ChemicalBook > CAS DataBase List > 2-Fluoro-N-[2-(2-methyl-1H-indol-3-yl)ethyl]benzamide

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

Product Name: 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 ，S7690;CK 666 (CK 0944666);CK-666, 10 mM in DMSO;Arp2/3 Complex Inhibitor I, CK-666;CK 666, Actin polymerization inhibitor;2-Fluoro-N-[2-(2-methyl-3-indolyl)ethyl]benzamide;2-Fluoro-N-[2-(2-methyl-1H-indol-3-yl)ethyl]benzamide;Benzamide, 2-fluoro-N-[2-(2-methyl-1H-indol-3-yl)ethyl]-
CBNumber: CB52518908
Molecular Formula: C18H17FN2O
Formula Weight: 296.34
MOL File: 442633-00-3.mol

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

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

Hazard Codes: Xi
Risk Statements: 36
Safety Statements: 26
WGK Germany: 3

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Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H319Causes serious eye irritation

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

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N-Bromosuccinimide Price

Sigma-Aldrich

Product number: SML0006
Product name: CK-666
Purity: ≥98% (HPLC), powder
Packaging: 5mg
Price: $136
Updated: 2025/07/31

Sigma-Aldrich

Product number: 182515
Product name: Arp2/3 Complex Inhibitor I, CK-666
Packaging: 25mg
Price: $231
Updated: 2025/07/31

Cayman Chemical

Product number: 29038
Product name: CK-666
Packaging: 1mg
Price: $32
Updated: 2024/03/01

Cayman Chemical

Product number: 29038
Product name: CK-666
Packaging: 5mg
Price: $86
Updated: 2024/03/01

Sigma-Aldrich

Product number: SML0006
Product name: CK-666
Purity: ≥98% (HPLC), powder
Packaging: 25mg
Price: $530
Updated: 2025/07/31

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2-Fluoro-N-[2-(2-methyl-1H-indol-3-yl)ethyl]benzamide Chemical Properties,Usage,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] B. J. NOLEN. Characterization of two classes of small molecule inhibitors of Arp2/3 complex[J]. Nature, 2009, 460 7258: 1031-1034. DOI:10.1038/nature08231
[2] JOHN H HENSON. Arp2/3 complex inhibition radically alters lamellipodial actin architecture, suspended cell shape, and the cell spreading process.[J]. Molecular Biology of the Cell, 2015, 26 5: 887-900. DOI:10.1091/mbc.e14-07-1244
[3] MINSEON PARK. Methamphetamine-induced occludin endocytosis is mediated by the Arp2/3 complex-regulated actin rearrangement.[J]. The Journal of Biological Chemistry, 2013: 33324-33334. DOI:10.1074/jbc.m113.483487
[4] SHAO-CHEN SUN. Actin nucleator Arp2/3 complex is essential for mouse preimplantation embryo development.[J]. Reproduction, fertility, and development, 2013, 25 4: 617-623. DOI:10.1071/rd12011
[5] YU.M. EFREMOV. Distinct impact of targeted actin cytoskeleton reorganization on mechanical properties of normal and malignant cells[J]. Biochimica et biophysica acta. Molecular cell research, 2015, 1853 11: Pages 3117-3125. DOI:10.1016/j.bbamcr.2015.05.008

2-Fluoro-N-[2-(2-methyl-1H-indol-3-yl)ethyl]benzamide Preparation Products And Raw materials

Raw materials

Preparation Products

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

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442633-00-3, 2-Fluoro-N-[2-(2-methyl-1H-indol-3-yl)ethyl]benzamideRelated Search:

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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]-

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CK 666, Actin polymerization inhibitor

CK-666, 10 mM in DMSO

2-Fluoro-N-[2-(2-methyl-3-indolyl)ethyl]benzamide

CK-666 ，S7690

442633-00-3