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

E. Mernyák, Johanna Szabó, Ildikó Bacsa, Judit Huber, G. Schneider, Renáta Minorics, Noémi Bózsity, I. Zupkó, Mónika Varga, Zsolt Bikádi, Eszter Hazai, J. 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 - 2014

Fingerprint

Cells
Cell Line
Estrone
Assays
Cytostatic Agents
Cyclization
Tubulin
Polymerization
Ether
Cisplatin
Inhibitory Concentration 50
Derivatives
Fibroblasts
Acids
Neoplasms
Molecules
In Vitro Techniques

Keywords

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

ASJC Scopus subject areas

  • Biochemistry
  • Clinical Biochemistry
  • Endocrinology
  • Molecular Biology
  • Organic Chemistry
  • Pharmacology
  • Medicine(all)

Cite this

Syntheses and antiproliferative effects of d-homo- and d-secoestrones. / Mernyák, E.; Szabó, Johanna; Bacsa, Ildikó; Huber, Judit; Schneider, G.; Minorics, Renáta; Bózsity, Noémi; Zupkó, I.; Varga, Mónika; Bikádi, Zsolt; Hazai, Eszter; Wölfling, J.

In: Steroids, Vol. 87, 2014, p. 128-136.

Research output: Contribution to journalArticle

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, vol. 87, pp. 128-136. https://doi.org/10.1016/j.steroids.2014.05.015
Mernyák, E. ; Szabó, Johanna ; Bacsa, Ildikó ; Huber, Judit ; Schneider, G. ; Minorics, Renáta ; Bózsity, Noémi ; Zupkó, I. ; Varga, Mónika ; Bikádi, Zsolt ; Hazai, Eszter ; Wölfling, J. / Syntheses and antiproliferative effects of d-homo- and d-secoestrones. In: Steroids. 2014 ; Vol. 87. pp. 128-136.
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