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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| Hydrogen peroxide enhances shedding of type I soluble tumor necrosis factor receptor from pulmonary epithelial cells. | 1999 Jan |
|
| Intracellular signaling pathways involved in acetaldehyde-induced collagen and fibronectin gene expression in human hepatic stellate cells. | 2001 May |
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| Vitamin E activates CRABP-II gene expression in cultured human fibroblasts, role of protein kinase C. | 2004 Jul 2 |
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| Regulation of proangiogenic factor CCN1 in cardiac muscle: impact of ischemia, pressure overload, and neurohumoral activation. | 2004 May 11 |
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| Effects of organochlorine insecticides on MAP kinase pathways in human HaCaT keratinocytes: key role of reactive oxygen species. | 2005 Aug |
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| Signalling pathways in the induction of proteasome expression by proteolysis-inducing factor in murine myotubes. | 2005 Jan |
|
| Piceatannol upregulates endothelial heme oxygenase-1 expression via novel protein kinase C and tyrosine kinase pathways. | 2006 Feb |
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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