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Chelerythrine

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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
  • phytochemical
  • reference standards from Chinese medicinal herbs (TCM).
  • standardized herbal extract
  • Natural Plant 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
InChI
InChI=1S/C21H18NO4/c1-22-10-16-13(6-7-17(23-2)21(16)24-3)14-5-4-12-8-18-19(26-11-25-18)9-15(12)20(14)22/h4-10H,11H2,1-3H3/q+1
InChIKey
LLEJIEBFSOEYIV-UHFFFAOYSA-N
SMILES
C[N+]1=CC2=C(C(OC)=CC=C2C2C=CC3C=C4OCOC4=CC=3C1=2)OC
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

Chemical Properties

Soluble in methanol and ethanol, with some solubility in water, insoluble in petroleum ether, chloroform and other solvents. Derived from the roots and leaves of Flying Dragon's Palm Blood [Toddalia asiatica (L.) Lam.

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.

in vivo

Chelerythrine (5 mg/kg, i.p., daily) attenuates partial unilateral ureteral obstruction (UUO) induced kidney injury, and restores renal function in neonatal rats[2].
Chelerythrine (1-10 mg/kg, i.p., at 24 and 1 h before injection of 100 μg/kg LPS) shows anti-inflammatory effects (increased survival rate, decreased serum nitrite and TNF-α level) in LPS induced mice endotoxic shock model[5].

Animal Model:Unilateral ureteral obstruction (UUO) induced neonatal rats[2]
Dosage:5 mg/kg
Administration:i.p., daily
Result:Attenuated kidney injury (Increased kidney weight and restored renal function).
Inhibited UUO-induced upregulated kidney injury molecule-1 expression, apoptosis, and renal fibrosis.

IC 50

PKC: 0.7 μM (IC50)

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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