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Details

Stereochemistry ACHIRAL
Molecular Formula C25H24N4O2
Molecular Weight 412.4846
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of GO-6850

SMILES

CN(C)CCCn1cc(c2ccccc21)C3=C(c4c[nH]c5ccccc45)C(=NC3=O)O

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 412.4846
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
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
Phorbol ester differentially regulates oxytocin receptor binding activity in hypothalamic cultured neurons and astrocytes.
2001 Apr
Signal transduction pathways for activation of extracellular signal-regulated kinase by arachidonic acid in rat neutrophils.
2001 Apr
Mechanisms of thrombin-induced MAPK activation associated with cell proliferation in human cultured tracheal smooth muscle cells.
2001 Apr
Levosimendan increases diastolic coronary flow in isolated guinea-pig heart by opening ATP-sensitive potassium channels.
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
Mechanism of action of the calcium-sensing receptor in human antral gastrin cells.
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
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
Altered expression of glutamate transporters under hypoxic conditions in vitro.
2001 Apr 15
Hypoxic enhancement of evoked noradrenaline release from the human neuroblastoma SH-SY5Y.
2001 Apr 18
Histamine-induced vasoconstriction involves phosphorylation of a specific inhibitor protein for myosin phosphatase by protein kinase C alpha and delta isoforms.
2001 Aug 3
Potent direct inhibition of mammalian phospholipase D isoenzymes by calphostin-c.
2001 Feb 27
Role of zinc in pulmonary endothelial cell response to oxidative stress.
2001 Jul
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
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
Calcium-sensing receptor activation induces intracellular calcium oscillations.
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
DNA binding of TEA/ATTS domain factors is regulated by protein kinase C phosphorylation in human choriocarcinoma cells.
2001 Jun 29
Progesterone effect mediated by the voltage-dependent calcium channel and protein kinase C on noncapacitated cryopreserved bovine spermatozoa.
2001 Mar
ATP stimulated cyclic AMP formation in bovine chromaffin cells is enhanced by neuropeptide Y.
2001 Mar
Induction of the monocytic differentiation of myeloid leukaemia cells by cotylenin A, a plant growth regulator.
2001 Mar
Vascular endothelial growth factor and the in vivo increase in plasma extravasation in the hamster cheek pouch.
2001 Mar
Cyclization strategies for the synthesis of macrocyclic bisindolylmaleimides.
2001 Mar 23
Upregulation of p21(WAF1/CIP1) leads to morphologic changes and esterase activity in TPA-mediated differentiation of human prostate cancer cell line TSU-Pr1.
2001 Mar 8
Saturated non-esterified fatty acids stimulate de novo diacylglycerol synthesis and protein kinase c activity in cultured aortic smooth muscle cells.
2001 May
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
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
Induction of embryonic dysmorphogenesis by high glucose concentration, disturbed inositol metabolism, and inhibited protein kinase C activity.
2001 May
Importance of PKC and PI3Ks in ethanol-induced contraction of cerebral arterial smooth muscle.
2001 May
Key role of PKC and Ca2+ in EGF protection of microtubules and intestinal barrier against oxidants.
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
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
Hypoxia alters the sensitivity of the L-type Ca(2+) channel to alpha-adrenergic receptor stimulation in the presence of beta-adrenergic receptor stimulation.
2001 May 25
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 Jun 26 04:54:39 UTC 2021
Edited
by admin
on Sat Jun 26 04:54:39 UTC 2021
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 Jun 26 04:54:39 UTC 2021 , Edited by admin on Sat Jun 26 04:54:39 UTC 2021
PRIMARY
EPA CompTox
133052-90-1
Created by admin on Sat Jun 26 04:54:39 UTC 2021 , Edited by admin on Sat Jun 26 04:54:39 UTC 2021
PRIMARY
DRUG BANK
DB03777
Created by admin on Sat Jun 26 04:54:39 UTC 2021 , Edited by admin on Sat Jun 26 04:54:39 UTC 2021
PRIMARY
FDA UNII
L79H6N0V6C
Created by admin on Sat Jun 26 04:54:39 UTC 2021 , Edited by admin on Sat Jun 26 04:54:39 UTC 2021
PRIMARY
CAS
133052-90-1
Created by admin on Sat Jun 26 04:54:39 UTC 2021 , Edited by admin on Sat Jun 26 04:54:39 UTC 2021
PRIMARY
WIKIPEDIA
Bisindolylmaleimide I
Created by admin on Sat Jun 26 04:54:39 UTC 2021 , Edited by admin on Sat Jun 26 04:54:39 UTC 2021
PRIMARY
Related Record Type Details
ACTIVE MOIETY