Ellipticine
featured

We are open as normal during COVID-19 pandemic. Order online, same day shipping out from North Carolina, USA

    WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 406537

CAS#: 519-23-3 (free base)

Description: Ellipticine is a DNA intercalating agent and a DNA topoisomerase II inhibitor. Ellipticine is an alkaloid first extracted from trees of the species Ochrosia elliptica and Rauvolfia sandwicensis,[5][6] which inhibits the enzyme topoisomerase II via intercalative binding to DNA. Ellipticine is a known intercalator, capable of entering a DNA strand between base pairs. In its intercalated state, ellipticine binds strongly[9] and lies parallel to the base pairs, increasing the superhelical density of the DNA. Intercalated ellipticine binds directly to topoisomerase II, an enzyme involved in DNA replication, inhibiting the enzyme and resulting in powerful antitumour activity.


Price and Availability

Size Price Shipping out time Quantity
10mg USD 80 Same day
25mg USD 150 Same day
50mg USD 250 Same day
100mg USD 450 Same day
200mg USD 750 Same day
500mg USD 1650 Same day
1g USD 2850 2 weeks
2g USD 4450 2 weeks
5g USD 6950 2 weeks
Inquire bulk and customized quantity

Pricing updated 2020-10-27. Prices are subject to change without notice.

Ellipticine, purity > 98%, is in stock. The same day shipping out after order is received.


Chemical Structure

img

Theoretical Analysis

MedKoo Cat#: 406537
Name: Ellipticine
CAS#: 519-23-3 (free base)
Chemical Formula: C17H14N2
Exact Mass: 246.1157
Molecular Weight: 246.31
Elemental Analysis: C, 82.90; H, 5.73; N, 11.37


Related CAS #: 519-23-3 (free base)   5081-48-1 (HCl)    

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


Technical Data

Appearance:
Yellow solid powder

Purity:
>98% (or refer to the Certificate of Analysis)

Certificate of Analysis:

Safety Data Sheet (SDS):

Shipping Condition:
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition:
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility:
Soluble in DMSO, not in water

Shelf Life:
>2 years if stored properly

Drug Formulation:
This drug may be formulated in DMSO

Stock Solution Storage:
0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code:
2934.99.9001


Additional Information

  
 
 
 


References

1: Lu H, Liu M, Lu W, Wang C, Wang G, Dong W, Wang X, Chen H, Tan C. Repurposing Ellipticine Hydrochloride to Combat Colistin-Resistant Extraintestinal Pathogenic E. coli (ExPEC). Front Microbiol. 2020 May 25;11:806. doi: 10.3389/fmicb.2020.00806. PMID: 32528422; PMCID: PMC7262907.

2: Costa de Oliveira R, Soares Pontes G, Kostyuk A, Coutinho Camargo GB, Dhyani A, Shvydenko T, Shvydenko K, Grafov A. Anticancer and Immunomodulatory Activities of a Novel Water-Soluble Derivative of Ellipticine. Molecules. 2020 May 1;25(9):2130. doi: 10.3390/molecules25092130. PMID: 32370100; PMCID: PMC7248987.

3: Li X, Ye C, Mulati M, Sun L, Qian F. Ellipticine blocks synergistic effects of IL-17A and TNF-α in epithelial cells and alleviates severe acute pancreatitis-associated acute lung injury. Biochem Pharmacol. 2020 Jul;177:113992. doi: 10.1016/j.bcp.2020.113992. Epub 2020 Apr 23. PMID: 32335141.

4: Zencir S, Hsieh MH, Hsu JS, Ergun Y, Chou GL, Li TK, Teng SC, Topcu Z. Selected ellipticine derivatives, known to target topoisomerase II, suppress the alternative lengthening of telomere (ALT) pathway in telomerase-negative cells. J Cancer Res Clin Oncol. 2020 Jul;146(7):1671-1676. doi: 10.1007/s00432-020-03213-x. Epub 2020 Apr 24. PMID: 32333143.

5: Márquez E, Mora JR, Flores-Morales V, Insuasty D, Calle L. Modeling the Antileukemia Activity of Ellipticine-Related Compounds: QSAR and Molecular Docking Study. Molecules. 2019 Dec 19;25(1):24. doi: 10.3390/molecules25010024. PMID: 31861689; PMCID: PMC6982814.

6: Tian LX, Li XY, Tang X, Zhou XY, Luo L, Ma XY, Tang WQ, Yu J, Ma W, Yang X, Yan J, Xu X, Liang HP. Ellipticine Conveys Protective Effects to Lipopolysaccharide-Activated Macrophages by Targeting the JNK/AP-1 Signaling Pathway. Inflammation. 2020 Feb;43(1):231-240. doi: 10.1007/s10753-019-01112-z. PMID: 31802382.

7: Dan VM, Varghese TS, Viswanathan G, Baby S. Ellipticine, its Derivatives: Re- evaluation of Clinical Suitability with the Aid of Drug Delivery Systems. Curr Cancer Drug Targets. 2020;20(1):33-46. doi: 10.2174/1568009619666190927150131. PMID: 31560288.

8: Dilek Ö, Patir S, Tilki T, Ertürk E. Total Synthesis of Olivacine and Ellipticine via a Lactone Ring-Opening and Aromatization Cascade. J Org Chem. 2019 Jun 21;84(12):7901-7916. doi: 10.1021/acs.joc.9b00706. Epub 2019 Jun 5. PMID: 31117560.

9: Lin J, Tang M, Zhao R, Du Q, Shen L, Du G, Zhang Y, Li Y, Pan X. Synthetic Optimization of Ellipticine and Antitumor Activity of Novel Hexacyclic Derivatives of Ellipticine. Curr Pharm Des. 2019;25(33):3578-3589. doi: 10.2174/1381612825666190404122650. PMID: 30947658.

10: Indra R, Černá T, Heger Z, Hraběta J, Wilhelm M, Dostálová S, Lengálová A, Martínková M, Adam V, Eckschlager T, Schmeiser HH, Arlt VM, Stiborová M. Ellipticine-loaded apoferritin nanocarrier retains DNA adduct-based cytochrome P450-facilitated toxicity in neuroblastoma cells. Toxicology. 2019 May 1;419:40-54. doi: 10.1016/j.tox.2019.03.009. Epub 2019 Mar 23. PMID: 30914192.

11: Kolarik M, Indra R, Adam V, Heger Z, Kopeckova K, Arlt VM, Stiborova M. Tyrosine kinase inhibitors vandetanib, lenvatinib and cabozantinib modulate oxidation of an anticancer agent ellipticine catalyzed by cytochromes P450 in vitro. Neuro Endocrinol Lett. 2019 Feb;39(7):515-524. PMID: 30860683.

12: Reed L, Indra R, Mrizova I, Moserova M, Schmeiser HH, Wolf CR, Henderson CJ, Stiborova M, Phillips DH, Arlt VM. Application of hepatic cytochrome b5/P450 reductase null (HBRN) mice to study the role of cytochrome b5 in the cytochrome P450-mediated bioactivation of the anticancer drug ellipticine. Toxicol Appl Pharmacol. 2019 Mar 1;366:64-74. doi: 10.1016/j.taap.2019.01.020. Epub 2019 Jan 25. PMID: 30685480; PMCID: PMC6382462.

13: Zsila F, Samsonov SA. Molecular interactions of the anticancer agent ellipticine with glycosaminoglycans by in silico analysis. Carbohydr Res. 2018 Jun 15;462:28-33. doi: 10.1016/j.carres.2018.03.014. Epub 2018 Apr 3. PMID: 29655053.

14: Cerna T, Hrabeta J, Eckschlager T, Frei E, Schmeiser HH, Arlt VM, Stiborová M. The Histone Deacetylase Inhibitor Valproic Acid Exerts a Synergistic Cytotoxicity with the DNA-Damaging Drug Ellipticine in Neuroblastoma Cells. Int J Mol Sci. 2018 Jan 5;19(1):164. doi: 10.3390/ijms19010164. PMID: 29304031; PMCID: PMC5796113.

15: Stiborová M, Indra R, Frei E, Kopečková K, Schmeiser HH, Eckschlager T, Adam V, Heger Z, Arlt VM, Martínek V. Cytochrome b5 plays a dual role in the reaction cycle of cytochrome P450 3A4 during oxidation of the anticancer drug ellipticine. Monatsh Chem. 2017;148(11):1983-1991. doi: 10.1007/s00706-017-1986-9. Epub 2017 Jul 4. PMID: 29104319; PMCID: PMC5653753.

16: Wen HL, Yang G, Dong QR. Ellipticine inhibits the proliferation and induces apoptosis in rheumatoid arthritis fibroblast-like synoviocytes via the STAT3 pathway. Immunopharmacol Immunotoxicol. 2017 Aug;39(4):219-224. doi: 10.1080/08923973.2017.1327963. Epub 2017 May 30. PMID: 28555524.

17: Kumarasamy VM, Sun D. Demonstration of a potent RET transcriptional inhibitor for the treatment of medullary thyroid carcinoma based on an ellipticine derivative. Int J Oncol. 2017 Jul;51(1):145-157. doi: 10.3892/ijo.2017.3994. Epub 2017 May 11. PMID: 28498409; PMCID: PMC5467785.

18: Nishiyama T, Hatae N, Mizutani M, Yoshimura T, Kitamura T, Miyano M, Fujii M, Satsuki N, Ishikura M, Hibino S, Choshi T. Concise synthesis and antiproliferative activity evaluation of ellipticine quinone and its analogs. Eur J Med Chem. 2017 Aug 18;136:1-13. doi: 10.1016/j.ejmech.2017.04.071. Epub 2017 Apr 28. PMID: 28477443.

19: Sulc M, Mrizova I, Cerna T, Frei E, Eckschlager T, Adam V, Kopeckova K, Stiborova M. Effectiveness of human cytochrome P450 3A4 present in liposomal and microsomal nanoparticles in formation of covalent DNA adducts by ellipticine. Neuro Endocrinol Lett. 2016 Dec 18;37(Suppl1):95-102. PMID: 28263536.

20: Tao S, Meng S, Zheng X, Xie L. ATM participates in the regulation of viability and cell cycle via ellipticine in bladder cancer. Mol Med Rep. 2017 Mar;15(3):1143-1148. doi: 10.3892/mmr.2017.6141. Epub 2017 Jan 24. PMID: 28138703; PMCID: PMC5367361.