Zerumbonoquinone 10 and zerumbonaminone 11 have been designed to release toxic moieties selectively and preferentially under reductive conditions. These compounds were synthesized by coupling the quinone delivery system with zerumbone alcohol 8 and amine 9. All compounds were evaluated for cytotoxicity against KB (non reductase overexpressing cells), NCI-H187 and MCF-7 (reductase overexpressing cells) and normal cells (Vero cells). Bioreductive compounds 10 and 11 were found to act as bioreductive anticancer agents exhibiting less cytotoxicity than the parents 8 and 9 in KB cells with good stability, and were partially bioreductively active against MCF-7 and NCI-H187 cells.
Keywords: Bioreductive, KB, NCI-H187, MCF-7, Zerumbone derivatives, Zingiber zerumbet Smith, Anticancer, sesquiterpene, antiproliferative, antileukemia, stereochemistry, tumor cells, tumor targeting drug delivery system (TDDS), intramolecular cyclization, non-toxic lactone species III
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