Evaluation of endogenous fatty acid amides and their synthetic analogues as potential anti-inflammatory leads

Hung The Dang, Gyeoung Jin Kang, Eun Sook Yoo, Jongki Hong, Jae Sue Choi, Hyung Sik Kim, Hae Young Chung, Jee H. Jung

Research output: Contribution to journalArticlepeer-review

30 Scopus citations

Abstract

A series of endogenous fatty acid amides and their analogues (1-78) were prepared, and their inhibitory effects on pro-inflammatory mediators (NO, IL-1β, IL-6, and TNF-α) in LPS-activated RAW264.7 cells were evaluated. Their inhibitory activity on the pro-inflammatory chemokine MDC in IFN-γ-activated HaCaT cells was also examined. The results showed that the activity is strongly dependent on the nature of the fatty acid part of the molecules. As expected, the amides derived from enone fatty acids showed significant activity and were more active than those derived from other types of fatty acids. A variation of the amine headgroup also altered bioactivity profile remarkably, possibly by modulating cell permeability. Regarding the amine part of the molecules, N-acyl dopamines exhibited the most potent activity (IC 50 ∼2 μM). This is the first report of the inhibitory activity of endogenous fatty acid amides and their analogues on the production of nitric oxide, cytokines (IL-1β, IL-6, and TNF-α) and the chemokine MDC. This study suggests that the enone fatty acid-derived amides (such as N-acyl ethanolamines and N-acyl amino acids) and N-acyl dopamines may be potential anti-inflammatory leads.

Original languageEnglish (US)
Pages (from-to)1520-1527
Number of pages8
JournalBioorganic and Medicinal Chemistry
Volume19
Issue number4
DOIs
StatePublished - Feb 15 2011

Keywords

  • Anti-inflammatory activity
  • Cytokines
  • Endogenous fatty acid amides
  • Enone fatty acids
  • Nitric oxide

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