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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

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

signalword

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

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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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Protein kinase C promotes cardiac fibrosis and heart failure by modulating galectin-3 expression
Song X, et al.
Biochimica et Biophysica Acta - Molecular Cell Research, 1853(2), 513-521 (2015)
Shi-Yang Li et al.
Scientific reports, 7(1), 15317-15317 (2017-11-12)
The present study was performed to explore the role of galanin and galanin receptor 1 (GalR 1) in nociceptive modulation in the central nucleus of amygdala (CeA) in normal rats and rats with neuropathy, and the involvement of GalR 1
W D Jarvis et al.
Cancer research, 54(7), 1707-1714 (1994-04-01)
The present studies were undertaken to characterize further the potential role of protein kinase C (PKC) in the regulation of apoptosis in HL-60 promyelocytic leukemia cells. The capacity of acute exposure to specific and nonspecific pharmacological inhibitors of PKC to
Doxazosin stimulates galectin-3 expression and collagen synthesis in HL-1 cardiomyocytes independent of protein kinase C pathway
Qian X, et al.
Frontiers in Pharmacology, 7, 495-495 (2016)
Rottlerin, a specific inhibitor of protein kinase C-delta, impedes barrier repair response by increasing intracellular free calcium
Ahn BK, et al.
The Journal of Investigative Dermatology, 126(6), 1348-1355 (2006)
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