Oleandrin | PBI-05204 | CAS#465-16-7 | Na/K-ATPase pump inhibitor

MedKoo Cat#: 202070 | Name: Oleandrin

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Oleandrin, also known as PBI-05204 , is a lipid soluble cardiac glycoside with potential antineoplastic activity. Upon administration, oleandrin specifically binds to and inhibits the alpha3 subunit of the Na/K-ATPase pump in human cancer cells. This may inhibit the phosphorylation of Akt, upregulate MAPK, inhibit NF-kb activation and inhibit FGF-2 export and may downregulate mTOR thereby inhibiting p70S6K and S6 protein expression. All of this may lead to an induction of apoptosis.

Chemical Structure

Oleandrin

CAS#465-16-7

Theoretical Analysis

MedKoo Cat#: 202070

Name: Oleandrin

CAS#: 465-16-7

Chemical Formula: C32H48O9

Exact Mass: 576.3298

Molecular Weight: 576.73

Elemental Analysis: C, 66.64; H, 8.39; O, 24.97

Price and Availability

Size	Price	Availability
100mg	USD 2,950.00	2 Weeks
200mg	USD 3,950.00	2 Weeks
500mg	USD 4,950.00	2 Weeks
1g	USD 5,950.00	2 Weeks
2g	USD 9,850.00	2 Weeks

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Related CAS #

No Data

Synonym

PBI05204; PBI 05204; PBI-05204; Oleandrin

IUPAC/Chemical Name

(3S,5R,9S,10S,13R,14S,16S)-14-hydroxy-3-(((2R,4S,5S,6S)-5-hydroxy-4-methoxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-10,13-dimethyl-17-(5-oxo-2,5-dihydrofuran-3-yl)hexadecahydro-1H-cyclopenta[a]phenanthren-16-yl acetate

InChi Key

JLPDBLFIVFSOCC-YBKPGLTNSA-N

InChi Code

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

SMILES Code

CC(O[C@H]1C[C@]2(O)C3CC[C@]4([H])C[C@@H](O[C@H]5C[C@H](OC)[C@@H](O)[C@H](C)O5)CC[C@]4(C)[C@@]3([H])CC[C@]2(C)C1C6=CC(OC6)=O)=O

Appearance

Solid powder

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO, not in water

Shelf Life

>2 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

More Info

Application: Detection in biological specimens Oleander extracts have been used as an instrument for both suicidal and homicidal poisonings. Oleandrin, the primary active constituent, may be quantified in serum, whole blood or urine to confirm a diagnosis of poisoning in hospitalized patients or to assist in the forensic investigation of a case of fatal overdosage. Most commercial immunoassays for digoxin or digitoxin will cross-react with the oleander glycosides and will suffice for clinical monitoring purposes, but forensic scientists generally rely on instrumental techniques such as liquid chromatography-mass spectrometry (Source: http://en.wikipedia.org/wiki/Oleandrin ).

Product Data

Product Data

Instruction

View handling instruction

Biological target:

Oleandrin (PBI-05204) inhibits the Na+, K+-ATPase activity with an IC50 of 620 nM.

In vitro activity:

The effects of oleandrin on α3 subunit intracellular distribution, cell death, proliferation, and EKR phosphorylation were examined in differentiated and undifferentiated human colon cancer CaCO-2 cells. Intriguingly, oleandrin exerted threefold stronger anti-proliferative activity in undifferentiated CaCO-2 cells (IC50, 8.25 nM) than in differentiated CaCO-2 cells (IC50, >25 nM). Oleandrin (10 to 20 nM) caused an autophagic cell death and altered ERK phosphorylation in undifferentiated but not in differentiated CaCO-2 cells. Reference: Mol Carcinog. 2014 Apr;53(4):253-63. https://pubmed.ncbi.nlm.nih.gov/23073998/

In vivo activity:

To this aim, mice were transplanted with human or murine glioma and analyzed for tumor progression upon oleandrin treatment. In both systems, oleandrin impaired glioma development, reduced tumor size, and inhibited cell proliferation. This study demonstrated that oleandrin does the following: (1) enhances the brain-derived neurotrophic factor (BDNF) level in the brain; (2) reduces both microglia/macrophage infiltration and CD68 immunoreactivity in the tumor mass; (3) decreases astrogliosis in peritumoral area; and (4) reduces glioma cell infiltration in healthy parenchyma. Reference: J Neurosci. 2017 Apr 5;37(14):3926-3939. https://pubmed.ncbi.nlm.nih.gov/28292827/

	Solvent	mg/mL	mM
Solubility
	DMSO	100.0	173.39
	Ethanol	10.0	17.34

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 576.73 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:

1. Eroğlu Güneş C, Seçer Çelik F, Seçme M, Elmas L, Dodurga Y, Kurar E. Glycoside oleandrin downregulates toll-like receptor pathway genes and associated miRNAs in human melanoma cells. Gene. 2022 Nov 15;843:146805. doi: 10.1016/j.gene.2022.146805. Epub 2022 Aug 11. PMID: 35964872. 2. Yang P, Cartwright C, Efuet E, Hamilton SR, Wistuba II, Menter D, Addington C, Shureiqi I, Newman RA. 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. doi: 10.1002/mc.21968. Epub 2012 Oct 16. PMID: 23073998; PMCID: PMC4442617. 3. Garofalo S, Grimaldi A, Chece G, Porzia A, Morrone S, Mainiero F, D'Alessandro G, Esposito V, Cortese B, Di Angelantonio S, Trettel F, Limatola C. The Glycoside Oleandrin Reduces Glioma Growth with Direct and Indirect Effects on Tumor Cells. J Neurosci. 2017 Apr 5;37(14):3926-3939. doi: 10.1523/JNEUROSCI.2296-16.2017. Epub 2017 Mar 14. PMID: 28292827; PMCID: PMC6596714. 4. Afaq F, Saleem M, Aziz MH, Mukhtar H. Inhibition of 12-O-tetradecanoylphorbol-13-acetate-induced tumor promotion markers in CD-1 mouse skin by oleandrin. Toxicol Appl Pharmacol. 2004 Mar 15;195(3):361-9. doi: 10.1016/j.taap.2003.09.027. PMID: 15020199.

In vitro protocol:

In vivo protocol:

1. Garofalo S, Grimaldi A, Chece G, Porzia A, Morrone S, Mainiero F, D'Alessandro G, Esposito V, Cortese B, Di Angelantonio S, Trettel F, Limatola C. The Glycoside Oleandrin Reduces Glioma Growth with Direct and Indirect Effects on Tumor Cells. J Neurosci. 2017 Apr 5;37(14):3926-3939. doi: 10.1523/JNEUROSCI.2296-16.2017. Epub 2017 Mar 14. PMID: 28292827; PMCID: PMC6596714. 2. Afaq F, Saleem M, Aziz MH, Mukhtar H. Inhibition of 12-O-tetradecanoylphorbol-13-acetate-induced tumor promotion markers in CD-1 mouse skin by oleandrin. Toxicol Appl Pharmacol. 2004 Mar 15;195(3):361-9. doi: 10.1016/j.taap.2003.09.027. PMID: 15020199.

1: Karwaciak I, Pastwińska J, Sałkowska A, Bachorz RA, Ratajewski M. Evaluation of the activity of cardiac glycosides on RORγ and RORγT nuclear receptors. Arch Biochem Biophys. 2024 Jul 4;759:110085. doi: 10.1016/j.abb.2024.110085. Epub ahead of print. PMID: 38971421. 2: Chakraborty S, Wei D, Tran M, Lang FF, Newman RA, Yang P. PBI-05204, a supercritical CO2 extract of Nerium oleander, suppresses glioblastoma stem cells by inhibiting GRP78 and inducing programmed necroptotic cell death. Neoplasia. 2024 Aug;54:101008. doi: 10.1016/j.neo.2024.101008. Epub 2024 May 31. PMID: 38823209; PMCID: PMC11177059. 3: Katoh M, Fujii T, Tabuchi Y, Shimizu T, Sakai H. Negative regulation of thyroid adenoma-associated protein (THADA) in the cardiac glycoside-induced anti-cancer effect. J Physiol Sci. 2024 Apr 1;74(1):23. doi: 10.1186/s12576-024-00914-7. PMID: 38561668; PMCID: PMC10985892. 4: Guo J, Yan YZ, Chen J, Duan Y, Zeng P. Identification of Hub Genes and Pathways of Middle Cerebral Artery Occlusion in Aged Rats Using the Gene Expression Omnibus Database. Crit Rev Immunol. 2024;44(4):1-12. doi: 10.1615/CritRevImmunol.2023051702. PMID: 38505917. 5: Fossum TW, Newman RA, Matos JR. Preliminary investigation of the safe dose of oleandrin when administered orally to Beagles. J Am Vet Med Assoc. 2024 Mar 19;262(7):966-972. doi: 10.2460/javma.23.11.0651. PMID: 38503057. 6: Pugliese N, Tinelli A, Crescenzo G, Nieddu M, Baralla E, Schiavone A, Zizzo N, Samarelli R, Dessì F, Circella E, Zizzadoro C, Saleh MS, Camarda A. Poisoning by Nerium oleander L. in Franconia Geese. Animals (Basel). 2024 Feb 14;14(4):612. doi: 10.3390/ani14040612. PMID: 38396580; PMCID: PMC10885877. 7: Kovačević T, Polić B, Ardalić TĆ, Petrović D, Stričević L, Rogulj M, Markić J. A suicide attempt by ingestion of oleander leaves and treatment with digoxin- specific Fab antibody fragments. Arh Hig Rada Toksikol. 2023 Dec 29;74(4):292-295. doi: 10.2478/aiht-2023-74-3752. PMID: 38146758; PMCID: PMC10750315. 8: Ayyappan S, N A, Toi PC. Accidental fatal poisoning in a child due to ingestion of Nerium oleander leaf. Forensic Sci Med Pathol. 2023 Dec 22. doi: 10.1007/s12024-023-00771-7. Epub ahead of print. PMID: 38133853. 9: Okuda H, Fukushima H, Nakatsukasa T, Yamamoto K, Kaizaki-Mitsumoto A, Numazawa S, Kamijo Y. Fatal poisoning due to ingestion of boiled oleander leaf extract. J Forensic Sci. 2024 Jan;69(1):351-354. doi: 10.1111/1556-4029.15393. Epub 2023 Sep 27. PMID: 37753820. 10: Sykes CA, Filigenzi M, Uzal FA, Poppenga RH. Yellow oleander (Thevetia peruviana) toxicosis in 4 goats. J Vet Diagn Invest. 2023 Sep;35(5):563-567. doi: 10.1177/10406387231186190. Epub 2023 Jul 26. PMID: 37496389; PMCID: PMC10467453. 11: Jensen GS, Yu L, Iloba I, Cruickshank D, Matos JR, Newman RA. Differential Activities of the Botanical Extract PBI-05204 and Oleandrin on Innate Immune Functions under Viral Challenge Versus Inflammatory Culture Conditions. Molecules. 2023 Jun 16;28(12):4799. doi: 10.3390/molecules28124799. PMID: 37375354; PMCID: PMC10302683. 12: Smer-Barreto V, Quintanilla A, Elliott RJR, Dawson JC, Sun J, Campa VM, Lorente-Macías Á, Unciti-Broceta A, Carragher NO, Acosta JC, Oyarzún DA. Discovery of senolytics using machine learning. Nat Commun. 2023 Jun 10;14(1):3445. doi: 10.1038/s41467-023-39120-1. PMID: 37301862; PMCID: PMC10257182. 13: Rashan LJ, Özenver N, Boulos JC, Dawood M, Roos WP, Franke K, Papasotiriou I, Wessjohann LA, Fiebig HH, Efferth T. Molecular Modes of Action of an Aqueous Nerium oleander Extract in Cancer Cells In Vitro and In Vivo. Molecules. 2023 Feb 16;28(4):1871. doi: 10.3390/molecules28041871. PMID: 36838857; PMCID: PMC9960564. 14: Carney N, Perry N, Garabedian J, Nagorny P. Development of α-Selective Glycosylation with l-Oleandral and Its Application to the Total Synthesis of Oleandrin. Org Lett. 2023 Feb 17;25(6):966-971. doi: 10.1021/acs.orglett.2c04358. Epub 2023 Feb 5. PMID: 36739571; PMCID: PMC10278664. 15: Sharma R, Singh S, Tewari N, Dey P. A toxic shrub turned therapeutic: The dichotomy of Nerium oleander bioactivities. Toxicon. 2023 Mar 1;224:107047. doi: 10.1016/j.toxicon.2023.107047. Epub 2023 Jan 25. PMID: 36706925. 16: Secer Celik F, Eroglu Gunes C, Kurar E. Cardiac Glycoside Oleandrin Suppresses EMT Ability in Endometrial Carcinoma Cells. Int J Mol Cell Med. 2023;12(3):220-228. doi: 10.22088/IJMCM.BUMS.12.3.220. PMID: 38751655; PMCID: PMC11092899. 17: Gao L, Zhao M, Mao Y, Zhang L, Wang X, Li S, Qin L, Xu J, Hu L, Qiao H. Localized Microsphere/Hydrogel for Tumor Immunotherapy of Cardiac Glycoside with Minimal Toxicity. ACS Appl Mater Interfaces. 2023 Jan 11;15(1):578-590. doi: 10.1021/acsami.2c18693. Epub 2022 Dec 20. PMID: 36539930. 18: Vaccaro S, Rossetti A, Porrazzo A, Camero S, Cassandri M, Pomella S, Tomaciello M, Macioce G, Pedini F, Barillari G, Marchese C, Rota R, Cenci G, Tombolini M, Newman RA, Yang P, Codenotti S, Fanzani A, Megiorni F, Festuccia C, Minniti G, Gravina GL, Vulcano F, Milazzo L, Marampon F. The botanical drug PBI-05204, a supercritical CO2 extract of Nerium oleander, sensitizes alveolar and embryonal rhabdomyosarcoma to radiotherapy in vitro and in vivo. Front Pharmacol. 2022 Dec 1;13:1071176. doi: 10.3389/fphar.2022.1071176. PMID: 36532747; PMCID: PMC9751381. 19: Eid S, Zerbes T, Williams D, Wang X, Sackmann C, Meier S, Dulin NO, Nagorny P, Schmitt-Ulms G. Identification of a Cardiac Glycoside Exhibiting Favorable Brain Bioavailability and Potency for Reducing Levels of the Cellular Prion Protein. Int J Mol Sci. 2022 Nov 26;23(23):14823. doi: 10.3390/ijms232314823. PMID: 36499150; PMCID: PMC9736291. 20: Eroğlu Güneş C, Seçer Çelik F, Seçme M, Elmas L, Dodurga Y, Kurar E. Glycoside oleandrin downregulates toll-like receptor pathway genes and associated miRNAs in human melanoma cells. Gene. 2022 Nov 15;843:146805. doi: 10.1016/j.gene.2022.146805. Epub 2022 Aug 11. PMID: 35964872.