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Figure 1.

Structure and pharmacophoric conformation of 21-BD.

(A) Chemical structure of ouabain, digoxin, and 21-BD. (B) Left: whole structure of Na,K-ATPase (PDB: 4HYT) showed in solid ribbon representation, where the alpha-helix, beta-sheets and turns are in red, blue and gray, respectively; right: highlight of the binding site with ouabain shown in tube representation. Dashed red lines indicate hydrogen bonds. Only polar hydrogen atoms were showed for a better visualization. Pharmacophoric conformation of, (C) digoxin and (D) 21-BD; polar and nonpolar interactions are depicted by magenta and green colors, respectively. Dashed lines indicate hydrogen bonds. Residue interactions are color coded as indicated in the inserted scale.

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Figure 2.

21-BD effect on Na,K-ATPase and Pdr5p activity.

(A) 21-BD competition of 3H-ouabain binding on HeLa cells; the control for maximal binding is represented with a white circle and a long dashed line, competition of ouabain and 21-BD is shown with blue and red circles respectively. (B) Inhibition of rat´s brain hemisphere Na,K-ATPase after 2 h incubation with digoxin (green circles) or 21-BD (red circles). (C) Effect of 21-BD on the Na,K-ATPase activity on proteins expressed in Sf9 insect cells, Na,K-ATPase activity was measured on Sf9 cells expressing the rat α1 β1 (orange circles) or β1 (red circles) after 15 min treatment with the indicated concentrations of 21-BD. (D) Dose-response curve for the effects of 21-DB on Na,K-ATPase activity of mouse kidney membrane preparations. E) Effect of 21-BD (red circles) or digoxin (green circles) on the activity of the Pdr5p transporter.

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Figure 3.

21-BD increases Na,K-ATPase expression in cancer cells.

(A) Na,K-ATPase activity after incubation of HeLa cells with 21-BD or digoxin for 48 h with different concentrations of 21-BD. B) mRNA content of the Na,K-ATPase α1 and β1 subunits of HeLa cells after 48 h incubation with various concentrations of 21-BD.

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Figure 4.

High concentrations of 21-BD reduce cell viability of HeLa and RKO.

HeLa (A) or RKO (B) cells were treated with digoxin (green symbols) or 21-BD (red symbols) for 24 (circles) or 48 (squares) h. Viability was measured by MTT reduction assay. 100 and 25 µM 21-BD induced the statistically significant reduction of HeLa and RKO viability, respectively (p<0.0084). Digoxin reduces HeLa viability starting with 150 µM for 24 h and 50 µM for 48 h (p<0.001). RKO cells have a higher sensitivity to digoxin that induces statistically significant differences starting from 1.6 µM for 48 h (p<0.0001).

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Figure 5.

21-BD induces apoptosis in HeLa and CHO-K1 cells.

(A) Score value obtained from the comet assay of CHO-K1 cells incubated 24 h with 21-BD at different concentrations (red circles). (B) Micronucleated cells percentage of CHO-K1 cultures incubated with 21-BD at different concentrations for 24 h. A 24 h incubation with 0.4 mM Methyl methanesulfonate (MMS) was used as a control (A, B, blue circles). (C) Apoptotic and necrotic HeLa cells after 24 h of incubation in control media (white bars), media with 50 µM 21-BD (red bars) or 2 µM digoxin (green bars) for 24 h. Apoptosis and necrosis were detected by flow cytometry ussing an annexin-V translocation assay and the incorporation of propidium iodide in to the nucleus, respectively. P<0.01.

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Figure 6.

21-BD regulates tight junctions.

MDCK cells were cultured in transwell permeable supports and treated with 5, 10 and 50 µM 21-BD. (A) TER was measured as a function of time. The control TER data (white circles, dotted line) averaged 183±8 Ω.cm2 (n = 13) and were normalized to 100%. 5 and 10 µM 21-BD provoke transient small increases of TER, while 50 µM 21-BD causes a stronger and a sustained TER increase (red circles). (B) MDCK cells were incubated 48 h with different concentrations of 21-BD (red symbols) or digoxin (green symbols). mRNA cell content of claudins -4 (circles) and -2 (triangles) were measured by quantitative real time PCR. (C) Protein cell content of the tight junction integral membrane proteins claudins -4 and -2 and the membrane-associated protein ZO-1 as a function of 21-BD concentration in the media for 48 h. Images from the left part of the figure C are representative immunoblots and the graph in the right part is the statistical analysis.

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Figure 7.

21-BD regulates tight junctiońs proteins localization.

Confluent monolayers of MDCK cells, grown on filters, were maintained in control medium (A, B, C) or treated with 50 µM 21-BD for 48 h (D, F, G) and processed for immunofluorescence, using antibodies against the TJs proteins: the integral membrane proteins claudin-4 (Cldn-4, A, D green) and claudin-2 (Cldcn-2, B, E red) and the peripheral membrane protein ZO-1 (C, E, red). Nuclei were stained with TOPRO (blue). 21-BD increases claudin-4 and ZO-1 expression at the tight junction (arrows) and in the cytoplasma (arrow heads), while simultaneously reduces the expression of claudin-2.

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Figure 8.

21-BD increases the expression of Na,K-ATPase in MDCK cells.

(A) Protein cell content of the α1 subunit of the Na,K-ATPase of confluent monolayers of MDCK cells grown on filters in control medium (white bar) or treated with different concentrations of 21-BD (red bars) for 48 h; upper part of the figure A shows representative immunoblots of the α1 subunit of the Na,K-ATPase and actin, the lower part the densitometric analysis. (B and C) Na,K-ATPase α1 subunit stained with a fluoresceinated antibody (B, C, white) or Topro (blue) to detect the nuclei.

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