GO-6850

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 Search

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

Description
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

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
Protein kinase C alpha 21 Target ID: CHEMBL299 Sources: https://www.ncbi.nlm.nih.gov/pubmed/1874734	Inhibitor 8504	20.0 nM [IC50]
Protein kinase C beta 22 Target ID: CHEMBL3045 Sources: https://www.ncbi.nlm.nih.gov/pubmed/1874734	Inhibitor 8504	17.0 nM [IC50]
Protein kinase C gamma 7 Target ID: CHEMBL2938 Sources: https://www.ncbi.nlm.nih.gov/pubmed/1874734	Inhibitor 8504	20.0 nM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Contact dermatitis 20 Sources: https://www.ncbi.nlm.nih.gov/pubmed/7473193	Primary		Basic research	Unknown Approved Use Unknown
Pulmonary edema 25 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24884662	Primary		Basic research	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Histamine-induced vasoconstriction involves phosphorylation of a specific inhibitor protein for myosin phosphatase by protein kinase C alpha and delta isoforms.	2001-08-03	11397799
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.	2001-07-01	11377403
Role of zinc in pulmonary endothelial cell response to oxidative stress.	2001-07	11404267
Post-ischemic PKC inhibition impairs myocardial calcium handling and increases contractile protein calcium sensitivity.	2001-07	11399253
Calyculin-A induces focal adhesion assembly and tyrosine phosphorylation of p125(Fak), p130(Cas), and paxillin in Swiss 3T3 cells.	2001-07	11382927
DNA binding of TEA/ATTS domain factors is regulated by protein kinase C phosphorylation in human choriocarcinoma cells.	2001-06-29	11313339
Phosphorylation of RGS9-1 by an endogenous protein kinase in rod outer segments.	2001-06-22	11292825
Protein kinase C-mediated down-regulation of MDR3 mRNA expression in Chang liver cells.	2001-06-01	11331069
TSH-induced differentiated functions correlate with enhancement of phosphotyrosine phosphatase activity in thyroid cells. Effect of phorbol 12-myristate 13-acetate.	2001-06	11375131
Possible involvement of Rho kinase in Ca2+ sensitization and mobilization by MCh in tracheal smooth muscle.	2001-06	11350801
Calcium-sensing receptor activation induces intracellular calcium oscillations.	2001-06	11350736
Hypoxia alters the sensitivity of the L-type Ca(2+) channel to alpha-adrenergic receptor stimulation in the presence of beta-adrenergic receptor stimulation.	2001-05-25	11375273
Receptor-mediated inhibition of G protein-coupled inwardly rectifying potassium channels involves G(alpha)q family subunits, phospholipase C, and a readily diffusible messenger.	2001-05-18	11279027
Novel gp91(phox) homologues in vascular smooth muscle cells : nox1 mediates angiotensin II-induced superoxide formation and redox-sensitive signaling pathways.	2001-05-11	11348997
Phosphorylation of murine homeodomain protein Dlx3 by protein kinase C.	2001-05-04	11343707
Saturated non-esterified fatty acids stimulate de novo diacylglycerol synthesis and protein kinase c activity in cultured aortic smooth muscle cells.	2001-05	11380080
Analysis of the signal pathways involved in the regulation of fatty acid synthase gene expression by insulin and somatotropin.	2001-05	11374539
Effects of insulin-like growth factor-1 on retinal endothelial cell glucose transport and proliferation.	2001-05	11359881
Extracellular ATP stimulates an inhibitory pathway towards growth factor-induced cRaf-1 and MEKK activation in astrocyte cultures.	2001-05	11359865
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.	2001-05	11343250
Protein kinase C regulation of dopamine transporter initiated by nicotinic receptor activation in slices of rat prefrontal cortex.	2001-05	11331413
Leukotriene D(4) affects localisation of vinculin in intestinal epithelial cells via distinct tyrosine kinase and protein kinase C controlled events.	2001-05	11329379
Induction of embryonic dysmorphogenesis by high glucose concentration, disturbed inositol metabolism, and inhibited protein kinase C activity.	2001-05	11320530
Importance of PKC and PI3Ks in ethanol-induced contraction of cerebral arterial smooth muscle.	2001-05	11299216
Key role of PKC and Ca2+ in EGF protection of microtubules and intestinal barrier against oxidants.	2001-05	11292590
Differential effects of growth hormone and insulin-like growth factor I on human endothelial cell migration.	2001-05	11287339
Pertussis toxin directly activates endothelial cell p42/p44 MAP kinases via a novel signaling pathway.	2001-05	11287337
Protein kinase C-mediated desensitization of the neurokinin 1 receptor.	2001-05	11287322
Hypoxic enhancement of evoked noradrenaline release from the human neuroblastoma SH-SY5Y.	2001-04-18	11311975
Targeted inhibition of calcineurin signaling blocks calcium-dependent reactivation of Kaposi sarcoma-associated herpesvirus.	2001-04-15	11290600
Altered expression of glutamate transporters under hypoxic conditions in vitro.	2001-04-15	11288147
Use of A-192621 to provide evidence for involvement of endothelin ET(B)-receptors in endothelin-1-mediated cardiomyocyte hypertrophy.	2001-04-13	11334846
Ischemic preconditioning upregulates vascular endothelial growth factor mRNA expression and neovascularization via nuclear translocation of protein kinase C epsilon in the rat ischemic myocardium.	2001-04-13	11304492
Modulation of rat erg1, erg2, erg3 and HERG K+ currents by thyrotropin-releasing hormone in anterior pituitary cells via the native signal cascade.	2001-04-01	11283231
Chemorepellent signaling through the PACAP/lysozyme receptor is mediated through cAMP and PKC in Tetrahymena thermophila.	2001-04	11401196
Protein kinase C alpha modulates the Ca2+ influx phase of the Ca2+ response to 1alpha,25-dihydroxy-vitamin-D3 in skeletal muscle cells.	2001-04	11383922
Phorbol ester differentially regulates oxytocin receptor binding activity in hypothalamic cultured neurons and astrocytes.	2001-04	11311739
Signal transduction pathways for activation of extracellular signal-regulated kinase by arachidonic acid in rat neutrophils.	2001-04	11310854
Mechanisms of thrombin-induced MAPK activation associated with cell proliferation in human cultured tracheal smooth muscle cells.	2001-04	11306243
Levosimendan increases diastolic coronary flow in isolated guinea-pig heart by opening ATP-sensitive potassium channels.	2001-04	11300649
The role of protein kinase C in the regulation of serotonin-2A receptor expression.	2001-04	11299321
Interaction of CD163 with the regulatory subunit of casein kinase II (CKII) and dependence of CD163 signaling on CKII and protein kinase C.	2001-04	11298324
Cyclization strategies for the synthesis of macrocyclic bisindolylmaleimides.	2001-03-23	11300896
Thrombin activates p38 mitogen-activated protein kinase in vascular smooth muscle cells.	2001-03-16	11388701
Upregulation of p21(WAF1/CIP1) leads to morphologic changes and esterase activity in TPA-mediated differentiation of human prostate cancer cell line TSU-Pr1.	2001-03-08	11313866
Progesterone effect mediated by the voltage-dependent calcium channel and protein kinase C on noncapacitated cryopreserved bovine spermatozoa.	2001-03	11350374
ATP stimulated cyclic AMP formation in bovine chromaffin cells is enhanced by neuropeptide Y.	2001-03	11287099
Protein kinase C-dependent and -independent inhibition of Ca(2+) influx by phorbol ester in rat pancreatic beta-cells.	2001-03	11282458
Potent direct inhibition of mammalian phospholipase D isoenzymes by calphostin-c.	2001-02-27	11327888
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	11401334

Patents

Sample Use Guides

In Vivo Use Guide

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 `Mon Mar 31 22:03:36 GMT 2025` Edited by `admin` on `Mon Mar 31 22:03:36 GMT 2025`
Record UNII	L79H6N0V6C
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

GO-6850

Common Name

English

GF109203X

Preferred 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

GF-109203X

Common Name

English

Code System Code Type Description

PUBCHEM

2396