Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C44H38O14 |
| Molecular Weight | 790.7641 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 2 / 2 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
COC1=CC(O)=C2C(=O)C(OC)=C(C[C@@H](C)OC(=O)OC3=CC=C(O)C=C3)C4=C2C1=C5C(OC)=CC(O)=C6C(=O)C(OC)=C(C[C@@H](C)OC(=O)C7=CC=CC=C7)C4=C56
InChI
InChIKey=SRJYZPCBWDVSGO-NHCUHLMSSA-N
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/t20-,21-/m1/s1
| Molecular Formula | C44H38O14 |
| Molecular Weight | 790.7641 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 2 / 2 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
Calphostin C (UCN-1028C), isolated compound from Cladosporium cladosporioides, is a cell permeable, potent and highly selective inhibitor of protein kinase C (IC50=0.05 uM). Calphostin C has been shown to compete at the DAG binding site and inhibit DGK (DAG kinase, DAGK). Calphostin inhibition of PKC is light dependent. At higher concentrations it inhibits myosin light chain kinase, PKA (cAMP-dependent protein kinase), protein kinase G, c-Src (pp60v-src protein TyK) (tyrosine kinase) and DGK. This compound also inhibits PC-PLD1 and -PLD2 (Phospholipase D1 and D2, PLD1 and PLD2). Calphostin C has been observed to induce apoptotic DNA fragmentation and cell death. This compound has demonstrated the ability to inhibit cardiac L-type Ca2+ channels. It has demonstrated the ability to Inhibit cardiac L-type calcium channel protein inhibitors. Calphostin C is an inhibitor of MYLK, PKA and PKD.
Originator
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Pentoxifylline and other protein kinase C inhibitors down-regulate HIV-LTR NF-kappa B induced gene expression. | 1994 Nov |
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| Protein kinase Cdelta-dependent induction of manganese superoxide dismutase gene expression by microtubule-active anticancer drugs. | 1998 Dec 18 |
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| Acetaldehyde enhances murine alpha2(I) collagen promoter activity by Ca2+-independent protein kinase C activation in cultured rat hepatic stellate cells. | 1999 Feb |
|
| Hydrogen peroxide enhances shedding of type I soluble tumor necrosis factor receptor from pulmonary epithelial cells. | 1999 Jan |
|
| Tumor necrosis factor-alpha stimulates attachment of small cell lung carcinoma to endothelial cells. | 1999 Mar |
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| Inducible expression of manganese superoxide dismutase by phorbol 12-myristate 13-acetate is mediated by Sp1 in endothelial cells. | 2000 Feb |
|
| Mechanism of doxorubicin-induced inhibition of sarcoplasmic reticulum Ca(2+)-ATPase gene transcription. | 2000 Jan 7-21 |
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| The transcription of the peroxisome proliferator-activated receptor alpha gene is regulated by protein kinase C. | 2001 Dec 15 |
|
| Protein kinase C-mediated down-regulation of MDR3 mRNA expression in Chang liver cells. | 2001 Jun 1 |
|
| Intracellular signaling pathways involved in acetaldehyde-induced collagen and fibronectin gene expression in human hepatic stellate cells. | 2001 May |
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| Noradrenaline and alpha-adrenergic signaling induce the hsp70 gene promoter in mollusc immune cells. | 2001 Oct |
|
| Induction of MnSOD gene by arachidonic acid is mediated by reactive oxygen species and p38 MAPK signaling pathway in human HepG2 hepatoma cells. | 2002 Jun 1 |
|
| Protein overload-induced NF-kappaB activation in proximal tubular cells requires H(2)O(2) through a PKC-dependent pathway. | 2002 May |
|
| High glucose stimulates synthesis of fibronectin via a novel protein kinase C, Rap1b, and B-Raf signaling pathway. | 2002 Nov 1 |
|
| Possible mechanisms underlying the mitogenic action of heptachlor in rat hepatocytes. | 2003 Dec 15 |
|
| The protein kinase C pathway plays a central role in the fibroblast growth factor-stimulated expression and transactivation activity of Runx2. | 2003 Jan 3 |
|
| Reactive oxygen species amplify protein kinase C signaling in high glucose-induced fibronectin expression by human peritoneal mesothelial cells. | 2004 Apr |
|
| Cadmium induces both pyruvate kinase and Na+/H+ exchanger activity through protein kinase C mediated signal transduction, in isolated digestive gland cells of Mytilus galloprovincialis (L.). | 2004 Apr |
|
| Involvement of mitogen-activated protein kinases and protein kinase C in cadmium-induced prostaglandin E2 production in primary mouse osteoblastic cells. | 2004 Aug 5 |
|
| Vitamin E activates CRABP-II gene expression in cultured human fibroblasts, role of protein kinase C. | 2004 Jul 2 |
|
| Abrogation of p21 expression by flavopiridol enhances depsipeptide-mediated apoptosis in malignant pleural mesothelioma cells. | 2004 Mar 1 |
|
| Regulation of proangiogenic factor CCN1 in cardiac muscle: impact of ischemia, pressure overload, and neurohumoral activation. | 2004 May 11 |
|
| Endothelins induce ETB receptor-mediated mechanical hypernociception in rat hindpaw: roles of cAMP and protein kinase C. | 2004 Oct 6 |
|
| Effects of organochlorine insecticides on MAP kinase pathways in human HaCaT keratinocytes: key role of reactive oxygen species. | 2005 Aug |
|
| Signalling pathways in the induction of proteasome expression by proteolysis-inducing factor in murine myotubes. | 2005 Jan |
|
| Signal pathway of cytokines produced by reactive oxygen species generated from phorbol myristate acetate-stimulated HMC-1 cells. | 2005 Jul |
|
| Activation of CREB by tauroursodeoxycholic acid protects cholangiocytes from apoptosis induced by mTOR inhibition. | 2005 Jun |
|
| Oxidant-mediated activation of cytosolic phospholipase a(2) in pulmonary endothelium: role of protein kinase C alpha and a pertussis toxin-sensitive protein. | 2005 May-Jun |
|
| Roles of protein kinase C, Ca2+, Pyk2, and c-Src in agonist activation of rat lacrimal gland p42/p44 MAPK. | 2006 Aug |
|
| Piceatannol upregulates endothelial heme oxygenase-1 expression via novel protein kinase C and tyrosine kinase pathways. | 2006 Feb |
|
| Mechanism of induction of muscle protein degradation by angiotensin II. | 2006 Jul |
|
| Induction of protein degradation in skeletal muscle by a phorbol ester involves upregulation of the ubiquitin-proteasome proteolytic pathway. | 2006 May 15 |
|
| peroxisome proliferator-activated receptor alpha activation-mediated regulation of endothelin-1 production via nitric oxide and protein kinase C signaling pathways in piglet cerebral microvascular endothelial cell culture. | 2007 Feb |
|
| NMDAR-nNOS generated zinc recruits PKCgamma to the HINT1-RGS17 complex bound to the C terminus of Mu-opioid receptors. | 2008 Oct |
|
| Tamoxifen inhibits TRPV6 activity via estrogen receptor-independent pathways in TRPV6-expressing MCF-7 breast cancer cells. | 2009 Dec |
|
| Superoxide production by NAD(P)H oxidase and mitochondria is increased in genetically obese and hyperglycemic rat heart and aorta before the development of cardiac dysfunction. The role of glucose-6-phosphate dehydrogenase-derived NADPH. | 2009 Jul |
|
| Regulation of gap junctional intercellular communication by TCDD in HMEC and MCF-7 breast cancer cells. | 2009 Mar 1 |
|
| Regulation of cerebrovascular endothelial peroxisome proliferator activator receptor alpha expression and nitric oxide production by clofibrate. | 2010 |
|
| Interpretation of the effects of protein kinase C inhibitors on human UDP-glucuronosyltransferase 1A (UGT1A) proteins in cellulo. | 2011 Jun |
|
| Hypoxia-induced up-regulation of aquaporin-1 protein in prostate cancer cells in a p38-dependent manner. | 2012 |
|
| Cadmium-induced apoptosis in the BJAB human B cell line: involvement of PKC/ERK1/2/JNK signaling pathways in HO-1 expression. | 2012 Oct 28 |
|
| Progesterone increases the activity of glutamate transporter type 3 expressed in Xenopus oocytes. | 2013 Sep 5 |
|
| Nicotine decreases the activity of glutamate transporter type 3. | 2014 Feb 10 |
Patents
Sample Use Guides
Mice: After intraperitoneal (i.p.) injection of a 40 mg/kg nontoxic bolus dose of calphostin C, the estimated Cmax was 2.9 uM, which is higher than the effective in vitro concentration of calphostin C against leukemic cells.
Route of Administration:
Intraperitoneal
In Vitro Use Guide
Curator's Comment: Glioma cell lines treated with calphostin C demonstrated a dose-dependent decrease (IC50 = 30 nM) in tumor invasiveness with a concomitant reduction in the activity of the MMP-2. https://www.ncbi.nlm.nih.gov/pubmed/8871536
Calphostin C inhibited PKC activity, increased the number of human glioma (U-373 MG) cells in S phase and produced strong cytotoxic effects (IC50 150 nM).
| Substance Class |
Chemical
Created
by
admin
on
Edited
Sat Dec 16 08:57:57 GMT 2023
by
admin
on
Sat Dec 16 08:57:57 GMT 2023
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| Record UNII |
I271P23G24
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| Record Status |
Validated (UNII)
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| Record Version |
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I271P23G24
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Calphostin C
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121263-19-2
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