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Details

Stereochemistry ACHIRAL
Molecular Formula C24H18N4O
Molecular Weight 378.4259
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of GO-6976

SMILES

CN1C2=C(C=CC=C2)C3=C1C4=C(C5=CC=CC=C5N4CCC#N)C6=C3C(=O)NC6

InChI

InChIKey=VWVYILCFSYNJHF-UHFFFAOYSA-N
InChI=1S/C24H18N4O/c1-27-17-9-4-2-7-14(17)20-21-16(13-26-24(21)29)19-15-8-3-5-10-18(15)28(12-6-11-25)23(19)22(20)27/h2-5,7-10H,6,12-13H2,1H3,(H,26,29)

HIDE SMILES / InChI

Molecular Formula C24H18N4O
Molecular Weight 378.4259
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
Curator's Comment: Description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/8486620 | https://www.ncbi.nlm.nih.gov/pubmed/21366551 | https://www.ncbi.nlm.nih.gov/pubmed/16956345

Indolocarbazole GO-6976 inhibited the calcium-dependent protein kinase C (PKC) isozymes alpha and beta 1. As PKC is a central enzyme that modulates numerous biological functions GO-6976 is extensively used as a tool for studying the involvement of PKC in signal transduction pathways. GO6976 was originally synthesized by Goedecke (formerly a subsidiary of Warner-Lambert, now Pfizer) in Germany. Preclinical investigations carried out by Goedecke have been for the potential treatment of HIV infections. Preclinical research with GO 6976 had been conducted by Biomol Inc. and Calbiochem in the USA as a potential treatment for cancer. No further information has been available for the compound therefore it is assumed that development has been discontinued. In addition to GO-6976 inhibition of PKC, it was reported that GO-6976 also inhibits JAK 2 and FLT3 tyrosine kinases and non-kinase transmembrane guanylyl cyclase.

CNS Activity

Curator's Comment: GO-6976 is CNS active in animals. No human data available.

Approval Year

PubMed

PubMed

TitleDatePubMed
Inhibition of protein kinase C mu by various inhibitors. Differentiation from protein kinase c isoenzymes.
1996 Aug 26
Lipoteichoic acid-induced cyclooxygenase-2 expression requires activations of p44/42 and p38 mitogen-activated protein kinase signal pathways.
2002 Aug 16
Direct targeting of human cytomegalovirus protein kinase pUL97 by kinase inhibitors is a novel principle for antiviral therapy.
2002 May
Arsenite stimulated glucose transport in 3T3-L1 adipocytes involves both Glut4 translocation and p38 MAPK activity.
2003 Oct
Phospholipase D is involved in oxidative stress-induced migration of vascular smooth muscle cells via tyrosine phosphorylation and protein kinase C.
2004 Apr 30
Expression of adhesion molecules by sphingosine 1-phosphate and histamine in endothelial cells.
2004 Feb 20
Cigarette smoke extract increases C5a receptor expression in human bronchial epithelial cells.
2005 Jul
Isoflurane induces a protein kinase C alpha-dependent increase in cell-surface protein level and activity of glutamate transporter type 3.
2005 May
Oxidant-mediated activation of cytosolic phospholipase a(2) in pulmonary endothelium: role of protein kinase C alpha and a pertussis toxin-sensitive protein.
2005 May-Jun
Regulation of skin microvasculature angiogenesis, cell migration, and permeability by a specific inhibitor of PKCalpha.
2006 Feb
Oxidative stress induces actin-cytoskeletal and tight-junctional alterations in hepatocytes by a Ca2+ -dependent, PKC-mediated mechanism: protective effect of PKA.
2006 Jun 1
Integration of P2Y receptor-activated signal transduction pathways in G protein-dependent signalling networks.
2006 Sep
The sarcoplasmic-endoplasmic reticulum Ca2+ ATPase 2b regulates the Ca2+ transients elicited by P2Y2 activation in PC Cl3 thyroid cells.
2006 Sep
Phosphorylation of TRPV1 by neurokinin-1 receptor agonist exaggerates the capsaicin-mediated substance P release from cultured rat dorsal root ganglion neurons.
2008 Dec
Heme oxygenase-1 mediates the anti-inflammatory effect of Curcumin within LPS-stimulated human monocytes.
2008 Jun
Tamoxifen inhibits tumor cell invasion and metastasis in mouse melanoma through suppression of PKC/MEK/ERK and PKC/PI3K/Akt pathways.
2009 Jul 15
Lead acetate induces EGFR activation upstream of SFK and PKCalpha linkage to the Ras/Raf-1/ERK signaling.
2009 Mar 1
Alpha-adrenergic signalling activates protein kinase D and causes nuclear efflux of the transcriptional repressor HDAC5 in cultured adult mouse soleus skeletal muscle fibres.
2009 Mar 1
Suppression of PMA-induced tumor cell invasion by dihydroartemisinin via inhibition of PKCalpha/Raf/MAPKs and NF-kappaB/AP-1-dependent mechanisms.
2010 Jun 15
Ursodeoxycholic acid is conjugated with taurine to promote secretin-stimulated biliary hydrocholeresis in the normal rat.
2011
Comprehensive assay of kinase catalytic activity reveals features of kinase inhibitor selectivity.
2011 Oct 30
P-cresol induces disruption of cardiomyocyte adherens junctions.
2013 Apr 5
Patents

Sample Use Guides

Unknown
Route of Administration: Other
Inflammation-induced multinucleation in cultured microglia was prevented by a protein kinase C (PKC) inhibitor GO-6976 (100 nM). Follicle-stimulating hormone (FSH ) significantly induced follicle-enclosed oocytes (FEOs) meiotic resumption, however, the induced effect of FSH was dose-dependently inhibited by Gö6976, and 100 nM Gö6976 completely blocked FSH function in oocyte meiotic resumption.
Substance Class Chemical
Created
by admin
on Fri Dec 15 19:17:46 GMT 2023
Edited
by admin
on Fri Dec 15 19:17:46 GMT 2023
Record UNII
B9IQO7JZ16
Record Status Validated (UNII)
Record Version
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Name Type Language
GO-6976
Common Name English
GOE-6976
Common Name English
12H-INDOLO(2,3-A)PYRROLO(3,4-C)CARBAZOLE-12-PROPANENITRILE, 5,6,7,13-TETRAHYDRO-13-METHYL-5-OXO-
Systematic Name English
Code System Code Type Description
CAS
136194-77-9
Created by admin on Fri Dec 15 19:17:47 GMT 2023 , Edited by admin on Fri Dec 15 19:17:47 GMT 2023
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WIKIPEDIA
Go 6976
Created by admin on Fri Dec 15 19:17:47 GMT 2023 , Edited by admin on Fri Dec 15 19:17:47 GMT 2023
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EPA CompTox
DTXSID70159731
Created by admin on Fri Dec 15 19:17:47 GMT 2023 , Edited by admin on Fri Dec 15 19:17:47 GMT 2023
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PUBCHEM
3501
Created by admin on Fri Dec 15 19:17:47 GMT 2023 , Edited by admin on Fri Dec 15 19:17:47 GMT 2023
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CHEBI
51913
Created by admin on Fri Dec 15 19:17:47 GMT 2023 , Edited by admin on Fri Dec 15 19:17:47 GMT 2023
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FDA UNII
B9IQO7JZ16
Created by admin on Fri Dec 15 19:17:47 GMT 2023 , Edited by admin on Fri Dec 15 19:17:47 GMT 2023
PRIMARY
Related Record Type Details
ACTIVE MOIETY