Basic information Safety Supplier Related

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

Basic information Safety Supplier Related

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]-
  • 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
CAS:
442633-00-3
MF:
C18H17FN2O
MW:
296.34
Mol File:
442633-00-3.mol
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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
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.
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Safety Information

Hazard Codes 
Xi
Risk Statements 
36
Safety Statements 
26
WGK Germany 
3
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2-Fluoro-N-[2-(2-methyl-1H-indol-3-yl)ethyl]benzamide Usage And Synthesis

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a member of the class of indoles that is 2-methyltryptamine in which a hydrogen attached to the primary amino group has been replaced by a 2-fluorobenzoyl group.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]benzamideSupplier

3B Pharmachem (Wuhan) International Co.,Ltd.
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821-50328103-801 18930552037
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3bsc@sina.com
ShangHai Caerulum Pharma Discovery Co., Ltd.
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18149758185 18149758185
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sales-cpd@caerulumpharma.com
Shanghai Macklin Biochemical Co.,Ltd.
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15221275939 15221275939
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shenlinxing@macklin.cn
Sigma-Aldrich
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021-61415566 800-8193336
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orderCN@merckgroup.com
EMMX Biotechnology LLC
Tel
888-539-0666
Email
info@emmx.com
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