ChemicalBook > CAS DataBase List > ELLIPTICINE

ELLIPTICINE

Product Name
ELLIPTICINE
CAS No.
519-23-3
Chemical Name
ELLIPTICINE
Synonyms
K00071;LP00531;CS-1794;icig770;CP-3025;CCG36483;CCG 36483;DB-052047;CCG-36483;LS-133282
CBNumber
CB6746832
Molecular Formula
C17H14N2
Formula Weight
246.31
MOL File
519-23-3.mol
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ELLIPTICINE Property

Melting point:
316-318°C
Boiling point:
379.31°C (rough estimate)
Density 
1.257±0.06 g/cm3 (20 ºC 760 Torr)
refractive index 
1.5794 (estimate)
storage temp. 
Keep in dark place,Sealed in dry,2-8°C
solubility 
DMSO: soluble
form 
Bright yellow solid
pka
16.59±0.40(Predicted)
color 
Light yellow to yellow
Merck 
13,3581
LogP
4.800
CAS DataBase Reference
519-23-3(CAS DataBase Reference)
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Safety

Hazard Codes 
T
Risk Statements 
25
Safety Statements 
45
RIDADR 
UN 3462 6.1/PG 3
WGK Germany 
3
RTECS 
UU8825000
HazardClass 
6.1(b)
PackingGroup 
III
Toxicity
LD50 in mice (mg/kg): 19.5-22.4 i.v.; 178-204 orally (Rakieten)
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Danger
Hazard statements

H301Toxic if swalloed

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P301+P310IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.

P405Store locked up.

P501Dispose of contents/container to..…

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
324688
Product name
Ellipticine
Packaging
10mg
Price
$113
Updated
2024/03/01
Cayman Chemical
Product number
18742
Product name
Ellipticine
Purity
≥98%
Packaging
5mg
Price
$57
Updated
2022/04/27
Cayman Chemical
Product number
18742
Product name
Ellipticine
Purity
≥98%
Packaging
10mg
Price
$85
Updated
2022/04/27
Cayman Chemical
Product number
18742
Product name
Ellipticine
Purity
≥98%
Packaging
25mg
Price
$198
Updated
2022/04/27
Cayman Chemical
Product number
18742
Product name
Ellipticine
Purity
≥98%
Packaging
50mg
Price
$338
Updated
2022/04/27
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ELLIPTICINE Chemical Properties,Usage,Production

Description

Ellipticine is an alkaloid isolated from Apocyanaceae plants that exhibits antitumor activities by intercalating into DNA and/or inhibiting DNA topoisomerase II. It forms covalent adducts in DNA after being enzymatically activated with cytochrome P450 isoforms (e.g., CYP3A4, CYP1A1, or CYP1A2) or by peroxidases in target tissues. Ellipticine has been shown to inhibit the proliferation of human breast adenocarcinoma MCF-7 cells, leukemia HL-60 and CCRF-CEM cells, neuroblastoma IMR-32, UKF-NB-3, and UKF-NB-4 cells, and U87MG glioblastoma cells with IC50 values ranging from 0.27-4.7 μM.

Uses

Ellipticine is a DNA intercalating agent and exhibits antitumor activities.

Definition

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

Synthesis Reference(s)

Journal of the American Chemical Society, 102, p. 1457, 1980 DOI: 10.1021/ja00524a059
The Journal of Organic Chemistry, 72, p. 7106, 2007 DOI: 10.1021/jo070774z
Tetrahedron Letters, 18, p. 4663, 1977 DOI: 10.1016/S0040-4039(01)83595-4

General Description

A topoisomerase II inhibitor. Acts as an intercalative alkaloid that stimulates topoisomerase II-mediated DNA breakage. Is also capable of uncoupling mitochondrial oxidative phosphorylation.

Biochem/physiol Actions

Cell permeable: yes

in vitro

treatment mammalian dna topoisomerase ii reaction mixture with ellipticine resulted in the stimulation of dna cleavage. the drug-stimulation of dna cleavage is related to the formation of a ternary complex between topoisomerase ii, dna, and ellipticine. ellipticine dose not inhibit enzyme-mediated dna religation, however, it stimulates dna breakage by enhancing the forward rate of cleavage [2]. ellipticine showed growth inhibition activity on l1210 lymphocytic leukemia cells with a ic50 of 0.99 μm [1].

in vivo

ellipticine was evaluated in p. berghei infected mice in the 4-day suppressive test. ellipticine had a 100% inhibition versus controls on days 5 and 7 at an oral dose of 50 mg/kg/day, and the mean survival time (mst) was more than 40 days [3].

IC 50

= 0.99 μm for l1210 lymphocytic leukemia cells [1]

Purification Methods

This DNA intercalator is purified by recrystallisation from CHCl3 or MeOH and is dried in vacuo. The UV max values in aqueous EtOH/HCl are at 241, 249, 307, 335 and 426nm. [Marini-Bettolo & Schmutz Helv Chim Acta 42 2146 1959.] The methiodide has m 360o(dec), with UV (EtOH/KOH) at 223, 242, 251, 311, 362 and 432nm. [Goodwin et al. J Am max Chem Soc 81 1903 1959, Beilstein 23/9 V 417.]

References

[1] paoletti c, cros s, xuong nd, lecointe p, moisand a. comparative cytotoxic and antitumoral effects of ellipticine derivatives on mouse l 1210 leukemia. chem biol interact. 1979 apr;25(1):45-58.
[2] tewey km, chen gl, nelson em, liu lf. intercalative antitumor drugs interfere with the breakage-reunion reaction of mammalian dna topoisomerase ii. j biol chem. 1984 jul 25;259(14):9182-7.
[3] rocha e silva lf, montoia a, amorim rc, melo mr, henrique mc, nunomura sm, costa mr, andrade neto vf, costa ds, dantas g, lavrado j, moreira r, paulo a, pinto ac, tadei wp, zacardi rs, eberlin mn, pohlit am. comparative in vitro and in vivo antimalarial activity of the indole alkaloids ellipticine, olivacine, cryptolepine and a synthetic cryptolepine analog. phytomedicine. 2012 dec 15;20(1):71-6.

ELLIPTICINE Preparation Products And Raw materials

Raw materials

Preparation Products

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View Lastest Price from ELLIPTICINE manufacturers

Henan Fengda Chemical Co., Ltd
Product
ELLIPTICINE 519-23-3
Price
US $10.00-2.00/KG
Min. Order
1KG
Purity
99%
Supply Ability
g-kg-tons, free sample is available
Release date
2024-04-28

519-23-3, ELLIPTICINERelated Search:

ELLIPTICINE Ellipticine acetomethylate N,N-diethyl-N'-(9-methoxy-5,11-dimethyl-6H-pyrido[4,3-b]carbazol-1-yl)propane-1,3-diamine 9-methoxy-5,11-dimethyl-6H-pyrido[4,3-b]carbazole 9-hydroxy-2,5,11-trimethyl-6H-pyrido[4,3-b]carbazolium iodide 5,11-dimethyl-6H-pyrido[4,3-b]carbazol-9-ol 5-(hydroxymethyl)-11-methyl-6H-pyrido(4,3-b)carbazole N-methylcarbamate ELLIPTICINE(REAGENT / STANDARD GRADE) Ellipticine, 9-Hydroxy-, HCl 8-nitroellipticine detalliptinium 9-aminoellipticine 9-METHOXY-2-METHYLELLIPTICINIUM ACETATE HYDRATE 5,11-Dimethyl-9-methoxy-N-propyl-6H-pyrido(4,3-b)carbazol-1-amine male ate ELLIPTICINE, 9-HYDROXY-, HYDROCHLORIDE 5,11-Dimethyl-N-ethyl-9-methoxy-6H-pyrido(4,3-b)carbazol-1-amine malea te 5,11-Dimethyl-9-methoxy-6H-pyrido(4,3-b)carbazol-1-amine maleate 1-((3-(Diethylamino)propyl)amino)-5,11-dimethyl-6H-pyrido(4,3-b)carbaz ol-9-ol

  • ELLIPTICINE
  • 5,11-DIMETHYLPYRIDO[4,3-B]CARBAZOLE
  • 5,11-DIMETHYLPYRIDO[4.3:B]CARBAZOLE
  • 5,11-DIMETHYL-6H-PYRIDO[4,3-B]CARBAZOLE
  • CCG 36483
  • CCG36483
  • CCG-36483
  • CCG-36483; CCG36483; CCG 36483; BRN-0221300; BRN0221300; BRN 0221300; DB-052047; K00071; LP00531; LS-133282; NSC 71795; NSC71795; NSC-71795; TCMDC-125546; VZ29809. ELLIPTECINE; ELLIPTICINE; ELLIPTISINE
  • DB-052047
  • Elliptisine
  • K00071
  • LP00531
  • LS-133282
  • TCMDC-125546
  • VZ29809. elliptecine
  • CS-1794
  • Ellipticine - CAS 519-23-3 - Calbiochem
  • 3-b)carbazole,5,11-dimethyl-6h-pyrido(
  • icig770
  • ELLIPTICINE, FOR FLUORESCENCE
  • ELLIPTICINE(RG)
  • ELLIPTICIN
  • PYRIDO(4,3-B)CARBAZOLE,5,11-DIMETHYL-
  • CP-3025
  • NSC-71795
  • Ellipticine Solution
  • 33668-12-1 (Hydrochloride)
  • 55042-50-7 (Tartrate)
  • 6H-Pyrido(4,3-B)carbazole, 5,11-dimethyl-
  • Brn 0221300
  • Ccris 2003
  • Ellipticine,5,11-Dimethyl-6H-pyrido[4,3-b]carbazole
  • 5,11-Dimethyl-6H-pyrido[4,3-b]carbazole Ellipticine
  • Ellipticine, ≥99%
  • Ellipticine,Inhibitor,NSC71795,NSC-71795,Topoisomerase,inhibit
  • 519-23-3
  • DNA metabolism
  • Fluorescent Probes, Labels, Particles and Stains
  • Fluorescent Stains
  • Nucleic Acid Stains
  • Nucleic Acid Stains For Flow Cytometry
  • DNA Repair Regulators
  • Cell Signaling and Neuroscience
  • Cell Biology
  • Apoptosis and Cell Cycle
  • Biochemicals and Reagents
  • BioChemical
  • Inhibitors
  • Alkaloids
  • Indoles and derivatives
  • Antitumour