ELLIPTICINE

Alkaloids

NP0014

519-23-3

ELLIPTICINE

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).

BRN 0221300; CCG-36483; CCRIS 2003; DB-052047; elliptecine; ellipticine; Elliptisine; K00071; LP00531; LS-133282; NSC 71795; NSC71795; NSC-71795; TCMDC-125546; VZ29809

246.31

C17H14N2

CC1=C2C(=C(C3=C1C=CN=C3)C)C4=CC=CC=C4N2

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

CTSPAMFJBXKSOY-UHFFFAOYSA-N

379.31°C (rough estimate)

316-318°C

0.98

1.257±0.06 g/cm3 (20°C 760 Torr)

DMSO: soluble

solid powder

Keep in dark place,Sealed in dry,2-8°C

White to Pale Yellow

ChEBI: A organic heterotetracyclic compound that is pyrido[4,3-b]carbazole carrying two methyl substituents at positions 5 and 11.

208-264-0

Solid

6.1(b)

T

13,3581

III

16.59±0.40(Predicted)

1.5794 (estimate)

UN 3462 6.1/PG 3

25

UU8825000

45

LD50 in mice (mg/kg): 19.5-22.4 i.v.; 178-204 orally (Rakieten)

3