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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
5-lipoxygenase is phosphorylated by p38 kinase-dependent MAPKAP kinases.
2000 May 9
High glucose stimulates Ca2+ uptake via cAMP and PLC/PKC pathways in primary cultured renal proximal tubule cells.
2001
Chemorepellent signaling through the PACAP/lysozyme receptor is mediated through cAMP and PKC in Tetrahymena thermophila.
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
Mechanism of action of the calcium-sensing receptor in human antral gastrin cells.
2001 Apr
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
Phosphorylation of the N-ethylmaleimide-sensitive factor is associated with depolarization-dependent neurotransmitter release from synaptosomes.
2001 Apr 13
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
Oxidized-LDL enhances coronary vasoconstriction by increasing the activity of protein kinase C isoforms alpha and epsilon.
2001 Feb
Ethanol activates NFkappaB DNA binding and p56lck protein tyrosine kinase in human osteoblast-like cells.
2001 Feb
Inhibition of depolarisation-evoked [(3)H]noradrenaline release from SH-SYFY human neuroblastoma cells by muscarinic (M1) receptors is not mediated by changes in [Ca(2+)].
2001 Feb 19
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
A potential role for protein kinase C-epsilon in regulating megakaryocytic lineage commitment.
2001 Jan 5
Role of zinc in pulmonary endothelial cell response to oxidative stress.
2001 Jul
Protein kinase C-mediated down-regulation of MDR3 mRNA expression in Chang liver cells.
2001 Jun 1
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
Sequential activation of heterotrimeric and monomeric G proteins mediates PLD activity in smooth muscle.
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
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
Stimulation of extracellular signal-regulated kinases and proliferation in rat osteoblastic cells by parathyroid hormone is protein kinase C-dependent.
2001 Mar 9
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
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
Phosphorylation of murine homeodomain protein Dlx3 by protein kinase C.
2001 May 4
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 16 08:24:51 UTC 2023
Edited
by admin
on Sat Dec 16 08:24:51 UTC 2023
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 16 08:24:51 UTC 2023 , Edited by admin on Sat Dec 16 08:24:51 UTC 2023
PRIMARY
EPA CompTox
DTXSID50157932
Created by admin on Sat Dec 16 08:24:51 UTC 2023 , Edited by admin on Sat Dec 16 08:24:51 UTC 2023
PRIMARY
DRUG BANK
DB03777
Created by admin on Sat Dec 16 08:24:51 UTC 2023 , Edited by admin on Sat Dec 16 08:24:51 UTC 2023
PRIMARY
FDA UNII
L79H6N0V6C
Created by admin on Sat Dec 16 08:24:51 UTC 2023 , Edited by admin on Sat Dec 16 08:24:51 UTC 2023
PRIMARY
CAS
133052-90-1
Created by admin on Sat Dec 16 08:24:51 UTC 2023 , Edited by admin on Sat Dec 16 08:24:51 UTC 2023
PRIMARY
WIKIPEDIA
Bisindolylmaleimide I
Created by admin on Sat Dec 16 08:24:51 UTC 2023 , Edited by admin on Sat Dec 16 08:24:51 UTC 2023
PRIMARY
Related Record Type Details
ACTIVE MOIETY