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Bioorg Med Chem. 2010 Mar 1;18(5):1899-909. doi: 10.1016/j.bmc.2010.01.037. Epub 2010 Jan 25.

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

Cai W, Hassani M, Karki R, Walter ED, Koelsch KH, Seradj H, Lineswala JP, Mirzaei H, York JS, Olang F, Sedighi M, Lucas JS, Eads TJ, Rose AS, Charkhzarrin S, Hermann NG, Beall HD, Behforouz M.

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Chemistry Department, Ball State University, Muncie, IN 47306, USA.

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.

Copyright 2010 Elsevier Ltd. All rights reserved.

PMID:: 20149966; [PubMed - indexed for MEDLINE]
PMCID:: PMC2841014

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Novel lavendamycin analogues as antitumor agents: synthesis, in vitro cytotoxicity, structure-metabolism, and computational molecular modeling studies with NAD(P)H:quinone oxidoreductase 1. [J Med Chem. 2005]
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Synthesis, metabolism and in vitro cytotoxicity studies on novel lavendamycin an...
Synthesis, metabolism and in vitro cytotoxicity studies on novel lavendamycin antitumor agents.
Bioorg Med Chem. 2010 Mar 1 ;18(5):1899-909. doi: 10.1016/j.bmc.2010.01.037. Epub 2010 Jan 25 .

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