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New oxygen-containing androstane derivatives: Synthesis and biological potential

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    0532722 - ÚEB 2021 RIV IN eng J - Journal Article
    Savić, M. P. - Kuzminac, I. Z. - Škorić, D. - Jakimov, D. S. - Rárová, Lucie - Sakač, M. N. - Djurendić, E. A.
    New oxygen-containing androstane derivatives: Synthesis and biological potential.
    Journal of chemical sciences. Roč. 132, č. 1 (2020), č. článku 98. ISSN 0974-3626. E-ISSN 0973-7103
    Institutional support: RVO:61389030
    Keywords : cytotoxicity * D-homo androstane lactones * in silico ADME studies * NMR analysis
    OECD category: Biochemistry and molecular biology
    Impact factor: 1.573, year: 2020
    Method of publishing: Open access
    http://doi.org/10.1007/s12039-020-01803-3

    New steroidal D-homo androstane derivatives with 5 beta,6 beta-epoxy-3,16-dicarbonyl, 6 alpha- and 6 beta-hydroxy-3,16-dicarbonyl and 3 beta,5 alpha-dihydroxy-6,16-dicarbonyl moieties were synthesized and confirmed by NMR spectroscopy. Novel and starting compounds were evaluated for their potential cytotoxicityin vitroagainst 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 5 beta,6 beta-epoxy-3,16-dicarbonyl moieties showed strong cytotoxic activity against colon adenocarcinoma (HT-29). In this work,in silicoADME properties of novel compounds were assessed by comparing calculated molecular properties with Lipinski, Veber, Egan, Ghose and Muegge criteria. Graphic abstract The synthesis and structure elucidation of new oxygen-containing androstane derivatives was reported. New derivatives were tested for theirin silicoADME properties and cytotoxicity against different human cancer cell lines.
    Permanent Link: http://hdl.handle.net/11104/0311134

     
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