Details
Stereochemistry | ACHIRAL |
Molecular Formula | C25H24N4O2 |
Molecular Weight | 412.4837 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CN(C)CCCN1C=C(C2=C1C=CC=C2)C3=C(C(=O)NC3=O)C4=CNC5=C4C=CC=C5
InChI
InChIKey=QMGUOJYZJKLOLH-UHFFFAOYSA-N
InChI=1S/C25H24N4O2/c1-28(2)12-7-13-29-15-19(17-9-4-6-11-21(17)29)23-22(24(30)27-25(23)31)18-14-26-20-10-5-3-8-16(18)20/h3-6,8-11,14-15,26H,7,12-13H2,1-2H3,(H,27,30,31)
Molecular Formula | C25H24N4O2 |
Molecular Weight | 412.4837 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
DescriptionSources: https://www.ncbi.nlm.nih.gov/pubmed/1874734
Sources: https://www.ncbi.nlm.nih.gov/pubmed/1874734
GF109203X (GO-6850) displayed high selectivity for protein kinase C (PKC) isoenzymes. GF109203X (GO-6850) is a competitive PKC inhibitor with respect to ATP. As PKC is a central enzyme that modulates numerous biological functions GF109203X is extensively used as a tool for studying the involvement of PKC in signal transduction pathways.
CNS Activity
Sources: https://www.ncbi.nlm.nih.gov/pubmed/26670183 | https://www.ncbi.nlm.nih.gov/pubmed/11786500
Curator's Comment: GF109203X (GO-6850) is CNS active in animals. No human data available.
Originator
Sources: https://www.ncbi.nlm.nih.gov/pubmed/1874734
Curator's Comment: Toullec et al., 1991. Laboratoires Glano, Centre de Recherches, 91951 Les Ulis, France
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL299 Sources: https://www.ncbi.nlm.nih.gov/pubmed/1874734 |
20.0 nM [IC50] | ||
Target ID: CHEMBL3045 Sources: https://www.ncbi.nlm.nih.gov/pubmed/1874734 |
17.0 nM [IC50] | ||
Target ID: CHEMBL2938 Sources: https://www.ncbi.nlm.nih.gov/pubmed/1874734 |
20.0 nM [IC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | Unknown Approved UseUnknown |
|||
Primary | Unknown Approved UseUnknown |
PubMed
Title | Date | PubMed |
---|---|---|
Suppression subtractive hybridization identifies high glucose levels as a stimulus for expression of connective tissue growth factor and other genes in human mesangial cells. | 1999 Feb 26 |
|
Protein tyrosine kinase-dependent regulation of adenylate cyclase and phosphatidylinositol 3-kinase activates the expression of glial fibrillary acidic protein upon induction of differentiation in rat c6 glioma. | 2001 |
|
Protein kinase C alpha modulates the Ca2+ influx phase of the Ca2+ response to 1alpha,25-dihydroxy-vitamin-D3 in skeletal muscle cells. | 2001 Apr |
|
Levosimendan increases diastolic coronary flow in isolated guinea-pig heart by opening ATP-sensitive potassium channels. | 2001 Apr |
|
Interaction of CD163 with the regulatory subunit of casein kinase II (CKII) and dependence of CD163 signaling on CKII and protein kinase C. | 2001 Apr |
|
Down-regulation of Na-K-Cl cotransport by protein kinase C is mediated by protein phosphatase 1 in pigmented ciliary epithelial cells. | 2001 Apr |
|
Human uterine myometrial smooth muscle cell proliferation and vascular endothelial growth-factor production in response to platelet-derived growth factor. | 2001 Apr |
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PLD pathway involved in carbachol-induced Cl- secretion: possible role of TNF-alpha. | 2001 Apr |
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Modulation of rat erg1, erg2, erg3 and HERG K+ currents by thyrotropin-releasing hormone in anterior pituitary cells via the native signal cascade. | 2001 Apr 1 |
|
Use of A-192621 to provide evidence for involvement of endothelin ET(B)-receptors in endothelin-1-mediated cardiomyocyte hypertrophy. | 2001 Apr 13 |
|
Purine and pyrimidine nucleotide-sensitive phospholipase A(2) in ampulla from frog semicircular canal. | 2001 Feb |
|
Differential actions of PKA and PKC in the regulation of glutamate release by group III mGluRs in the entorhinal cortex. | 2001 Feb |
|
Regulation of phosphate uptake in primary cultured rabbit renal proximal tubule cells by glucocorticoids: evidence for nongenomic as well as genomic mechanisms. | 2001 Feb |
|
Involvement of protein kinase C in the presynaptic nicotinic modulation of [(3)H]-dopamine release from rat striatal synaptosomes. | 2001 Feb |
|
Upregulation of angiotensin-converting enzyme by vascular endothelial growth factor. | 2001 Feb |
|
Adenosine triphosphate-evoked cytosolic calcium oscillations in human granulosa-luteal cells: role of protein kinase C. | 2001 Feb |
|
Monocytes are differentially activated through HLA-DR, -DQ, and -DP molecules via mitogen-activated protein kinases. | 2001 Feb 15 |
|
Inhibition of depolarisation-evoked [(3)H]noradrenaline release from SH-SYFY human neuroblastoma cells by muscarinic (M1) receptors is not mediated by changes in [Ca(2+)]. | 2001 Feb 19 |
|
The stimulation of MAP kinase by 1,25(OH)(2)-vitamin D(3) in skeletal muscle cells is mediated by protein kinase C and calcium. | 2001 Feb 28 |
|
Phorbol ester-induced inhibition of potassium currents in rat sensory neurons requires voltage-dependent entry of calcium. | 2001 Jan |
|
A proposed mechanism for the potentiation of cAMP-mediated acid secretion by carbachol. | 2001 Jan |
|
Selective secretion of protein kinase C isozymes by thrombin-stimulated human platelets. | 2001 Jan 12 |
|
p53-independent elevation of p21 expression by PMA results from PKC-mediated mRNA stabilization. | 2001 Jan 12 |
|
Angiotensin AT(1) and AT(2) receptors differentially regulate angiopoietin-2 and vascular endothelial growth factor expression and angiogenesis by modulating heparin binding-epidermal growth factor (EGF)-mediated EGF receptor transactivation. | 2001 Jan 19 |
|
Differential sensitivity of breast cancer cells to tumor necrosis factor-alpha: involvement of protein kinase C. | 2001 Jan 26 |
|
Calyculin-A induces focal adhesion assembly and tyrosine phosphorylation of p125(Fak), p130(Cas), and paxillin in Swiss 3T3 cells. | 2001 Jul |
|
The effect of aliphatic, naphthenic, and aromatic hydrocarbons on production of reactive oxygen species and reactive nitrogen species in rat brain synaptosome fraction: the involvement of calcium, nitric oxide synthase, mitochondria, and phospholipase A. | 2001 Jul 1 |
|
Protein kinase C-mediated down-regulation of MDR3 mRNA expression in Chang liver cells. | 2001 Jun 1 |
|
ATP stimulated cyclic AMP formation in bovine chromaffin cells is enhanced by neuropeptide Y. | 2001 Mar |
|
Protein kinase C-dependent and -independent inhibition of Ca(2+) influx by phorbol ester in rat pancreatic beta-cells. | 2001 Mar |
|
Induction of the monocytic differentiation of myeloid leukaemia cells by cotylenin A, a plant growth regulator. | 2001 Mar |
|
Ceramide-induced cell death in the prostate cancer cell line LNCaP has both necrotic and apoptotic features. | 2001 Mar 1 |
|
Sp1-p53 heterocomplex mediates activation of HTLV-I long terminal repeat by 12-O-tetradecanoylphorbol-13-acetate that is antagonized by protein kinase C. | 2001 Mar 1 |
|
Cyclization strategies for the synthesis of macrocyclic bisindolylmaleimides. | 2001 Mar 23 |
|
Extracellular signal-regulated kinase and the small GTP-binding protein p21Rac1 are involved in the regulation of gene transcription by angiotensin II. | 2001 Mar-Apr |
|
Saturated non-esterified fatty acids stimulate de novo diacylglycerol synthesis and protein kinase c activity in cultured aortic smooth muscle cells. | 2001 May |
|
Tauroursodeoxycholic acid inserts the apical conjugate export pump, Mrp2, into canalicular membranes and stimulates organic anion secretion by protein kinase C-dependent mechanisms in cholestatic rat liver. | 2001 May |
|
Protein kinase C regulation of dopamine transporter initiated by nicotinic receptor activation in slices of rat prefrontal cortex. | 2001 May |
|
Leukotriene D(4) affects localisation of vinculin in intestinal epithelial cells via distinct tyrosine kinase and protein kinase C controlled events. | 2001 May |
|
Pertussis toxin directly activates endothelial cell p42/p44 MAP kinases via a novel signaling pathway. | 2001 May |
|
Protein kinase C-mediated desensitization of the neurokinin 1 receptor. | 2001 May |
|
Novel gp91(phox) homologues in vascular smooth muscle cells : nox1 mediates angiotensin II-induced superoxide formation and redox-sensitive signaling pathways. | 2001 May 11 |
|
Receptor-mediated inhibition of G protein-coupled inwardly rectifying potassium channels involves G(alpha)q family subunits, phospholipase C, and a readily diffusible messenger. | 2001 May 18 |
|
Down-regulation of intrinsic P-glycoprotein expression in multicellular prostate tumor spheroids by reactive oxygen species. | 2001 May 18 |
|
Phosphorylation of murine homeodomain protein Dlx3 by protein kinase C. | 2001 May 4 |
Patents
Sample Use Guides
In a murine model of delayed type hypersensitivity, GF109203X (GO-6850) inhibited dinitrofluorobenzene-induced contact dermatitis with and ID50 value of 150 micrograms/ear.
Intrahippocampal GF109203X (GO-6850) 0.3-30 pg/site modulates memory reconsolidation in rats. Rats that were pretreated with GF109203X (GO-6850) 0.12 mg/kg by intramuscular injection had less pulmonary edema induced by the high tidal volume ventilation.
Route of Administration:
Other
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/8904648
After pretreatment of cells with GF109203X (GO-6850) (5 microM, 45 min), the histamine (100 microM)-induced initial rise in [Ca2+]i, representing Ca2+ mobilization from internal stores, was inhibited in in DDT1 MF-2 smooth muscle cells.
Substance Class |
Chemical
Created
by
admin
on
Edited
Sat Dec 16 08:24:51 GMT 2023
by
admin
on
Sat Dec 16 08:24:51 GMT 2023
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Record UNII |
L79H6N0V6C
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Record Status |
Validated (UNII)
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Record Version |
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-
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DTXSID50157932
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DB03777
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L79H6N0V6C
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133052-90-1
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Bisindolylmaleimide I
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