CAS Number465-16-7
SynonymsCorrigen; OLEANDRIN; Neriolin; Cholesteryl-methyl-ether; Cholesterin-methylether; Folinerin; Cholesterin-monomethylether; EINECS 207-361-5
Molecular FormulaC32H48O9
Molecular Weight576.72
Density1.26
Boiling Point693.7±55.0 °C at 760 mmHg
Melting Point250ºC
Symbol
Signal WordWarning
| Chemical & Physical Properties | |
|---|---|
| CAS Number | 465-16-7 |
| Catalog No. | 2A-2189697 |
| Chinese Name | 欧夹竹桃苷 |
| Synonyms | Corrigen; OLEANDRIN; Neriolin; Cholesteryl-methyl-ether; Cholesterin-methylether; Folinerin; Cholesterin-monomethylether; EINECS 207-361-5 |
| Molecular Formula | C32H48O9 |
| Molecular Weight | 576.72 |
| Density | 1.26 |
| Boiling Point | 693.7±55.0 °C at 760 mmHg |
| Melting Point | 250ºC |
| Storage Condition | The warehouse is low-temperature, ventilated, dry, |
| Application | Oleandrin inhibits Na+, K+-ATPase activity with an IC50 of 620 nM. |
| PubChem ID | 16643571 |
| SMILES | COC1CC(OC2CCC3(C)C(CCC4C3CCC3(C)C(C5=CC(=O)OC5)C(OC(C)=O)CC43O)C2)OC(C)C1O |
| InChI | InChI=1S/C32H48O9/c1-17-29(35)24(37-5)14-27(39-17)41-21-8-10-30(3)20(13-21)6-7-23-22(30)9-11-31(4)28(19-12-26(34)38-16-19)25(40-18(2)33)15-32(23,31)36/h12,17,20-25,27-29,35-36H,6-11,13-16H2,1-5H3/t17-,20?,21-,22?,23?,24-,25-,27-,28-,29-,30-,31+,32-/m0/s1 |
| InChI Key | JLPDBLFIVFSOCC-XYXFTTADSA-N |
| NACRES Code | NA.24 |
| UNSPSC | 41116107 |
| Hazard Symbols | transportation |
| Bioactivity | Oleandrin inhibits the Na+, K+-ATPase activity with an IC50 of 620 nM. Related Catalog Signaling Pathways >> Membrane Transporter/Ion Channel >> Na+/K+ ATPase Research Areas >> Cancer 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. Chemical & Physical Properties 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 InChIKey JLPDBLFIVFSOCC-XYXFTTADSA-N SMILES COC1CC(OC2CCC3(C)C(CCC4C3CCC3(C)C(C5=CC(=O)OC5)C(OC(C)=O)CC43O)C2)OC(C)C1O |
| Use of | Oleandrin inhibits the Na+, K+-ATPase activity with an IC50 of 620 nM. Properties Articles25 Name oleandrin Synonym More Synonyms Oleandrin Biological Activity Description Oleandrin inhibits the Na+, K+-ATPase activity with an IC50 of 620 nM. Related Catalog Signaling Pathways >> Membrane Transporter/Ion Channel >> Na+/K+ ATPase Research Areas >> Cancer IC50: 620 nM (Na+, K+-ATPase)[1]. 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. Chemical & Physical Properties Molecular Formula C32H48O9 Exact Mass 576.329834 PSA 120.75000 Index of Refraction 1.567 InChIKey JLPDBLFIVFSOCC-XYXFTTADSA-N |
| Transport Info | Product name: Purity: 98.0% |
| MSDS Transport Info | Module 14. Shipping information 14.1 UN dangerous goods number European Dangerous Regulations for land transport: 2811 International Dangerous Regulations for sea transport: 2811 International Dangerous Regulations for air transport: 2811 14.2 Names specified by the United Nations (UN) European Land Transport Dangerous Regulations: TOXIC SOLID, ORGANIC, N.O.S. (16β-Acetoxy-3β-(2,6-dideoxy-3-O-methyl-L-arabino- hexopyranosyloxy)-14-hydroxycard-20(22)-enolide) IMDG: TOXIC SOLID, ORGANIC, N.O.S. (16β-Acetoxy-3β-(2,6-dideoxy-3-O-methyl-L-arabino- hexopyranosyloxy)-14-hydroxycard-20(22)-enolide) International air transport hazard regulations: Toxic solid, organic, n.o.s. (16β-Acetoxy-3β-(2,6-dideoxy-3-O-methyl-L-arabino- hexopyranosyloxy)-14-hydroxycard-20(22)-enolide) 14.3 Transport hazard categories European Land Transport Danger Regulations: 6.1 International Maritime Transport Danger Regulations: 6.1 International Air Transport Danger Regulations: 6.1 14.4 Package group European Dangerous Regulations for land transport: II International Dangerous Regulations for sea transport: II International Dangerous Regulations for air transport: II 14.5 Environmental hazards European Land Transport Dangerous Regulations: No International Maritime Transport Dangerous Regulations Maritime Pollutants: No International Air Transport Risk Regulations: No 14.6 Special reminder to users No data available |
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