Towards the Synthesis of a Polyamine Perylenebisimide Derivative for Intercalation into Quadruplex DNA

May, Bobby (2017) Towards the Synthesis of a Polyamine Perylenebisimide Derivative for Intercalation into Quadruplex DNA. Undergraduate thesis, under the direction of Daniell Mattern from Chemistry and Biochemistry, University of Mississippi.

Preview

Text BobbyLMay Thesis PDF.pdf Download (20MB) | Preview

Abstract

Perylenebisimide intercalation in G-quadruplex DNA is an area of study that has increasing interest in cancer research. The ability of perylenebisimides to interrupt the structures of the G4 DNA on the end of telomeres has allowed for the observation of how the variable-regions of the perylenebisimide can have differing effects on anticancer properties. The purpose of this experiment was to synthesize a perylenebisimide with the intentions of observing its intercalating properties with G-quadruplex DNA. In order to accomplish this, dibenzylamine was substituted onto chloroacetonitrile through an SN2 reaction to produce 2-(dibenzylamino)acetonitrile. The 2-(dibenzylamino)acetonitrile was then reduced with LAH to yield N,N–dibenzylethane-1,2-diamine. The final step involved the transformation of the perylene-3,4,9,10-tetracarboxylic dianhydride into the targeted perylenebisimide derivative. While the first two steps were determined to be successful, the final molecule was not isolated in a pure state, despite subtle NMR signals that hinted to the synthesis of the molecule. Despite falling short of completion, with more time and a few more changes to the reactions when the project continues, a perylenebisimide derivative could be obtained that would potentially have unique effects when intercalated into G-quadruplex DNA.

Actions (login required)

View Item