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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
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
Chemorepellent signaling through the PACAP/lysozyme receptor is mediated through cAMP and PKC in Tetrahymena thermophila.
2001 Apr
Signal transduction pathways for activation of extracellular signal-regulated kinase by arachidonic acid in rat neutrophils.
2001 Apr
The role of protein kinase C in the regulation of serotonin-2A receptor expression.
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
Synergistic induction of apoptosis in human leukemia cells (U937) exposed to bryostatin 1 and the proteasome inhibitor lactacystin involves dysregulation of the PKC/MAPK 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
Ischemic preconditioning upregulates vascular endothelial growth factor mRNA expression and neovascularization via nuclear translocation of protein kinase C epsilon in the rat ischemic myocardium.
2001 Apr 13
Targeted inhibition of calcineurin signaling blocks calcium-dependent reactivation of Kaposi sarcoma-associated herpesvirus.
2001 Apr 15
Histamine-induced vasoconstriction involves phosphorylation of a specific inhibitor protein for myosin phosphatase by protein kinase C alpha and delta isoforms.
2001 Aug 3
Vascular endothelial growth factor enhances the expression of urokinase receptor in human endothelial cells via protein kinase C activation.
2001 Feb
Oxidized-LDL enhances coronary vasoconstriction by increasing the activity of protein kinase C isoforms alpha and epsilon.
2001 Feb
Ethanol activates NFkappaB DNA binding and p56lck protein tyrosine kinase in human osteoblast-like cells.
2001 Feb
Use of protein kinase C inhibitors results in rapid [Mg(2+)](i) mobilization in primary cultured rat aortic smooth muscle cells: are certain kinase C isoforms natural homeostatic regulators of cystolic free Mg(2+).
2001 Feb 16
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
Potent direct inhibition of mammalian phospholipase D isoenzymes by calphostin-c.
2001 Feb 27
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
Modulation of H2 histamine receptor-mediated cAMP generation and granulocytic differentiation by extracellular nucleotides via activation of protein kinase C.
2001 Jan
Modulation of noradrenaline-induced microvascular constriction by protein kinase inhibitors.
2001 Jan
p53-independent elevation of p21 expression by PMA results from PKC-mediated mRNA stabilization.
2001 Jan 12
Differential sensitivity of breast cancer cells to tumor necrosis factor-alpha: involvement of protein kinase C.
2001 Jan 26
Role of zinc in pulmonary endothelial cell response to oxidative stress.
2001 Jul
Post-ischemic PKC inhibition impairs myocardial calcium handling and increases contractile protein calcium sensitivity.
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
TSH-induced differentiated functions correlate with enhancement of phosphotyrosine phosphatase activity in thyroid cells. Effect of phorbol 12-myristate 13-acetate.
2001 Jun
Possible involvement of Rho kinase in Ca2+ sensitization and mobilization by MCh in tracheal smooth muscle.
2001 Jun
Protein kinase C-mediated down-regulation of MDR3 mRNA expression in Chang liver cells.
2001 Jun 1
Phosphorylation of RGS9-1 by an endogenous protein kinase in rod outer segments.
2001 Jun 22
Progesterone effect mediated by the voltage-dependent calcium channel and protein kinase C on noncapacitated cryopreserved bovine spermatozoa.
2001 Mar
Protein kinase C-dependent and -independent inhibition of Ca(2+) influx by phorbol ester in rat pancreatic beta-cells.
2001 Mar
Vascular endothelial growth factor and the in vivo increase in plasma extravasation in the hamster cheek pouch.
2001 Mar
Angiotensin AT(1) receptor phosphorylation and desensitization in a hepatic cell line. Roles of protein kinase c and phosphoinositide 3-kinase.
2001 Mar
Sequential activation of heterotrimeric and monomeric G proteins mediates PLD activity in smooth muscle.
2001 Mar
G-protein-coupled receptor kinase 3- and protein kinase C-mediated desensitization of the PACAP receptor type 1 in human Y-79 retinoblastoma cells.
2001 Mar
Ceramide-induced cell death in the prostate cancer cell line LNCaP has both necrotic and apoptotic features.
2001 Mar 1
Cyclization strategies for the synthesis of macrocyclic bisindolylmaleimides.
2001 Mar 23
Glycated serum albumin-induced vascular smooth muscle cell proliferation through activation of the mitogen-activated protein kinase/extracellular signal-regulated kinase pathway by protein kinase C.
2001 Mar 9
Analysis of the signal pathways involved in the regulation of fatty acid synthase gene expression by insulin and somatotropin.
2001 May
Effects of insulin-like growth factor-1 on retinal endothelial cell glucose transport and proliferation.
2001 May
Extracellular ATP stimulates an inhibitory pathway towards growth factor-induced cRaf-1 and MEKK activation in astrocyte cultures.
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
Importance of PKC and PI3Ks in ethanol-induced contraction of cerebral arterial smooth muscle.
2001 May
Differential effects of growth hormone and insulin-like growth factor I on human endothelial cell migration.
2001 May
Pertussis toxin directly activates endothelial cell p42/p44 MAP kinases via a novel signaling pathway.
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
Down-regulation of intrinsic P-glycoprotein expression in multicellular prostate tumor spheroids by reactive oxygen species.
2001 May 18
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