ChemicalBook CAS DataBase List 3895-92-9

3895-92-9

Name	CHELERYTHRINE CHLORIDE
CAS	3895-92-9
EINECS(EC#)	223-444-9
Molecular Formula	C21H18ClNO4
MDL Number	MFCD00060717
Molecular Weight	383.82
MOL File	3895-92-9.mol

Synonyms

TODDALIN CHELERYTHRINE CHELERYTHRIN CL Chelerythrine Cl TODDALIN CHLORIDE CHELERYTHRIN CHLORIDE Chelerythrine cloride Chelerythrine chloride CHELERYTHRINE CHLORIDE(P) CHELERYTHRINE CHLORIDE(RG) Chelerythrine chloride,98% chelerythrinehydrochloride 1,2-DIMETHOXY-12,[1,3]-BENZODIOXOLO[5,6-C]PHENANTHRIDINIUM CHLORIDE 3)benzodioxolo(5,6-c)phenanthridinium,1,2-dimethoxy-12-methyl-(chloride 1,2-DIMETHOXY-12-METHYL[1,3]BENZODIOXOLO[5,6-C]PHENANTHRIDINIUM CHLORIDE 1,2-Dimethoxy-N-methyl-[1,3]benzodioxolo[5,6-c]phenanthridinium chloride [1,3]Benzodioxolo[5,6-c]phenanthridiniuM, 1,2-diMethoxy-12-Methyl-, chloride [1,3]Benzodioxolo[5,6-c]phenanthridinium, 1,2-dimethoxy-12-methyl-, chloride (1:1) 1,2-diMethoxy-12-Methyl-[1,3]dioxolo[4',5':4,5]benzo[1,2-c]phenanthridin-12-iuM chloride Chelerythrine chloride1,2-Dimethoxy-N-methyl-[1,3]benzodioxolo[5,6-c]phenanthridinium chloride

Chemical Properties

Appearance	yellow to orange solid
Melting point	195-205 °C
storage temp.	−20°C
solubility	DMSO: ≥10 mg/mL
form	powder
color	yellow to orange
Water Solubility	water: 1mg/mL DMSO: 10mg/mL
Stability:	Hygroscopic
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
InChIKey	WEEFNMFMNMASJY-UHFFFAOYSA-M
SMILES	Cl.COc1ccc2-c3ccc4cc5OCOc5cc4c3[N](C)=Cc2c1OC

Safety Data

Symbol(GHS)	GHS07
Signal word	Warning
Hazard statements	H302+H312+H332-H315-H319-H335
Precautionary statements	P261-P280-P301+P312-P302+P352+P312-P304+P340+P312-P305+P351+P338
Hazard Codes	Xn,Xi
Risk Statements	20/21/22-36/37/38-36/37 less more
Safety Statements	26-36-36/37 less more
RIDADR	UN 1544PSN1 6.1 / PGII
WGK Germany	3
RTECS	FL9200000
HS Code	29349990
Storage Class	11 - Combustible Solids
Hazard Classifications	Acute Tox. 4 Dermal Acute Tox. 4 Inhalation Acute Tox. 4 Oral Eye Irrit. 2 Skin Irrit. 2 STOT SE 3
Toxicity	mouse,LD50,intravenous,18500ug/kg (18.5mg/kg),Planta Medica. Vol. 43, Pg. 161, 1981. less more

Hazard Information

Chemical Properties

yellow to orange solid

Description

Chelerythrine is a potent, cell permeable inhibitor of protein kinase C (IC₅₀ = 660 nM) that does not inhibit tyrosine protein kinases, cAMP-dependent protein kinase, or calcium/calmodulin-dependent protein kinase. Chelerythrine also inhibits Bcl-xL function (IC₅₀ = 1.5 μM) by displacing Bax binding, inducing apoptosis in several cancer cell lines. Chelerythrine can also have PKC-independent effects, activate p38 MAP kinase and JUNK signaling pathways, and induce apoptosis in cancer cells both in vitro and in vivo.

Uses

Chelerythrine Chloride is a cell permeable protein kinase C (PKC) inhibitor.

General Description

Naturally occurring alkaloid. Cell-permeable, selective inhibitor of protein kinase C (IC₅₀ = 660 nM). Acts on the catalytic domain irrespective of the attachment of the regulatory domain. Material is a competitive inhibitor with respect to the phosphate acceptor and a non-competitive inhibitor with respect to ATP. Over ten-fold more potent than H-7, HCl (Cat. No. 371955). Inhibits thromboxane formation and phosphoinositide metabolism in platelets. Also induces apoptotic DNA fragmentation and cell death in HL-60 human promyelocytic leukemia cells.

Biochem/physiol Actions

Cell permeable: yes

storage

Store at -20°C

References

1. j. m. herbert, j. m. augereau, j. gleye and j. p. maffrand, biochem biophys res commun 1990, 172, 993-999. 2. w. d. jarvis, a. j. turner, l. f. povirk, r. s. traylor and s. grant, cancer res 1994, 54, 1707-1714. 3. j. vrba, p. dolezel, j. vicar, m. modriansky and j. ulrichova, toxicol in vitro 2008, 22, 1008-1017. 4. m. vogler, k. weber, d. dinsdale, i. schmitz, k. schulze-osthoff, m. j. dyer and g. m. cohen, cell death differ 2009, 16, 1030-1039. 5. r. yu, s. mandlekar, t. h. tan and a. n. kong, j biol chem 2000, 275, 9612-9619. 6. s. yamamoto, k. seta, c. morisco, s. f. vatner and j. sadoshima, j mol cell cardiol 2001, 33, 1829-1848.

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