1-(3,6-DIBROMO-9H-CARBAZOL-9-YL)-3-(DIMETHYLAMINO)PROPAN-2-OL Property

Melting point:

153-155

Boiling point:

320.2±22.0 °C(Predicted)

Density 

1.62±0.1 g/cm3(Predicted)

storage temp. 

2-8°C

solubility 

DMSO: soluble10mg/mL, clear

pka

14.40±0.20(Predicted)

form 

White solid

color 

white to beige

Stability:

Stable for 2 years from date of purchase as supplied. Solutions in DMSO or ethanol may be stored at -20° for up to 3 months.

Safety

Hazard Codes 

Xi,T

Risk Statements 

25

Safety Statements 

45

RIDADR 

UN 2811 6.1 / PGIII

WGK Germany 

3

Hazard Note 

Irritant

HazardClass 

6.1

HS Code 

2933998090

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

Hazard statements

H301Toxic if swalloed

H413May cause long lasting harmful effects to aquatic life

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P273Avoid release to the environment.

P301+P310IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.

P405Store locked up.

P501Dispose of contents/container to..…

1-(3,6-DIBROMO-9H-CARBAZOL-9-YL)-3-(DIMETHYLAMINO)PROPAN-2-OL Chemical Properties,Usage,Production

Description

Wiskostatin (253449-04-6) is a selective, reversible inhibitor of neural Wiskott-Aldrich syndrome protein (N-WASP) activity1. Binds to the regulatory domain of N-WASP and inhibits activation of Arp2/3 complex by forcing N-WASP into an inactive conformation2. Inhibits PIP2-induced actin polymerization (EC50=4 μM). Wiskostatin perturbs agrin-elicited acetylcholine receptor clustering3. Inhibits the formation of dendritic spines and synapses in hippocampal neurons.

Uses

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)

Definition

ChEBI: 1-(3,6-dibromocarbazol-9-yl)-3-(dimethylamino)propan-2-ol is a member of the class of carbazoles that is 1-(carbazol-9-yl)-3-(dimethylamino)propan-2-ol bearing two additional bromo substituents at positions 3 and 6 on the carbazole ring system. It is a member of carbazoles, an organobromine compound, a secondary alcohol and a tertiary amino compound.

General Description

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

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.

storage

+4°C

References

1) Peterson et al. (2002), Small molecules, big impact: a history of chemical inhibitors and the cytoskeleton; Chem. Biol., 9 1275 2) Peterson et al. (2004), Chemical inhibition of N-WASP by stabilization of a native autoinhibited conformation; Nat. Struct. Mol. Biol., 11 747 3) Cartaud et al. (2011), Agrin triggers the clustering of raft-associated acetylcholine receptors through actin cytoskeleton reorganization; Biol. Cell., 103 287 4) Wegner et al. (2008), N-wasp and the arp2/3 complex are critical regulators of actin in the development of dendritic spines and synapses; J. Biol. Chem., 283 15912