2-Fluoro-N-[2-(2-methyl-1H-indol-3-yl)ethyl]benzamide
Synonym(s):;2-Fluoro-N-[2-(2-methyl-1H-indol-3-yl)ethyl]-benzamide;
- CAS NO.:442633-00-3
- Empirical Formula: C18H17FN2O
- Molecular Weight: 296.34
- MDL number: MFCD03036271
- SAFETY DATA SHEET (SDS)
- Update Date: 2023-06-30 15:45:59
What is 2-Fluoro-N-[2-(2-methyl-1H-indol-3-yl)ethyl]benzamide?
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.
The Uses of 2-Fluoro-N-[2-(2-methyl-1H-indol-3-yl)ethyl]benzamide
CK-666 may be used to study Arp2/3-mediated structural changes in cells.
What are the applications of Application
CK 666 is an inhibitor of the Arp2/3 complex
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a member of the class of indoles that is 2-methyltryptamine in which a hydrogen attached to the primary amino group has been replaced by a 2-fluorobenzoyl group.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
Properties of 2-Fluoro-N-[2-(2-methyl-1H-indol-3-yl)ethyl]benzamide
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. |
Safety information for 2-Fluoro-N-[2-(2-methyl-1H-indol-3-yl)ethyl]benzamide
Computed Descriptors for 2-Fluoro-N-[2-(2-methyl-1H-indol-3-yl)ethyl]benzamide
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