2-Fluoro-N-[2-(2-methyl-1H-indol-3-yl)ethyl]benzamide

2-Fluoro-N-[2-(2-methyl-1H-indol-3-yl)ethyl]benzamide
  • CAS No.:442633-00-3

Important Notice

  1. This product is a chemical product/pharmaceutical intermediate. It is not a drug, an active pharmaceutical ingredient (API), or a pharmaceutical-grade material. It has not been granted a drug approval number or a Chemical Drug Substance Approval Notice, has not passed drug-related review and approval, and is not manufactured, tested, or released in accordance with pharmaceutical GMP.
  2. This product is intended solely for non-clinical research, process development, quality studies, further chemical processing, or chemical synthesis. It must not be used in drug-product manufacturing, clinical trials, clinical diagnosis, or administration to humans or animals, or be sold, used as an input, submitted for regulatory filing, or released as an API or pharmaceutical material.
  3. The purchaser must not use this product, or supply it to another party, for personal consumption, sports or fitness, weight loss, health supplements, food, or animal feed.
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2-Fluoro-N-[2-(2-methyl-1H-indol-3-yl)ethyl]benzamide Basic information
Product Name:2-Fluoro-N-[2-(2-methyl-1H-indol-3-yl)ethyl]benzamide
Synonyms:2-Fluoro-N-[2-(2-methyl-1H-indol-3-yl)ethyl]benzamide;CK 666;CK-0944666;Arp2/3 Complex Inhibitor I, CK-666;CK 666 (CK 0944666);Benzamide, 2-fluoro-N-[2-(2-methyl-1H-indol-3-yl)ethyl]-
CAS:442633-00-3
MF:C18H17FN2O
MW:296.34
EINECS:
Product Categories:
Mol File:442633-00-3.mol
2-Fluoro-N-[2-(2-methyl-1H-indol-3-yl)ethyl]benzamide Chemical Properties
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
pka13.86±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
Hazard Codes Xi
Risk Statements 36
Safety Statements 26
WGK Germany 3
MSDS Information
2-Fluoro-N-[2-(2-methyl-1H-indol-3-yl)ethyl]benzamide Usage And Synthesis
DescriptionCK-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.
UsesCK-666 may be used to study Arp2/3-mediated structural changes in cells.
General DescriptionA 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 ActionsCK-666 binds to Arp2/3 complex, stabilizes the inactive state of the complex and prevents its movement into active conformation.
References1) 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

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