1-(3,6-DIBROMO-9H-CARBAZOL-9-YL)-3-(DIMETHYLAMINO)PROPAN-2-OL
Synonym(s):1-(3,6-dibromocarbazol-9-yl)-3-(dimethylamino)propan-2-ol;Wiskostatin - CAS 253449-04-6 - Calbiochem
- CAS NO.:253449-04-6
- Empirical Formula: C17H18Br2N2O
- Molecular Weight: 426.15
- MDL number: MFCD00218393
- SAFETY DATA SHEET (SDS)
- Update Date: 2024-11-19 23:02:33
What is 1-(3,6-DIBROMO-9H-CARBAZOL-9-YL)-3-(DIMETHYLAMINO)PROPAN-2-OL?
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.
The Uses of 1-(3,6-DIBROMO-9H-CARBAZOL-9-YL)-3-(DIMETHYLAMINO)PROPAN-2-OL
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)
What are the applications of Application
Wiskostatin is a selective inhibitor of actin filament assembly
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
Properties of 1-(3,6-DIBROMO-9H-CARBAZOL-9-YL)-3-(DIMETHYLAMINO)PROPAN-2-OL
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 information for 1-(3,6-DIBROMO-9H-CARBAZOL-9-YL)-3-(DIMETHYLAMINO)PROPAN-2-OL
Signal word | Danger |
Pictogram(s) |
Skull and Crossbones Acute Toxicity GHS06 |
GHS Hazard Statements |
H301:Acute toxicity,oral H413:Hazardous to the aquatic environment, long-term hazard |
Precautionary Statement Codes |
P264:Wash hands thoroughly after handling. P264:Wash skin thouroughly after handling. P270:Do not eat, drink or smoke when using this product. P273:Avoid release to the environment. P301+P310:IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician. P405:Store locked up. P501:Dispose of contents/container to..… |
Computed Descriptors for 1-(3,6-DIBROMO-9H-CARBAZOL-9-YL)-3-(DIMETHYLAMINO)PROPAN-2-OL
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