| Identification | Back Directory | [Name]
2-Fluoro-N-[2-(2-methyl-1H-indol-3-yl)ethyl]benzamide | [CAS]
442633-00-3 | [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]- | [Molecular Formula]
C18H17FN2O | [MDL Number]
MFCD03036271 | [MOL File]
442633-00-3.mol | [Molecular Weight]
296.34 |
| Chemical Properties | Back Directory | [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 | [form ]
powder | [pka]
13.86±0.46(Predicted) | [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. | [InChI]
1S/C18H17FN2O/c1-12-13(14-6-3-5-9-17(14)21-12)10-11-20-18(22)15-7-2-4-8-16(15)19/h2-9,21H,10-11H2,1H3,(H,20,22) | [InChIKey]
UXRKUKRXVWJFER-UHFFFAOYSA-N | [SMILES]
Cc1[nH]c2ccccc2c1CCNC(=O)c3ccccc3F |
| Hazard Information | Back Directory | [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a member of the class of indoles that is 2-methyltryptamine in which a hydrogen attached to the primary amino group has been replaced by a 2-fluorobenzoyl group.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 |
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BOC Sciences
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1-631-485-4226; 16314854226 |
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https://www.bocsci.com |
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Sigma-Aldrich
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021-61415566 800-8193336 |
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https://www.sigmaaldrich.cn |
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