614316
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.
Synonyme(s) :
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
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About This Item
Formule empirique (notation de Hill):
C15H17ClFNO4S
Numéro CAS:
Poids moléculaire :
361.82
Code UNSPSC :
12352200
Nomenclature NACRES :
NA.77
Produits recommandés
Niveau de qualité
Pureté
≥98% (HPLC)
Forme
solid
Fabricant/nom de marque
Calbiochem®
Conditions de stockage
OK to freeze
protect from light
Couleur
white to yellow-white
Solubilité
DMSO: 100 mg/mL
Conditions d'expédition
wet ice
Température de stockage
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
Clé InChI
LEEIJTHMHDMWLJ-CQSZACIVSA-N
Description générale
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).
Actions biochimiques/physiologiques
Cell permeable: yes
Primary Target
TLR4
TLR4
Reversible: yes
Conditionnement
Packaged under inert gas
Avertissement
Toxicity: Harmful (C)
Reconstitution
Following reconstitution, aliquot and freeze (-70°C). Stock solutions are stable for up to 1 year at -70°C. Use only fresh DMSO.
Autres remarques
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.
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.
Informations légales
CALBIOCHEM is a registered trademark of Merck KGaA, Darmstadt, Germany
Code de la classe de stockage
11 - Combustible Solids
Classe de danger pour l'eau (WGK)
WGK 2
Point d'éclair (°F)
Not applicable
Point d'éclair (°C)
Not applicable
Certificats d'analyse (COA)
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