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ProductsBack/Etoposide [33419-42-0]
Chemical Structure
Chemical Structure
Chemical Structure

Etoposide [33419-42-0]

Research Use Only
AG-CR1-3572
AdipoGen Life Sciences
CAS Number33419-42-0
DownloadMSDS
Product group Chemicals
Estimated Purity>98%
Molecular Weight588.6
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Overview

  • Supplier
    AdipoGen Life Sciences
  • Product Name
    Etoposide
  • Delivery Days Customer
    10
  • CAS Number
    33419-42-0
  • Certification
    Research Use Only
  • Estimated Purity
    >98%
  • Hazard Information
    Danger
  • Molecular Formula
    C29H32O13
  • Molecular Weight
    588.6
  • Scientific Description
    Chemical. CAS: 33419-42-0. Formula: C29H32O13. MW: 588.6. Semisynthetic derivative of podophyllotoxin. Potent anti-cancer compound. Induces apoptosis in normal and tumor cell lines. 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. p53 activator. Blocks the cell cycle between the end of the S phase and the early G2 phase. Oncoprotein Mdm2 synthesis inhibitor. Apoptosis inducer through the cytochrome c/Apaf-1/caspase-9 pathway and the Fas-mediated death signaling pathway. Cell cycle checkpoint activator. Affects gene expression at different levels (chromatin remodeling, transcription and alternative splicing). Chemotherapeutic compound used in cancers. Used in conditioning regimen prior to a bone marrow or blood stem cell transplantation. Highly effective in mobilizing stem cells - 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]
  • 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
  • Storage Instruction
    RT
  • UNSPSC
    12352200

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)