SML1443

L48H37

≥98% (HPLC)

• Synonym(s): (3E,5E)-1-ethyl-3,5-bis[(2,3,4-trimethoxyphenyl)methylidene]piperidin-4-one, 1-Ethyl-3,5-bis(3,4,5-trimethoxybenzylidene)piperidin-4-one, 1-Ethyl-3,5-bis[(2,3,4-trimethoxyphenyl)methylene]-4-piperidinone
• Empirical Formula (Hill Notation): C₂₇H₃₃NO₇
• CAS Number: 939318-04-4
• Molecular Weight: 483.55
• UNSPSC Code: 12352200
• PubChem Substance ID: 329825883
• NACRES: NA.77

Properties

• Quality Level: 100
• assay: ≥98% (HPLC)
• form: powder
• color: white to beige
• solubility: DMSO: 2 mg/mL, clear (warmed)
• storage temp.: 2-8°C
• SMILES string: O=C(/C(CN(CC)C/1)=C/C2=C(OC)C(OC)=C(OC)C=C2)C1=C\C3=CC=C(OC)C(OC)=C3OC
• InChI: 1S/C27H33NO7/c1-8-28-15-19(13-17-9-11-21(30-2)26(34-6)24(17)32-4)23(29)20(16-28)14-18-10-12-22(31-3)27(35-7)25(18)33-5/h9-14H,8,15-16H2,1-7H3/b19-13+,20-14+
• InChI key: XLPNFINERWLGNC-IWGRKNQJSA-N

Description

Application

L48H37 has been used as a myeloid differentiator protein 2 (MD2) antagonist/inhibitor:

• to investigate intracellular signaling of LPS in signal transduction pathways via endosomic toll-like receptor 4 (TLR4) in colonic epithelium
• to determine its anti-cancer effects in pancreatic ductal adenocarcinoma (PDAC)
• to study its effects on lipopolysaccharide (LPS) and palmitate CC chemokine ligand 2 (CCL2) responses in normal kidney proximal tubule cells

Biochem/physiol Actions

L48H37 can stimulate apoptosis and prevent proliferation in pancreatic cancer cells, especially in the absence of histone-lysine N-methyltransferase 2D (KMT2D). It has an unsaturated monoketone structure, which helps to enhance its stability and anti-cancer effects. L48H37 may possess an anti-neoplastic effect on human pancreatic ductal adenocarcinoma (PDAC) cells.

L48H37 is a potent and chemically stable anti-inflammatory curcumin analog that inhibits LPS-induced inflammation through the myeloid differentiation 2 (MD-2) and toll-like receptor 4 (TLR4) complex. L48H37 is a potent MD2 inhibitor that binds to the hydrophobic region of MD-2 and blocks the interaction between MD2 and LPS. L48H37 significantly improves survival and protected lung injury in LPS-induced septic mice.

Safety Information

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