Synthesis and cytotoxicity of novel simplified eleutherobin analogues as potential antitumour agents

被引：6
|
作者：
Sosonyuk, Sergey E. [1 ]
Peshich, Anita [1 ]
Tutushkina, Anastasia V. [1 ]
Khlevin, Dmitry A. [1 ]
Lozinskaya, Natalia A. [1 ,2 ]
Gracheva, Yulia A. [1 ]
Glazunova, Valeria A. [3 ]
Osolodkin, Dmitry I. [1 ,4 ,5 ]
Semenova, Marina N. [6 ]
Semenov, Victor V. [7 ]
Palyulin, Vladimir A. [1 ,2 ]
Proskurnina, Marina V. [1 ,2 ]
Shtil, Alexander A. [1 ,3 ]
Zefirov, Nikolay S. [1 ,2 ]
机构：
[1] Lomonosov Moscow State Univ, Dept Chem, 1-3 Leninskie Gory, Moscow 119991, Russia
[2] Russian Acad Sci, Inst Physiologically Act Cpds, 1 Severniy Proezd, Chernogolovka 142432, Moscow Region, Russia
[3] Blokhin Natl Med Ctr Oncol, 24 Kashirskoye Shosse, Moscow 115478, Russia
[4] RAS, FSBSI Chumakov FSC R&D IBP, 8 Bd 1 Poselok Inst Poliomielita, Moscow 108819, Russia
[5] Sechenov First Moscow State Med Univ, Inst Translat Med & Biotechnol, Moscow 119991, Russia
[6] Russian Acad Sci, Inst Dev Biol, Moscow, Russia
[7] Russian Acad Sci, Zelinsky Inst Organ Chem, Moscow, Russia
来源：
ORGANIC & BIOMOLECULAR CHEMISTRY | 2019年 / 17卷 / 10期
关键词：
RING CLOSING METATHESIS; SEA-URCHIN EMBRYO; TUBULIN; PROTEIN;
D O I：
10.1039/c8ob02915f
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Mixed simplified structures containing the paclitaxel and eleutherobin pharmacophore moieties were analyzed using molecular docking techniques and synthesized based on adamantane and 8-oxabicyclo[3.2.1]octane scaffolds. The crucial role of substituents' stereochemistry in biological activity is discussed. At micromolar concentrations the selected analogues interfered with tubulin dynamics in vitro and in a living organism. Furthermore, new compounds were cytotoxic against human tumour cell lines. The simplified eleutherobin analogues may be considered as prototypes of a new class of antitumour agents.
引用
收藏
页码：2792 / 2797
页数：6
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