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 20 Target ID: CHEMBL299 Sources: https://www.ncbi.nlm.nih.gov/pubmed/1874734	Inhibitor 8228	20.0 nM [IC50]
Protein kinase C beta 21 Target ID: CHEMBL3045 Sources: https://www.ncbi.nlm.nih.gov/pubmed/1874734	Inhibitor 8228	17.0 nM [IC50]
Protein kinase C gamma 6 Target ID: CHEMBL2938 Sources: https://www.ncbi.nlm.nih.gov/pubmed/1874734	Inhibitor 8228	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 24 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24884662	Primary		Basic research	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
5-lipoxygenase is phosphorylated by p38 kinase-dependent MAPKAP kinases.	2000 May 9	10779545
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
Chemorepellent signaling through the PACAP/lysozyme receptor is mediated through cAMP and PKC in Tetrahymena thermophila.	2001 Apr	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 Apr	11383922
Down-regulation of Na-K-Cl cotransport by protein kinase C is mediated by protein phosphatase 1 in pigmented ciliary epithelial cells.	2001 Apr	11273665
Mechanism of action of the calcium-sensing receptor in human antral gastrin cells.	2001 Apr	11266377
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	11283231
Use of A-192621 to provide evidence for involvement of endothelin ET(B)-receptors in endothelin-1-mediated cardiomyocyte hypertrophy.	2001 Apr 13	11334846
Targeted inhibition of calcineurin signaling blocks calcium-dependent reactivation of Kaposi sarcoma-associated herpesvirus.	2001 Apr 15	11290600
Altered expression of glutamate transporters under hypoxic conditions in vitro.	2001 Apr 15	11288147
Hypoxic enhancement of evoked noradrenaline release from the human neuroblastoma SH-SY5Y.	2001 Apr 18	11311975
Histamine-induced vasoconstriction involves phosphorylation of a specific inhibitor protein for myosin phosphatase by protein kinase C alpha and delta isoforms.	2001 Aug 3	11397799
Interactions between 2-fluoroadenine 9-beta-D-arabinofuranoside and the kinase inhibitor UCN-01 in human leukemia and lymphoma cells.	2001 Feb	11234887
Ethanol activates NFkappaB DNA binding and p56lck protein tyrosine kinase in human osteoblast-like cells.	2001 Feb	11182374
Differential actions of PKA and PKC in the regulation of glutamate release by group III mGluRs in the entorhinal cortex.	2001 Feb	11160494
Monocytes are differentially activated through HLA-DR, -DQ, and -DP molecules via mitogen-activated protein kinases.	2001 Feb 15	11160273
Potent direct inhibition of mammalian phospholipase D isoenzymes by calphostin-c.	2001 Feb 27	11327888
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	11223176
A proposed mechanism for the potentiation of cAMP-mediated acid secretion by carbachol.	2001 Jan	11121387
Selective secretion of protein kinase C isozymes by thrombin-stimulated human platelets.	2001 Jan 12	11162508
Role of zinc in pulmonary endothelial cell response to oxidative stress.	2001 Jul	11404267
Post-ischemic PKC inhibition impairs myocardial calcium handling and increases contractile protein calcium sensitivity.	2001 Jul	11399253
Calyculin-A induces focal adhesion assembly and tyrosine phosphorylation of p125(Fak), p130(Cas), and paxillin in Swiss 3T3 cells.	2001 Jul	11382927
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	11377403
TSH-induced differentiated functions correlate with enhancement of phosphotyrosine phosphatase activity in thyroid cells. Effect of phorbol 12-myristate 13-acetate.	2001 Jun	11375131
Possible involvement of Rho kinase in Ca2+ sensitization and mobilization by MCh in tracheal smooth muscle.	2001 Jun	11350801
Calcium-sensing receptor activation induces intracellular calcium oscillations.	2001 Jun	11350736
Protein kinase C-mediated down-regulation of MDR3 mRNA expression in Chang liver cells.	2001 Jun 1	11331069
Progesterone effect mediated by the voltage-dependent calcium channel and protein kinase C on noncapacitated cryopreserved bovine spermatozoa.	2001 Mar	11350374
Induction of the monocytic differentiation of myeloid leukaemia cells by cotylenin A, a plant growth regulator.	2001 Mar	11260075
Sequential activation of heterotrimeric and monomeric G proteins mediates PLD activity in smooth muscle.	2001 Mar	11171620
Modulation of cyclin D1 and its signaling components by the phorbol ester TPA and the tyrosine phosphatase inhibitor vanadate.	2001 Mar	11169972
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	11166332
Ceramide-induced cell death in the prostate cancer cell line LNCaP has both necrotic and apoptotic features.	2001 Mar 1	11241551
Thrombin activates p38 mitogen-activated protein kinase in vascular smooth muscle cells.	2001 Mar 16	11388701
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	11237743
Saturated non-esterified fatty acids stimulate de novo diacylglycerol synthesis and protein kinase c activity in cultured aortic smooth muscle cells.	2001 May	11380080
Analysis of the signal pathways involved in the regulation of fatty acid synthase gene expression by insulin and somatotropin.	2001 May	11374539
Effects of insulin-like growth factor-1 on retinal endothelial cell glucose transport and proliferation.	2001 May	11359881
Extracellular ATP stimulates an inhibitory pathway towards growth factor-induced cRaf-1 and MEKK activation in astrocyte cultures.	2001 May	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 May	11343250
Protein kinase C regulation of dopamine transporter initiated by nicotinic receptor activation in slices of rat prefrontal cortex.	2001 May	11331413
Leukotriene D(4) affects localisation of vinculin in intestinal epithelial cells via distinct tyrosine kinase and protein kinase C controlled events.	2001 May	11329379
Pertussis toxin directly activates endothelial cell p42/p44 MAP kinases via a novel signaling pathway.	2001 May	11287337
Novel gp91(phox) homologues in vascular smooth muscle cells : nox1 mediates angiotensin II-induced superoxide formation and redox-sensitive signaling pathways.	2001 May 11	11348997
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	11375273
Phosphorylation of murine homeodomain protein Dlx3 by protein kinase C.	2001 May 4	11343707

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 `Thu Jul 06 13:50:54 UTC 2023` Edited by `admin` on `Thu Jul 06 13:50:54 UTC 2023`
Record UNII	L79H6N0V6C
Record Status	`Validated (UNII)`
Record Version

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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