2-Methoxyestradiol is a 17-beta estradiol derivative with antitumor activity. Due to low bioavailability, a new estrogen analogue was in silico-designed. The latter, a sulphamoylated analogue of 2-methoxyestradiol, was evaluated for its potential antiproliferative effect by means of expression microarray analysis and transmission electron microscopy in the highly metastatic breast adenocarcinoma (MDA-MB-231) cell line. Data indicate changes in gene expression pertaining to induction of apoptosis and autophagy as types of cell death, arrest of the cell cycle, and impairment of the cytoskeleton and induction of reactive oxygen species. Transmission electron microscopy confirmed morphological characteristics of apoptosis and autophagy. Altered cell cycle- and cytoskeletal-related gene expression profiles demonstrated that the estradiol analogue acts as an antimitotic agent in this highly metastatic breast cell line. Data also showed that the newly designed estrogen analogue exerts an antiproliferative effect in this cancer cell line culminating in both apoptosis and autophagy as type of cell death paving the way for further investigations into its potential as anticancer agent. ; Cancer Association of South Africa, the Struwig Germeshuysen Trust, RESCOM (Research Council of the University of Pretoria), National Research Foundation and The Medical Research Council. ; http://www.biomedres.info ; hb2015