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Description: TLR4 signaling inhibitor
Chemical Name: (R)-Ethyl 6-(N-(2-chloro-4-fluorophenyl)sulfamoyl)cyclohex-1-enecarboxylate
Purity: ≥98% (HPLC)
Biological Activity for TAK 242
TAK 242 is a toll-like receptor 4 (TLR4) signaling inhibitor. Binds to intracellular domain of TLR4. Inhibits LPS-induced cytokine production in vitro (IC50 values are 1.3, 1.3 and 3.2 nM for IL-6, TNFα and NO production). Reduces lesion volume in a mouse model of cerebral cavernous malformations (CCMs). Also attenuates increased cytokine levels in a mouse sepsis model, when given in combination with ceftazidime. Cell permeable.
Technical Data for TAK 242
| M. Wt | 361.82 |
| Formula | C15H17ClFNO4S |
| Storage | Store at -20°C |
| Purity | ≥98% (HPLC) |
| CAS Number | 243984-11-4 |
| PubChem ID | 11703255 |
| InChI Key | LEEIJTHMHDMWLJ-CQSZACIVSA-N |
| Smiles | CCOC(C1=CCCC[C@H]1S(=O)(NC2=C(C=C(C=C2)F)Cl)=O)=O |
The technical data provided above is for guidance only. For batch specific data refer to the Certificate of Analysis.
Tocris products are intended for laboratory research use only, unless stated otherwise.
Solubility Data for TAK 242
| Solvent | Max Conc. mg/mL | Max Conc. mM | |
|---|---|---|---|
| Solubility | |||
| DMSO | 36.18 | 100 | |
| ethanol | 36.18 | 100 |
Preparing Stock Solutions for TAK 242
The following data is based on the product molecular weight 361.82. Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass | 1 mg | 5 mg | 10 mg |
|---|---|---|---|
| 1 mM | 2.76 mL | 13.82 mL | 27.64 mL |
| 5 mM | 0.55 mL | 2.76 mL | 5.53 mL |
| 10 mM | 0.28 mL | 1.38 mL | 2.76 mL |
| 50 mM | 0.06 mL | 0.28 mL | 0.55 mL |
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Product Datasheets for TAK 242
References for TAK 242
References are publications that support the biological activity of the product.
Yamada et al (2005) Discovery of novel and potent small-molecule inhibitors of NO and cytokine production as antisepsis agents: synthesis and biological activity of alkyl 6-(N-substituted sulfamoyl)cyclohex-1-ene-1-carboxylate. J.Med.Chem. 48 7457 PMID: 16279805
Ii et al (2006) A novel cyclohexene derivative, ethyl (6R)-6-[N-(2-Chloro-4-fluorophenyl)sulfamoyl]cyclohex-1-ene-1-carboxylate (TAK-242), selectively inhibits toll-like receptor 4-mediated cytokine production through suppression of intracellular signal Mol.Pharmacol. 69 1288 PMID: 16373689
Tang et al (2017) Endothelial TLR4 and the microbiome drive cerebral cavernous malformations. Nature 545 305 PMID: 28489816
Takashima et al (2009) Analysis of binding site for the novel small-molecule TLR4 signal transduction inhibitor TAK-242 and its therapeutic effect on mouse sepsis model. Br.J.Pharmacol. 157 1250 PMID: 19563534
If you know of a relevant reference for TAK 242, please let us know.
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Keywords: TAK 242, TAK 242 supplier, TAK242, toll, like, receptor, TLR4, signaling, inhibitor, inhibits, sepsis, cell, permeable, Toll-like, Receptors, 6587, Tocris Bioscience
6 Citations for TAK 242
Citations are publications that use Tocris products. Selected citations for TAK 242 include:
Grigoryeva et al (2021) Human macrophages utilize a wide range of pathogen recognition receptors to recognize Legionella pneumophila, including Toll-Like Receptor 4 engaging Legionella lipopolysaccharide and the Toll-like Receptor 3 nucleic-acid sensor PLoS 17 e1009781 PMID: 34280250
Avadhesha et al (2023) TLR4 activation by lysozyme induces pain without inflammation. Front Immunol 14 1065226 PMID: 37197666
Titus Ikusya et al (2022) Bodyweight, locomotion, and behavioral responses of the naked mole rat (Heterocephalus glaber) to lipopolysaccharide administration. J Comp Physiol A Neuroethol Sens Neural Behav Phys 208 493-504 PMID: 35731263
Harpal S et al (2022) Asprosin Exerts Pro-Inflammatory Effects in THP-1 Macrophages Mediated via the Toll-like Receptor 4 (TLR4) Pathway. Int J Mol Sci 24 PMID: 36613673
Emre et al (2022) Opioid Antagonist Nanodrugs Successfully Attenuate the Severity of Ischemic Stroke. Mol Pharm 19 2254-2267 PMID: 35506882
Robert A et al (2022) Human platelets display dysregulated sepsis-associated autophagy, induced by altered LC3 protein-protein interaction of the Vici-protein EPG5. Autophagy 18 1534-1550 PMID: 34689707
Do you know of a great paper that uses TAK 242 from Tocris? Please let us know.
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