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208725

Sigma-Aldrich

Calphostin C, Cladosporium cladosporioides

A cell permeable, highly specific inhibitor of protein kinase C (IC₅₀ = 50 nM) that interacts with the protein′s regulatory domain by competing at the binding site of diacylglycerol and phorbol esters.

Synonym(s):

Calphostin C, Cladosporium cladosporioides, UCN-1028c

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About This Item

Empirical Formula (Hill Notation):
C44H38O14
CAS Number:
121263-19-2
Molecular Weight:
790.76
MDL number:
MFCD00133155
UNSPSC Code:
12352200

Quality Level

100

Assay

≥95% (HPLC)

form

lyophilized solid

manufacturer/tradename

Calbiochem®

storage condition

OK to freeze
protect from light

color

light brown

solubility

DMSO: 1 mg/mL
ethanol: soluble

shipped in

ambient

storage temp.

2-8°C

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/h7-15,18-21,45,48-49H,16-17H2,1-6H3

InChI key

LSUTUUOITDQYNO-UHFFFAOYSA-N

General description

A cell permeable, highly specific inhibitor of protein kinase C (IC50 = 50 nM) that interacts with the protein’s regulatory domain by competing at the binding site of diacylglycerol and phorbol esters. Does not compete with Ca2+ or phospholipids. At higher concentrations inhibits myosin light chain kinase (IC50 >5 µM), protein kinase A (IC50 >50 µM), protein kinase G (IC50 >25 µM), and p60v-src (IC50 >50 µM). Induces apoptotic DNA fragmentation and cell death in HL-60 human promyelocytic leukemia cells. Requires brief exposure to light for activation.
Cell-permeable, highly specific inhibitor of protein kinase C (IC50 = 50 nM) that interacts with the protein′s regulatory domain by competing at the binding site of diacylglycerol and phorbol esters. At higher concentrations inhibits myosin light chain kinase (IC50 >5 µM), protein kinase A (IC50 >50 µM), protein kinase G (IC50 >25 µM), and p60v-src protein tyrosine kinase (IC50 >50 µM). Does not compete with Ca2+ or phospholipids. Also induces apoptotic DNA fragmentation and cell death in HL-60 human promyelocytic leukemia cells. Inhibition of PKC is dependent on exposure to light in cell-free systems. Ordinary fluorescent light is sufficient for full activation.

Biochem/physiol Actions

Cell permeable: yes
Primary Target
PKC
Product does not compete with ATP.
Reversible: no
Target IC50: 50 nM against protein kinase C

Warning

Toxicity: Standard Handling (A)

Reconstitution

Following reconstitution, aliquot and freeze (-20°C). Stock solutions are stable for up to 6 months at -20°C.

Other Notes

Jarvis, W.D., et al. 1994. Cancer Res.54, 1707.
Svetlov, S., and Nigami, S. 1993. Biochim. Biophys. Acta 1177, 75.
Gopalakrishna, R., et al. 1992. FEBS Lett. 314, 149.
Shimamato, H., et al. 1992. Br. J. Pharmacol.107, 282.
Bruns, R.F., et al. 1991. Biochem. Biophys. Res. Commun.176, 288.
Tamaoki, T., et al. 1990. Biotechnology8, 732.
Kobayashi, E., et al. 1989. Biochem. Biophys. Res. Commun.159, 548.

Legal Information

CALBIOCHEM is a registered trademark of Merck KGaA, Darmstadt, Germany

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

JAN Code

208725-100UG:
208725-UG:
208725-50UG:

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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