Syntheses and antiproliferative effects of d-homo- and d-secoestrones

Erzsébet Mernyák, Johanna Szabó, Ildikó Bacsa, Judit Huber, Gyula Schneider, Renáta Minorics, Noémi Bózsity, István Zupkó, Mónika Varga, Zsolt Bikádi, Eszter Hazai, János Wölfling

Research output: Contribution to journalArticle

9 Citations (Scopus)

Abstract

Substituted and/or heterocyclic d-homoestrone derivatives were synthetized via the intramolecular cyclization of a δ-alkenyl-d-secoaldehyde, -d-secoalcohol or -d-secocarboxylic acid of estrone 3-benzyl ether. The d-secoalcohol was modified at three sites in the molecule. The in vitro antiproliferative activities of the new d-homo- and d-secoestrone derivatives were determined on HeLa, MCF-7, A431 and A2780 cells through use of MTT assay. d-Homoalcohols 3 and 5 displayed cell line-selective cytostatic effects against ovarian and cervical cell lines, respectively. Two d-secoestrones (6 and 12c) proved to be effective, with IC50 values comparable with those of the reference agent cisplatin. A selected compound (6) was tested by tubulin polymerization assay and its cancer specificity was additionally determined by using noncancerous human fibroblast cells.

Original languageEnglish
Pages (from-to)128-136
Number of pages9
JournalSteroids
Volume87
DOIs
Publication statusPublished - Sep 2014

Keywords

  • Antiproliferative effect
  • Homoestrone
  • MTT assay
  • Secoestrone
  • Tubulin polymerization

ASJC Scopus subject areas

  • Biochemistry
  • Molecular Biology
  • Endocrinology
  • Pharmacology
  • Clinical Biochemistry
  • Organic Chemistry

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  • Cite this

    Mernyák, E., Szabó, J., Bacsa, I., Huber, J., Schneider, G., Minorics, R., Bózsity, N., Zupkó, I., Varga, M., Bikádi, Z., Hazai, E., & Wölfling, J. (2014). Syntheses and antiproliferative effects of d-homo- and d-secoestrones. Steroids, 87, 128-136. https://doi.org/10.1016/j.steroids.2014.05.015