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C6303

Sigma-Aldrich

Calphostin C from Cladosporium cladosporioides

≥90% (HPLC), powder

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Synonym(s):
UCN-1028c
Empirical Formula (Hill Notation):
C44H38O14
CAS Number:
Molecular Weight:
790.76
MDL number:
UNSPSC Code:
12352200
PubChem Substance ID:
NACRES:
NA.77

biological source

microbial (Cladosporium cladosporioides)

Quality Level

Assay

≥90% (HPLC)

form

powder

color

red to brown

solubility

DMF: 1 mg/mL
DMSO: 1 mg/mL
ethanol: 1 mg/mL

storage temp.

−20°C

SMILES string

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

InChI

1S/C44H38O14/c1-20(56-43(50)22-10-8-7-9-11-22)16-25-31-32-26(17-21(2)57-44(51)58-24-14-12-23(45)13-15-24)42(55-6)40(49)34-28(47)19-30(53-4)36(38(32)34)35-29(52-3)18-27(46)33(37(31)35)39(48)41(25)54-5/h7-15,18-21,45-47H,16-17H2,1-6H3

InChI key

SRJYZPCBWDVSGO-UHFFFAOYSA-N

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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.

Features and Benefits

This compound is featured on the Phospholipase D and PKC pages of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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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M Begemann et al.
Anticancer research, 18(5A), 3139-3152 (1998-12-22)
Protein kinase C (PKC) is a central component in signal transduction and growth control and might be an appropriate target for the chemotherapy of human brain tumors. This study demonstrates that the staurosporine derivative Ro 31-8220, a potent PKC inhibitor
T Tamaoki et al.
Bio/technology (Nature Publishing Company), 8(8), 732-735 (1990-08-01)
Potent and specific inhibitors of protein kinase C have been found in streptomyces and fungi: Staurosporine, an alkaloid from Streptomyces sp., is the most potent inhibitor of protein kinases with an IC50 in the nanomolar range. UCN-01 (7-hydroxy staurosporine), isolated
Yang Chen et al.
Annals of translational medicine, 10(3), 132-132 (2022-03-15)
The currently available treatment methods are ineffective in reducing mortality or improving outcomes in acute lung injury (ALI). The activation of protein kinase C alpha (PKCα) has recently been implicated in ALI development. We explored the potential therapeutic outcomes of
R F Bruns et al.
Biochemical and biophysical research communications, 176(1), 288-293 (1991-04-15)
Calphostin C, a secondary metabolite of the fungus Cladosporium cladosporioides, inhibits protein kinase C by competing at the binding site for diacylglycerol and phorbol esters. Calphostin C is a polycyclic hydrocarbon with strong absorbance in the visible and ultraviolet ranges.
I Ozaki et al.
The Journal of biological chemistry, 274(9), 5310-5317 (1999-02-20)
Apoptosis was induced in human glioma cell lines by exposure to 100 nM calphostin C, a specific inhibitor of protein kinase C. Calphostin C-induced apoptosis was associated with synchronous down-regulation of Bcl-2 and Bcl-xL as well as activation of caspase-3

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