Name: Wiskostatin
Brand: SIGMA

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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

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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 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

GHS06

signalword

Danger

hcodes

H301,H413

pcodes

P264 - P270 - P273 - P301 + P310 - P405 - P501

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_germany

WGK 3

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