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

页码：2792 / 2797

页数：6

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