Synthesis of steroid analogs of tubuloclustin, their cytotoxicity and effect on microtubules of A549 carcinoma cells


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Synthesis of analogs of tubuloclustin (N-(7-adamant-2-yloxy-7-oxoheptanoyl)-N-deacetylcolchicine (1)) with the colchicine fragment replaced with 2-methoxyestradiol scaffold attached via phenolic hydroxy group was described. Esters 3a–c exhibit moderate cytotoxicity (EC50 = 5–6 μmol L–1) and exert a weak effect on the microtubule network in A549 human lung carcinoma cells similar to the clustering effect of tubuloclustin and its derivatives. Conjugates 6a–c and 7a–c with the phenolic ester bond are low stable and compounds 7a–c are inactive to the microtubules of A549 cells, while compounds 6a–c cause an unusual effect of curling of the microtubules.

Sobre autores

E. Nurieva

Department of Chemistry, M. V. Lomonosov Moscow State University

Email: olgaz@org.chem.msu.ru
Rússia, 1 Leninskie Gory, Moscow, Russian Federation, 119991

N. Zefirov

Department of Chemistry, M. V. Lomonosov Moscow State University; Institute of Physiologically Active Compounds, Russian Academy of Sciences

Email: olgaz@org.chem.msu.ru
Rússia, 1 Leninskie Gory, Moscow, Russian Federation, 119991; 1 Severnyi proezd, Chernogolovka, Moscow Region, Russian Federation, 142432

A. Mamaeva

Department of Chemistry, M. V. Lomonosov Moscow State University

Email: olgaz@org.chem.msu.ru
Rússia, 1 Leninskie Gory, Moscow, Russian Federation, 119991

B. Wobith

Institute of Biological Sciences, University of Rostock

Email: olgaz@org.chem.msu.ru
Alemanha, Rostock, 18106

S. Kuznetsov

Institute of Biological Sciences, University of Rostock

Email: olgaz@org.chem.msu.ru
Alemanha, Rostock, 18106

O. Zefirova

Department of Chemistry, M. V. Lomonosov Moscow State University; Institute of Physiologically Active Compounds, Russian Academy of Sciences

Autor responsável pela correspondência
Email: olgaz@org.chem.msu.ru
Rússia, 1 Leninskie Gory, Moscow, Russian Federation, 119991; 1 Severnyi proezd, Chernogolovka, Moscow Region, Russian Federation, 142432

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