W2270

Wiskostatin

• Synonym(s): 1-(3,6-dibromocarbazol-9-yl)-3-(dimethylamino)propan-2-ol
• Empirical Formula (Hill Notation): C₁₇H₁₈Br₂N₂O
• CAS Number: 253449-04-6
• Molecular Weight: 426.15
• NACRES: NA.77
• PubChem Substance ID: 329830469
• UNSPSC Code: 12352200
• MDL number: MFCD00218393
• Assay: ≥98% (HPLC)
• Form: powder

Properties

• assay: ≥98% (HPLC)
• Quality Segment: 100
• 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

Description

General description

Wiskostatin is a dibrominated carbazole. The N-alkylated side chain has a chiral hydroxyl group and a terminal tertiary amine.[1]

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[2]
• as a neural (N)-WASP inhibitor in cultured neurons[3] and in the human embryonic kidney (HEK293) cells expressing HA-Parkin[4]
• 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)[5]

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).[1]

Safety Information

• 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: WGK 3