CAY10614

• CAT Number: R064520
• CAS Number: 1202208-36-3
• Molecular Formula: C42H78INO2
• Molecular Weight: 755.995
• Purity: ≥95%
• Synonyms: N-cyclopentyl-N,N-dimethyl-3,4-bis(tetradecyloxy)-benzenemethanaminium, iodide
• Target: Toll-like Receptor (TLR)
• Storage: -20°C
• IUPAC Name: cyclopentyl-[[3,4-di(tetradecoxy)phenyl]methyl]-dimethylazanium;iodide
• InChI: InChI=1S/C42H78NO2.HI/c1-5-7-9-11-13-15-17-19-21-23-25-29-35-44-41-34-33-39(38-43(3,4)40-31-27-28-32-40)37-42(41)45-36-30-26-24-22-20-18-16-14-12-10-8-6-2;/h33-34,37,40H,5-32,35-36,38H2,1-4H3;1H/q+1;/p-1
• InChIKey: UXOPVNPWTUWUEA-UHFFFAOYSA-M
• SMILES: CCCCCCCCCCCCCCOC1=C(C=C(C=C1)C[N+](C)(C)C2CCCC2)OCCCCCCCCCCCCCC.[I-]

Lipid A is a lipid-<wbr></wbr>rich component of endotoxin, also known as lipopolysaccharide (LPS), which in turn is part of the outer membrane of Gram-<wbr></wbr>negative bacteria. Lipid A activates toll-<wbr></wbr>like receptor 4 (TLR4), initiating an immune response. CAY10614 is an antagonist of lipid A activation of TLR4, exhibiting an IC50 value of 1.68 μM in a cell-<wbr></wbr>based assay using modified human embryonic kidney (HEK) cells. It does not significantly affect HEK cell viability. In a model of sepsis, CAY10614 dramatically and significantly improves survival of mice given intraperitoneal LPS.

Reference

1.Piazza, M.,Rossini, C.,Fiorentina, S.D., et al. Glycolipids and benzylammonium lipids as novel antisepsis agents: Synthesis and biological characterization. Journal of Medicinal Chemistry 52, 1209-1213 (2009).