Etoposide

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Cat.No. 1226 - Etoposide | C29H32O13 | CAS No. 33419-42-0
Description: Topoisomerase II inhibitor
Chemical Name: [5R-[5α,5aβ,8aα,9β(R*)]]-9-[(4,6-Ο-Ethylidene-β-D-glucopyranosyl)oxy]-5,8,8a,9-tetrahydro-5-(4-hydroxy-3,5-dimethoxyphenyl)furo[3',4':6,7]naphtho[2,3-d]-1,3-dioxol-6-(5aH)-one
Purity: ≥99% (HPLC)
Datasheet
Citations (4)
Reviews (1)
Literature

Biological Activity

Topoisomerase II inhibitor (IC50 = 59.2 μM).

Compound Libraries

Etoposide is also offered as part of the Tocriscreen Plus and Tocriscreen Library of FDA-Approved Compounds. Find out more about compound libraries available from Tocris.

Technical Data

M. Wt 588.56
Formula C29H32O13
Storage Store at RT
Purity ≥99% (HPLC)
CAS Number 33419-42-0
PubChem ID 36462
InChI Key VJJPUSNTGOMMGY-MRVIYFEKSA-N
Smiles OC(C(OC)=C3)=C(OC)C=[C@@]3[C@@H]2C1=CC6=C(OCO6)C=C1[C@@H](O[C@]4([H])O[C@@](CO[C@@H](C)O7)([H])[C@]7([H])[C@H](O)[C@H]4O)[C@@H]5[C@@H]2[C@](OC5)=O

The technical data provided above is for guidance only. For batch specific data refer to the Certificate of Analysis.

Tocris products are intended for laboratory research use only, unless stated otherwise.

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 58.86 100

Preparing Stock Solutions

The following data is based on the product molecular weight 588.56. 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 1.7 mL 8.5 mL 16.99 mL
5 mM 0.34 mL 1.7 mL 3.4 mL
10 mM 0.17 mL 0.85 mL 1.7 mL
50 mM 0.03 mL 0.17 mL 0.34 mL

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Product Datasheets

Certificate of Analysis / Product Datasheet
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References

References are publications that support the biological activity of the product.

Burden et al (1996) Toposiomerase II.etoposide interactions direct the formation of drug-induced enzyme-DNA cleavage complexes. J.Biol.Chem. 271 29238 PMID: 8910583

Hande et al (1998) Etoposide: four decades of development of a topoisomerase II inhibitor. Eur.J.Cancer 34 1514 PMID: 9893622

Terada et al (1993) Antitumor agents.3.Synthesis and biological activity of 4β-alkyl derivatives containing hydroxy, amino, and amido groups of 4'-O-demethyl-4-desoxypodophyllotoxin as antitumor agents. J.Med.Chem. 36 1689 PMID: 8389875


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Keywords: Etoposide, Etoposide supplier, Topoisomerase, II, inhibitors, inhibits, DNA, Isomerases, VP16, chemotherapeutics, 1226, Tocris Bioscience

⚠ WARNING: This product can expose you to chemicals including Etoposide, which is known to the State of California to cause cancer. For more information, go to www.P65Warnings.ca.gov

4 Citations for Etoposide

Citations are publications that use Tocris products. Selected citations for Etoposide include:

Long et al (2019) Novel peptide dermaseptin-PS1 exhibits anticancer activity via induction of intrinsic apoptosis signalling. J Cell Mol Med 23 1300 PMID: 30461197

Maswadeh et al (2015) Etoposide incorporated into camel milk phospholipids liposomes shows increased activity against fibrosarcoma in a mouse model. Eur J Cancer 2015 743051 PMID: 25821817

Nicolson (2014) Recombinant adeno-associated virus utilizes host cell nuclear import machinery to enter the nucleus. J Virol 88 4132 PMID: 24478436

Li et al (2013) Transmembrane Protein 214 (TMEM214) mediates endoplasmic reticulum stress-induced caspase 4 enzyme activation and apoptosis. J Biol Chem 288 17908 PMID: 23661706


Do you know of a great paper that uses Etoposide from Tocris? Please let us know.

Reviews for Etoposide

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Etoposide inhibits growth of melanoma cell line at micromolar concentrations.
By Anonymous on 02/07/2019
Assay Type: In Vitro
Species: Human
Cell Line/Tissue: SK-MEL-28

Used for killing assay for in vitro cell culture. Cells were cultured for 24 hours before the addition of the compound into the media at low micromolar concentrations (indicated by the arrow).

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Literature in this Area

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Cancer

Cancer Research Product Guide

A collection of over 750 products for cancer research, the guide includes research tools for the study of:

  • Cancer Metabolism
  • Epigenetics in Cancer
  • Receptor Signaling
  • Cell Cycle and DNA Damage Repair
  • Angiogenesis
  • Invasion and Metastasis
Cell Cycle & DNA Damage Repair

Cell Cycle & DNA Damage Repair Poster

In normal cells, each stage of the cell cycle is tightly regulated, however in cancer cells many genes and proteins that are involved in the regulation of the cell cycle are mutated or over expressed. Adapted from the 2015 Cancer Product Guide, Edition 3, this poster summarizes the stages of the cell cycle and DNA repair. It also highlights strategies for enhancing replicative stress in cancer cells to force mitotic catastrophe and cell death.