Calphostin C

AdipoGen Life Sciences
Product Code: AG-CN2-0430
CodeSizePrice
AG-CN2-0430-C100100 ug£190.00
Quantity:
Prices exclude any Taxes / VAT

Overview

Regulatory Status: RUO
Shipping:
Ambient
Storage:
-20°C

Images

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Chemical Structure

Chemical Structure

Further Information

Alternate Names/Synonyms:
UCN 1028C; PKF115-584; Cal-C
Appearance:
Dark red to brown solid.
CAS:
121263-19-2
EClass:
32160000
Form (Short):
liquid
Handling Advice:
Keep cool and dry.Protect from light when in solution.
InChi:
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
InChiKey:
SRJYZPCBWDVSGO-UHFFFAOYSA-N
Long Description:
Chemical. CAS: 121263-19-2. Formula: C44H38O14. MW: 790.8. Isolated from Cladosporium cladosporioides sp. Potent and highly specific cell permeable protein kinase C (PKC) inhibitor. The inhibition of PKC is light-dependent. PKA, PKG, DAG kinase, phospholipase D1 and D2, myosin light chain kinase and c-Src inhibitor. Anticancer compound. Inhibits cell proliferation and strongly induces apoptosis in vitro. Inducer of endoplasmic reticulum ER-stress. Shown to directly and potently block L-type Ca channels. Calphostin C specifically inhibits contraction-stimulated glucose transport but not insulin-stimulated glucose transport in skeletal muscle. Wnt/beta-catenin/lef-1 signaling inhibitor. beta-catenin/TCF antagonist. Inhibits Wnt-activated genes in a dose-dependent fashion
MDL:
MFCD00133155
Molecular Formula:
C44H38O14
Molecular Weight:
790.8
Package Type:
Vial
Product Description:
Potent and highly specific cell permeable protein kinase C (PKC) inhibitor [1]. The inhibition of PKC is light-dependent. PKA, PKG, DAG kinase, phospholipase D1 and D2, myosin light chain kinase and c-Src inhibitor. Anticancer compound. Inhibits cell proliferation and strongly induces apoptosis in vitro. Inducer of endoplasmic reticulum ER-stress. Shown to directly and potently block L-type Ca channels. Calphostin C specifically inhibits contraction-stimulated glucose transport but not insulin-stimulated glucose transport in skeletal muscle. Wnt/beta-catenin/lef-1 signaling inhibitor. beta-catenin/TCF antagonist. Inhibits Wnt-activated genes in a dose-dependent fashion
Purity:
>95% (HPLC)
SMILES:
COC1=C2C3=C(OC)C=C(O)C4=C3C(C(CC(C)OC(=O)C3=CC=CC=C3)=C(OC)C4=O)=C3C(CC(C)OC(=O)OC4=CC=C
Solubility Chemicals:
Soluble in ethanol, methanol, DMSO or dimethylformamide. Poorly soluble in water.
Source / Host:
Isolated from Cladosporium cladosporioides.
Transportation:
Non-hazardous
UNSPSC Category:
Natural Products/Extracts
UNSPSC Number:
12352200
Use & Stability:
Stable for at least 1 year after receipt when stored at -20°C. After reconstitution protect from light at -20°C.

References

Calphostins (UCN-1028), novel and specific inhibitors of protein kinase C. I. Fermentation, isolation, physico-chemical properties and biological activities: E. Kobayashi, et al.; J. Antibiot. (Tokyo) 42, 1470 (1989) | Calphostins, novel and specific inhibitors of protein kinase C. II. Chemical structures: T. Iida, et al.; J. Antibiot. (Tokyo). 42, 1475 (1989) | Use and specificity of staurosporine, UCN-01, and calphostin C as protein kinase inhibitors: T. Tamaoki, et al.; Methods Enzymol. 201, 340 (1991) | Inhibition of protein kinase C by calphostin C is light-dependent: R.F. Burns, et al.; BBRC 176, 288 (1991) | Calphostin C, a specific protein kinase C inhibitor, activates human neutrophils: effect on phospholipase A2 and aggregation: S. Svetlov & S. Nigam; Biochim. Biophys. Acta 1177, 75 (1993) | Inhibition of diacylglycerol kinase by the antitumor agent calphostin C. Evidence for similarity between the active site of diacylglycerol kinase and the regulatory site of protein kinase C: C. Redman, et al.; Biochem. Pharmacol. 50, 235 (1995) | Calphostin C, a widely used protein kinase C inhibitor, directly and potently blocks L-type Ca channels: H.C. Hartzell & A. Rinderknecht; Am. J. Physiol. 270, C1293 (1996) | Calphostin C synergistically induces apoptosis with VP-16 in lymphoma cells which express abundant phosphorylated Bcl-2 protein: M. Murata, et al.; Cell. Mol. Life Sci. 53, 737 (1997) | Calphostin C induces selective disassembly of the Golgi complex by a protein kinase C-independent mechanism: M. Alonso, et al.; Eur. J. Cell Biol. 76, 93 (1998) | Growth inhibition induced by Ro 31-8220 and calphostin C in human glioblastoma cell lines is associated with apoptosis and inhibition of CDC2 kinase: M Begemann, et al.; Anticancer Res. 18, 3139 (1998) | Calphostin C triggers calcium-dependent apoptosis in human acute lymphoblastic leukemia cells: D.M. Zhu, et al.; Clin. Cancer Res. 4, 2967 (1998) | Calphostin C is an inhibitor of contraction, but not insulin-stimulated glucose transport, in skeletal muscle: J. Ihlemann, et al.; Acta Physiol. Scand. 167, 69 (1999) | Pharmacokinetic features and metabolism of calphostin C, a naturally occurring perylenequinone with antileukemic activity: C.L. Chen, et al.; Pharm. Res. 16, 1003 (1999) | Potent direct inhibition of mammalian phospholipase D isoenzymes by calphostin-c: V.A. Sciorra, et al.; Biochemistry 40, 2640 (2001) | Calphostin C as a rapid and strong inducer of apoptosis in human coronary artery smooth muscle cells: K.D. Krueger, et al.; Int. Immunopharmacol. 13, 1751 (2003) | Calphostin-C induction of vascular smooth muscle cell apoptosis proceeds through phospholipase D and microtubule inhibition: X.L. Zheng, et al.; J. Biol. Chem. 279, 7112 (2004) | Small-molecule antagonists of the oncogenic Tcf/beta-catenin protein complex: M. Lepourcelet, et al.; Cancer Cell. 5, 91 (2004) | Golgi complex disassembly caused by light-activated calphostin C involves MAPK and PKA: J.A. Morgado-Diaz, et al.; Tissue Cell 39, 161 (2007) | Killing of cancer cells by the photoactivatable protein kinase C inhibitor, calphostin C, involves induction of endoplasmic reticulum stress: A. Kaul & W.A Maltese; Neoplasia 11, 823 (2009) | Small molecule inhibitors of Wnt/beta-catenin/lef-1 signaling induces apoptosis in chronic lymphocytic leukemia cells in vitro and in vivo: R.K. Gandhirajan, et al.; Neoplasia 12, 326 (2010) | Investigation of 3-aryl-pyrimido[5,4-e][1,2,4]triazine-5,7-diones as small molecule antagonists of beta-catenin/TCF transcription: J. Zeller, et al.; Bioorg. Med. Chem. Lett. 23, 5814 (2013)