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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
Structure of GO-6850

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)

HIDE SMILES / InChI

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

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

Curator's Comment: GF109203X (GO-6850) is CNS active in animals. No human data available.

Originator

Curator's Comment: Toullec et al., 1991. Laboratoires Glano, Centre de Recherches, 91951 Les Ulis, France

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
20.0 nM [IC50]
17.0 nM [IC50]
20.0 nM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
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
PLD pathway involved in carbachol-induced Cl- secretion: possible role of TNF-alpha.
2001 Apr
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
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 Sat Dec 16 08:24:51 GMT 2023
Edited
by admin
on Sat Dec 16 08:24:51 GMT 2023
Record UNII
L79H6N0V6C
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
GO-6850
Common Name English
1H-PYRROLE-2,5-DIONE, 3-(1-(3-(DIMETHYLAMINO)PROPYL)-1H-INDOL-3-YL)-4-(1H-INDOL-3-YL)-
Systematic Name English
BISINDOLYLMALEIMIDE I
Common Name English
GF109203X
Code English
GF-109203X
Common Name English
Code System Code Type Description
PUBCHEM
2396
Created by admin on Sat Dec 16 08:24:51 GMT 2023 , Edited by admin on Sat Dec 16 08:24:51 GMT 2023
PRIMARY
EPA CompTox
DTXSID50157932
Created by admin on Sat Dec 16 08:24:51 GMT 2023 , Edited by admin on Sat Dec 16 08:24:51 GMT 2023
PRIMARY
DRUG BANK
DB03777
Created by admin on Sat Dec 16 08:24:51 GMT 2023 , Edited by admin on Sat Dec 16 08:24:51 GMT 2023
PRIMARY
FDA UNII
L79H6N0V6C
Created by admin on Sat Dec 16 08:24:51 GMT 2023 , Edited by admin on Sat Dec 16 08:24:51 GMT 2023
PRIMARY
CAS
133052-90-1
Created by admin on Sat Dec 16 08:24:51 GMT 2023 , Edited by admin on Sat Dec 16 08:24:51 GMT 2023
PRIMARY
WIKIPEDIA
Bisindolylmaleimide I
Created by admin on Sat Dec 16 08:24:51 GMT 2023 , Edited by admin on Sat Dec 16 08:24:51 GMT 2023
PRIMARY
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ACTIVE MOIETY