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465-16-7

465-16-7 structure
465-16-7 structure
Name oleandrin
Synonyms (3β,5β,16β)-16-(acetyloxy)-3-[(2,6-dideoxy-3-O-methyl-α-L-arabino-hexopyranosyl)oxy]-14-hydroxycard-20(22)-enolide
Corrigen
OLEANDRIN
Neriolin
(3β,5β,16β)-16-Acetoxy-3-[(2,6-dideoxy-3-O-methyl-α-L-arabino-hexopyranosyl)oxy]-14-hydroxycard-20(22)-enolide
Cholesteryl-methyl-ether
Card-20(22)-enolide, 16-(acetyloxy)-3-((2,6-dideoxy-3-O-methyl-α-L-arabino-hexopyranosyl)oxy)-14-hydroxy-, (3β,5β,16β)-
Cholesterin-methylether
Card-20(22)-enolide, 16-(acetyloxy)-3-[(2,6-dideoxy-3-O-methyl-α-L-arabino-hexopyranosyl)oxy]-14-hydroxy-, (3β,5β,16β)-
(3b,5b,16b)-16-(Acetyloxy)-3-[(2,6-dideoxy-3-O-methyl-a-L-arabino-hexopyranosyl)oxy]-14-hydroxycard-20(22)-enolide
Folinerin
Cholesterin-monomethylether
EINECS 207-361-5
Description Oleandrin inhibits the Na+, K+-ATPase activity with an IC50 of 620 nM.
Related Catalog
Target

IC50: 620 nM (Na+, K+-ATPase)[1].

In Vitro Study of Na,K-ATPase inhibition shows an IC50 (nM) of 620 for Oleandrin. The inhibition of Na,K-ATPase by Oleandrin confirms that it likely exert its toxic effect through inhibition of sodium pump activity[1]. When treated with a series of concentrations of Oleandrin (0.2-25 nM), the undifferentiated CaCO-2 cells are sensitive as evidenced by an IC50 of 8.25 nM. In contrast, a maximum growth inhibition of only 20% is reached in differentiated CaCO-2 cells even though they are treated with Oleandrin concentrations as high as 25 nM[2].
In Vivo The effect of Oleandrin is investigated on glioma growth in vivo. To this aim, SCID or C57BL/6 mice are transplanted, respectively, with human U87MG (5×104), U251, GBM19 (5×105), or murine (syngeneic) GL261 (7.5×104) cells into the right striatum and, after 10 d, treated daily with intraperitoneal Oleandrin for an additional 7 d. Oleandrin significantly reduces tumor sizes in human and murine glioma cell models in vivo in a dose-dependent way. High concentrations of Oleandrin (3 mg/kg) are fatal in both models, as expected from the known lethal dose for rodents. Doses of Oleandrin below the lethal dose (0.3 mg/kg) significantly increase the survival time from 32.6±1.4 d to 53.8±9.6 d in mice injected with U87MG cells (n=5-11; p<0.01, log-rank test) and from 23.37±1.2 d to 34.38±3.3 d (n=5-11; p<0.01, log rank test) in mice injected with GL261 cells[3].
Cell Assay Undifferentiated wild-type and well-differentiated CaCO-2 cells are treated with a range of concentrations of Oleandrin (0.2-25 nM). After 48 h, cells are labeled with BrdU and relative cell proliferation is determined with a BrdU Cell Proliferation Kit[2].
Animal Admin Mice[3] After tumor cell injection, SCID or C57BL/6 mice are monitored daily. The end point is determined by lack of physical activity or death. The mean survival time is calculated using the Kaplan-Meier method and statistical analysis is performed using a log-rank test. For cotreatment with Temozolomide (TMZ), 10 d after tumor injection, mice are treated with Oleandrin (0.03, 0.3, or 3 mg/kg/daily, i.p.), TMZ (50 mg/kg, i.p., every 2 d for a total of 4 times with a stop of 2 weeks) or both. The dosing scheme is chosen starting from these data to be reasonably sure that a constant concentration of drug is maintained along the experiment. Animals used in Kaplan-Meier survival studies receive up to four TMZ cycles.
References

[1]. Jortani SA, et al. Inhibition of Na,K-ATPase by oleandrin and oleandrigenin, and their detection by digoxin immunoassays. Clin Chem. 1996 Oct;42(10):1654-8.

[2]. Yang P, et al. Cellular location and expression of Na+, K+-ATPase α subunits affect the anti-proliferative activity of oleandrin. Mol Carcinog. 2014 Apr;53(4):253-63.

[3]. Garofalo S, et al. The Glycoside Oleandrin Reduces Glioma Growth with Direct and Indirect Effects on Tumor Cells. J Neurosci. 2017 Apr 5;37(14):3926-3939.
Density 1.26
Boiling Point 693.7±55.0 °C at 760 mmHg
Melting Point 250ºC
Molecular Formula C32H48O9
Molecular Weight 576.718
Flash Point 217.2±25.0 °C
Exact Mass 576.329834
PSA 120.75000
LogP 2.30
Vapour Pressure 0.0±4.9 mmHg at 25°C
Index of Refraction 1.567
Symbol GHS06 GHS08
GHS06, GHS08
Signal Word Danger
Hazard Statements H300 + H330-H373
Precautionary Statements P260-P264-P284-P301 + P310-P310
Hazard Codes T
Risk Phrases 23/24/25
Safety Phrases 22-36/37/39-45
RIDADR UN 2811
RTECS FH4585000
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title: CAS No. 465-16-7 | Chemsrc address: https://m.chemsrc.com/en/baike/178564.html

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