1-(3,6-DIBROMO-9H-CARBAZOL-9-YL)-3-(DIMETHYLAMINO)PROPAN-2-OL
- Product Name
- 1-(3,6-DIBROMO-9H-CARBAZOL-9-YL)-3-(DIMETHYLAMINO)PROPAN-2-OL
- CAS No.
- 253449-04-6
- Chemical Name
- 1-(3,6-DIBROMO-9H-CARBAZOL-9-YL)-3-(DIMETHYLAMINO)PROPAN-2-OL
- Synonyms
- WISKOSTATIN;Wiskostatin, N-WASP inhibitor;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;3,6-Dibromo-α-[(dimethylamino)methyl]-9H-carbazole-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]-
- CBNumber
- CB4347723
- Molecular Formula
- C17H18Br2N2O
- Formula Weight
- 426.15
- MOL File
- 253449-04-6.mol
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.
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..…
N-Bromosuccinimide Price
- Product number
- 681525
- Product name
- Wiskostatin
- Packaging
- 1mg
- Price
- $166
- Updated
- 2024/03/01
- Product number
- 681525
- Product name
- Wiskostatin
- Packaging
- 5mg
- Price
- $437
- Updated
- 2024/03/01
- Product number
- J67015
- Product name
- Wiskostatin
- Purity
- 99%
- Packaging
- 10mg
- Price
- $156
- Updated
- 2021/12/16
- Product number
- 15047
- Product name
- Wiskostatin
- Purity
- ≥98%
- Packaging
- 1mg
- Price
- $68
- Updated
- 2024/03/01
- Product number
- 15047
- Product name
- Wiskostatin
- Purity
- ≥98%
- Packaging
- 5mg
- Price
- $116
- Updated
- 2024/03/01
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
1-(3,6-DIBROMO-9H-CARBAZOL-9-YL)-3-(DIMETHYLAMINO)PROPAN-2-OL Preparation Products And Raw materials
Raw materials
Preparation Products
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