Synthesis and evaluation of small molecule DNA-interactive compounds : total synthesis of (±)-NNN-5'-acetate, synthesis of skipped benzimidazolium aza-enediynes, and synthesis of a series of C2-aryl UK-1 analogs

Description

Small-molecule DNA interactive compounds are critical as both carcinogens and therapeutic agents. In this research, a synthetic precursor to a known carcinogen, (±)-N’-nitrosonicotine-5’-acetate was synthesized, and its interactions with DNA were evaluated by polyacrylamide gel electrophoresis and electrospray-ionization mass spectrometry. A library of skipped benzimidazolium aza-enediynes which selectively target unmethylated cytosines in presence of unmethylated cytosines were synthesized, and their biological properties were evaluated in a nicking assay and cytotoxicity study. Finally, a series of structural analogs to a antineoplastic agent, UK-1, were synthesized via a biaryl coupling at C2 on the benzoxazole. / text

Links & Downloads

1. http://hdl.handle.net/2152/ETD-UT-2009-08-384

Tags

UK-1

Aza-enediyne

Cytotoxicity

N-nitrosonornicotine-5'-acetate

NNN-OAc

Tobacco carcinogens

Methylcytosine

Additional Fields

Identifer	oai:union.ndltd.org:UTEXAS/oai:repositories.lib.utexas.edu:2152/ETD-UT-2009-08-384
Date	25 February 2011
Creators	Marriner, Gwendolyn Ann
Contributors	Kerwin, Sean M.
Source Sets	University of Texas
Language	English
Detected Language	English
Type	thesis
Format	application/pdf