Title page for ETD etd-05192010-125546

Type of Document Master's Thesis
Author van der Aa, Eveline Maria
Author's Email Address
URN etd-05192010-125546
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
  • gene delivery
  • water-soluble
  • hydrogen bonding
  • electrostatic interactions
  • nucleobase
  • polyelectrolyte
Date of Defense 2010-05-05
Availability unrestricted
Wide 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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