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 18 Target ID: CHEMBL299 Sources: https://www.ncbi.nlm.nih.gov/pubmed/1874734	Inhibitor 8146	20.0 nM [IC50]
Protein kinase C beta 21 Target ID: CHEMBL3045 Sources: https://www.ncbi.nlm.nih.gov/pubmed/1874734	Inhibitor 8146	17.0 nM [IC50]
Protein kinase C gamma 6 Target ID: CHEMBL2938 Sources: https://www.ncbi.nlm.nih.gov/pubmed/1874734	Inhibitor 8146	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
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	11264178
Differential actions of PKA and PKC in the regulation of glutamate release by group III mGluRs in the entorhinal cortex.	2001 Feb	11160494
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
Modulation of noradrenaline-induced microvascular constriction by protein kinase inhibitors.	2001 Jan	11191837
Modulation of inducible nitric oxide synthase expression in rat intestinal cells by colon tumor promoters.	2001 Jan	11115551
Differential sensitivity of breast cancer cells to tumor necrosis factor-alpha: involvement of protein kinase C.	2001 Jan 26	11162606
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
TSH-induced differentiated functions correlate with enhancement of phosphotyrosine phosphatase activity in thyroid cells. Effect of phorbol 12-myristate 13-acetate.	2001 Jun	11375131
Protein kinase C-mediated down-regulation of MDR3 mRNA expression in Chang liver cells.	2001 Jun 1	11331069
Phosphorylation of RGS9-1 by an endogenous protein kinase in rod outer segments.	2001 Jun 22	11292825
Modulation of cyclin D1 and its signaling components by the phorbol ester TPA and the tyrosine phosphatase inhibitor vanadate.	2001 Mar	11169972
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	11222091
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	11150863
Leukotriene D(4) affects localisation of vinculin in intestinal epithelial cells via distinct tyrosine kinase and protein kinase C controlled events.	2001 May	11329379
Induction of embryonic dysmorphogenesis by high glucose concentration, disturbed inositol metabolism, and inhibited protein kinase C activity.	2001 May	11320530
Key role of PKC and Ca2+ in EGF protection of microtubules and intestinal barrier against oxidants.	2001 May	11292590
Differential effects of growth hormone and insulin-like growth factor I on human endothelial cell migration.	2001 May	11287339
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
Down-regulation of intrinsic P-glycoprotein expression in multicellular prostate tumor spheroids by reactive oxygen species.	2001 May 18	11279018

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 `Sat Dec 17 23:09:29 UTC 2022` Edited by `admin` on `Sat Dec 17 23:09:29 UTC 2022`
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