1-(3,6-DIBROMO-9H-CARBAZOL-9-YL)-3-(DIMETHYLAMINO)PROPAN-2-OL

ChemicalBook > CAS DataBase List > 1-(3,6-DIBROMO-9H-CARBAZOL-9-YL)-3-(DIMETHYLAMINO)PROPAN-2-OL

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 - 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]-;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
CBNumber: CB4347723
Molecular Formula: C17H18Br2N2O
Formula Weight: 426.15
MOL File: 253449-04-6.mol

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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.

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Safety

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

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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..…

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N-Bromosuccinimide Price

Sigma-Aldrich

Product number: 681525
Product name: Wiskostatin
Packaging: 1mg
Price: $166
Updated: 2024/03/01

Sigma-Aldrich

Product number: 681525
Product name: Wiskostatin
Packaging: 5mg
Price: $437
Updated: 2024/03/01

Alfa Aesar

Product number: J67015
Product name: Wiskostatin
Purity: 99%
Packaging: 10mg
Price: $156
Updated: 2021/12/16

Cayman Chemical

Product number: 15047
Product name: Wiskostatin
Purity: ≥98%
Packaging: 1mg
Price: $68
Updated: 2024/03/01

Cayman Chemical

Product number: 15047
Product name: Wiskostatin
Purity: ≥98%
Packaging: 5mg
Price: $116
Updated: 2024/03/01

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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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253449-04-6, 1-(3,6-DIBROMO-9H-CARBAZOL-9-YL)-3-(DIMETHYLAMINO)PROPAN-2-OLRelated Search:

BKM120 (NVP-BKM120, Buparlisib) S-Trityl-L-cysteine ANSAMITOCIN P-3 2-Fluoro-N-[2-(2-methyl-1H-indol-3-yl)ethyl]benzamide SALOR-INT L144428-1EA 1-(3,6-DIBROMO-CARBAZOL-9-YL)-3-PYRROLIDIN-1-YL-PROPAN-2-OL 1-(3,6-DIBROMO-CARBAZOL-9-YL)-3-[4-(4-FLUORO-PHENYL)-PIPERAZIN-1-YL]-PROPAN-2-OL SALOR-INT L150053-1EA (+)-1-(3,6-DIBROMOCARBAZOL-9-YL)-3-PIPERAZIN-1-YL-PROPAN-2-OL, BIS TFA 3,6-DIBROMO-ALPHA-(1-PIPERAZINYLMETHYL)-9H-CARBAZOLE-9-ETHANOL DIHYDROCHLORIDE 1-(4-[2-HYDROXY-3-(1,3,6-TRIBROMO-9H-CARBAZOL-9-YL)PROPYL]PIPERAZINO)-3-(1,3,6-TRIBROMO-9H-CARBAZOL-9-YL)PROPAN-2-OL DIHYDROCHLORIDE 1-(3,6-DIBROMO-9H-CARBAZOL-9-YL)-3-(DIMETHYLAMINO)PROPAN-2-OL

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%

9H-Carbazole-9-ethanol, 3,6-dibromo-α-[(dimethylamino)methyl]-

3,6-Dibromo-α-[(dimethylamino)methyl]-9H-carbazole-9-ethanol

Wiskostatin,neuronal,ATP,irreversible,Arp2/3 Complex,inhibit,N-WASP,selective,Inhibitor,Actin-related protein 2/3 complex,actin polymerization

253449-04-6

C17H18Br2N2O

Inhibitors