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 a benzophenanthridine alkaloid derived from the plant Chelidonium majus (greater celandine) and is also found in the root of Zanthoxylum simulans. It is a potent, selective, and cell-permeable protein kinase C inhibitor, acting as an efficient antagonist of G-protein-coupled CB1 receptors and an independent activator of MAPK pathways. Chelerythrine Chloride exhibits a variety of biological activities, including antiplatelet, anti-inflammatory, antibacterial, and antitumor effects. Notably, it has been reported to induce apoptosis in HL-60 human promyelocytic leukemia cells and several other cancer cell lines, with its mechanism involving the inhibition of the binding of BclXL to Bax or Bad.

Uses

Used in Pharmaceutical Industry:
Chelerythrine Chloride is used as a research compound for its various biological activities, particularly in the development of treatments for cancer. Its ability to induce apoptosis in cancer cells and inhibit specific protein interactions makes it a valuable tool in the study and potential treatment of various malignancies.
Used in Neuroscience Research:
As an efficient antagonist of G-protein-coupled CB1 receptors, Chelerythrine Chloride is used in neuroscience research to study the role of these receptors in various physiological processes and their potential as therapeutic targets for conditions such as pain, addiction, and mood disorders.
Used in Cell Signaling Studies:
Due to its role as an independent activator of MAPK pathways, Chelerythrine Chloride is utilized in cell signaling research to understand the complex interactions between various signaling molecules and their impact on cellular processes, including cell growth, differentiation, and apoptosis.
Used in Anti-Inflammatory and Antibacterial Applications:
Chelerythrine Chloride's anti-inflammatory and antibacterial properties make it a potential candidate for the development of new treatments for inflammatory conditions and bacterial infections. Its use in these applications is currently under investigation in various research settings.

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

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.