Type of Document Master's Thesis Author van der Aa, Eveline Maria Author's Email Address URN etd-05192010-125546 Title SYNTHESIS AND CHARACTERIZATION OF NUCLEOBASE-CONTAINING POLYELECTROLYTES FOR GENE DELIVERY Degree Master of Science Department Chemistry Advisory Committee
Advisor Name Title Timothy E. Long Committee Chair Robert E. Moore Committee Member Theresa M. Reineke Committee Member Keywords
- gene delivery
- hydrogen bonding
- electrostatic interactions
Date of Defense 2010-05-05 Availability unrestricted AbstractWide literature precedence exists for polymers containing electrostatic interactions and
polymers containing hydrogen bonding motifs, however the combination of electrostatic
and hydrogen bonding interactions is not widely investigated in current literature.
Polyelectrolytes containing hydrogen bonding groups are expected to exhibit properties
of both classes of supramolecular interactions. A series of adenine- and thyminecontaining
PDMAEMA and tert-butyl acrylate copolymers were synthesized to
investigate the effect of incorporating hydrogen bonding groups into a polyelectrolyte.
Incorporation of the styrenic nucleobases significantly affected the solubility of these
copolymers on aqueous solutions and showed salt-triggerability with higher contents of
these groups. Polyelectrolytes are capable of binding and condensing DNA through
electrostatic interactions with the negatively charged phosphate groups of the DNA
backbone; however a high degree of cytotoxicity is also often observed for these gene
delivery systems. The high level of cytotoxicity is attributed to high degree of cationic
character for the polyplexes formed with these systems according to the proton-sponge
hypothesis. One method of reducing the overall cationic character for these systems is
incorporation of non-electrostatic binding mechanisms such as hydrogen bonding. A
series of nucleobase-containing PDMAEMA copolymers were utilized in order to
investigate the effect of incorporation of these groups on the cell viability, binding
efficiency, and transfection efficiency of PDMAEMA.
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