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In the present work, diastereoselective ring\u2010opening of mono\u2010 and polyoxiranes, containing a cyclooctane core, by azide\u2010anion was performed to yield a series of azidoalcohols with different types of symmetry. The products were involved in copper\u2010catalyzed azyde\u2010alkyne cycloaddition (CuAAC) reaction with ethinylestradiol and ethinyltestosterone, and the resulting steroids and steroid dimers with triazole linkers were screened for their antiproliferative activity via (3\u2010(4,5\u2010dimethylthiazol\u20102\u2010yl)2,5\u2010diphenyl tetrazolium bromide) assay. All the compounds revealed cytotoxicity toward several cancer cell lines. The effect of the most potent compound, containing two estradiol moieties, on the microtubules (MT) dynamics was investigated by immunofluorescent microscopy. The disruption of the majority of interphase cell cytoplasmic MT and mitotic event disturbances in the presence of the studied compound were observed. The latter effect caused the appearance of numerous multinucleated cells.<\/jats:p>","DOI":"10.1002\/ardp.202400483","type":"journal-article","created":{"date-parts":[[2024,7,30]],"date-time":"2024-07-30T22:46:15Z","timestamp":1722379575000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":3,"title":["Mono\u2010 and bis(steroids) containing a cyclooctane core: Synthesis, antiproliferative activity, and action on cell cytoskeleton microtubules"],"prefix":"10.1002","volume":"357","author":[{"given":"Olga V.","family":"Ryzhikova","sequence":"first","affiliation":[{"name":"Department of Chemistry Lomonosov Moscow State University Moscow Russia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Aleksandra S.","family":"Churkina","sequence":"additional","affiliation":[{"name":"A.N. Belozersky Institute of Physico\u2010Chemical Biology Lomonosov Moscow State University Moscow Russia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Kseniya N.","family":"Sedenkova","sequence":"additional","affiliation":[{"name":"Department of Chemistry Lomonosov Moscow State University Moscow Russia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Daiana V.","family":"Savchenkova","sequence":"additional","affiliation":[{"name":"Department of Chemistry Lomonosov Moscow State University Moscow Russia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Anton S.","family":"Shakhov","sequence":"additional","affiliation":[{"name":"A.N. Belozersky Institute of Physico\u2010Chemical Biology Lomonosov Moscow State University Moscow Russia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Svetlana V.","family":"Lavrushkina","sequence":"additional","affiliation":[{"name":"A.N. 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