SYNTHESIS OF POLYMERIC MATERIALS FOR DRUG DELIVERY AND INDUSTRIAL APPLICATIONS Public Deposited

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  • March 19, 2019
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  • Kramer, Stephanie
    • Affiliation: College of Arts and Sciences, Department of Chemistry
Abstract
  • This dissertation reports the synthesis of polymeric materials for industrial and medicinal applications. Depending on their chemical structure, polymers have different properties and applications. Polyolefins, used in packaging and films, are one of the most highly produced polymeric materials in industry, whereas only a handful of polymeric materials are in the market for drug delivery. The first part of this thesis presents a method to deoxygenate linear polyols producing branched polyolefins. In Chapter 2, linear polyols, such as poly(vinyl alcohol) (PVA), are hydrosilylatively deoxygenated using catalytic amounts of B(C6F5)3 and a reducing hydrosilane. Following reduction, a highly branched, predominantly saturated structure is obtained. Depending on the alcohol-protecting group and the hydrosilane used, the branch numbers can exceed 200 branches per 1000 carbons. The branching microstructure is also dependent on the protecting group and silane. For instance, the deoxygenation of TMS-protected PVA with diethylsilane produced a polymer with different branch types when compared to the polymer that results from the deoxygenation of TES-protected PVA. The B(C6F5)3-catalyzed deoxygenation was applied to a triblock system wherein the central block was a 1,5-polyol structure to produce otherwise inaccessible triblock polymers with an amorphously branched interior block (Chapter 3). The starting polymer was obtained by sequential hydroboration/oxidation of poly(styrene-b-butadiene-b-styrene) (SBS), which converts the polybutadiene block into a 1,5-polyol block. The hydroxylated SBS polymer was then completely deoxygenated to yield a novel triblock polymer with a highly branched interior, with the branching being predominantly butyl or longer chains as established by 13C-NMR spectroscopy. The structure-property relationships of this new triblock system still need to be investigated and compared to SBS. The second section of this thesis discusses an alternative drug delivery approach utilizing nanoscale coordination polymers (NCPs). Chapter 4 presents the synthesis of Ca(II) and Mn(II)-based NCP formulations containing a cisplatin prodrug. Coating the NCPs with a lipid bilayer stabilized both of these formulations. Drug release profiles demonstrated sustained cisplatin release from the NCPs. Drug loadings of 20% for Ca-based NCP and 25% for Mn-NCP were determined. Due to the exceptionally high drug loadings and nanoscale size, these cisplatin NCPs are promising drug delivery candidates.
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  • In Copyright
Advisor
  • Gagne, Michel
  • Brookhart, Maurice
  • Templeton, Joseph
  • Waters, Marcey
  • Schauer, Cynthia
Degree
  • Doctor of Philosophy
Degree granting institution
  • University of North Carolina at Chapel Hill Graduate School
Graduation year
  • 2015
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Place of publication
  • Chapel Hill, NC
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