ELLIPTICINE

For Research Use Only.
Category
Alkaloids
Cat.No.
NP0014
CAS
519-23-3
Product Name
ELLIPTICINE
Structure

Product Details

Description
Ellipticine is a DNA intercalating agent and a DNA topoisomerase II inhibitor. Ellipticine is also a natural product, isolated in 1959 from the Australian evergreen tree of the Apocynaceae family. Ellipticine was found to be an extremely promising anticancer drug. The planar polycyclic structure was found to interact with DNA through intercalation, exhibiting a high DNA binding affinity (10(6) M(-1)). The presence of protonatable ring nitrogens distinguished ellipticine from other simple intercalators. Both monocationic and uncharged species were found to be present under physiological conditions. The positive charge stabilized the binding of ellipticine to nucleic acids, while the more lipophilic uncharged compound was shown to readily penetrate membrane barriers. The structural nature of these compounds offers a plausible basis for the implication of multiple modes of action, including DNA binding, interactions with membrane barriers, oxidative bioactivation and modification of enzyme function; most notably that of topoisomerase II and telomerase. (Curr Med Chem Anticancer Agents. 2004 Mar;4(2):149-72).
Synonyms
BRN 0221300; CCG-36483; CCRIS 2003; DB-052047; elliptecine; ellipticine; Elliptisine; K00071; LP00531; LS-133282; NSC 71795; NSC71795; NSC-71795; TCMDC-125546; VZ29809
Molecular Weight
246.31
Molecular Formula
C17H14N2
Canonical SMILES
CC1=C2C(=C(C3=C1C=CN=C3)C)C4=CC=CC=C4N2
InChI
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
InChIKey
CTSPAMFJBXKSOY-UHFFFAOYSA-N
Boiling Point
379.31°C (rough estimate)
Melting Point
316-318°C
Purity
0.98
Density
1.257±0.06 g/cm3 (20°C 760 Torr)
Solubility
DMSO: soluble
Appearance
solid powder
Storage
Keep in dark place,Sealed in dry,2-8°C
Color
White to Pale Yellow
Definition
ChEBI: A organic heterotetracyclic compound that is pyrido[4,3-b]carbazole carrying two methyl substituents at positions 5 and 11.
EINECS
208-264-0
Form
Solid
Hazard Class
6.1(b)
Hazard Codes
T
Merck
13,3581
Packing Groups
III
pKa
16.59±0.40(Predicted)
Refractive Index
1.5794 (estimate)
RIDADR
UN 3462 6.1/PG 3
Risk Statements
25
RTECS
UU8825000
Safety Statements
45
Toxicity
LD50 in mice (mg/kg): 19.5-22.4 i.v.; 178-204 orally (Rakieten)
WGK Germany
3
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