2-Fluoro-N-[2-(2-methyl-1H-indol-3-yl)ethyl]benzamide
- CAS No.
- 442633-00-3
- Chemical Name:
- 2-Fluoro-N-[2-(2-methyl-1H-indol-3-yl)ethyl]benzamide
- Synonyms
- CK 666;CK-0944666;CK 666 (CK 0944666);Arp2/3 Complex Inhibitor I, CK-666;2-Fluoro-N-[2-(2-methyl-1H-indol-3-yl)ethyl]benzamide;Benzamide, 2-fluoro-N-[2-(2-methyl-1H-indol-3-yl)ethyl]-;Inhibitor,HIV,meshwork,CK-666,Actin-related protein 2/3 complex,allosteric,CK 666,state,effector,active,inhibit,CK666,trabecular,Human immunodeficiency virus,Arp2/3 Complex
- CBNumber:
- CB52518908
- Molecular Formula:
- C18H17FN2O
- Molecular Weight:
- 296.34
- MDL Number:
- MFCD03036271
- MOL File:
- 442633-00-3.mol
Boiling point | 528.2±50.0 °C(Predicted) |
---|---|
Density | 1.235±0.06 g/cm3(Predicted) |
storage temp. | 2-8°C |
solubility | DMSO: ≥25mg/mL |
pka | 13.86±0.46(Predicted) |
form | powder |
color | white to tan |
Stability | Stable for 1 year from date of purchase as supplied. Solutions in DMSO or ethanol may be stored at -20°C for up to 3 months. |
2-Fluoro-N-[2-(2-methyl-1H-indol-3-yl)ethyl]benzamide price More Price(20)
Manufacturer | Product number | Product description | CAS number | Packaging | Price | Updated | Buy |
---|---|---|---|---|---|---|---|
Sigma-Aldrich | SML0006 | CK-666 ≥98% (HPLC), powder | 442633-00-3 | 5mg | $132 | 2024-03-01 | Buy |
Sigma-Aldrich | 182515 | Arp2/3 Complex Inhibitor I, CK-666 | 442633-00-3 | 25mg | $225 | 2024-03-01 | Buy |
Cayman Chemical | 29038 | CK-666 | 442633-00-3 | 1mg | $32 | 2024-03-01 | Buy |
Cayman Chemical | 29038 | CK-666 | 442633-00-3 | 5mg | $86 | 2024-03-01 | Buy |
Sigma-Aldrich | SML0006 | CK-666 ≥98% (HPLC), powder | 442633-00-3 | 25mg | $516 | 2024-03-01 | Buy |
2-Fluoro-N-[2-(2-methyl-1H-indol-3-yl)ethyl]benzamide Chemical Properties,Uses,Production
Description
CK-666 (442633-00-3) is a potent, selective and reversible inhibitor of ARP2/3 complex (actin related proteins 2 and 3) with an IC50?= 4 μM for human ARP2/3.1?Blocks actin nucleation and radically alters lamellipodial actin architecture, suspended cell shape and the cell spreading process.2 CK-666 attenuates BBB dysfunction induced by methamphetamine.3?It is an important new tool for studying actin assembly and the diverse range of actin-related processes in normal4 and pathophysiology5.
Uses
CK-666 may be used to study Arp2/3-mediated structural changes in cells.
Definition
ChEBI: CK-666 is a member of the class of indoles that is 2-methyltryptamine in which a hydrogen attached to the primary amino group has been replaced by a 2-fluorobenzoyl group. It is a cell-permeable inhibitor of actin assembly mediated by actin-related protein Arp2/3 complex which works by binding to Arp2/3 complex, stabilising the inactive state of the complex and preventing its movement into the active conformation. It has a role as an actin polymerisation inhibitor. It is a member of indoles, an organofluorine compound and a member of benzamides.
General Description
A cell-permeable indolyl-fluorobenzamide compound that selectively inhibits actin assembly mediated by actin-related protein Arp2/3 complex of human, bovine, fission yeast S. pombe, and budding yeast S. cerevisiae origin (IC50 = 4, 17, 5, and 12 μM, respectively), without affecting S. pombe formin domain Cdc12(FH2)-mediated or the spontaneous actin polymerization. Shown to inhibit the actin filament "comet tails" formation around intracellular Listeria in infected SKOV3 cells (IC50 = 7 μM) in a reversible manner. Structrual studies indicate that CK-666 targets a pocket formed between subdomain 4 of Arp2 and subdomain 1 of Arp3, preventing Arp2/3 from shifting into an active conformation upon N-WASP-VCA binding. CK-666 and CK-869 (Cat. No. 182516) exhibit different modes of binding, resulting in their different yeast cross-reactivities. CK-689 (Cat. No. 182517) can serve as a negative control.
Biochem/physiol Actions
CK-666 binds to Arp2/3 complex, stabilizes the inactive state of the complex and prevents its movement into active conformation.
storage
Store at -20°C
References
1) Nolan et al. (2009), Characterization of two classes of small molecule inhibitors of Arp2/3 complex; Nature, 460 1031 2) Henson et al. (2015), Arp2/3 complex inhibition radically alters lamellipodial actin architecture, suspended cell shape, and the cell spreading process; Mol. Biol. Cell, 26 887 3) Park et al. (2013), Methamphetamine-induced occluding endocytosis is mediated by the Arp2/3 complex-regulated actin rearrangement; J. Biol. Chem., 288 33324 4) Sun et al. (2013), Actin nucleator Arp2/3 complex is essential for mouse preimplantation embryo development; Reprod. Fertil. Dev., 25 617 5) Efremov et al. (2015), Distinct impact of targeted actin cytoskeleton reorganization on mechanical properties of normal and malignant cells; Biochim. Biophys. Acta, 1853 (11PtB) 3117
2-Fluoro-N-[2-(2-methyl-1H-indol-3-yl)ethyl]benzamide Preparation Products And Raw materials
Raw materials
Preparation Products
2-Fluoro-N-[2-(2-methyl-1H-indol-3-yl)ethyl]benzamide Suppliers
Supplier | Tel | Country | ProdList | Advantage | |
---|---|---|---|---|---|
TargetMol Chemicals Inc. | +1-781-999-5354 +1-00000000000 | marketing@targetmol.com | United States | 19892 | 58 |
Career Henan Chemica Co | +86-0371-86658258 +8613203830695 | laboratory@coreychem.com | China | 30250 | 58 |
Aladdin Scientific | +1-+1(833)-552-7181 | sales@aladdinsci.com | United States | 57511 | 58 |
3B Pharmachem (Wuhan) International Co.,Ltd. | 821-50328103-801 18930552037 | 3bsc@sina.com | China | 15848 | 69 |
ShangHai Caerulum Pharma Discovery Co., Ltd. | 18149758185 | sales-cpd@caerulumpharma.com | China | 3466 | 58 |
Shanghai Macklin Biochemical Co.,Ltd. | 15221275939 15221275939 | shenlinxing@macklin.cn | China | 16168 | 55 |
Sigma-Aldrich | 021-61415566 800-8193336 | orderCN@merckgroup.com | China | 51471 | 80 |
EMMX Biotechnology LLC | 888-539-0666 | info@emmx.com | United States | 8449 | 60 |
Shanghai EFE Biological Technology Co., Ltd. | 021-65675885 18964387627 | info@efebio.com | China | 9806 | 58 |
Tianjin Kailiqi Biotechnology Co., Ltd. | 15076683720 | klq@cw-bio.com | China | 4192 | 55 |