EllipticineA DNA intercalating inhibitor of Topo II

Ellipticine (CAS 519-23-3)

Ellipticine | CAS 519-23-3 is rated 5.0 out of 5 by 1.
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Application: A DNA intercalating inhibitor of Topo II
CAS Number: 519-23-3
Purity: ≥98%
Molecular Weight: 246.31
Molecular Formula: C17H14N2
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* Refer to Certificate of Analysis for lot specific data (including water content).
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Ellipticine is a polyaromatic small molecule DNA intercalator, demonstrated to inhibit Topo II (DNA topoisomerase II) and to form covalent adducts with DNA. The formation of Ellipticine-DNA adducts is correlated to cytotoxicity and these adducts are suggested to interfere with DNA replication in the S phase. Antineoplastic effects are demonstrated with Ellipticine. Processing of Ellipticine by cytochrome p450 produces the adduct forming metabolites 13- and 12-hydroxyellipticine, and Ellipticine is described to inhibit cytochrome p450 CYP1A1 activity. Ellipticine was also shown to block p53 protein phosphorylation.


References

1. Froelich-Ammon, S.J., et al. 1995. J. Biol. Chem. 270: 14998-15004. PMID: 7797481
2. Ohashi, M., et al. 1995. Jpn. J. Cancer Res. 86: 819-827. PMID: 7591958
3. Chang, C.Y. and Puga, A. 1998. Mol. Cell. Biol. 18: 525-535. PMID: 9418899
4. Poljaková, J., et al. 2009. Biochem. Pharmacol. 77: 1466-1479. PMID: 19426684

Appearance :
Bright yellow solid
Physical State :
Solid
Solubility :
Soluble in DMSO, ethanol, and methanol. Insoluble in water.
Storage :
Store at 4° C
Melting Point :
174.19° C (Predicted)
Boiling Point :
~495.4° C at 760 mmHg (Predicted)
Density :
~1.3 g/cm3 (Predicted)
Refractive Index :
n20D 1.78
IC50 :
Breast carcinoma cells: IC50 = 0.1 µg/mL (Homo sapiens); Vero (Kidney cells): IC50 = 0.2 µg/mL (Chlorocebus aethiops); HIV-1: IC50 = 30.1 µM
pK Values :
pKb: 7.03
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
WGK Germany :
3
RTECS :
UU8825000
PubChem CID :
3213
Merck Index :
14: 3548
MDL Number :
MFCD00010524
EC Number :
208-264-0
Beilstein Registry :
221300
SMILES :
CC1=C2C(=C(C3=C1C=CN=C3)C)C4=CC=CC=C4N2

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Ellipticine  Product Citations

See how others have used Ellipticine. Click on the entry to view the PubMed entry .

Citations 1 to 3 of 3 total

PMID: # 28623690  Siebert, MN. et al. 2017. Aquat. Toxicol. 189: 142-149.

PMID: # 27769881  Siebert, MN. et al. 2017. Comp. Biochem. Physiol. B, Biochem. Mol. Biol. 203: 115-121.

PMID: # 28555524  Wen, HL. et al. 2017. Immunopharmacol Immunotoxicol. 39: 219-224.

Citations 1 to 3 of 3 total
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Rated 5 out of 5 by from Poljakova et al Poljakova et al. (PubMed ID 19426684) found that ellipticine, an antineoplastic agent, formed covalent DNA adducts that conferred cytotoxicity to neurobalstoma cells.
Date published: 2015-07-03
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