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Synthesis, metabolism and in vitro cytotoxicity studies on novel lavendamycin antitumor agents. 2010
Wen Cai, and
Mary Hassani, and
Rajesh Karki, and
Ervin D Walter, and
Katherine H Koelsch, and
Hassan Seradj, and
Jayana P Lineswala, and
Hamid Mirzaei, and
Jeremy S York, and
Fatemeh Olang, and
Minoo Sedighi, and
Jennifer S Lucas, and
Thomas J Eads, and
Anthony S Rose, and
Sahba Charkhzarrin, and
Nicholas G Hermann, and
Howard D Beall, and
Mohammad Behforouz
Chemistry Department, Ball State University, Muncie, IN 47306, USA.
A series of lavendamycin analogues with two, three or four substituents at the C-6, C-7 N, C-2', C-3' and C-11' positions were synthesized via short and efficient methods and evaluated as potential NAD(P)H:quinone oxidoreductase (NQO1)-directed antitumor agents. The compounds were prepared through Pictet-Spengler condensation of the desired 2-formylquinoline-5,8-diones with the required tryptophans followed by further needed transformations. Metabolism and toxicity studies demonstrated that the best substrates for NQO1 were also the most selectively toxic to NQO1-rich tumor cells compared to NQO1-deficient tumor cells.
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