17(E)-Picolinylidene androstane derivatives as potential inhibitors of prostate cancer cell growth: Antiproliferative activity and molecular docking studies

被引：28
|
作者：
Ajdukovic, Jovana J. [1 ]
Djurendic, Evgenija A. [1 ]
Petri, Edward T. [3 ]
Klisuric, Olivera R. [2 ]
Celic, Andjelka S. [3 ]
Sakac, Marija N. [1 ]
Jakimov, Dimitar S. [4 ]
Gasi, Katarina M. Penov [1 ]
机构：
[1] Univ Novi Sad, Fac Sci, Dept Chem Biochem & Environm Protect, Novi Sad 21000, Serbia
[2] Univ Novi Sad, Fac Sci, Dept Phys, Novi Sad 21000, Serbia
[3] Univ Novi Sad, Fac Sci, Dept Biol & Ecol, Novi Sad 21000, Serbia
[4] Oncol Inst Vojvodina, Novi Sad 21204, Serbia
来源：
BIOORGANIC & MEDICINAL CHEMISTRY | 2013年 / 21卷 / 23期
关键词：
Androstane; 17 alpha-Picolyl and 17(E)-picolinylidene derivatives; Synthesis; Antiproliferative activity; Antitumor; Virtual screening; Molecular docking; BIOLOGICAL EVALUATION; ANTITUMOR-ACTIVITY; 17-PICOLYL; PHARMACOKINETICS; DETERMINANTS; INDUCTION; ESTROGEN; DESIGN;
D O I：
10.1016/j.bmc.2013.09.063
中图分类号：
Q5 [生物化学]; Q7 [分子生物学];
学科分类号：
071010 ; 081704 ;
摘要：
We report a rapid and efficient synthesis of A-ring modified 17 alpha-picolyl and 17(E)-picolinylidene androstane derivatives from dehydroepiandrosterone. Compounds were validated spectroscopically and structurally characterized by X-ray crystallography. Virtual screening by molecular docking against clinical targets of steroidal anticancer drugs (ER alpha, AR, Aromatase and CYP17A1) suggests that 17(E)-picolinylidene, but not 17 alpha-picolyl androstanes could specifically interact with CYP17A1 (17 alpha-hydroxylase) with similar geometry and affinity as Abiraterone, a 17-pyridinyl androstane drug clinically used in the treatment of prostate cancer. In addition, several 17(E)-picolinylidene androstanes demonstrated selective antiproliferative activity against PC3 prostate cancer cells, which correlates with Abiraterone antiproliferative activity and predicted CYP17A1 binding affinities. Based on these preliminary results, 17(E)-picolinylidene androstane derivatives could be a promising starting point for the development of new compounds for the treatment of prostate cancer. (C) 2013 Elsevier Ltd. All rights reserved.
引用
收藏
页码：7257 / 7266
页数：10
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