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W2270

Sigma-Aldrich

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:
253449-04-6
Molecular Weight:
426.15
MDL number:
MFCD00218393
UNSPSC Code:
12352200
PubChem Substance ID:
329830469
NACRES:
NA.77

Assay

≥98% (HPLC)

form

powder

color

white to beige

solubility

DMSO: 10 mg/mL, clear

storage temp.

2-8°C

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

InChI key

XUBJEDZHBUPBKL-UHFFFAOYSA-N

General description

Wiskostatin is a dibrominated carbazole. The N-alkylated side chain has a chiral hydroxyl group and a terminal tertiary amine.

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 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).

Pictograms

Skull and crossbones
GHS06

Signal Word

Danger

Hazard Statements

H301,H413

Hazard Classifications

Acute Tox. 3 Oral - Aquatic Chronic 4

Storage Class Code

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK

WGK 3

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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
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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