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W2270

Sigma-Aldrich

Wiskostatin

Synonyme(s) :

1-(3,6-dibromocarbazol-9-yl)-3-(dimethylamino)propan-2-ol

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About This Item

Formule empirique (notation de Hill):
C17H18Br2N2O
Numéro CAS:
253449-04-6
Poids moléculaire :
426.15
Numéro MDL:
MFCD00218393
Code UNSPSC :
12352200
ID de substance PubChem :
329830469
Nomenclature NACRES :
NA.77

Pureté

≥98% (HPLC)

Forme

powder

Couleur

white to beige

Solubilité

DMSO: 10 mg/mL, clear

Température de stockage

2-8°C

Chaîne SMILES 

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

Clé InChI

XUBJEDZHBUPBKL-UHFFFAOYSA-N

Description générale

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)

Actions biochimiques/physiologiques

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).

Pictogrammes

Skull and crossbones
GHS06

Mention d'avertissement

Danger

Mentions de danger

H301,H413

Classification des risques

Acute Tox. 3 Oral - Aquatic Chronic 4

Code de la classe de stockage

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

Classe de danger pour l'eau (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
Astrid Escudero-Esparza et al.
Journal of experimental & clinical cancer research : CR, 31, 43-43 (2012-05-09)
Recent studies have shown dysregulation in TJ structure of several cancers including breast. Claudin-5 is a protein member of the TJ structure expressed in both endothelial and epithelial cells. This study examined the level of expression and distribution of Claudin-5
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
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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