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New oxygen-containing androstane derivatives: Synthesis and biological potential

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Abstract

New steroidal D-homo androstane derivatives with 5β,6β-epoxy-3,16-dicarbonyl, 6α- and 6β-hydroxy-3,16-dicarbonyl and 3β,5α-dihydroxy-6,16-dicarbonyl moieties were synthesized and confirmed by NMR spectroscopy. Novel and starting compounds were evaluated for their potential cytotoxicity in vitro against seven human cancer cell lines (MCF-7, MDA-MB-231, PC3, HeLa, HT-29, A549 and CEM) and one human noncancerous cell line (MRC-5). The most sensitive cell line was MDA-MB-231 derived from female reproductive tissue, wherein all compounds showed moderate to strong cytotoxic activity. Also, new compound with 5β,6β-epoxy-3,16-dicarbonyl moieties showed strong cytotoxic activity against colon adenocarcinoma (HT-29). In this work, in silico ADME properties of novel compounds were assessed by comparing calculated molecular properties with Lipinski, Veber, Egan, Ghose and Muegge criteria.

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The synthesis and structure elucidation of new oxygen-containing androstane derivatives was reported. New derivatives were tested for their in silico ADME properties and cytotoxicity against different human cancer cell lines.

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Acknowledgements

The authors thank the Ministry of Education, Science and Technological Development of the Republic of Serbia (Grant No. 172021). This work was also supported by the European Regional Development Fund – Project ENOCH (No. CZ.02.1.01/0.0/0.0/16_019/0000868).

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Authors and Affiliations

  1. Department of Chemistry, Biochemistry and Environmental Protection, Faculty of Sciences, University of Novi Sad, Trg Dositeja Obradovića 3, 21000, Novi Sad, Serbia

    Marina P Savić, Ivana Z Kuzminac, Dušan Đ Škorić, Marija N Sakač & Evgenija A Djurendić

  2. Oncology Institute of Vojvodina, Faculty of Medicine, University of Novi Sad, Put Dr Goldmana 4, 21204, Sremska Kamenica, Serbia

    Dimitar S Jakimov

  3. Laboratory of Growth Regulators, Faculty of Science and Institute of Experimental Botany, Palacký University and the Czech Academy of Sciences, Šlechtitelů 27, 78371, Olomouc, Czech Republic

    Lucie Rárová

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  1. Marina P Savić
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Correspondence to Marina P Savić.

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Savić, M.P., Kuzminac, I.Z., Škorić, D.Đ. et al. New oxygen-containing androstane derivatives: Synthesis and biological potential. J Chem Sci 132, 98 (2020). https://doi.org/10.1007/s12039-020-01803-3

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