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Merck

W2270

Wiskostatin

Synonyme(s) :

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

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A propos de cet article

Formule empirique (notation de Hill) :
C17H18Br2N2O
Numéro CAS:
Poids moléculaire :
426.15
NACRES:
NA.77
PubChem Substance ID:
UNSPSC Code:
12352200
MDL number:
Assay:
≥98% (HPLC)
Form:
powder
Quality level:
Service technique
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assay

≥98% (HPLC)

Quality Level

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).


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Danger

hcodes

Hazard Classifications

Acute Tox. 3 Oral - Aquatic Chronic 4

Classe de stockage

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
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
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