Etoposide

CHF 40.00
In stock
AG-CR1-3572-M02525 mgCHF 40.00
AG-CR1-3572-M100100 mgCHF 90.00
AG-CR1-3572-51005 x 100 mgCHF 380.00
More Information
Product Details
Synonyms VP-16-213; NSC 141540
Product Type Chemical
Properties
Formula

C29H32O13

MW 588.6
Merck Index 14: 3886
CAS 33419-42-0
RTECS KC0190000
Source/Host Chemicals Semisynthetic derivative of podophyllotoxin.
Purity Chemicals ≥98% (HPLC)
Appearance White to off-white powder.
Solubility Soluble in DMSO, ethanol, methanol or dimethylformamide.
InChi Key VJJPUSNTGOMMGY-MRVIYFEKSA-N
Smiles [H][C@]12COC(=O)[C@]1([H])[C@H](C1=CC(OC)=C(O)C(OC)=C1)C1=C(C=C3OCOC3=C1)[C@H]2O[C@]1([H])O[C@]2([H])CO[C@@H](C)O[C@@]2([H])[C@H](O)[C@H]1O
Shipping and Handling
Shipping AMBIENT
Short Term Storage +20°C
Long Term Storage +20°C
Handling Advice Protect from light and moisture.
Use/Stability Stable for at least 2 years after receipt when stored at +20°C.
Store solutions in DMSO at 4°C.
After reconstitution, prepare aliquots and store at -20°C.
Documents
MSDS Download PDF
Product Specification Sheet
Datasheet Download PDF
  • Potent anti-cancer compound. Induces apoptosis in normal and tumor cell lines [1, 5].
  • DNA Topoisomerase II activity inhibitor. Increases Topo II-mediated DNA breakage primarily by inhibiting the ability of the enzyme to religate cleaved nucleic acid molecules. Does not lead to immediate block of DNS synthesis, induces a progressive inhibition of DNA replication [2, 4, 6].
  • p53 activator [3].
  • Blocks the cell cycle between the end of the S phase and the early G2 phase [2, 8].
  • Oncoprotein Mdm2 synthesis inhibitor [7].
  • Apoptosis inducer through the cytochrome c/Apaf-1/caspase-9 pathway and the Fas-mediated death signaling pathway [9, 10].
  • Cell cycle checkpoint activator. Affects gene expression at different levels (chromatin remodeling, transcription and alternative splicing) [11, 14, 15].
  • Chemotherapeutic compound used in cancers [12, 13].
  • Used in conditioning regimen prior to a bone marrow or blood stem cell transplantation [16].
  • Highly effective in mobilizing stem cells [17]
Product References
  1. The podophyllotoxin derivatives VP16-213 and VM26: B.F. Issell; Cancer Chemother. Pharmacol. 7, 73 (1982)
  2. Topoisomerase-specific drug sensitivity in relation to cell cycle progression: K.C. Chow & W.E. Ross; Mol. Cell. Biol. 7, 3119 (1987)
  3. Increases in sequence specific DNA binding by p53 following treatment with chemotherapeutic and DNA damaging agents: R.B. Tishler, et al.; Cancer Res. 53, 2212 (1993)
  4. Topoisomerase II-etoposide interactions direct the formation of drug-induced enzyme-DNA cleavage complexes: D.A. Burden, et al.; J. Biol. Chem. 271, 29238 (1996)
  5. Cell death induced by topoisomerase-targeted drugs: more questions than answers: S.H. Kaufmann; Biochim. Biophys. Acta 1400, 195 (1998) (Review)
  6. Etoposide: four decades of development of a topoisomerase II inhibitor: K.R. Hande; Eur. J. Cancer 34, 1514 (1998) (Review)
  7. Differential regulation of p21waf-1/cip-1 and Mdm2 by etoposide: etoposide inhibits the p53-Mdm2 autoregulatory feedback loop: E.L. Arriola, et al.; Oncogene 18, 1081 (1999)
  8. Early caspase activation in leukemic cells subject to etoposide-induced G2-M arrest: evidence of commitment to apoptosis rather than mitotic cell death: R.J. Sleiman & B.W. Stewart; Clin. Cancer Res. 6, 3756 (2000)
  9. Ordering of ceramide formation, caspase activation, and Bax/Bcl-2 expression during etoposide-induced apoptosis in C6 glioma cells: M. Sawada, et al.; Cell Death Differ. 7, 761 (2000)
  10. Distinct pathways for stimulation of cytochrome c release by etoposide: J.D. Robertson, et al.; J. Biol. Chem. 275, 32438 (2000)
  11. Deacetylase activity associates with topoisomerase II and is necessary for etoposide-induced apoptosis: C.A. Johnson, et al.; J. Biol. Chem. 276, 4539 (2001)
  12. Etoposide: discovery and medicinal chemistry: P. Meresse, et al.; Curr. Med. Chem. 11, 2443 (2004) (Review)
  13. Etoposide, topoisomerase II and cancer: E.L. Baldwin & N. Osheroff; Curr. Med. Chem. Anticancer Agents 5, 363 (2005) (Review)
  14. The dispersal of replication proteins after Etoposide treatment requires the cooperation of Nbs1 with the ataxia telangiectasia Rad3-related/Chk1 pathway: R. Rossi, et al.; Cancer Res. 66, 1675 (2006)
  15. Cellular response to etoposide treatment: A. Montecucco & G. Biamonti; Cancer Lett. 252, 9 (2007) (Review)
  16. Chemomobilization with Etoposide is Highly Effective in Patients with Multiple Myeloma and Overcomes the Effects of Age and Prior Therapy: W.A. Wood, et al.; Biol. Blood Marrow. Transplant. 17, 141 (2011)
  17. The aging effect of chemotherapy on cultured human mesenchymal stem cells. S. Buttiglieri, et al.; Exp. Hematol. 39, 1171 (2011)
© 2017 Adipogen Life Sciences. Pictures: © 2012 Martin Oeggerli. All Rights Reserved.