| Identification | Back Directory | [Name]
1-(3,6-DIBROMO-9H-CARBAZOL-9-YL)-3-(DIMETHYLAMINO)PROPAN-2-OL | [CAS]
253449-04-6 | [Synonyms]
WISKOSTATIN
Wiskostatin - CAS 253449-04-6 - Calbiochem
1-(3,6-dibromocarbazol-9-yl)-3-(dimethylamino)propan-2-ol
3,6-Dibromo-α-[(dimethylamino)methyl]-9H-cabazole-9-ethanol
1-(3,6-DIBROMO-9H-CARBAZOL-9-YL)-3-(DIMETHYLAMINO)PROPAN-2-OL
9H-Carbazole-9-ethanol, 3,6-dibromo-α-[(dimethylamino)methyl]-
1-(3,6-Dibromo-9H-carbazol-9-yl)-3-(dimethylamino)propan-2-ol 97%
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 | [Molecular Formula]
C17H18Br2N2O | [MDL Number]
MFCD00218393 | [MOL File]
253449-04-6.mol | [Molecular Weight]
426.15 |
| Chemical Properties | Back Directory | [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 | [form ]
White solid | [pka]
14.40±0.20(Predicted) | [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 Data | Back Directory | [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 Information | Back Directory | [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]
A selective, reversible inhibitor of N-WASP (neural Wiskott-Aldrich syndrome protein) that selectively blocks actin filament assembly. Appears to bind to N-WASP, stabilize the autoinhibited conformation and prevent the activation of Arp2/3 (actin-related protein 2/3) complex. | [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 |
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Sigma-Aldrich
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