Synthesis, biological evaluation, and modeling studies of 1,3-disubstituted cyclobutane-containing analogs of combretastatin A4

被引：11

作者：

Malashchuk, Andrii ^{[1
,2
]}

Chernykh, Anton, V ^{[1
]}

Hurmach, Vasyl V. ^{[1
,2
]}

Platonov, Maxim O. ^{[1
]}

Onopchenko, Oleksandra ^{[3
]}

Zozulya, Sergey ^{[3
]}

Daniliuc, Constantin G. ^{[4
]}

Dobrydnev, Alexey, V ^{[1
,2
]}

Kondratov, Ivan S. ^{[1
,5
]}

Moroz, Yuriy S. ^{[2
,6
]}

Grygorenko, Oleksandr O. ^{[1
,2
]}

机构：

[1] Enamine Ltd, Www Enamine Net, Chervonotkatska St 78, UA-02094 Kiev, Ukraine

[2] Taras Shevchenko Natl Univ Kyiv, Volodymyrska St 60, UA-01601 Kiev, Ukraine

[3] Bienta Enamine Ltd, Www Bienta Net, Chervonotkatska St 78, UA-02094 Kiev, Ukraine

[4] Westfalische Wilhelms Univ Munster, Organ Chem Inst, Corrensstr 40, D-48149 Munster, Germany

[5] NAS Ukraine, Inst Bioorgan Chem & Petrochem, Murmanska St 1, UA-02660 Kiev, Ukraine

[6] Chemspace, Ilukstes Iela 38-5, LV-1082 Riga, Latvia

来源：

JOURNAL OF MOLECULAR STRUCTURE | 2020年 / 1210卷

关键词：

Combretastatin; Tubulin; Molecular dynamics; Conformational restriction; Cyclobutane; NATURAL-PRODUCTS; A-4; ANALOGS; COLCHICINE; TUBULIN; DERIVATIVES; POTENT; INHIBITORS; PHOSPHATE; TRIAL;

D O I：

10.1016/j.molstruc.2020.128025

中图分类号：

O64 [物理化学（理论化学）、化学物理学];

学科分类号：

070304 ; 081704 ;

摘要：

With the aim of circumventing the adverse cis/trans-isomerization of combretastatin A4 (CA4), a naturally occurring tumor-vascular disrupting agent, we designed novel CA4 analogs bearing 1,3-disubstituted cyclobutane moiety instead of the cis-stilbene unit of the parent compound. The corresponding cis and trans cyclobutane-containing derivatives were prepared as pure diastereomers. The structure of the target compounds was confirmed by X-ray diffraction study. The title compounds were evaluated for their cytotoxic properties in human cancer cell lines HepG2 (hepatocarcinoma) and SK-N-DZ (neuroblastoma), and the overall activity was found in micromolar range. Molecular docking studies and molecular dynamics simulation within the colchicine binding site of tubulin were in good agreement with the obtained cytotoxicity data. (C) 2020 Elsevier B.V. All rights reserved.

引用

页数：9

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