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In the present study, two different series of organoselenocyanates (<jats:bold>15\u2009a\u201315\u2009c<\/jats:bold> and <jats:bold>16\u2009a\u201316\u2009c<\/jats:bold>) incorporating crucial heterocyclic pharmacophores such as 2,4\u2010thiazolidine\u20101,3\u2010dione and 1,2,3\u2010triazole were rationally designed. The organoselenocyanates were synthesized using multi\u2010step organic synthesis and investigated for their anticancer activities against triple\u2010negative breast cancer cells. Based on the preliminary anti\u2010proliferative activities and the selectivity index towards cancer cells over the normal cells, 2,4\u2010thiazolidine\u20101,3\u2010dione\u2010based selenocyanate <jats:bold>15\u2009a<\/jats:bold> was identified as the lead analogue for detailed investigations. In addition to the anti\u2010migratory activity, compound <jats:bold>15\u2009a<\/jats:bold> induced G1\u2010phase arrest of the cell cycle and led to early apoptosis. Further studies on the redox balance of MDA\u2010MB\u2010231 cells indicated the antioxidant nature of <jats:bold>15\u2009a<\/jats:bold> with the quenching of ROS level and upregulation of TrxR1 expression. Detailed mechanistic investigations with the expression levels of key\u2010cancer marker proteins revealed that the selenocyanate <jats:bold>15\u2009a<\/jats:bold> induced the activation of ERK pathway by upregulating <jats:italic>p<\/jats:italic>\u2010ERK expression with the subsequent downregulation of <jats:italic>p<\/jats:italic>\u2010Akt and c\u2010Myc levels leading to the inhibition of cellular proliferation. Therefore, the primary outcomes of the study would be valuable in the development of chemotherapeutic agents towards the treatment of triple\u2010negative breast cancer.<\/jats:p>","DOI":"10.1002\/chem.202403026","type":"journal-article","created":{"date-parts":[[2024,12,4]],"date-time":"2024-12-04T09:32:21Z","timestamp":1733304741000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":5,"title":["Synthesis of Thiazolidinedione\u2010 and Triazole\u2010Linked Organoselenocyanates and Evaluation of Anticancer Activities Against Breast Cancer with Mechanistic Investigations"],"prefix":"10.1002","volume":"31","author":[{"ORCID":"https:\/\/orcid.org\/0009-0003-2349-6651","authenticated-orcid":false,"given":"Nikita","family":"Pal","sequence":"first","affiliation":[{"name":"Department of Chemistry Indian Institute of Technology Guwahati  781039 Guwahati, Assam India"},{"name":"Department of Chemical Engineering Indian Institute of 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