Homologous series of novel adamantane–colchicine conjugates: synthesis and cytotoxic effect on human cancer cells

Abstract

Homologues of N-[7-(adamantan-1-yloxy)-7-oxoheptanoyl]-N-deacetylcolchicine with sequential shift of the ester group in the chain connecting colchicine and adamantane moieties were synthesized to find an optimal position of this group. All homologues possessed very high cytotoxicity to human lung carcinoma cell line A549 demonstrating a weak dependence of toxic activity on the ester group position. The cytotoxicity (EC50 = 5.9 nm) of the most active compound was close to that of clinically used anti-tubulin anticancer drug taxol.