Ellipticine
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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.


Chemical Structure

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

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

Price and Availability

Size Price Availability Quantity
10.0mg USD 80.0 Same day
25.0mg USD 150.0 Same day
50.0mg USD 250.0 Same day
100.0mg USD 450.0 Same day
200.0mg USD 750.0 Same day
500.0mg USD 1650.0 Same day
1.0g USD 2850.0 2 weeks
2.0g USD 4450.0 2 weeks
5.0g USD 6950.0 2 weeks
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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

Appearance: Yellow solid powder

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

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

Biological target: Ellipticine (NSC 71795) is an antineoplastic agent which inhibits DNA topoisomerase II activities.
In vitro activity: Ellipticine treatment significantly inhibited the viability and proliferation of RA-FLSs (rheumatoid arthritis fibroblast-like synoviocytes) in a concentration-dependent manner. In contrast, ellipticine exposure did not alter the viability of normal human FLSs. Moreover, ellipticine triggered significant apoptosis and increased caspase-3 activity in RA-FLSs. Mechanistically, ellipticine reduced the phosphorylation of STAT3 and downregulated the expression of Mcl-1, cyclin D1 and Bcl-2. Luciferase reporter assay demonstrated that ellipticine treatment led to a significant inhibition of STAT3-mediated transcriptional activity in RA-FLSs. Overexpression of constitutively active STAT3 reversed the suppressive effects of ellipticine on RA-FLSs, which was accompanied by restoration of Mcl-1, cyclin D1 and Bcl-2. Reference: Immunopharmacol Immunotoxicol. 2017 Aug;39(4):219-224. https://www.tandfonline.com/doi/abs/10.1080/08923973.2017.1327963?journalCode=iipi20
In vivo activity: The capacity of ellipticine to form DNA adducts was investigated in vivo. Male Wistar rats were treated with ellipticine, and DNA from various organs was analyzed by (32)P postlabeling. Ellipticine-specific DNA adduct patterns were detected in most test organs. The highest level of DNA adducts was found in liver (19.7 adducts per 10(7) nucleotides), followed by spleen, lung, kidney, heart and brain. One major and one minor ellipticine-DNA adducts were found in DNA of all these organs of rats exposed to ellipticine. The predominant adduct formed in rat tissues in vivo was identical to the deoxyguanosine adduct generated in DNA by ellipticine in vitro as shown by cochromatography in 2 independent systems. Correlation studies showed that the formation of this major DNA adduct in vivo is mediated by CYP3A1- and CYP1A-dependent reactions. The results show the formation of CYP-mediated covalent DNA adducts by ellipticine in vivo and confirm the formation of covalent DNA adducts as a new mode of ellipticine action. Reference: Int J Cancer. 2003 Dec 20;107(6):885-90. https://onlinelibrary.wiley.com/doi/full/10.1002/ijc.11511

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO:PBS (pH 7.2) (1:3) 0.25 1.01
DMF 10.0 40.6
Ethanol 1.0 4.06

Preparing Stock Solutions

The following data is based on the product molecular weight 246.31 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol: 1. 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. 2. Chen Q, Liu J, Zhuang Y, Bai LP, Yuan Q, Zheng S, Liao K, Khan MA, Wu Q, Luo C, Liu L, Wang H, Li T. Identification of an IKKβ inhibitor for inhibition of inflammation in vivo and in vitro. Pharmacol Res. 2019 Nov;149:104440. doi: 10.1016/j.phrs.2019.104440. Epub 2019 Aug 31. PMID: 31479750. 3. Stiborová M, Breuer A, Aimová D, Stiborová-Rupertová M, Wiessler M, Frei E. DNA adduct formation by the anticancer drug ellipticine in rats determined by 32P postlabeling. Int J Cancer. 2003 Dec 20;107(6):885-90. doi: 10.1002/ijc.11511. PMID: 14601046.
In vitro protocol: 1. 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. 2. Chen Q, Liu J, Zhuang Y, Bai LP, Yuan Q, Zheng S, Liao K, Khan MA, Wu Q, Luo C, Liu L, Wang H, Li T. Identification of an IKKβ inhibitor for inhibition of inflammation in vivo and in vitro. Pharmacol Res. 2019 Nov;149:104440. doi: 10.1016/j.phrs.2019.104440. Epub 2019 Aug 31. PMID: 31479750.
In vivo protocol: 1. Stiborová M, Breuer A, Aimová D, Stiborová-Rupertová M, Wiessler M, Frei E. DNA adduct formation by the anticancer drug ellipticine in rats determined by 32P postlabeling. Int J Cancer. 2003 Dec 20;107(6):885-90. doi: 10.1002/ijc.11511. PMID: 14601046. 2. Chen Q, Liu J, Zhuang Y, Bai LP, Yuan Q, Zheng S, Liao K, Khan MA, Wu Q, Luo C, Liu L, Wang H, Li T. Identification of an IKKβ inhibitor for inhibition of inflammation in vivo and in vitro. Pharmacol Res. 2019 Nov;149:104440. doi: 10.1016/j.phrs.2019.104440. Epub 2019 Aug 31. PMID: 31479750.

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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.



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