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614316

Sigma-Aldrich

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.

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Synonym(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
Empirical Formula (Hill Notation):
C15H17ClFNO4S
CAS Number:
Molecular Weight:
361.82
NACRES:
NA.77

Quality Level

assay

≥98% (HPLC)

form

solid

manufacturer/tradename

Calbiochem®

storage condition

OK to freeze
protect from light

color

white to yellow-white

solubility

DMSO: 100 mg/mL

shipped in

wet ice

storage temp.

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

InChI key

LEEIJTHMHDMWLJ-CQSZACIVSA-N

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This Item
4894795.08336420351
vibrant-m

614316

TLR4 Inhibitor, TAK-242

vibrant-m

489479

LSD1 Inhibitor IV, RN-1, 2HCl

vibrant-m

5.08336

TAK-242

vibrant-m

420351

ICMT Inhibitor II, FTPAT

assay

≥98% (HPLC)

assay

≥97% (HPLC)

assay

≥98% (HPLC)

assay

≥98% (HPLC)

manufacturer/tradename

Calbiochem®

manufacturer/tradename

Calbiochem®

manufacturer/tradename

Calbiochem®

manufacturer/tradename

Calbiochem®

form

solid

form

solid

form

liquid

form

solid

solubility

DMSO: 100 mg/mL

solubility

DMSO: 2.5 mg/mL, water: 2.5 mg/mL

solubility

-

solubility

DMSO: 50 mg/mL

storage condition

OK to freeze, protect from light

storage condition

OK to freeze, desiccated (hygroscopic), protect from light

storage condition

OK to freeze, avoid repeated freeze/thaw cycles, desiccated (hygroscopic), protect from light

storage condition

OK to freeze, protect from light

General description

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).

Biochem/physiol Actions

Cell permeable: yes
Primary Target
TLR4
Reversible: yes

Packaging

Packaged under inert gas

Warning

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.

Other Notes

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.

Legal Information

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

Storage Class

11 - Combustible Solids

wgk_germany

WGK 2

flash_point_f

Not applicable

flash_point_c

Not applicable


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