253449-04-6

Basic information

• Product Name: 1-(3,6-DIBROMO-9H-CARBAZOL-9-YL)-3-(DIMETHYLAMINO)PROPAN-2-OL
• Synonyms: 1-(3,6-DIBROMO-9H-CARBAZOL-9-YL)-3-(DIMETHYLAMINO)PROPAN-2-OL;WISKOSTATIN;9H-Carbazole-9-ethanol, 3,6-dibroMo-alpha-[(diMethylaMino)Methyl]-;3,6-Dibromo-9-[3-(dimethylamino)-2-hydroxyprop-1-yl]-9H-carbazole, 3-(3,6-Dibromo-9H-carbazol-9-yl)-N,N-dimethyl-2-hydroxypropylamine;1-(3,6-dibromocarbazol-9-yl)-3-(dimethylamino)propan-2-ol
• CAS NO: 253449-04-6
• Molecular Formula: C17H18Br2N2O
• Molecular Weight: 426.15
• Product Categories: Inhibitors
• Mol File: 253449-04-6.mol
• Article Data: 0

Chemical Properties

• Melting Point: 153-155
• Boiling Point: 320.2 °C at 760 mmHg
• Flash Point: 147.4 °C
• Appearance: white to beige/
• Density: 1.62 g/cm³
• Vapor Pressure: 0.000134mmHg at 25°C
• Refractive Index: 1.657
• Storage Temp.: 2-8°C
• Solubility: DMSO: soluble10mg/mL, clear
• PKA: 14.40±0.20(Predicted)
• 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.
• CAS DataBase Reference: 1-(3,6-DIBROMO-9H-CARBAZOL-9-YL)-3-(DIMETHYLAMINO)PROPAN-2-OL(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(3,6-DIBROMO-9H-CARBAZOL-9-YL)-3-(DIMETHYLAMINO)PROPAN-2-OL(253449-04-6)
• EPA Substance Registry System: 1-(3,6-DIBROMO-9H-CARBAZOL-9-YL)-3-(DIMETHYLAMINO)PROPAN-2-OL(253449-04-6)

Safety Data

• Hazard Codes: Xi,T
• Statements: 25
• Safety Statements: 45
• RIDADR: UN 2811 6.1 / PGIII
• WGK Germany: 3
• HazardClass: 6.1
• Hazardous Substances Data: 253449-04-6(Hazardous Substances Data)

Usage

Description

1-(3,6-DIBROMO-9H-CARBAZOL-9-YL)-3-(DIMETHYLAMINO)PROPAN-2-OL, also known as Wiskostatin, is a dibrominated carbazole with a chiral hydroxyl group and a terminal tertiary amine. It is a selective, reversible inhibitor of neural Wiskott-Aldrich syndrome protein (N-WASP) activity, binding to the regulatory domain of N-WASP and inhibiting the activation of the Arp2/3 complex. Wiskostatin has been shown to inhibit PIP2-induced actin polymerization and perturb agrin-elicited acetylcholine receptor clustering.

Uses

Used in Cellular and Molecular Research:
1-(3,6-DIBROMO-9H-CARBAZOL-9-YL)-3-(DIMETHYLAMINO)PROPAN-2-OL is used as a small-molecule inhibitor for investigating the role of N-WASP in various cellular processes. It is particularly useful in studying the effects of N-WASP on actin polymerization, receptor clustering, and synapse formation.
Used in Human Osteosarcoma U2OS Cells and Mouse-Tail Fibroblast Cell Lines:
1-(3,6-DIBROMO-9H-CARBAZOL-9-YL)-3-(DIMETHYLAMINO)PROPAN-2-OL is used as a neural (N)-WASP inhibitor to study the effects of N-WASP inhibition on cellular processes in human osteosarcoma U2OS cells and mouse-tail fibroblast cell lines.
Used in Cultured Neurons and Human Embryonic Kidney (HEK293) Cells Expressing HA-Parkin:
1-(3,6-DIBROMO-9H-CARBAZOL-9-YL)-3-(DIMETHYLAMINO)PROPAN-2-OL is used as a neural (N)-WASP inhibitor to investigate the role of N-WASP in the formation of dendritic spines and synapses in hippocampal neurons, as well as its effects on the actin-related protein 2/3 complex (Arp 2/3) in the context of vascular endothelial growth factor (VEGF) signaling.
Used in Dorsal Root Ganglion (DRG) Cells:
1-(3,6-DIBROMO-9H-CARBAZOL-9-YL)-3-(DIMETHYLAMINO)PROPAN-2-OL is used as a neural (N)-WASP inhibitor in DRG cells to further explore the effects of N-WASP on cellular processes and its potential role in various cellular signaling pathways.

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.

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

InChI:InChI=1/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