N. A. Zefirov, M. Hoppe, I. V. Kuznetsova, N. A. Chernyshov, Yu. K. Grishin, O. A. Maloshitskaya, S. A. Kuznetsov, O. N. Zefirova, “Homologous series of novel adamantane–colchicine conjugates: synthesis and cytotoxic effect on human cancer cells”, Mendeleev Commun., 2018, Volume 28, Issue 3,Pages <nobr>308

This article is cited in 9 papers

Communications

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

N. A. Zefirov^ab, M. Hoppe^c, I. V. Kuznetsova^a, N. A. Chernyshov^a, Yu. K. Grishin^a, O. A. Maloshitskaya^a, S. A. Kuznetsov^c, O. N. Zefirova^ab

^a Department of Chemistry, M.V. Lomonosov Moscow State University, Moscow, Russian Federation
^b Institute of Physiologically Active Compounds, Federal Research Center of Problems of Chemical Physics and Medicinal Chemistry, Russian Academy of Sciences, Chernogolovka, Moscow Region, Russian Federation
^c Institute of Biological Sciences, Cell Biology and Biosystems Technology, University of Rostock, Rostock, Germany

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=5.9nm) of the most active compound was close to that of clinically used anti-tubulin anticancer drug taxol.

Language: English

DOI: 10.1016/j.mencom.2018.05.027