W2270
Wiskostatin
Synonym(s):
1-(3,6-dibromocarbazol-9-yl)-3-(dimethylamino)propan-2-ol
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About This Item
Empirical Formula (Hill Notation):
C17H18Br2N2O
CAS Number:
Molecular Weight:
426.15
NACRES:
NA.77
PubChem Substance ID:
UNSPSC Code:
12352200
MDL number:
InChI key
XUBJEDZHBUPBKL-UHFFFAOYSA-N
SMILES string
CN(C)CC(O)Cn1c2ccc(Br)cc2c3cc(Br)ccc13
InChI
1S/C17H18Br2N2O/c1-20(2)9-13(22)10-21-16-5-3-11(18)7-14(16)15-8-12(19)4-6-17(15)21/h3-8,13,22H,9-10H2,1-2H3
assay
≥98% (HPLC)
form
powder
color
white to beige
solubility
DMSO: 10 mg/mL, clear
storage temp.
2-8°C
Quality Level
Related Categories
Application
Wiskostatin has been used:
- as a small-molecule inhibitor of Wiskott-Aldrich syndrome protein (WASP) in human osteosarcoma U2OS cells and mouse-tail fibroblast cell lines
- as a neural (N)-WASP inhibitor in cultured neurons and in the human embryonic kidney (HEK293) cells expressing HA-Parkin
- as a neural (N)-WASP inhibitor in dorsal root ganglion (DRG) cells to investigate vascular endothelial growth factor (VEGF) effect on the actin related protein 2/3 complex (Arp 2/3)
Biochem/physiol Actions
Wiskostatin is a selective inhibitor of N-WASP, a ubiquitously expressed member of the Wiskott-Aldrich Syndrome protein (WASp) family that regulates actin polymerization.
Wiskostatin is a selective inhibitor of N-WASP, a ubiquitously expressed member of the Wiskott-Aldrich Syndrome protein (WASp) family that regulates actin polymerization. Wiskostatin inhibits actin-dependent cellular functions, including migration, transmembrane transport and phagocytosis.
Wiskostatin mediates the inhibition of cytokinesis. It interacts with WASP especially at the regulatory guanosine-5′-triphosphate (GTP)ase-binding domain (GBD).
General description
Wiskostatin is a dibrominated carbazole. The N-alkylated side chain has a chiral hydroxyl group and a terminal tertiary amine.
signalword
Danger
hcodes
Hazard Classifications
Acute Tox. 3 Oral - Aquatic Chronic 4
Storage Class
6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects
wgk
WGK 3
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Guillaume Bompard et al.
BMC cell biology, 9, 42-42 (2008-08-01)
Cytokinesis is the final step of cell division taking place at the end of mitosis during which the cytoplasmic content and replicated chromosomes of a cell are equally partitioned between the two daughter cells. This process is achieved by the
Chaohong Liu et al.
PLoS biology, 11(11), e1001704-e1001704 (2013-11-14)
Negative regulation of receptor signaling is essential for controlling cell activation and differentiation. In B-lymphocytes, the down-regulation of B-cell antigen receptor (BCR) signaling is critical for suppressing the activation of self-reactive B cells; however, the mechanism underlying the negative regulation
Alexis Cotto-Rosario et al.
Microorganisms, 10(11) (2022-11-25)
New therapeutic agents for cryptosporidiosis are a critical medical need. The marine organic compound, tartrolon E (trtE), is highly effective against multiple apicomplexan parasites, including Cryptosporidium. Understanding the mechanism of action of trtE is required to advance in the drug
R Wollman et al.
Nature cell biology, 14(12), 1261-1269 (2012-11-13)
The actin cortex both facilitates and hinders the exocytosis of secretory granules. How cells consolidate these two opposing roles was not well understood. Here we show that antigen activation of mast cells induces oscillations in Ca(2+) and PtdIns(4,5)P(2) lipid levels
Jeffrey R Peterson et al.
Nature structural & molecular biology, 11(8), 747-755 (2004-07-06)
Current drug discovery efforts focus primarily on proteins with defined enzymatic or small molecule binding sites. Autoregulatory domains represent attractive alternative targets for small molecule inhibitors because they also occur in noncatalytic proteins and because allosteric inhibitors may avoid specificity
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