Structures of tested compounds, all compounds possess <i>trans</i> conformation except compounds 19 and 20.

<p>Structures of tested compounds, all compounds possess <i>trans</i> conformation except compounds 19 and 20.</p

Effect estrogen active compounds 15 and 18 and estrogen inactive compounds 11 and 12 on mitochondrial activity (MTT assay), cell mass (SRB assay) and LDH release in estrogen dependent MCF-7 and estrogen independent MDA-MB-231 cells.

<p>Cells were exposed to increasing concentrations of tested compounds for 72 h before performing the assay. Data are reported as % of control and are the means±SEM.</p

Binding site of 18 (central panel and in green in the others) and comparison with the binding mode of estradiol (Left panel, blue) and ligand AIJ (PDB accession code 1xp9) derived from the dihydrobenzoxathiin scaffold (Right panel, cyan)

<p>Binding site of 18 (central panel and in green in the others) and comparison with the binding mode of estradiol (Left panel, blue) and ligand AIJ (PDB accession code 1xp9) derived from the dihydrobenzoxathiin scaffold (Right panel, cyan)</p

Induction of estrogenic activity of HEK293 cells transfected with ER-α receptor by compounds with selective (A) and no selective (B) toxicity against MCF-7 cells. (C) Estrogenic activity of defined compounds toward MCF-7 cell line.

<p>* <i>p</i> < 0.05 compared to the control cells treated with β-estradiol.</p

SEM images of β-CD (A), RU (B), RU-β-CD (C).

<p>SEM images of β-CD (A), RU (B), RU-β-CD (C).</p

Parameters characterizing the concentration of free radicals described by equation 4.

<p>Parameters characterizing the concentration of free radicals described by <a href="http://www.plosone.org/article/info:doi/10.1371/journal.pone.0120858#pone.0120858.e004" target="_blank">equation 4</a>.</p

Two possible ways of inclusion of rutin into β-CD (A) and the structural parts of routine which can interact with β-CD during complex creation (B).

<p>Two possible ways of inclusion of rutin into β-CD (A) and the structural parts of routine which can interact with β-CD during complex creation (B).</p

Estrogenic and cytotoxic activity of tested compounds in HEK293 cells transfected with wild type ERα receptor or plasmids bearing mutated versions of ERα.

<p><b>A</b>.- HEK293 were transfected with wild type ERα receptor or Erα W383A and W383S plasmids and an ER dependent luciferase reporter gene. Results are expressed as mean ± SEM (n = 8). * <i>p</i> < 0.05 was considered statistically significant. <b>B</b>.- HEK293 were transfected mock-transfected or transfected with wild type ERα or Erα W383S plasmids. 48 h after transfection, cells were incubated in the presence of increasing concentrations of compounds 18 for 72 h and cell viability was measured by MTT assay. Results are reported as % viability based on the untreated control cells normalized to 100% viable. Results represent means ± SEM (n = 8). * <i>p</i> <0.05 versus mock-transfected untransfected cells. # p<0.05 versus ERα W383S transfected cells.</p

DSC spectra of RU (black) and RU-β-CD (red).

<p>DSC spectra of RU (black) and RU-β-CD (red).</p

FT-IR absorption spectra for β-CD (red), RU (black) and RU-β-CD complex (blue).

<p>FT-IR absorption spectra for β-CD (red), RU (black) and RU-β-CD complex (blue).</p