Chelerythrine chloride

Specifications / Handling

More Information
Product Details
Synonyms	NSC 36405; 1,2-Dimethoxy-N-methyl-[1,3]benzodioxolo[5,6-c]phenanthridinium chloride
Product Type	Chemical
Properties
Formula	C₂₁H₁₈ClNO₄
MW	383.8
Merck Index	14: 2051
CAS	3895-92-9
RTECS	FL9200000
Purity Chemicals	≥98% (NMR)
Appearance	Yellow to dark yellow solid.
Solubility	Soluble in DMSO, ethanol, methanol or water (2mg/ml warm).
Identity	Determined by ¹H-NMR.
InChi Key	WEEFNMFMNMASJY-UHFFFAOYSA-M
Smiles	[Cl-].COC1=C(OC)C2=C(C=C1)C1=C(C3=C(C=C1)C=C1OCOC1=C3)[N+](C)=C2
Shipping and Handling
Shipping	AMBIENT
Short Term Storage	+4°C
Long Term Storage	-20°C
Handling Advice	Protect from light when in solution.
Use/Stability	Stable for at least 2 years after receipt when stored at -20°C.
Documents
MSDS	Download PDF
Product Specification Sheet
Datasheet	Download PDF

Product-specific References

Description

Cell permeable potent inhibitor of protein kinase C. Does not inhibit tyrosine protein kinases, cAMP-dependent protein kinase or calcium/calmodulin-dependent protein kinase [1, 5].
Antiplatelet, anti-inflammatory, antibacterial and antitumor compound [1, 2, 9, 12, 15].
Apoptosis inducer in cancer cells in vitro and in vivo [3, 9].
Activates MAPK and JUNK signaling pathways [4, 8].
Affects translocation of PKC from cytosol to plasma membrane [6].
Neurite outgrowth stimulator [7].
Inhibits binding of Bcl_XL to Bak (IC50 = 1.5 μM) or Bad proteins and stimulates apoptosis in several cancer cell lines [10, 13].
Blocks human P2X7 receptor [11].
Induces cell cycle arrest in G1 phase [14].
Specific cyclooxygenase-2 inhibitor [15].

Product References

Chelerythrine is a potent and specific inhibitor of protein kinase C: J.M. Herbert, et al.; BBRC 172, 993 (1990)
Antiplatelet effects of chelerythrine chloride isolated from Zanthoxylum simulans: F.N. Ko, et al.; Biochim. Biophys. Acta 1052, 360 (1990)
Induction of apoptotic DNA fragmentation and cell death in HL-60 human promyelocytic leukemia cells by pharmacological inhibitors of protein kinase C: W.D. Jarvis, et al.; Cancer Res. 54, 1707 (1994)
Role of c-jun in human myeloid leukemia cell apoptosis induced by pharmacological inhibitors of protein kinase C: A.J. Freemerman, et al.; Mol. Pharmacol. 49, 788 (1996)
Angoline and chelerythrine, benzophenanthridine alkaloids that do not inhibit protein kinase C: S.K. Lee, et al.; J. Biol. Chem. 273, 19829 (1998)
Inhibition of protein kinase C translocation from cytosol to membrane by chelerythrine: M.D. Chao, et al.; Planta Med. 64, 662 (1998)
Axonal transport is inhibited by a protein kinase C inhibitor in cultured isolated mouse dorsal root ganglion cells: H. Hiruma, et al.; Brain. Res. 826, 135 (1999)
Activation of p38 and c-Jun N-terminal kinase pathways and induction of apoptosis by chelerythrine do not require inhibition of protein kinase C: R. Yu, et al.; J. Biol. Chem. 275, 9612 (2000)
In vitro and in vivo activity of protein kinase C inhibitor chelerythrine chloride induces tumor cell toxicity and growth delay in vivo: S.J. Chmura, et al.; Clin. Cancer Res. 6, 737 (2000)
Identification of chelerythrine as an inhibitor of BclXL function: S.L. Chan, et al.; J. Biol. Chem. 278, 20453 (2003)
Chelerythrine and other benzophenanthridine alkaloids block the human P2X7 receptor: A.N. Shemon, et al.; Br. J. Pharmacol. 142, 1015 (2004)
The effect of chelerythrine on cell growth, apoptosis, and cell cycle in human normal and cancer cells in comparison with sanguinarine: J. Malikova, et al.; Cell Biol. Toxicol. 22, 439 (2006)
Chelerythrine induces apoptosis through a Bax/Bak-independent mitochondrial mechanism: K.F. Wan, et al.; J. Biol. Chem. 283, 8423 (2008)
Chelerythrine and dihydrochelerythrine induce G1 phase arrest and bimodal cell death in human leukemia HL-60 cells: J. Vrba, et al.; Toxicol. In Vitro. 22, 1008 (2008)
Effects of chelerythrine, a specific inhibitor of cyclooxygenase-2, on acute inflammation in mice: X.F. Niu, et al.; Fitoterapia 82, 620 (2011)

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