Synthesis of Tetrahydropyran-2-carboxylic Acid Derivatives of Lipid A Containing an Olefin in Their Chains and Their LPS-Antagonistic Activities

doi:10.1246/BCSJ.76.2341

Paper

Synthesis of Tetrahydropyran-2-carboxylic Acid Derivatives of Lipid A Containing an Olefin in Their Chains and Their LPS-Antagonistic Activities

Published Dec 15, 2003 · Yukiko Watanabe, M. Shiozaki, Daisuke Tanaka

Bulletin of the Chemical Society of Japan

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Abstract

Four tetrahydropyran-2-carboxylic acid derivatives with 3-(tetradec-7-enyloxy)tetradecyl chains instead of 3-(tetradecanoyloxy)tetradecanoyl chains in lipid A were synthesized and their biological activities toward human U937 cells, human whole blood cells and mouse peritoneal resident macrophages were measured. These compounds showed LPS-antagonistic activity toward these three kinds of cells. The IC50 values (nM) (1 M = 1 mol dm−3) of these four compounds (21, 21′, 24 and 24′) toward human monoblastic U937 cells were 2.2, 1.0, 0.017 and 0.055, respectively. However, the LPS-antagonistic activities (IC50 values) of these four compounds toward human whole blood cells were only 0.28, 0.21, 0.81 and 0.58 μM, respectively. The IC50 values (μM) toward mouse peritoneal resident macrophages were 2.49, 0.49, 0.91 and 0.69, respectively.

In Vitro Study

Study Snapshot

Four tetrahydropyran-2-carboxylic acid derivatives with olefin chains in lipid A show LPS-antagonistic activity against human U937 cells, human whole blood cells, and mouse peritoneal resident macrophages.

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

Paper

Synthesis of Tetrahydropyran-2-carboxylic Acid Derivatives of Lipid A Containing an Olefin in Their Chains and Their LPS-Antagonistic Activities

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Citations

Syntheses of glucose derivatives of E5564-related compounds and their LPS-antagonistic activities.

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