Adamantyl-substituted ligands of colchicine binding site in tubulin: different effects on microtubule network in cancer cells

  • Nikolai A. Zefirov
  • Yulia A. Evteeva
  • Birgit Wobith
  • Sergei A. Kuznetsov
  • Olga N. Zefirova
Original Research


Four novel conjugates of adamantane connected at a bridgehead position via four-bond linker to structurally different ligands interacting with colchicine binding site of tubulin were synthesized. All compounds were found to inhibit cancer cell proliferation and, notably, to promote the formation of different atypical tubulin assemblies — clusters, curly, or “entangled” microtubules. The distinction in the observed effects for conceptually equivalent structural templates can be partially explained on the basis of computer molecular modeling.


Tubulin polymorphism “Entangled” microtubules Adamantane Colchicine binding site Human lung carcinoma cells A549 


Funding information

This work was supported by Russian Fund of Fundamental Research (project no. №18-03-00524) and the German organization DAAD (German Academic Exchange Service) under the auspices of a collaborative agreement between Moscow and Rostock Universities.

Compliance with ethical standards

Conflict of interest

The authors declare that they have no conflicts of interest.


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Copyright information

© Springer Science+Business Media, LLC, part of Springer Nature 2018

Authors and Affiliations

  • Nikolai A. Zefirov
    • 1
    • 2
  • Yulia A. Evteeva
    • 1
  • Birgit Wobith
    • 3
  • Sergei A. Kuznetsov
    • 3
  • Olga N. Zefirova
    • 1
    • 2
  1. 1.Lomonosov Moscow State UniversityMoscowRussian Federation
  2. 2.Institute of Physiologically active compoundsRussian Academy of SciencesMoscowRussian Federation
  3. 3.Institute of Biological SciencesUniversity of RostockRostockGermany

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