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C2932

Sigma-Aldrich

Chelerythrine chloride

≥95% (TLC), powder

Synonym(s):

1,2-Dimethoxy-N-methyl(1,3)benzodioxolo(5,6-c)phenanthridinium chloride, Toddaline chloride

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About This Item

Empirical Formula (Hill Notation):
C21H18ClNO4
CAS Number:
3895-92-9
Molecular Weight:
383.82
MDL number:
MFCD00060717
UNSPSC Code:
12352200
PubChem Substance ID:
24278305
NACRES:
NA.77

biological source

plant

Quality Level

100

Assay

≥95% (TLC)

form

powder

color

yellow to orange

mp

213.0-214.0  °C

solubility

DMSO: 2 mg/mL

storage temp.

−20°C

SMILES string

Cl.COc1ccc2-c3ccc4cc5OCOc5cc4c3[N](C)=Cc2c1OC

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

InChI key

SUPBMPBJXZDANZ-UHFFFAOYSA-N

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General description

Chelerythrine chloride (CHE), a benzophenanthridine alkaloid is an inhibitor of protein kinase C (PKC). It is the active component of Macleaya cordata.

Application

Chelerythrine chloride has been used:
  • as a supplement in heat-inactivated late-embryo extract or late-embryo extract to inhibit protein kinase C (PKC) activity
  • for in vitro Xenopus experiments
  • as a PKC inhibitor in HL-1 cells, to block the PKC pathway to study its effects on doxazosin-induced galectin-3 and collagen expression

Biochem/physiol Actions

Chelerythrine chloride (CHE) is capable of preventing the growth and apoptosis in human gastric cancer BGC-823 cells. It possesses several biological effects and also can induce the phosphorylation of a ~20 kDa protein present in the mitochondrial fraction of the rat retina.

Features and Benefits

This compound is featured on the P2 Receptors: P2X Ion Channel Family and PKC pages of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Classifications

Acute Tox. 4 Dermal - Acute Tox. 4 Inhalation - Acute Tox. 4 Oral - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Regulatory Information

监管及禁止进口产品

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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A E Eckly-Michel et al.
European journal of pharmacology, 324(1), 85-88 (1997-04-11)
Chelerythrine, a potent inhibitor of protein kinase C, was evaluated for its effect on cyclic nucleotide phosphodiesterases (PDE) isolated from bovine aorta. Chelerythrine activated basal PDE2 and inhibited activated PDE2, PDE4 and PDE5. The effect of chelerythrine (10 microM) was
Stimulation by chelerythrine of the phosphorylation of the amino acid serine in an~20 kDa protein present in the mitochondrial fraction of the rat retina
Lombardini JB
Biochemical Pharmacology, 52(2), 253-257 (1996)
Win Sen Heng et al.
Molecules (Basel, Switzerland), 25(1) (2020-01-16)
Plant secondary metabolites have been seen as alternatives to seeking new medicines for treating various diseases. Phytochemical scientists remain hopeful that compounds isolated from natural sources could help alleviate the leading problem in oncology-the lung malignancy that kills an estimated
PKC-mediated phosphorylation of nuclear lamins at a single serine residue regulates interphase nuclear size in Xenopus and mammalian cells
Edens LJ, et al.
Molecular Biology of the Cell, 28(10), 1389-1399 (2017)
Chelerythrine chloride from Macleaya cordata induces growth inhibition and apoptosis in human gastric cancer BGC-823 cells
Zhang Z, et al.
Acta Pharmaceutica Sinica. B, 2(5), 464-471 (2012)
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