614316

TAK-242

≥98% (HPLC), solid, TLR4 inhibitor, Calbiochem^®

• Sinónimos: TLR4 Inhibitor, TAK-242, Ethyl-(6 R)-6-(N-(2-chloro-4-fluorophenyl)sulfamoyl)cyclohex-1-ene-1-carboxylate, Ethyl-(6R)-6-(N-(2-chloro-4-fluorophenyl)sulfamoyl)cyclohex-1-ene-1-carboxylate
• Fórmula empírica (notación de Hill): C₁₅H₁₇ClFNO₄S
• Número de CAS: 243984-11-4
• Peso molecular: 361.82
• Código UNSPSC: 12352200
• NACRES: NA.77

Propiedades

• product name: TLR4 Inhibitor, TAK-242, TAK-242; CAS 243984-11-4; is a cell-permeable compound that selectively binds to Cys747 of TLR4 and selectively disrupts its interaction with adaptor molecules TIRAP and TRAM.
• Nivel de calidad: 100
• Análisis: ≥98% (HPLC)
• formulario: solid
• fabricante / nombre comercial: Calbiochem^®
• condiciones de almacenamiento: OK to freeze; protect from light
• color: white to yellow-white
• solubilidad: DMSO: 100 mg/mL
• Condiciones de envío: wet ice
• temp. de almacenamiento: 2-8°C
• InChI: 1S/C15H17ClFNO4S/c1-2-22-15(19)11-5-3-4-6-14(11)23(20,21)18-13-8-7-10(17)9-12(13)16/h5,7-9,14,18H,2-4,6H2,1H3/t14-/m1/s1
• Clave InChI: LEEIJTHMHDMWLJ-CQSZACIVSA-N

Descripción

Descripción general

A cell-permeable cyclohexenecarboxylate that disrupts TLR4 interaction with adaptor molecules TIRAP and TRAM by selectively binding to TLR4, but not TLR1-3 or TLR5-10, via TLR4 intracellular Cys747 residue. Shown to effectively inhibit TLR4-mediated signaling events, including LPS-induced NO and inflammatory cytokines production in murine RAW264.7 macrophages (IC₅₀ = 1.8, 1.3, and 1.9 nM, respectively, against NO, IL-6, and TNF-α production), TLR4/TIRAP-dependent NF-κB activity as well as TLR4/TIRAP- and TLR4/TRAM-dependent ISRE activity (IC₅₀<300 nM) in HEK293-hTLR4/MD2-CD14 transfected with either TIRAP or TRAM. When administered at an i.v. dose of 3 mg/kg, TAK-242 is reported to completely prevent LPS- (7 mg/kg, i.p.) induced death in mice in vivo. Complete elimination of septic shock-induced death can be extended to live E. coli-infected mice when co-administered with ceftazidime (3 mg/kg TAK-242 and 20 mg/kg ceftazidime, i.v.).

A cell-permeable cyclohexenecarboxylate that disrupts TLR4, but not TLR1-3 or TLR5-10, interaction with adaptor molecules TIRAP and TRAM via direct binding to TLR4 intracellular Cys747 residue.Shown to effectively inhibit TLR4-mediated cellular events (IC₅₀ = 1.8, 1.3, and 1.9 nM, respectively, against LPS-induced NO, IL-6, and TNF-α production in murine RAW264.7 macrophages) in vitro and completely prevent LPS- (7 mg/kg, i.p.) induced death in mice (3 mg/kg; i.v.) in vivo. Also available as a 25 mM solution in DMSO (Cat. No. 508336).

Acciones bioquímicas o fisiológicas

Cell permeable: yes

Primary Target
TLR4

Reversible: yes

Envase

Packaged under inert gas

Advertencia

Toxicity: Harmful (C)

Reconstitución

Following reconstitution, aliquot and freeze (-70°C). Stock solutions are stable for up to 1 year at -70°C. Use only fresh DMSO.

Otras notas

Matsunaga, N., et al. 2011. Mol. Pharmacol.79, 34.
Takashima, K., et al. 2009. Br. J. Pharmacol.157, 1250.
Li, M., et al. 2006. Mol. Pharmacol.69, 1288.
Yamada, M., et al. 2005. J. Med. Chem.48, 7457.

Información legal

CALBIOCHEM is a registered trademark of Merck KGaA, Darmstadt, Germany

Información de seguridad

• Código de clase de almacenamiento: 11 - Combustible Solids
• Clase de riesgo para el agua (WGK): WGK 2
• Punto de inflamabilidad (°F): Not applicable
• Punto de inflamabilidad (°C): Not applicable