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

Nikolay Alekseevich Zefirov 1, 2
Nikolay Alekseevich Zefirov
Marius Hoppe 3
Marius Hoppe
Irina V Kuznetsova 1
Irina V Kuznetsova
Nikita Aleksandrovich Chernyshov 1
Nikita Aleksandrovich Chernyshov
Olga Aleksandrovna Maloshitskaya
Sergei A Kuznetsov 3
Sergei A Kuznetsov
Ol'ga Nikolaevna Zefirova 1, 2
Ol'ga Nikolaevna Zefirova
Published 2018-04-27
CommunicationVolume 28, Issue 3, 308-310
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Zefirov N. A. et al. Homologous series of novel adamantane–colchicine conjugates: synthesis and cytotoxic effect on human cancer cells // Mendeleev Communications. 2018. Vol. 28. No. 3. pp. 308-310.
GOST all authors (up to 50) Copy
Zefirov N. A., Hoppe M., Kuznetsova I. V., Chernyshov N. A., Grishin Y. K., Maloshitskaya O. A., Kuznetsov S. A., Zefirova O. N. Homologous series of novel adamantane–colchicine conjugates: synthesis and cytotoxic effect on human cancer cells // Mendeleev Communications. 2018. Vol. 28. No. 3. pp. 308-310.
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TY - JOUR
DO - 10.1016/j.mencom.2018.05.027
UR - https://mendcomm.colab.ws/publications/10.1016/j.mencom.2018.05.027
TI - Homologous series of novel adamantane–colchicine conjugates: synthesis and cytotoxic effect on human cancer cells
T2 - Mendeleev Communications
AU - Zefirov, Nikolay Alekseevich
AU - Hoppe, Marius
AU - Kuznetsova, Irina V
AU - Chernyshov, Nikita Aleksandrovich
AU - Grishin, Yuri Konstantinovich
AU - Maloshitskaya, Olga Aleksandrovna
AU - Kuznetsov, Sergei A
AU - Zefirova, Ol'ga Nikolaevna
PY - 2018
DA - 2018/04/27
PB - Mendeleev Communications
SP - 308-310
IS - 3
VL - 28
ER -
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@article{2018_Zefirov,
author = {Nikolay Alekseevich Zefirov and Marius Hoppe and Irina V Kuznetsova and Nikita Aleksandrovich Chernyshov and Yuri Konstantinovich Grishin and Olga Aleksandrovna Maloshitskaya and Sergei A Kuznetsov and Ol'ga Nikolaevna Zefirova},
title = {Homologous series of novel adamantane–colchicine conjugates: synthesis and cytotoxic effect on human cancer cells},
journal = {Mendeleev Communications},
year = {2018},
volume = {28},
publisher = {Mendeleev Communications},
month = {Apr},
url = {https://mendcomm.colab.ws/publications/10.1016/j.mencom.2018.05.027},
number = {3},
pages = {308--310},
doi = {10.1016/j.mencom.2018.05.027}
}
MLA
Cite this
MLA Copy
Zefirov, Nikolay Alekseevich, et al. “Homologous series of novel adamantane–colchicine conjugates: synthesis and cytotoxic effect on human cancer cells.” Mendeleev Communications, vol. 28, no. 3, Apr. 2018, pp. 308-310. https://mendcomm.colab.ws/publications/10.1016/j.mencom.2018.05.027.

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.

References

1.
10.1016/j.mencom.2018.05.027_bib0005
The Practice of Medicinal Chemistry, 2003
2.
Marrazzo A., Pappalardo A., Prezzavento O., Vittorio F.
Arkivoc, 2004
3.
Design and Synthesis of Novel Dimeric Morphinan Ligands for κ and μ Opioid Receptors
Neumeyer J.L., Zhang A., Xiong W., Gu X., Hilbert J.E., Knapp B.I., Negus S.S., Mello N.K., Bidlack J.M.
Journal of Medicinal Chemistry, 2003
4.
Synthesis and SAR requirements of adamantane–colchicine conjugates with both microtubule depolymerizing and tubulin clustering activities
Zefirova O.N., Nurieva E.V., Shishov D.V., Baskin I.I., Fuchs F., Lemcke H., Schröder F., Weiss D.G., Zefirov N.S., Kuznetsov S.A.
Bioorganic and Medicinal Chemistry, 2011
5.
Novel antimitotic agents related to tubuloclustin: synthesis and biological evaluation
Zefirova O.N., Nurieva E.V., Wobith B., Gogol V.V., Zefirov N.A., Ogonkov A.V., Shishov D.V., Zefirov N.S., Kuznetsov S.A.
Molecular Diversity, 2017
6.
Synthesis and Characterization of a Cobalamin−Colchicine Conjugate as a Novel Tumor-Targeted Cytotoxin
Bagnato J.D., Eilers A.L., Horton R.A., Grissom C.B.
Journal of Organic Chemistry, 2004
8.
Vasilenko D.A., Averina E.B., Zefirov N.A., Wobith B., Grishin Y.K., Rybakov V.B., Zefirova O.N., Kuznetsova T.S., Kuznetsov S.A., Zefirov N.S.
Mendeleev Communications, 2017
9.
Vostrikov N.S., Lobko I.F., Spirikhin L.V., Vakhitova Y.V., Pivnitsky K.K., Miftakhov M.S.
Mendeleev Communications, 2017
10.
Pentapeptide analogs of somatostatin containing a thiazolidine fragment: synthesis and cytotoxic activity
Balaev A.N., Osipov V.N., Okhmanovich K.A., Ruchko E.A., Baryshnikova M.A., Khachatryan D.S.
Russian Chemical Bulletin, 2016
11.
Adamantane acid esters with alkoxyaryl alcohols: Synthesis, antiproliferative activity, and influence on microtubule network of tumor cells
Zefirov N.A., Nurieva E.V., Pikulina Y.A., Ogon´kov A.V., Wobith B., Kuznetsov S.A., Zefirova O.N.
Russian Chemical Bulletin, 2017
12.
What is an apoptotic index measuring? A commentary