Date of Award

2011-01-01

Degree Name

Master of Science

Department

Chemistry

Advisor(s)

Juan C. Noveron

Abstract

The synthesis of materials via molecular self-assembly is a powerful bottom-up approach for fabricating matter in the nano- and micro-meter scales. This methodology involves the spontaneous and reversible organization of small molecules that interact with one another to create larger structures driven by non-covalent interactions such as hydrogen bonding, hydrophobic forces and metal-ligand coordination interactions. In this thesis, the design, synthesis and characterization of a new set of molecules that spontaneously self-organize in water to form three-dimensional nanoscale toroidal structures was investigated. These supramolecular structures were designed with an intrinsic affinity to bind and condense DNA strands with the intent to deliver exogenous oligonucleotides into mammalian cells.

The new molecules presented are based on soluble coordination polymers of Cu(II) derived from 1,4,7,10-tetraazacyclododecane, 1,4,7-triazacyclononane, and 4,4'-trimethylenedipyridyl connecting units. They formed Cu-polymers [1,3-Di(4-pyridyl)propane) bis(1,4,7-triazacyclononane) copper(II) triflate] (7), and [(Tetraethyleglycol-di-isonicotinic acid)decanoic acid(1,4,7,10- tetraazacyclododecane) copper(II)] (8).

The head group of 7 was characterized with X-ray crystallography.

The new class of metallo-liposomes was used as a DNA delivery system and demonstrated to be effective for the transfection of pEGFP-N1 plasmid into HEK 293-T cells. Using optical fluorescent microscopy and X-ray crystallography data, we demonstrate that metal-ion coordination and lipid alkane interdigitation mediate the self-assembly of these molecules, and that intracellular conditions reverse this type of supramolecular organization.

Language

en

Provenance

Received from ProQuest

File Size

90 pages

File Format

application/pdf

Rights Holder

Alejandro Arzola-Rubio

Included in

Biochemistry Commons

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