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 (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]-;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
- CBNumber
- CB52518908
- Molecular Formula
- C18H17FN2O
- Formula Weight
- 296.34
- MOL File
- 442633-00-3.mol
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.
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.
N-Bromosuccinimide Price
- Product number
- SML0006
- Product name
- CK-666
- Purity
- ≥98% (HPLC), powder
- Packaging
- 5mg
- Price
- $132
- Updated
- 2024/03/01
- Product number
- 182515
- Product name
- Arp2/3 Complex Inhibitor I, CK-666
- Packaging
- 25mg
- Price
- $225
- Updated
- 2024/03/01
- Product number
- 29038
- Product name
- CK-666
- Packaging
- 1mg
- Price
- $32
- Updated
- 2024/03/01
- Product number
- 29038
- Product name
- CK-666
- Packaging
- 5mg
- Price
- $86
- Updated
- 2024/03/01
- Product number
- SML0006
- Product name
- CK-666
- Purity
- ≥98% (HPLC), powder
- Packaging
- 25mg
- Price
- $516
- Updated
- 2024/03/01
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) 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
Raw materials
Preparation Products
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