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Chelerythrine

Basic information Description References Safety Supplier Related

Chelerythrine Basic information

Product Name:
Chelerythrine
Synonyms:
  • 1,2-Dimethoxy-N-methyl-[1,3]benzodioxolo[5,6-c]phenanthridinium chloride
  • Chelerythrine chloride
  • CHELERYTHRINE(TODDALINE)(RG)
  • 1,2-dimethoxy-12-methyl[1,3]benzodioxolo[5,6-c]phenanthridinium
  • chelerythrine/toddaline
  • 1,2-Dimethoxy-12-methyl[1,3]benzodioxolo[5,6-c]phenanthridin-12-ium
  • 2,3-(Epoxymethanoxy)-5-methyl-7,8-dimethoxybenzo[c]phenanthridine-5-ium
  • Cheleritrine
CAS:
34316-15-9
MF:
C21H18NO4+
MW:
348.37192
EINECS:
251-930-0
Product Categories:
  • chemical reagent
  • pharmaceutical intermediate
  • Natural Plant Extract
  • phytochemical
  • reference standards from Chinese medicinal herbs (TCM).
  • standardized herbal extract
Mol File:
34316-15-9.mol
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Chelerythrine Chemical Properties

Melting point:
195-205°C
Boiling point:
496.37°C (rough estimate)
Density 
1.2985 (rough estimate)
refractive index 
1.5614 (estimate)
storage temp. 
Desiccate at -20°C
solubility 
Chloroform (Slightly, Sonicated), DMSO (Slightly, Sonicated), Methanol (Slightly)
form 
Solid
color 
Light Yellow to Dark Orange
Stability:
Hygroscopic
LogP
-0.401 (est)
CAS DataBase Reference
34316-15-9(CAS DataBase Reference)
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Safety Information

Hazard Codes 
Xn
Risk Statements 
20/21/22
Safety Statements 
36/37
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Chelerythrine Usage And Synthesis

Description

Chelerythrine chloride is the chloride form of Chelerythrine chloride which is a benzophenanthridine alkaloid isolated from the plant Chelidonium majus (greater celandine). It is a kind of potent, selective, and cell-permeable protein kinase C inhibitor, an efficient antagonist of G-protein-coupled CB1 receptors, and an independent activator of MAPK pathways. It has a wide range of biological activities including antiplatelet, anti-inflammatory, antibacterial and antitumor effects. It has reported of that it is capable of inducing apoptosis in HL-60 human promyelocytic leukemia cells and several other cancer cell lines. The underlying mechanism is through its effects of inhibiting the binding of BclXL to Bax or Bad.

References

https://en.wikipedia.org/wiki/Chelerythrine
https://www.scbt.com/scbt/product/chelerythrine-chloride-3895-92-9
https://www.tocris.com/dispprod.php?ItemId=2342#.WQmZVVNsgZQ

Uses

Chelerythrine Chloride is a cell permeable protein kinase C (PKC) inhibitor.

Definition

ChEBI: A benzophenanthridine alkaloid isolated from the root of Zanthoxylum simulans, Chelidonium majus L., and other Papaveraceae.

Biological Activity

Potent, cell-permeable inhibitor of protein kinase C (IC 50 = 660 nM); competitive with respect to the phosphate acceptor and non-competitive with respect to ATP. Has a wide range of biological activities, including antiplatelet, anti-inflammatory, antibacterial and antitumor effects. Activates MAPK pathways, independent of PKC inhibition. Inhibits binding of BclXL to Bak (IC 50 = 1.5 μ M) or Bad proteins and stimulates apoptosis.

Purification Methods

Chelerythrine crystallises from CHCl3 on addition of MeOH [Manske Can J Res 21B 140 1943, UV: Hruban et al. Coll Czech Chem Commun 35 3420 1970]. The pseudo base is colourless while the salts are yellow in aqueous solution and are fluorescent.

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