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| 1-(3,6-DIBROMO-9H-CARBAZOL-9-YL)-3-(DIMETHYLAMINO)PROPAN-2-OL 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;9H-Carbazole-9-ethanol, 3,6-dibroMo-alpha-[(diMethylaMino)Methyl]-;WISKOSTATIN;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;3,6-Dibromo-α-[(dimethylamino)methyl]-9H-cabazole-9-ethanol;Wiskostatin - CAS 253449-04-6 - Calbiochem;1-(3,6-Dibromo-9H-carbazol-9-yl)-3-(dimethylamino)propan-2-ol 97% | | CAS: | 253449-04-6 | | MF: | C17H18Br2N2O | | MW: | 426.15 | | EINECS: | | Product Categories: | Inhibitors | | Mol File: | 253449-04-6.mol |
| 1-(3,6-DIBROMO-9H-CARBAZOL-9-YL)-3-(DIMETHYLAMINO)PROPAN-2-OL Chemical Properties |
| 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. |
| 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 |
| 1-(3,6-DIBROMO-9H-CARBAZOL-9-YL)-3-(DIMETHYLAMINO)PROPAN-2-OL Usage And Synthesis |
| 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)
| | 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. | | 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 |
| 1-(3,6-DIBROMO-9H-CARBAZOL-9-YL)-3-(DIMETHYLAMINO)PROPAN-2-OL Preparation Products And Raw materials |
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