Chelerythrine chloride, Cell-permeable protein kinase C inhibitor

Key facts

CAS number

3895-92-9

Purity

>98%

Form

Solid

form

Molecular weight

383.8 Da

Molecular formula

C₂₁H₁₈ClNO₄

PubChem

72311

Nature

Synthetic

Solubility

Soluble in DMSO to 10 mM

Soluble in water to 10 mM

Biochemical name

Chelerythrine chloride

Biological description

Cell-permeable, selective inhibitor of protein kinase C (IC₅₀ = 0.66 μM); Competitive with respect to the phosphate acceptor and non-competitive with respect to ATP. Activates MAPK pathways, independent of PKC inhibition. Inhibits Bcl_XL function (IC₅₀ = 1.5 μM) by displacing Bax binding, inducing apoptosis in several cancer cell lines.

Canonical smiles

C[N+]1=C2C(=C3C=CC(=C(C3=C1)OC)OC)C=CC4=CC5=C(C=C42)OCO5.[Cl-]

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

InChiKey

WEEFNMFMNMASJY-UHFFFAOYSA-M

IUPAC Name

1,2-dimethoxy-12-methyl-[1,3]benzodioxolo[5,6-c]phenanthridin-12-ium;chloride