ChemicalBook CAS DataBase List 121263-19-2

121263-19-2

Name	CALPHOSTIN C
CAS	121263-19-2
Molecular Formula	C44H38O14
MDL Number	MFCD00133155
Molecular Weight	790.76
MOL File	121263-19-2.mol

Synonyms

UCN-1028C PKF 115-584 CALPHOSTIN C Cladochrome E He Ding C Carver (R)-Calphostin C Calphostin C,98% Calphostin CUCN-1028C UCN 1028 C, PKF 115-384 Calphostin C(UCN 1028C, PKF 115584) CALPHOSTIN C, CLADOSPORIUM CLADOSPORIOIDES C,CalphostinCfroMCladosporiuMcladosporioide CALPHOSTIN C FROM CLADOSPORIUMCLADOSPORI OIDES 4,9-Dihydroxy-12-[(R)-2-(4-hydroxyphenyloxy)carbonyloxypropyl]-2,6,7,11-tetramethoxy-1-[(R)-2-benzoyloxypropyl]perylene-3,10-dione 1-[(R)-2-(4-Hydroxyphenoxycarbonyloxy)propyl]-2,6,7,11-tetramethoxy-4,9-dihydroxy-12-[(R)-2-(benzoyloxy)propyl]-3,10-dihydroperylene-3,10-dione 2-[12-[2-(BENZOYLOXY)PROPYL]-3,10-DIHYDRO-4,9-DIHYDROXY-2,6,7,11-TETRAMETHOX Y-3,10-DIOXO-1-PERYLENYL]-1-METHYLETHYL CARBONIC ACID 4-HYDROXYPHENYL ESTER (1R)-2-[12-[(2R)-2-(Benzoyloxy)propyl]-3,10-dihydro-4,9-dihydroxy-2,6,7,11-tetramethoxy-3,10-dioxo-1-perylenyl]-1-methylethylcarbonicacid4-hydroxyphenylester Carbonic acid,(1R)-2-[12-[(2R)-2-(benzoyloxy)propyl]-3,10-dihydro-4,9-dihydroxy-2,6,7,11-tetramethoxy-3,10-dioxo-1-perylenyl]-1-methylethyl4-hydroxyphenyl ester, stereoisomer

Chemical Properties

Appearance	Dark red solid
Boiling point	1039.8±65.0 °C(Predicted)
density	1.48±0.1 g/cm3(Predicted)
storage temp.	−20°C
solubility	DMF: 1 mg/mL
form	powder
pka	7.30±0.20(Predicted)
color	red to brown
biological source	microbial (Cladosporium cladosporioides)
InChIKey	SRJYZPCBWDVSGO-UHFFFAOYSA-N
SMILES	COc1cc(O)c2C(=O)C(OC)=C(CC(C)OC(=O)Oc3ccc(O)cc3)c4c5C(CC(C)OC(=O)c6ccccc6)=C(OC)C(=O)c7c(O)cc(OC)c(c57)c1c24

Safety Data

Hazard Codes	Xn
Risk Statements	20/21/22-36/37/38 less more
Safety Statements	24/25-36-26 less more
WGK Germany	3
HS Code	29209010
Storage Class	11 - Combustible Solids
Hazardous Substances Data	121263-19-2(Hazardous Substances Data)

Hazard Information

Chemical Properties

Dark red solid

Uses

Calphostin C (CGP049090) is a perylenequinione isolated from the fungus, Cladosporium cladosporioides. Calphostin C is a potent and specific inhibitor of protein kinase C (PKC), with inhibition being light dependent. Calphostin C inhibits cell proliferation and induces apoptosis in vitro. Calphostin C is an antagonist of Tcf4/b-catenin signalling, inhibiting the expression of survivin and inducing apoptosis in several tumour cell lines.

Uses

Calphostin C (PKF115-584) is a perylenequinione isolated from the fungus, Cladosporium cladosporioides. Calphostin C is a potent and specific inhibitor of protein kinase C (PKC), with inhibition being light dependent. Calphostin C inhibits cell proliferation and induces apoptosis in vitro. Calphostin C is an antagonist of Tcf4/b-catenin signalling, inhibiting the expression of survivin and inducing apoptosis in several tumor cell lines.

Biological Activity

Potent, selective and photo-dependent inhibitor of protein kinase C that targets the regulatory domain (IC 50 = 50 nM). Displays > 1000-fold selectivity over other protein kinases such as cAMP-dependent protein kinase and tyrosine-specific protein kinase. Inhibits cell proliferation of malignant glioma cells in light-treated conditions in vitro (IC 50 ~ 40-60 nM).

Biochem/physiol Actions

Highly specific inhibitor of protein kinase C (IC50 = 50 nM); requires light for activation. At higher concentrations (100 nM or greater), it has been shown to inhibit cell proliferation and induce apoptosis in vitro.

storage

+4°C (desiccate)

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