WARNING: This product is for research use only, not for human or veterinary use.
MedKoo CAT#: 406537
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 ).
MedKoo Cat#: 406537
Chemical Formula: C17H14N2
Exact Mass: 246.1157
Molecular Weight: 246.31
Elemental Analysis: C, 82.90; H, 5.73; N, 11.37
Synonym: CCG-36483; CCG36483; CCG 36483; DB-052047; K00071; LP00531; LS-133282; NSC 71795; NSC71795; NSC-71795; TCMDC-125546; VZ29809; Elliptecine; Ellipticine; Elliptisine.
IUPAC/Chemical Name: 5,11-dimethyl-6H-pyrido[4,3-b]carbazole
InChi Key: CTSPAMFJBXKSOY-UHFFFAOYSA-N
InChi Code: 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
SMILES Code: CC1=C(C=NC=C2)C2=C(C)C(N3)=C1C4=C3C=CC=C4
1: Savorani C, ManfÃ© V, Biskup E, Gniadecki R. Ellipticine Induces Apoptosis In T-cell Lymphoma Via Oxidative DNA Damage. Leuk Lymphoma. 2014 Jun 5:1-20. [Epub ahead of print] PubMed PMID: 24898668.
2: Stiborova M, Cerna V, Moserova M, Arlt VM, Frei E. The effect of benzo[a]pyrene on metabolic activation of anticancer drug ellipticine in mice. Neuro Endocrinol Lett. 2013;34 Suppl 2:43-54. PubMed PMID: 24362092.
3: Wang H, Yang L, Rempel GL. Preparation of pH-responsive polymer core-shell nanospheres for delivery of hydrophobic antineoplastic drug ellipticine. Macromol Biosci. 2014 Feb;14(2):166-72. doi: 10.1002/mabi.201300333. Epub 2013 Sep 16. PubMed PMID: 24106137.
4: Pandrangi SL, Chikati R, Chauhan PS, Kumar CS, Banarji A, Saxena S. Effects of ellipticine on ALDH1A1-expressing breast cancer stem cells--an in vitro and in silico study. Tumour Biol. 2014 Jan;35(1):723-37. doi: 10.1007/s13277-013-1099-y. Epub 2013 Aug 28. PubMed PMID: 23982874.
5: Masood F, Chen P, Yasin T, Fatima N, Hasan F, Hameed A. Encapsulation of Ellipticine in poly-(3-hydroxybutyrate-co-3-hydroxyvalerate) based nanoparticles and its in vitro application. Mater Sci Eng C Mater Biol Appl. 2013 Apr 1;33(3):1054-60. doi: 10.1016/j.msec.2012.11.025. Epub 2012 Nov 28. PubMed PMID: 23827542.
6: Ghosh S, Kar A, Chowdhury S, Dasgupta D. Ellipticine binds to a human telomere sequence: an additional mode of action as a putative anticancer agent? Biochemistry. 2013 Jun 18;52(24):4127-37. doi: 10.1021/bi400080t. Epub 2013 Jun 4. PubMed PMID: 23697684.
7: Stiborova M, Poljakova J, Eckschlager T, Kizek R, Frei E. Analysis of covalent ellipticine- and doxorubicin-derived adducts in DNA of neuroblastoma cells by the Â³Â²P-postlabeling technique. Biomed Pap Med Fac Univ Palacky Olomouc Czech Repub. 2012 Jun;156(2):115-21. doi: 10.5507/bp.2012.043. PubMed PMID: 22837132.
8: Wu Y, Sadatmousavi P, Wang R, Lu S, Yuan YF, Chen P. Self-assembling peptide-based nanoparticles enhance anticancer effect of ellipticine in vitro and in vivo. Int J Nanomedicine. 2012;7:3221-33. doi: 10.2147/IJN.S31858. Epub 2012 Jun 28. PubMed PMID: 22802684; PubMed Central PMCID: PMC3396387.
9: Poljakova J, Hrebackova J, Dvorakova M, Moserova M, Eckschlager T, Hrabeta J, GÃ¶ttlicherova M, Kopejtkova B, Frei E, Kizek R, Stiborova M. Anticancer agent ellipticine combined with histone deacetylase inhibitors, valproic acid and trichostatin A, is an effective DNA damage strategy in human neuroblastoma. Neuro Endocrinol Lett. 2011;32 Suppl 1:101-16. PubMed PMID: 22167207.
10: ProchÃ¡zka P, Libra A, ZemanovÃ¡ Z, HřebačkovÃ¡ J, PoljakovÃ¡ J, Hraběta J, Bunček M, StiborovÃ¡ M, Eckschlager T. Mechanisms of ellipticine-mediated resistance in UKF-NB-4 neuroblastoma cells. Cancer Sci. 2012 Feb;103(2):334-41. doi: 10.1111/j.1349-7006.2011.02137.x. Epub 2011 Nov 29. PubMed PMID: 22040216.