5.08336

TAK-242

InSolution, ≥98%, 25 mM in DMSO, TLR4 inhibitor

• Synonym(e): InSolution TLR4 Inhibitor, TAK-242, Ethyl-(6R)-6-(N-(2-chloro-4-fluorophenyl)sulfamoyl)cyclohex-1-ene-1-carboxylate, (R)-Ethyl 6-(N-(2-chloro-4-fluorophenyl)sulfamoyl)cyclohex-1-enecarboxylate, TLR4 Inhibitor, TAK-242 InSolution, TLR4 Inhibitor, TAK-242 InSolution, Ethyl-(6R)-6-(N-(2-chloro-4-fluorophenyl)sulfamoyl)cyclohex-1-ene-1-carboxylate, (R)-Ethyl 6-(N-(2-chloro-4-fluorophenyl)sulfamoyl)cyclohex-1-enecarboxylate
• Empirische Formel (Hill-System): C₁₅H₁₇ClFNO₄S
• CAS-Nummer: 243984-11-4
• Molekulargewicht: 361.82
• UNSPSC-Code: 12352200
• NACRES: NA.77

Eigenschaften

• Qualitätsniveau: 100
• Assay: ≥98% (HPLC)
• Form: liquid
• Hersteller/Markenname: Calbiochem^®
• Lagerbedingungen: OK to freeze; avoid repeated freeze/thaw cycles; desiccated (hygroscopic); protect from light
• Lagertemp.: −70°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
• InChIKey: LEEIJTHMHDMWLJ-CQSZACIVSA-N

Beschreibung

Allgemeine Beschreibung

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.).

Biochem./physiol. Wirkung

Cell permeable: yes

Primary Target
TLR4

Reversible: no

Verpackung

Packaged under inert gas

Warnhinweis

Toxicity: Standard Handling (A)

Physikalische Form

A 25 mM (2 mg/221 µL) sterile-filtered solution of TLR4 Inhibitor, TAK-242 (Cat. No. 614316) in DMSO.

Rekonstituierung

Following initial thaw, aliquot and freeze (-70°C). Aliquots are stable for up to 1 year at -70°C.

Sonstige Hinweise

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.

Rechtliche Hinweise

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

Sicherheitshinweise

• Lagerklassenschlüssel: 10 - Combustible liquids
• WGK: WGK 1
• Flammpunkt (°F): 188.6 °F - (refers to pure substance)
• Flammpunkt (°C): 87 °C - (refers to pure substance)