| Identification | More | [Name]
Chelerythrine chloride | [CAS]
34316-15-9 | [Synonyms]
CHELERYTHRINE(TODDALINE)(RG)
1,2-dimethoxy-12-methyl[1,3]benzodioxolo[5,6-c]phenanthridinium
1,2-Dimethoxy-N-methyl-[1,3]benzodioxolo[5,6-c]phenanthridinium chloride
Chelerythrine chloride
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 | [EINECS(EC#)]
251-930-0 | [Molecular Formula]
C21H18NO4+ | [MDL Number]
MFCD00060717 | [Molecular Weight]
348.372 | [MOL File]
34316-15-9.mol |
| Chemical Properties | Back Directory | [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) |
| Safety Data | Back Directory | [Hazard Codes ]
Xn | [Risk Statements ]
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed . | [Safety Statements ]
S36/37:Wear suitable protective clothing and gloves . |
| Questions And Answer | Back Directory | [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
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| Hazard Information | Back Directory | [Chemical Properties]
It is soluble in methanol and ethanol, has a certain solubility in water, and is insoluble in solvents such as petroleum ether and chloroform. It is derived from the roots and leaves of the Rutaceae plant 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.
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| [IC 50]
PKC: 0.7 μM (IC50) | [storage]
Store at 2-8°C | [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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