Chelerythrine chloride

Chelerythrine is a benzophenanthridine alkaloid extracted from the plant Greater celandine (Chelidonium majus). It is a potent, selective, and cell-permeable protein kinase C inhibitor

Product information

CAS Number: 3895-92-9

Molecular Weight: 383.82

Formula: C21H18ClNO4

Synonym:

NSC-36405

NSC 36405

NSC36405

Related CAS Number:

34316-15-9 (free base)

478-03-5 (OH-)

3895-92-9 (HCl)

Chemical Name: 1, 2-dimethoxy-12-methyl-[1, 3]dioxolo[4', 5':4, 5]benzo[1, 2-c]phenanthridin-12-ium chloride

Smiles: [Cl-].C[N+]1=CC2=C(OC)C(=CC=C2C2=CC=C3C=C4OCOC4=CC3=C12)OC

InChiKey: WEEFNMFMNMASJY-UHFFFAOYSA-M

InChi: InChI=1S/C21H18NO4.ClH/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;1H/q+1;/p-1

Technical Data

Appearance: Solid Power.

Purity: ≥98% (or refer to the Certificate of Analysis)

Solubility: Soluble in DMSO, not in water

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical or refer to Certificate of Analysis

Storage Condition: Dry, dark and -20 ^oC for 1 year or refer to the Certificate of Analysis.

Shelf Life: ≥360 days if stored properly.

Stock Solution Storage: 0 - 4 ^oC for 1 month or refer to the Certificate of Analysis.

Drug Formulation: To be determined.

HS Tariff Code: 382200

How to use

In Vitro:

Chelerythrine inhibits the BclXL-Bak BH3 peptide binding with IC50 of 1.5 μM and displaces Bax, a BH3-containing protein, from BclXL. Mammalian cells treated with Chelerythrine undergoes apoptosis with characteristic features that suggest involvement of the mitochondrial pathway. Chelerythrine treatment inhibits LPS-induced TNF-α level and NO production in LPS-induced murine peritoneal macrophages through selective inhibition of p38 mitogen-activated protein kinase (MAPK) and extracellular signal-regulated protein kinases 1 and 2 (ERK1/2) activation. Moreover, the effects of chelerythrine on NO and cytokine TNF-α production can possibly be explained by the role of p38 MAPK and ERK1/2 in the regulation of inflammatory mediators expression. Chelerythrine shows cytotoxic effect on the human monocytic leukaemia cells with LD50 value of 3.46 μM. Two hours after LPS stimulation, cells influenced by sanguinarine and Chelerythrine significantly decline the CCL-2 expression by a factors of 3.5 and 1.9. Chelerythrine chloride significantly enhances the phosphorylation of ERK1/2 in a dose-dependent manner. In addition, chelerythrine chloride inhibits the phosphorylation of p38.

In Vivo:

Chelerythrine displays significant anti-inflammatory effects in experimentally induced mice endotoxic shock model in vivo through inhibition of LPS-induced tumor necrosis factor-alpha (TNF-α) level and nitric oxide (NO) production in serum. Chelerythrine chloride (5 mg/kg/day, i.p.) induces apoptosis of RCC cells without significant toxicity to mice. Chelerythrine Chloride treatment leads to a dose-dependent accumulation of p53.

References:

1. Gao ZQ, Han BH, Sha HF, Shi ZY, Yang XH, Feng JX. [Effects of a protein kinase C inhibitor combined with cisplatin on non-small cell lung cancer.]. Zhonghua Jie He He Hu Xi Za Zhi. 2010 Apr;33(4):284-8. Chinese. PubMed PMID: 20646461.
2. Lu DQ, Chen Y, Li T, Li BL. [Role of protein kinase C in protecting rats against pulmonary ischemia reperfusion injury through opening of mitochondrial ATP sensitive potassium channel]. Sichuan Da Xue Xue Bao Yi Xue Ban. 2010 May;41(3):436-40. Chinese. PubMed PMID: 20629316.
3. Alloatti G, Arnoletti E, Bassino E, Penna C, Perrelli MG, Ghé C, Muccioli G. Obestatin affords cardioprotection to the ischemic/reperfused isolated rat heart and inhibits apoptosis in cultures of similarly stressed cardiomyocytes. Am J Physiol Heart Circ Physiol. 2010 Jun 4. [Epub ahead of print] PubMed PMID: 20525876.
4. Wang HJ, Jiang HL, Chen XH, Lin PY, Zhu YC, Tao LL. [The anti-apoptosis effect of erythropoietin on neonatal rat cardiocytes during hypoxia/reoxygenation injury and its possible mechanism.]. Zhongguo Wei Zhong Bing Ji Jiu Yi Xue. 2010 May;22(5):302-5. Chinese. PubMed PMID: 20519083.
5. Adão-Novaes J, de Cássia Belem Guterrres C, Linden R, Sholl-Franco A. Rod photoreceptor cell death is induced by okadaic acid through activation of PKC and L-type voltage-dependent Ca2+ channels and prevented by IGF-1. Neurochem Int. 2010 Sep;57(2):128-35. Epub 2010 May 11. PubMed PMID: 20466029.
6. Zhang S, Li H, Yang SJ. Tribulosin protects rat hearts from ischemia/reperfusion injury. Acta Pharmacol Sin. 2010 Jun;31(6):671-8. Epub 2010 May 10. PubMed PMID: 20453871.

Products are for research use only. Not for human use.