Synthesis and electrochemical, spectral, and biological evaluation of novel 9,10-anthraquinone derivatives containing piperidine unit as potent antiproliferative agents

Paweł Niedziałkowski , Elżbieta Czaczyk , Joanna Jarosz , Anna Wcisło , Wioleta Białobrzeska , Joanna Wietrzyk , Tadeusz Ossowski

Abstract

The present study describes the synthesis and electrochemical, spectral and biological evaluation of new 9,10-anthraquinone derivatives containing one or two piperidine units incorporated in the different positions of the anthraquinone scaffold. The authors focused their efforts on the characterization of the obtained derivatives using the NMR and IR techniques and on the analysis of the molecules properties using the UV-VIS spectroscopy in the DMSO solution. Additionally, the electrochemical investigation of the compounds was performed using the cyclic voltammetry at the GC (glassy carbon) electrode in the DMSO solution. The primary aim of this study was to determine the antiproliferative activity of the obtained compounds. All novel anthraquinone derivatives containing piperidine unit in the structure were tested in vitro against four human cancer cell linesdHL-60, LoVo, HL-60/MX2, LoVo/Dxdwhich the latter two are drug-resistant. The tests also included the in vitro analyses of the antiproliferative activities against BALB/3T3 normal mouse fibroblasts cell lines. The results led to an interesting observation concerning the selectivitydall the derivatives exhibit potential anticancer activity against leukemic drug-resistant cell lines. Moreover, the most active compound 1-(piperidin-1-yl)-9,10-anthraquinone 1 inhibited also the proliferation of the colon cancer cell lines, distinctly overcoming the drug-resistance. Its activity towards the cancer cell lines was 5e8 times higher than the activity against normal fibroblasts cell line, which can suggest its selectivity towards cancer cells.
Author Paweł Niedziałkowski (FCh / DACh / LSCh)
Paweł Niedziałkowski,,
- Laboratory of Supramolecular Chemistry
, Elżbieta Czaczyk (FCh / DACh / LSCh)
Elżbieta Czaczyk,,
- Laboratory of Supramolecular Chemistry
, Joanna Jarosz
Joanna Jarosz,,
-
, Anna Wcisło (FCh / DOCh / LChB)
Anna Wcisło,,
- Laboratory of Chemistry of Biopolymers
, Wioleta Białobrzeska (FCh / DACh / LSCh)
Wioleta Białobrzeska,,
- Laboratory of Supramolecular Chemistry
, Joanna Wietrzyk
Joanna Wietrzyk,,
-
, Tadeusz Ossowski (FCh / DACh / LSCh)
Tadeusz Ossowski,,
- Laboratory of Supramolecular Chemistry
Journal seriesJournal of Molecular Structure, ISSN 0022-2860, (A 20 pkt)
Issue year2019
Vol1175
Pages488-495
Publication size in sheets0.5
Keywords in English9,10-anthraquinone derivatives, electrochemistry, UV-Vis, piperidine, ntiproliferative activity, cytotoxicity
DOIDOI:10.1016/j.molstruc.2018.07.070
URL https://doi.org/10.1016/j.molstruc.2018.07.070
Languageen angielski
Score (nominal)20
ScoreMinisterial score = 20.0, 21-09-2018, ArticleFromJournal
Ministerial score (2013-2016) = 20.0, 21-09-2018, ArticleFromJournal
Publication indicators WoS Impact Factor: 2016 = 1.753 (2) - 2016=1.561 (5)
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