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AdipoGen Life Sciences
Etoposide
30
CHF
CHF 30.00
In stock
AG-CR1-3572-M02525 mgCHF 30.00
AG-CR1-3572-M100100 mgCHF 70.00
AG-CR1-3572-51005 x 100 mgCHF 280.00
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 |
Description
- 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
- The podophyllotoxin derivatives VP16-213 and VM26: B.F. Issell; Cancer Chemother. Pharmacol. 7, 73 (1982)
- Topoisomerase-specific drug sensitivity in relation to cell cycle progression: K.C. Chow & W.E. Ross; Mol. Cell. Biol. 7, 3119 (1987)
- 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)
- 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)
- Cell death induced by topoisomerase-targeted drugs: more questions than answers: S.H. Kaufmann; Biochim. Biophys. Acta 1400, 195 (1998) (Review)
- Etoposide: four decades of development of a topoisomerase II inhibitor: K.R. Hande; Eur. J. Cancer 34, 1514 (1998) (Review)
- 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)
- 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)
- 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)
- Distinct pathways for stimulation of cytochrome c release by etoposide: J.D. Robertson, et al.; J. Biol. Chem. 275, 32438 (2000)
- Deacetylase activity associates with topoisomerase II and is necessary for etoposide-induced apoptosis: C.A. Johnson, et al.; J. Biol. Chem. 276, 4539 (2001)
- Etoposide: discovery and medicinal chemistry: P. Meresse, et al.; Curr. Med. Chem. 11, 2443 (2004) (Review)
- Etoposide, topoisomerase II and cancer: E.L. Baldwin & N. Osheroff; Curr. Med. Chem. Anticancer Agents 5, 363 (2005) (Review)
- 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)
- Cellular response to etoposide treatment: A. Montecucco & G. Biamonti; Cancer Lett. 252, 9 (2007) (Review)
- 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)
- The aging effect of chemotherapy on cultured human mesenchymal stem cells. S. Buttiglieri, et al.; Exp. Hematol. 39, 1171 (2011)