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https://open.uns.ac.rs/handle/123456789/31267
Title: | Synthesis, structural analysis and antitumor activity of novel 17α-picolyl and 17(E)-picolinylidene A-modified androstane derivatives | Authors: | Ajduković Jovana Penov-Gaši Katarina Jakimov Dimitar Klisurić Olivera Jovanović-Šanta Suzana Sakač Marija Aleksić Lidija Djurendić Evgenija |
Issue Date: | 2015 | Journal: | Bioorganic and Medicinal Chemistry | Abstract: | © 2015 Elsevier Ltd. All rights reserved.. The heterocyclic ring at C-17 position of the androstane compounds plays an important role in biological activity. The aim of the present study was to synthesize and evaluate potential antitumor activity of different A-modified 17α-picolyl and 17(E)-picolinylidene androstane derivatives. In several synthetic steps, novel derivatives bearing the hydroximino, nitrile or lactame functions in A-ring were synthesized and characterized according to the spectral data, by mass analysis as well as XRD analysis (compounds 6, 13 and 15). The structurally most promising compounds 6, 11-17 were investigated as antitumor agents. The in vitro antiproliferative activity was evaluated against six human cancer cell lines: estrogen receptor negative (ER-) breast adenocarcinoma (MDA-MB-231); estrogen receptor positive (ER+) breast adenocarcinoma (MCF-7); prostate cancer (PC-3); human cervical carcinoma (HeLa); lung adenocarcinoma (A549) and colon adenocarcinoma (HT-29) using MTT assay. The results of the 48 h incubation time in vitro tests showed that compound 15 was the most effective against PC-3 (IC50 6.6 μM), compound 17 against MCF-7 (IC50 7.9 μM) cells, while compound 16 exhibited strong antiproliferative effect against both, MCF-7 (IC50 1.7 μM) and PC-3 (IC50 8.7 μM) cancer cells. It was also found that compounds 16 and 17 induced apoptosis in MCF-7 cells (dicyano derivative 17 stronger then dioxime 16 and reference formestane), with no distinct changes in the cell cycle of MCF-7 cells. | URI: | https://open.uns.ac.rs/handle/123456789/31267 | ISSN: | 0968-0896 | DOI: | 10.1016/j.bmc.2015.02.001 |
Appears in Collections: | PMF Publikacije/Publications |
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