| 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 | [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 | [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. | [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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