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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
Putative conventional protein kinase C inhibitor Gödecke 6976 [12-(2-cyanoethyl)-6,7,12,13-tetrahydro-13-methyl-5-oxo-5H-indolo(2,3-a)pyrrolo(3,4-c)-carbazole] stimulates transglutaminase activity in primary mouse epidermal keratinocytes.
2002 Jul
Differential modulation of CaV2.3 Ca2+ channels by Galphaq/11-coupled muscarinic receptors.
2004 Feb
Gefitinib ("Iressa", ZD1839) inhibits SN38-triggered EGF signals and IL-8 production in gastric cancer cells.
2005 Apr
Cigarette smoke extract increases C5a receptor expression in human bronchial epithelial cells.
2005 Jul
Hypotonic shock mediation by p38 MAPK, JNK, PKC, FAK, OSR1 and SPAK in osmosensing chloride secreting cells of killifish opercular epithelium.
2005 Mar
Aldose reductase pathway mediates JAK-STAT signaling: a novel axis in myocardial ischemic injury.
2005 May
Immunomodulatory drugs (IMiDs) increase the production of IL-2 from stimulated T cells by increasing PKC-theta activation and enhancing the DNA-binding activity of AP-1 but not NF-kappaB, OCT-1, or NF-AT.
2005 Oct
Corticotropin-releasing hormone inhibits progesterone production in cultured human placental trophoblasts.
2006 Dec
Activation of ROS/NF-kappaB and Ca2+/CaM kinase II are necessary for VCAM-1 induction in IL-1beta-treated human tracheal smooth muscle cells.
2009 May 15
Nucleotide oligomerization domain 1 is a dominant pathway for NOS2 induction in vascular smooth muscle cells: comparison with Toll-like receptor 4 responses in macrophages.
2010 Aug
Angiotensin II inhibits activity of human organic anion transporter 3 through activation of protein kinase Calpha: accelerating endocytosis of the transporter.
2010 Feb 10
Zinc-triggered induction of tissue plasminogen activator by brain-derived neurotrophic factor and metalloproteinases.
2011 Sep
A broad activity screen in support of a chemogenomic map for kinase signalling research and drug discovery.
2013 Apr 15
Oxidative stress parameters induced by exposure to either cadmium or 17β-estradiol on Mytilus galloprovincialis hemocytes. The role of signaling molecules.
2014 Jan
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 Sat Dec 17 02:31:05 UTC 2022
Edited
by admin
on Sat Dec 17 02:31:05 UTC 2022
Record UNII
B9IQO7JZ16
Record Status Validated (UNII)
Record Version
  • Download
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 Sat Dec 17 02:31:05 UTC 2022 , Edited by admin on Sat Dec 17 02:31:05 UTC 2022
PRIMARY
WIKIPEDIA
Go 6976
Created by admin on Sat Dec 17 02:31:05 UTC 2022 , Edited by admin on Sat Dec 17 02:31:05 UTC 2022
PRIMARY
EPA CompTox
DTXSID70159731
Created by admin on Sat Dec 17 02:31:05 UTC 2022 , Edited by admin on Sat Dec 17 02:31:05 UTC 2022
PRIMARY
PUBCHEM
3501
Created by admin on Sat Dec 17 02:31:05 UTC 2022 , Edited by admin on Sat Dec 17 02:31:05 UTC 2022
PRIMARY
CHEBI
51913
Created by admin on Sat Dec 17 02:31:05 UTC 2022 , Edited by admin on Sat Dec 17 02:31:05 UTC 2022
PRIMARY
FDA UNII
B9IQO7JZ16
Created by admin on Sat Dec 17 02:31:05 UTC 2022 , Edited by admin on Sat Dec 17 02:31:05 UTC 2022
PRIMARY
Related Record Type Details
ACTIVE MOIETY