Date of Graduation

Summer 2014

Degree

Master of Science in Chemistry

Department

Chemistry

Committee Chair

Reza Herati

Keywords

dendrons, PEGylation, linear dendritic copolymers, PEG, critical micelle concentration, RNA, nuclear magnetic resonance, fluorescence spectroscopy

Subject Categories

Chemistry

Abstract

The synthesis and characterization of novel copolymers consisting of a linear block of methoxypoly(ethylene glycol) (mPEG) and a dendrimeric block with potential biomedical applications are described. Based on the structure of each polymer, they can either function as encapsulating agents in drug delivery or complexing agents in gene therapy. The first polymer was constructed with allyl glycidal ether, L-cysteine, and ethylene diamine. Another dendron was built from allyl chloride and 3-mercapto-1,2-propanediol, resulting in a polymer with alkene functionalities at the periphery, later functionalized with cysteamine. A final dendron was assembled from methyl gallate, allyl bromide, and cysteamine to produce a poly(ether-amide-sulfide) dendron also containing terminal alkenes. The synthetic work was confirmed using a combination of NMR, MALDI-TOF, IR, and elemental analysis. Critical micelle concentration (CMC) was used to evaluate the encapsulation properties of the copolymers resulting in values as low as 32 mg/mL. DLS was used to measure the average size of the polymers in solution. Gel shift provided an evaluation of RNA binding at various N/P ratios and indicated an N/P ratio of 5 was adequate for one polymer. Circular dichroism was used to measure the chiral nature of RNA and indicated the secondary structure remained intact at high N/P ratios for all polymers.

Copyright

© Wesley Aaron Dowler

Campus Only

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