Etoposide (VP-16)Inhibits DNA synthesis via topoisomerase II inhibition

Etoposide (VP-16) (CAS 33419-42-0)

Etoposide (VP-16) | CAS 33419-42-0 is rated 5.0 out of 5 by 1.
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Application: Inhibits DNA synthesis via topoisomerase II inhibition
CAS Number: 33419-42-0
Purity: ≥99%
Molecular Weight: 588.6
Molecular Formula: C29H32O13
* Refer to Certificate of Analysis for lot specific data (including water content).
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Etoposide (VP-16) is a Topo II (topoisomerase II) inhibitor that is widely used as an apoptosis inducer. Etoposide exhibits antineoplastic and anti-mitotic properties, as well as, inhibits DNA synthesis and induces double-strand and single-strand DNA breaks. Etoposide is cell-cycle dependent and cell-cycle specific to late S and G2 phases, activates p53, resulting in upregulated expression of TRAIL-R2 (DR5) and Bak to overcome TRAIL resistance in Bax-deficient human colon carcinoma cancer cells. Etoposide (VP-16) is an inhibitor of NCoA-3.


References

1. Fearnhead, H.O., et al. 1994. Biochem. Pharmacol. 48: 1073-1079. PMID: 7945400
2. de Jong, R.S., et al. 1995. Anticancer Res. 15: 2319-2330. PMID: 8572646
3. Hainsworth, J.D. and Greco, F.A. 1995. Ann. Oncol. 6: 325-341. PMID: 7619747

Usage :
Store solutions in DMSO at 4°C. For long term storage prepare aliquots and store at -20°C.
Physical State :
Solid
Solubility :
Soluble in DMSO (30 mg/ml), dimethyl formamide, ethyl ether, chloroform:methanol (1:1), methanol (slightly), acetone (slightly), water (<1 mg/ml) at 25° C, and ethanol (<1 mg/ml) at 25° C.
Storage :
Store at room temperature
Melting Point :
236-251° C (lit.)
Boiling Point :
~798.1° C at 760 mmHg (Predicted)
Density :
1.56 g/cm3 (Predicted)
Refractive Index :
n20D 1.66 (Predicted)
Optical Activity :
α20/D -110.5°, c = 0.6 in chloroform
IC50 :
Topoisomerase II: IC50 = 59.2 µM; Topoisomerase II: IC50 = 0.81 µM (HeLa cell ); KB cells: IC50 = 1.1 µM (human); DNA topoisomerase II alpha: IC50 = 75700 nM (Homo sapiens); MCF7 (Breast carcinoma cells): IC50 = 100000 nM (Homo sapiens)
pK Values :
pKa: 9.8
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
WGK Germany :
3
RTECS :
KC0190000
PubChem CID :
36462
Merck Index :
14: 3886
MDL Number :
MFCD00869325
EC Number :
251-509-1
SMILES :
C[C@@H]1OC[C@@H]2[C@@H](O1)[C@@H]([C@H]([C@@H](O2)O[C@H]3[C@H]4COC(=O)[C@@H]4[C@@H](C5=CC6=C(C=C35)OCO6)C7=CC(=C(C(=C7)OC)O)OC)O)O

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Etoposide (VP-16)  Product Citations

See how others have used Etoposide (VP-16). Click on the entry to view the PubMed entry .

Citations 1 to 10 of 26 total

PMID: # 28420874  Özeş, AR. et al. 2017. Sci Rep. 7: 894.

PMID: # 28339648  Pendergraft, SS. et al. 2017. Biol. Reprod. 96: 720-732.

PMID: # 28379541  Aslani, F. et al. 2017. Mol. Hum. Reprod. 23: 370-380.

PMID: # 28942258  Hercog, K. et al. 2017. Chemosphere. 189: 319-329.

PMID: # 29100012  Zhou, W. et al. 2017. Cell Stem Cell. 21: 591-603.e4.

PMID: # 27248664  Ambati, SR. et al. 2016. Oncotarget. 7: 43062-43075.

PMID: # 27814544  Isidori, M. et al. 2016. Environ. Pollut. 219: 275-287.

PMID: # 26971211  Ferre-Aracil, J. et al. 2016. The Science of the total environment. 556: 70-9.

PMID: # 27852435  Lopez-Mosqueda, J. et al. 2016. Elife. 5:

PMID: # 26201655  Kovács, R. et al. 2015. Environmental science and pollution research international.

Citations 1 to 10 of 26 total
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Rated 5 out of 5 by from An increase in the expression of phosphorylated An increase in the expression of phosphorylated p53 was observed by WB when comparing untreated MCF cells with those that have been treated with Etoposide. -SCBT QC
Date published: 2015-04-23
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