5.32583

TLR1/TLR2 Agonist II, CU-T12-9

• Synonym(s): TLR1/TLR2 Agonist II, CU-T12-9, N-Methyl-4-nitro-2-(4-(4-(trifluoromethyl)phenyl)-1H-imidazol-1-yl)aniline, CUT129
• Empirical Formula (Hill Notation): C₁₇H₁₃F₃N₄O₂
• CAS Number: 1821387-73-8
• Molecular Weight: 362.31
• MDL number: MFCD30182292
• UNSPSC Code: 12352200
• NACRES: NA.77
• Assay: ≥98% (HPLC)
• Form: powder
• Storage condition: OK to freeze, protect from light

Properties

• assay: ≥98% (HPLC)
• Quality Segment: 100
• form: powder
• manufacturer/tradename: Calbiochem^®
• storage condition: OK to freeze, protect from light
• color: yellow
• solubility: DMSO: 50 mg/mL
• storage temp.: 2-8°C
• SMILES string: FC(F)(F)c1ccc(cc1)c2nc[n](c2)c3c(ccc(c3)[N+](=O)[O-])NC
• InChI: 1S/C17H13F3N4O2/c1-21-14-7-6-13(24(25)26)8-16(14)23-9-15(22-10-23)11-2-4-12(5-3-11)17(18,19)20/h2-10,21H,1H3
• InChI key: LITXVDAFEYLWQE-UHFFFAOYSA-N

Description

General description

A non-cytotoxic (up to 100 µM) diphenyl-substituted imidazole compound that exhibits high affinity toward both TLR1 & TLR2 (K_D = 182 nM & 478 nM, respectively) and induces TLR1/2 heterodimerization, effectively completing against Pam₃CSK₄ (Cat. No. 506350) for TLR1/2 binding (K_i = 45.4 nM; [Pam3] = 20 mg/mL; [TLR1/2] = 80 nM). Shown to potently induce secreted embryonic alkaline phosphatase (SEAP) production from human TLR2-, but not TLR3-, 4-, 5-, 7-, 8-, transfected HEK293 (EC₅₀ = 52.9 nM) in an NF-κB inhibitor Triptolide-(Cat. No. 645900) blockable manner via selective TLR1/2, but not TLR2/6, heterodimer activation. Reported to induce comparable NF-κB-dependent reporter transcription as 100 ng/mL Pam₃CSK₄ when administered to human macrophage U937 cultures at 5 µM concentration (24 h) and effectively trigger NO production in both murine Raw 264.7 and primary rat macrophage cultures (EC_max = 1.2 & 0.4 µM, respectively; 24 h), blockable by TLR1/2 antagonist CU-CPT22 (Cat. No. 614305), but not TLR4 antagonist TAK-242 (Cat. No. 614316 & 508336). Likewise, both CU-T12-9 and Pam₃CSK₄ (1 µM & 50 ng/mL, respectively) are demonstrated to induce similar time-dependent induction of TLR1, TLR2, TNF-α, iNOS, IL-10 mRNA in Raw 264.7 cells.

Biochem/physiol Actions

Primary Target
TLR1/TLR2

Reversible: yes

Preparation Note

Following reconstitution, aliquot and freeze (-20°C). Stock solutions are stable for up to 3 months at -20°C.

Other Notes

Cheng, K., et al. 2014. Manuscript in preparation.

Legal Information

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

Disclaimer

Toxicity: Standard Handling (A)

Safety Information

• Storage Class: 11 - Combustible Solids
• wgk: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable