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Synthesis and cytotoxicity of novel simplified eleutherobin analogs as potential antitumor agents

Sergey Sosonyuk,  Anita Peshich,  Anastasia Tutushkina,  Dmitry Khlevin,  Natalia Alexandrovna Lozinskaya,  Yulia Gracheva,  Valeria Glazunova,  Dmitry I. Osolodkin,  Marina Semenova,  Victor Semenov,  Vladimir A Palyulin,  Marina Proskurnina,  Alexander Shtil  and  Nikolay S. Zefirov 

Abstract

Mixed simplified structures containing the paclitaxel and eleutherobin pharmacophore moieties were analyzed using molecular docking simulation (software package SYBYL) and synthesized based on adamantane and 8-oxabicyclo[3.2.1]octane scaffolds. The cytotoxic activity of new compounds against three cancer cell lines revealed and the crucial role of substituents stereochemistry for compounds biological activity was discussed. Found examples of compounds with low micromolar cytotoxicity caused cell rounding indicative of interaction of compounds with microtubules. The compound influence on sea urchin embryogenesis associated with microtubule dynamics was also determined.

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Publication details

The article was received on 22 Nov 2018, accepted on 11 Feb 2019 and first published on 11 Feb 2019


Article type: Paper
DOI: 10.1039/C8OB02915F
Citation: Org. Biomol. Chem., 2019, Accepted Manuscript

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    Synthesis and cytotoxicity of novel simplified eleutherobin analogs as potential antitumor agents

    S. Sosonyuk, A. Peshich, A. Tutushkina, D. Khlevin, N. A. Lozinskaya, Y. Gracheva, V. Glazunova, D. I. Osolodkin, M. Semenova, V. Semenov, V. A. Palyulin, M. Proskurnina, A. Shtil and N. S. Zefirov, Org. Biomol. Chem., 2019, Accepted Manuscript , DOI: 10.1039/C8OB02915F

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