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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 analogsMarriner, Gwendolyn Ann 25 February 2011 (has links)
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
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