Synthesis, metabolism and in vitro cytotoxicity studies on novel lavendamycin antitumor agents.

Abstract

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.

DOI: 10.1016/j.bmc.2010.01.037

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@article{Cai2010SynthesisMA, title={Synthesis, metabolism and in vitro cytotoxicity studies on novel lavendamycin antitumor agents.}, author={Wen H. 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 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}, journal={Bioorganic & medicinal chemistry}, year={2010}, volume={18 5}, pages={1899-909} }