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One analog induced cell cycle disturbance supported by flow cytometry and both estrone analogs increased hypodiploid populations. The compounds enhanced tubulin polymerization in vitro and suppressed breast cancer migration and invasion using wound healing and Boyden chamber assays. Luciferase reporter assays indicated strong estrogenic activity, supporting hormone-independent malignancy potential.",{"@graph":69,"@context":122},[70,84,105],{"@type":71,"itemListElement":72},"BreadcrumbList",[73,77,79,82],{"item":74,"name":75,"@type":76,"position":8},"https://docshare.wps.com","Home","ListItem",{"item":78,"name":9,"@type":76,"position":14},"https://docshare.wps.com/document/",{"item":80,"name":35,"@type":76,"position":81},"https://docshare.wps.com/document/healthcare/",3,{"item":83,"name":65,"@type":76,"position":19},"https://docshare.wps.com/document/antiproliferative-and-antimetastatic-properties-of-16-azidomethyl-substituted-3-o-benzyl-estrone-analogs/380459/",{"url":83,"name":65,"@type":85,"image":86,"author":91,"headline":65,"publisher":94,"fileFormat":97,"inLanguage":63,"description":67,"dateModified":98,"datePublished":99,"encodingFormat":97,"isAccessibleForFree":100,"interactionStatistic":101},"DigitalDocument",{"url":87,"@type":88,"width":89,"height":90},"https://docshare.wps.com/thumbnails/antiproliferative-and-antimetastatic-properties-of-16-azidomethyl-substituted-3-o-benzyl-estrone-analogs/380459.png","ImageObject",300,407,{"name":92,"@type":93},"Terk","Person",{"url":74,"name":95,"@type":96},"DocShare","Organization","application/pdf","2026-10-25","2026-09-24",true,{"@type":102,"interactionType":103,"userInteractionCount":24},"InteractionCounter",{"@type":104},"ViewAction",{"@type":106,"mainEntity":107},"FAQPage",[108,114,118],{"name":109,"@type":110,"acceptedAnswer":111},"What compounds were tested for antiproliferative and antimetastatic activity?","Question",{"text":112,"@type":113},"Four diastereomers of 16-azidomethyl substituted 3-O-benzyl estradiol and two estrone analogs (16AABE and 16BABE) were tested against human gynecological cancer cell lines.","Answer",{"name":115,"@type":110,"acceptedAnswer":116},"How did the analogs affect breast cancer cell growth and cell cycle?",{"text":117,"@type":113},"Both estrone analogs increased hypodiploid populations, and 16AABE caused cell cycle disturbance as evidenced by flow cytometry.",{"name":119,"@type":110,"acceptedAnswer":120},"Which experiments supported the antimetastatic effects of the estrone analogs?",{"text":121,"@type":113},"Inhibition of migration and invasive ability was supported by wound healing and Boyden chamber assays, along with in vitro tubulin polymerization changes.","https://schema.org",{"og:url":83,"og:type":124,"og:title":65,"og:site_name":95,"og:description":67},"article",{"robots":126,"canonical":83},"index,follow",{"doc_id":128,"site_id":62},380459,1791028898,{"code":4,"msg":5,"data":131},{"doc_id":128,"user_id":132,"nickname":92,"user_avatar":133,"doc_module":4,"category_id":34,"category_name":35,"doc_title":65,"doc_description":67,"doc_content":134,"file_id":135,"file_url":136,"file_type":137,"file_size":138,"view_count":24,"is_deleted":4,"is_public":8,"is_downloadable":8,"audit_status":8,"page_count":139,"language":140,"language_code":63,"site_id":62,"html_lang":63,"table_of_contents":141,"faqs":142,"seo_title":143,"seo_description":67,"update_tm":144,"read_time":36},1099525198933,"https://ap-avatar.wpscdn.com/davatar_155a257f0dc6eb9ab79c44ca47cae57d","Article  \nAntiproliferative and Antimetastatic Properties of  \n16-Azidomethyl Substituted 3-O-Benzyl Estrone Analogs †  \nSeyyed Ashkan Senobar Tahaei 1, 􀂁gnes Kulm¡ny 1, Ren¡ta Minorics 1, Anita Kiss 2, Zolt¡n Szabâ 3, P²ter Germ¡n 1, G¡bor J. Szebeni 4, Nikolett G²mes 4, Erzs²bet Merny¡k 2,* and Istv¡n Zupkâ 1,5, *  \nCitation: Senobar Tahaei, S.A.; Kulmány, Á.; Minorics, R.; Kiss, A.; Szabó, Z.; Germán, P.; Szebeni, G.J.; Gémes, N.; Mernyák, E.; Zupkó, I. Antiproliferative and Antimetastatic Properties of 16-Azidomethyl Substituted 3-O-Benzyl Estrone Analogs. Int. J. Mol. Sci. 2023, 24, 13749. [https://doi.org/10.3390/](https://doi.org/10.3390/)[ ](https://doi.org/10.3390/)ijms241813749  \nAcademic Editor: Jack A. Tuszynski  \nReceived: 20 July 2023  \nRevised: 31 August 2023  \nAccepted: 1 September 2023  \nPublished: 6 September 2023  \nCopyright: © 2023 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license ([https://](https://)[ ](https://)[creativecommons.org/licenses/by/](creativecommons.org/licenses/by/)[ ](creativecommons.org/licenses/by/)[4.0/](4.0/)) .  \n1 Institute of Pharmacodynamics and Biopharmacy, University of Szeged, H-6720 Szeged, Hungary  \n2 Department of Inorganic, Organic and Analytical Chemistry, University of Szeged, H-6720 Szeged, Hungary  \n3 Department of Medicinal Chemistry, University of Szeged, H-6720 Szeged, Hungary  \n4 Laboratory of Functional Genomics, Biological Research Centre, H-6726 Szeged, Hungary  \n5 Interdisciplinary Centre of Natural Products, University of Szeged, H-6720 Szeged, Hungary  \n* [Correspondence: bobe@chem.u-szeged.hu](Correspondence: bobe@chem.u-szeged.hu) (E.M.); [zupko.istvan@szte.hu](zupko.istvan@szte.hu) (I.Z.)† Dedicated to the memory of Professor Gyula Schneider.  \nAbstract: Four diastereomers of 16-azidomethyl substituted 3-O-benzyl estradiol (1–4) and their two estrone analogs (16AABE and 16BABE) were tested for their antiproliferative properties against human gynecological cancer cell lines. The estrones were selected for additional experiments based on their outstanding cell growth-inhibiting activities. Both compounds increased hypodiploid populations of breast cancer cells, and 16AABE elicited cell cycle disturbance as evidenced by flow cytometry. The two analogs substantially increased the rate of tubulin polymerization in vitro. 16AABE and 16BABE inhibited breast cancer cells' migration and invasive ability, as evidenced by wound healing and Boyden chamber assays. Since both estrone analogs exerted remarkable estrogenic activities, as documented by a luciferase reporter gene assay, they can be considered as promising drug candidates for hormone-independent malignancies.  \nKeywords: estrone analogs; antiproliferative effect; metastasis; apoptosis; tubulin polymerization; breast cancer  \n1. Introduction  \nCancer is prominent cause of death worldwide, with mortality rates comparable to those of stroke and coronary heart disease. According to the latest update from the International Agency for Research on Cancer (IARC) database, 19.3 million new cancer cases and almost 10 million cancer-related deaths occurred globally in 2020 . Moreover, the global cancer burden is expected to reach 28.4 million cases by 2040, corresponding to a 47% rise in all cancer cases. Lung cancer is the leading cause of cancer death, responsible for 18% of tumor-related mortality, followed by colorectal (9.4%), liver (8.3%), stomach (7.7%), and female breast (6.9%) cancers. Concerning the incidence of different female tumors, breast carcinomas are the most common, accounting for 24.5% of all new cases. Altogether, 38.9% of new cancer cases in females involve gynecological malignancies [1] . The 2.26 million breast cancer cases diagnosed in 2020 show unequal geographical distribution, with the highest age-standardized incidence rate in Europe (69.7/100,000) and the lowes","cbCaipVy6QIAIgOc","https://ap.wps.com/l/cbCaipVy6QIAIgOc","pdf",17448116,16,"English","# Abstract\n# Introduction\n## Cancer burden and epidemiology\n## Need for innovative anticancer options\n## Steroid-based anticancer research background","[{\"question\":\"What compounds were tested for antiproliferative and antimetastatic activity?\",\"answer\":\"Four diastereomers of 16-azidomethyl substituted 3-O-benzyl estradiol and two estrone analogs (16AABE and 16BABE) were tested against human gynecological cancer cell lines.\"},{\"question\":\"How did the analogs affect breast cancer cell growth and cell cycle?\",\"answer\":\"Both estrone analogs increased hypodiploid populations, and 16AABE caused cell cycle disturbance as evidenced by flow cytometry.\"},{\"question\":\"Which experiments supported the antimetastatic effects of the estrone analogs?\",\"answer\":\"Inhibition of migration and invasive ability was supported by wound healing and Boyden chamber assays, along with in vitro tubulin polymerization changes.\"}]","Antiproliferative and Antimetastatic Properties of 16-Azidomethyl Substituted 3-O-Benzyl Estrone Analogs | PDF",1790240277]