N. A. Zefirov, L. Gädert, A. R. Fatkulin, V. M. Shibilev, G. M. Butov, V. M. Mokhov, S. A. Kuznetsov, O. N. Zefirova, “Tubuloclustin analogues with ether moiety: synthesis and evaluation of tubulin clustering and antimitotic activity in cancer cells”, Mendeleev Commun., 30:1 (2020), 106

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Mendeleev Communications, 2020, Volume 30, Issue 1, Pages 106–108
DOI: https://doi.org/10.1016/j.mencom.2020.01.035 (Mi mendc1116)

This article is cited in 9 scientific papers (total in 9 papers)

Communications

Tubuloclustin analogues with ether moiety: synthesis and evaluation of tubulin clustering and antimitotic activity in cancer cells

N. A. Zefirov^ab, L. Gädert^c, A. R. Fatkulin^a, V. M. Shibilev^a, G. M. Butov^d, V. M. Mokhov^e, 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
^d Volzhsky Polytechnic Institute (Branch), Volgograd State Technical University, Volzhsky, Russian Federation
^e Volgograd State Technical University, Volgograd, Russian Federation

Full-text PDF (1771 kB) Citations (9)

DOI: https://doi.org/10.1016/j.mencom.2020.01.035

Graphic abstract: Tubuloclustin analogues with ether moiety: synthesis and evaluation of tubulin clustering and antimitotic activity in cancer cells

Abstract: New analogues of anticancer agent tubuloclustin N-[7-(adamantan-1-yloxy)-7-heptanoyl]-N-deacetylcolchicine with ether moiety in the linker between colchicine and adamantine fragments were synthesized from w-(adamantan-1-yloxy)alkan- 1-ols. These compounds effectively inhibited growth of human lung carcinoma cell line A549 (IC₅₀=5–15.5nM), induced both apoptosis and formation of tubulin clusters. The conjugates lacking ester carbonyl in the linker exhibit improved metabolic stability and are promising for further cytotoxicity studies in vivo.

Keywords: adamantane, dehydroadamantane, colchicine, tubuloclustin, metabolic stability, tubulin, colchicine binding site, depolymerisation of microtubules, carcinoma A549 cell line..

Document Type: Article

Language: English

*Supplementary materials:*
		Supplementary_data_1.pdf	(490.1 Kb)

Citation: N. A. Zefirov, L. Gädert, A. R. Fatkulin, V. M. Shibilev, G. M. Butov, V. M. Mokhov, S. A. Kuznetsov, O. N. Zefirova, “Tubuloclustin analogues with ether moiety: synthesis and evaluation of tubulin clustering and antimitotic activity in cancer cells”, Mendeleev Commun., 30:1 (2020), 106–108

Linking options:

https://www.mathnet.ru/eng/mendc1116

https://www.mathnet.ru/eng/mendc/v30/i1/p106

This publication is cited in the following 9 articles:

V. M. Mokhov, G. M. Butov, I. A. Novakov, “1,3-DEHYDROADAMANTANE AND ITS DERIVATIVES: A VERSATILE SYNTHETIC PLATFORM FOR PREPARATION OF FUNCTIONAL COMPOUNDS WITH A CAGE STRUCTURE. A REVIEW”, Doklady Rossijskoj akademii nauk. Himiâ, nauki o materialah., 511:1 (2023), 3
V. M. Mokhov, G. M. Butov, I. A. Novakov, “1,3-Dehydroadamantane and Its Derivatives: A Versatile Synthetic Platform for the Preparation of Functional Compounds with a Cage Structure. A Review”, Dokl Chem, 511:1 (2023), 149
A. A. Alexeev, E. V. Nurieva, I. A. Elisseev, E. R. Milaeva, K. A. Lyssenko, O. N. Zefirova, “Bicyclic isothioureas for conjugation with tubulin targeted anticancer agents”, Mendeleev Commun., 32:6 (2022), 766–768
N. A. Zefirov, A. Glassl, E. V. Radchenko, A. N. Borovik, V. V. Stanishevskiy, E. R. Milaeva, S. A. Kuznetsov, O. N. Zefirova, “Podophyllotoxin esters with alicyclic residues: an insight into the origin of microtubule-curling effect in cancer cells”, Mendeleev Commun., 32:2 (2022), 173–175
N. A. Zefirov, A. V. Mamaeva, A. I. Krasnoperova, Yu. A. Evteeva, E. R. Milaeva, S. A. Kuznetsov, O. N. Zefirova, “Novel analogs of 5-hydroxymethyl-2-methoxyphenyl adamantane-1-acetate: synthesis, biotesting, and molecular modeling”, Russ Chem Bull, 70:3 (2021), 549
N.A. Zefirov, A.V. Mamaeva, E.V. Radchenko, E.R. Milaeva, S.A. Kuznetsov, O.N. Zefirova, “Conjugate of podophyllotoxin with chlorambucil: synthesis, biological testing and molecular modeling”, BIOMED KHIM, 67:3 (2021), 289
E. V. Nurieva, N. A. Zefirov, N. S. Temnyakova, S. A. Kuznetsov, O. N. Zefirova, “C(7)-Derivatives of colchicine with guanosine and biphenyl moieties: molecular modeling, synthesis, and tubulin clustering effect in cancer cells”, Russ Chem Bull, 69:11 (2020), 2222
N. A. Zefirov, Yu. A. Evteeva, A. I. Krasnoperova, A. V. Mamaeva, E. R. Milaeva, S. A. Kuznetsov, O. N. Zefirova, “Tubulin targeted antimitotic agents based on adamantane lead compound: synthesis, SAR and molecular modeling”, Mendeleev Commun., 30:4 (2020), 421–423
E. V. Nurieva, N. A. Zefirov, N. Fritsch, E. R. Milaeva, S. A. Kuznetsov, O. N. Zefirova, “Molecular design and synthesis of new heterobivalent compounds based on chlorambucil and colchicine”, Mendeleev Commun., 30:6 (2020), 706–708

Citing articles in Google Scholar: Russian citations, English citations
Related articles in Google Scholar: Russian articles, English articles

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