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Sigma-Aldrich

TAK-242

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

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

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About This Item

Empirical Formula (Hill Notation):
C15H17ClFNO4S
CAS Number:
Molecular Weight:
361.82
UNSPSC Code:
12352200
NACRES:
NA.77

Pricing and availability is not currently available.

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.

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

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This Item
Z676772Z676721Z676705
feature

Empty reload rack, for 1000ul tips

feature

barrier, low retention: no, Reload insert, Tip design ART 1000XL

feature

barrier, low retention: no, Reload insert, Tip design ART 200

feature

DNase free, RNase free, barrier, endotoxin free, low retention: no, Hinged rack, Tip design ART 100E

sterility

non-sterile

sterility

sterile

sterility

sterile

sterility

sterile

packaging

pack of 32 ea

packaging

pack of 4800 ea (50 inserts of 96 tips)

packaging

pack of 4800 ea (50 inserts of 96 tips)

packaging

pack of 4800 ea (50 hinged racks of 96 tips)

technique(s)

PCR: suitable

technique(s)

PCR: suitable

technique(s)

PCR: suitable

technique(s)

PCR: suitable

size

, large

size

-

size

-

size

-

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 Code

11 - Combustible Solids

WGK

WGK 2

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable


Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Anna Stierschneider et al.
International journal of molecular sciences, 22(17) (2021-09-11)
Augmented Toll-like receptor 4 (TLR4) expression was found in nearly 70% of patients with pancreatic adenocarcinoma, which is correlated with increased tumorigenesis and progression. In this study, we engineered a new light-oxygen-voltage-sensing (LOV) domain-based optogenetic cell line (opto-TLR4 PANC-1) that
Qianqian Zheng et al.
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Tetyana P Buzhdygan et al.
Journal of neuroinflammation, 18(1), 63-63 (2021-03-03)
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Ying Lu et al.
Frontiers in molecular neuroscience, 15, 859558-859558 (2022-08-16)
TLR4 and Cx43 signaling in dorsal spinal cord has been shown to be involved in the development of neuropathic pain. However, it is not clear whether TLR4 signaling is associated with the expression of MCP-1, CXCL1, and Cx43 in LPS
Su Ui Lee et al.
Cytokine, 131, 155116-155116 (2020-05-11)
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