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324688

Sigma-Aldrich

Ellipticine

A cell-permeable antitumor alkaloid that acts as an inhibitor of topoisomerase II and acts as an intercalative agent that stimulates topoisomerase II-mediated DNA breakage.

Synonym(s):

Ellipticine, 5,11-Dimethyl-6H-pyrido[4,3-b]carbazole

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About This Item

Empirical Formula (Hill Notation):
C17H14N2
CAS Number:
519-23-3
Molecular Weight:
246.31
UNSPSC Code:
12352200
NACRES:
NA.77

Quality Level

100

Assay

≥99% (HPLC)

form

solid

manufacturer/tradename

Calbiochem®

storage condition

OK to freeze

color

bright yellow

solubility

ethanol: 1 mg/mL
DMSO: 5 mg/mL

shipped in

ambient

storage temp.

2-8°C

InChI

1S/C17H14N2/c1-10-14-9-18-8-7-12(14)11(2)17-16(10)13-5-3-4-6-15(13)19-17/h3-9,19H,1-2H3

InChI key

CTSPAMFJBXKSOY-UHFFFAOYSA-N

General description

A cell-permeable antitumor alkaloid that acts as an inhibitor of topoisomerase II and acts as an intercalative agent that stimulates topoisomerase II-mediated DNA breakage. Is also capable of uncoupling mitochondrial oxidative phosphorylation.
A topoisomerase II inhibitor. Acts as an intercalative alkaloid that stimulates topoisomerase II-mediated DNA breakage. Is also capable of uncoupling mitochondrial oxidative phosphorylation.

Biochem/physiol Actions

Cell permeable: yes
Primary Target
topoisomerase 2
Product does not compete with ATP.
Reversible: no

Warning

Toxicity: Toxic & Carcinogenic / Teratogenic (G)

Reconstitution

Following reconstitution, aliquot and freeze (-20°C). Stock solutions are stable for up to 3 months at -20°C.

Other Notes

Due to the nature of the Hazardous Materials in this shipment, additional shipping charges may be applied to your order. Certain sizes may be exempt from the additional hazardous materials shipping charges. Please contact your local sales office for more information regarding these charges.
Froelich-Ammon, S.J., et al. 1995. J. Biol. Chem. 270, 14998.
Schwaller, M.A., et al. 1995. J. Biol. Chem.270, 22709.
Pommier, Y., et al. 1985. Biochemistry24, 6406.

Legal Information

CALBIOCHEM is a registered trademark of Merck KGaA, Darmstadt, Germany

Pictograms

Skull and crossbones
GHS06

Signal Word

Danger

Hazard Statements

H301

Hazard Classifications

Acute Tox. 3 Oral

Storage Class Code

6.1C - Combustible, acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK

WGK 3

Certificates of Analysis (COA)

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M A Schwaller et al.
The Journal of biological chemistry, 270(39), 22709-22713 (1995-09-29)
Ellipticine is an antitumor alkaloid capable of uncoupling mitochondrial oxidative phosphorylation. It behaves as a lipophilic weak base with pK = 7.40. We have investigated its molecular mode of action using several of its isomers with pK ranging between 5.8
S J Froelich-Ammon et al.
The Journal of biological chemistry, 270(25), 14998-15004 (1995-06-23)
Although a number of drugs currently in use for the treatment of human cancers act by stimulating topoisomerase II-mediated DNA breakage, little is known regarding interactions between these agents and the enzyme. To further define the mechanism of drug action
Y Pommier et al.
Biochemistry, 24(23), 6406-6410 (1985-11-05)
Intercalator-induced DNA double-strand breaks (DSB) presumably represent topoisomerase II DNA cleavage sites in mammalian cells. Isolated L1210 cell nuclei were used to determine the saturability of this reaction at high drug concentrations. 4'-(9-Acridinylamino)methanesulfon-m-anisidide (m-AMSA) and 5-iminodaunorubicin (5-ID) both produced DSB

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