34316-15-9

Basic information

• Product Name: Chelerythrine chloride
• 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;3895-92-9 (Chloride)
• CAS NO: 34316-15-9
• Molecular Formula: C₂₁H₁₈NO₄
• Molecular Weight: 348.37192
• EINECS: 251-930-0
• Product Categories: Natural Plant Extract;chemical reagent;pharmaceutical intermediate;phytochemical;reference standards from Chinese medicinal herbs (TCM).;standardized herbal extract
• Mol File: 34316-15-9.mol
• Article Data: 2

Chemical Properties

• Melting Point: 195-205°C
• Boiling Point: 496.37°C (rough estimate)
• Appearance: /
• 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
• Stability: Hygroscopic
• CAS DataBase Reference: Chelerythrine chloride(CAS DataBase Reference)
• NIST Chemistry Reference: Chelerythrine chloride(34316-15-9)
• EPA Substance Registry System: Chelerythrine chloride(34316-15-9)

Safety Data

• Hazard Codes: Xn
• Statements: 20/21/22
• Safety Statements: 36/37
• Hazardous Substances Data: 34316-15-9(Hazardous Substances Data)

Usage

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

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.

InChI:InChI=1/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

Upstream product

• 180411-11-4 6-bromonaphtho[2,3-d][1,3]dioxol-5-ol 
• 6880-91-7 12,13-dihydrochelerythrine 
• 91-16-7 1,2-dimethoxybenzene 
• 175844-54-9 6-bromo-2,3-dimethoxybenzyl bromide 
• 4463-33-6 1,2-dimethoxy-3-methylbenzene 
• 41303-45-1 6,7-methylenedioxy-1-tetralone 
• 180411-09-0 6,6-dibromo-7,8-dihydro-6H-naphtho[2,3-d][1,3]dioxol-5-one 
• 180411-13-6 2-(6-bromo-naphtho[2,3-d][1,3]dioxol-5-yloxy)-2-methylpropionamide 
• 213698-51-2 N-(6-bromonaphtho[2,3-d][1,3]dioxol-5-yl)-2-hydroxy-2-methylpropionamide 
• 180411-17-0 2-bromo-6,7-methylenedioxy-1-naphthylamine 
• 74866-17-4 3,4-dimethoxy-2-methyl-1-bromobenzene 
• 87264-52-6 allocryptopine N-oxide 

Downstream Products

• 15575-49-2 6-acetonyldihydrochelerythrine 
• 28342-33-8 oxychelerythrine 
• 125226-39-3 6-ethoxydihydrochelerythrine 
• 21080-31-9 6-methoxy-5,6-dihydrochelerythrine 

Relevant articles and documents

Dihydrochelerythrine and its derivatives: Synthesis and their application as potential G-quadruplex DNA stabilizing agents

A convenient route was envisaged toward the synthesis of dihydrochelerythrine (DHCHL), 4 by intramolecular Suzuki coupling of 2-bromo-N-(2-bromobenzyl)-naphthalen-1-amine derivative 5 via in situ generated arylborane. This compound was converted to (±)-6-acetonyldihydrochelerythrine (ADC), 3 which was then resolved by chiral prep-HPLC. Efficiency of DHCHL for the stabilization of promoter quadruplex DNA structures and a comparison study with the parent natural alkaloid chelerythrine (CHL), 1 was performed. A thorough investigation was carried out to assess the quadruplex binding affinity by using various biophysical and biochemical studies and the binding mode was explained by using molecular modeling and dynamics studies. Results clearly indicate that DHCHL is a strong G-quadruplex stabilizer with affinity similar to that of the parent alkaloid CHL. Compounds ADC and DHCHL were also screened against different human cancer cell lines. Among the cancer cells, (±)-ADC and its enantiomers showed varied (15-48%) inhibition against human colorectal cell line HCT116 and breast cancer cell line MDA-MB-231 albeit low enantio-specificity in the inhibitory effect; whereas DHCHL showed 30% inhibition against A431 cell line only, suggesting the compounds are indeed cancer tissue specific.