemulsion technique to synthesize thymol/carvacrol-loaded nanoparticles with high loading capacity (≈50% w/w), excellent encapsulation efficiencies (>95%), and potent antimicrobial activity. In the following chapters, new pro-antimicrobial networks via degradable acetals (PANDAs) were fabricated as a new paradigm for the sequestration and triggered release of volatile, antimicrobial aldehydes. PANDAs are crosslinked networks in which every crosslink junction contains a degradable acetal linkage. When PANDAs are exposed to neutral to acidic conditions (pH < 8), the PANDAs undergo surface erosion and exhibit sustained aldehyde release from days to months. Chapter IV details the fabrication of PANDAs with a synthetic aldehyde, chlorobenzaldehyde, while chapter V emphases on the use of the plant-derived, p-anisaldehyde (an extract from star anise). In both chapters, the synthesis of PANDAs, thermal/mechanical properties, aldehyde release kinetics, as well as antimicrobial efficacy and cytotoxicity were elucidated.

ORCID ID

0000-0001-9831-358X

Download

Share

COinS