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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
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
Differential actions of PKA and PKC in the regulation of glutamate release by group III mGluRs in the entorhinal cortex.
2001 Feb
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 noradrenaline-induced microvascular constriction by protein kinase inhibitors.
2001 Jan
Modulation of inducible nitric oxide synthase expression in rat intestinal cells by colon tumor promoters.
2001 Jan
Differential sensitivity of breast cancer cells to tumor necrosis factor-alpha: involvement of protein kinase C.
2001 Jan 26
Post-ischemic PKC inhibition impairs myocardial calcium handling and increases contractile protein calcium sensitivity.
2001 Jul
Calyculin-A induces focal adhesion assembly and tyrosine phosphorylation of p125(Fak), p130(Cas), and paxillin in Swiss 3T3 cells.
2001 Jul
TSH-induced differentiated functions correlate with enhancement of phosphotyrosine phosphatase activity in thyroid cells. Effect of phorbol 12-myristate 13-acetate.
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
Modulation of cyclin D1 and its signaling components by the phorbol ester TPA and the tyrosine phosphatase inhibitor vanadate.
2001 Mar
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
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
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
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
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 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
  • 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 17 23:09:29 UTC 2022 , Edited by admin on Sat Dec 17 23:09:29 UTC 2022
PRIMARY
EPA CompTox
DTXSID50157932
Created by admin on Sat Dec 17 23:09:29 UTC 2022 , Edited by admin on Sat Dec 17 23:09:29 UTC 2022
PRIMARY
DRUG BANK
DB03777
Created by admin on Sat Dec 17 23:09:29 UTC 2022 , Edited by admin on Sat Dec 17 23:09:29 UTC 2022
PRIMARY
FDA UNII
L79H6N0V6C
Created by admin on Sat Dec 17 23:09:29 UTC 2022 , Edited by admin on Sat Dec 17 23:09:29 UTC 2022
PRIMARY
CAS
133052-90-1
Created by admin on Sat Dec 17 23:09:29 UTC 2022 , Edited by admin on Sat Dec 17 23:09:29 UTC 2022
PRIMARY
WIKIPEDIA
Bisindolylmaleimide I
Created by admin on Sat Dec 17 23:09:29 UTC 2022 , Edited by admin on Sat Dec 17 23:09:29 UTC 2022
PRIMARY
Related Record Type Details
ACTIVE MOIETY