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
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About This Item
Empirical Formula (Hill Notation):
C27H33NO7
CAS Number:
Molecular Weight:
483.55
UNSPSC Code:
12352200
PubChem Substance ID:
NACRES:
NA.77
Assay:
≥98% (HPLC)
Form:
powder
Quality Segment
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
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 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.
L48H37 is a potent and chemically stable anti-inflammatory curcumin analog.
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.
Storage Class
11 - Combustible Solids
WGK
WGK 3
Flash Point (°F)
Not applicable
Flash Point (°C)
Not applicable
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