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
- Molecular Weight:
- 426.15
- MDL Number:
- MFCD00218393
- MOL File:
- 253449-04-6.mol
- MSDS File:
- SDS
| 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. |
1-(3,6-DIBROMO-9H-CARBAZOL-9-YL)-3-(DIMETHYLAMINO)PROPAN-2-OL price More Price(25)
| Manufacturer | Product number | Product description | CAS number | Packaging | Price | Updated | Buy |
|---|---|---|---|---|---|---|---|
| Sigma-Aldrich | 681525 | Wiskostatin | 253449-04-6 | 1mg | $166 | 2024-03-01 | Buy |
| Sigma-Aldrich | 681525 | Wiskostatin | 253449-04-6 | 5mg | $437 | 2024-03-01 | Buy |
| Alfa Aesar | J67015 | Wiskostatin 99% | 253449-04-6 | 10mg | $156 | 2021-12-16 | Buy |
| Cayman Chemical | 15047 | Wiskostatin ≥98% | 253449-04-6 | 1mg | $68 | 2024-03-01 | Buy |
| Cayman Chemical | 15047 | Wiskostatin ≥98% | 253449-04-6 | 5mg | $116 | 2024-03-01 | Buy |
1-(3,6-DIBROMO-9H-CARBAZOL-9-YL)-3-(DIMETHYLAMINO)PROPAN-2-OL Chemical Properties,Uses,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
1-(3,6-DIBROMO-9H-CARBAZOL-9-YL)-3-(DIMETHYLAMINO)PROPAN-2-OL Suppliers
| Supplier | Tel | Country | ProdList | Advantage | |
|---|---|---|---|---|---|
| TargetMol Chemicals Inc. | +1-781-999-5354 +1-00000000000 | marketing@targetmol.com | United States | 19892 | 58 |
| Aceschem Inc. | +1-817863-6948 +1-（817）863-6948 | sales@aceschem.com | United States | 19639 | 58 |
| Aladdin Scientific | +1-833-552-7181 | sales@aladdinsci.com | United States | 57511 | 58 |
| J & K SCIENTIFIC LTD. | 010-82848833 400-666-7788 | jkinfo@jkchemical.com | China | 94838 | 76 |
| Nanjing Chemlin Chemical Co., Ltd | 025-83697070 | info@chemlin.com.cn | China | 18088 | 64 |
| Thermo Fisher Scientific | 800-810-5118 | cnchemical@thermofisher.com | China | 17779 | 75 |
| 9ding chemical ( Shanghai) Limited | 4009209199 | sales@9dingchem.com | China | 22519 | 55 |
| Sigma-Aldrich | 021-61415566 800-8193336 | orderCN@merckgroup.com | China | 51471 | 80 |
| Shanghai EFE Biological Technology Co., Ltd. | 021-65675885 18964387627 | info@efebio.com | China | 9709 | 58 |
| Target molecule Corp. | 857-239-0968 | service1@targetmol.com | United States | 2559 | 60 |
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