Honors Theses
Date of Award
2013
Document Type
Undergraduate Thesis
Department
Chemistry and Biochemistry
First Advisor
Daniell Mattern
Relational Format
Dissertation/Thesis
Abstract
Deoxyribonucleic acid (DNA) can exist in a quadruplex arrangement that requires an abundance of guanine residues [2]. The structures of various quadruplexes have been revealed, in vitro, and, more recently, in vivo [4,5]. Guanine quadruplexes are thermo dynamically stable. It is postulated that quadruplex destabilization facilitates a conformational change in the structure that could serve as a switch for gene expression [5]. This principle is the basis for targeting quadruplexes with organic, small-molecule binding and stabilizing agents. Quadruplexes may play an important role in regulating the expression of many genes, including those implicated in cancer. Stabilization of the quadruplex contained in the promoter of many oncogenes decreases their expression [10]. The binding and stabilization of small molecules with quadruplex DNA has been widely reported in the literature [ 10,11,12,13]. Of particular interest are perylene tetracarboxylic diimides containing side chains that are cationic at physiological pH. Most of these molecules reported in the literature are symmetrical, meaning they contain the same heteroatom-substituted side chain on both ends of the central perylene structure. We have designed both symmetrical and unsymmetrical, hydrosoluble perylenediimide derivatives, intending to increase their solubility and affinity for G-quadruplex DNA. Here, we report our attempts to synthesize a bis-imide with an increased side-chain heteroatom (amine) content that could provide more ionic character at physiological pH than has been previously examined.
Recommended Citation
Matrick, Andrew Jacob, "Polycationic Perylenebisimides for G-Quadruplex Binding" (2013). Honors Theses. 2062.
https://egrove.olemiss.edu/hon_thesis/2062
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