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C2932

Sigma-Aldrich

Chelerythrine chloride

≥95% (TLC), powder

Synonyme(s) :

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

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About This Item

Formule empirique (notation de Hill):
C21H18ClNO4
Numéro CAS:
3895-92-9
Poids moléculaire :
383.82
Numéro MDL:
MFCD00060717
Code UNSPSC :
12352200
ID de substance PubChem :
24278305
Nomenclature NACRES :
NA.77

Source biologique

plant

Niveau de qualité

100

Pureté

≥95% (TLC)

Forme

powder

Couleur

yellow to orange

Pf

213.0-214.0  °C

Solubilité

DMSO: 2 mg/mL

Température de stockage

−20°C

Chaîne SMILES 

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

Clé InChI

SUPBMPBJXZDANZ-UHFFFAOYSA-N

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Description générale

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

Actions biochimiques/physiologiques

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.

Caractéristiques et avantages

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.

Pictogrammes

Exclamation mark
GHS07

Mention d'avertissement

Warning

Classification des risques

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

Organes cibles

Respiratory system

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Certificats d'analyse (COA)

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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)
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)
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
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
Yudong Yao et al.
Neuropharmacology, 64, 37-44 (2012-08-01)
PKMζ is an autonomously active, atypical protein kinase C (aPKC) isoform that is both necessary and sufficient for maintaining long-term potentiation (LTP) and long-term memory. The myristoylated ζ-pseudosubstrate peptide, ZIP, potently inhibits PKMζ biochemically in vitro, within cultured cells, and
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