Potential anti-inflammatory actions of the elmiric (lipoamino) acids

Abstract

A library of amino acid-fatty acid conjugates (elmiric acids) was synthesized and evaluated for activity as potential anti-inflammatory agents. The compounds were tested in vitro for their effects on cell proliferation and prostaglandin production and compared with their effects on in vivo models of inflammation. LPS stimulated RAW 267.4 mouse macrophage cells was the in vitro model and phorbol ester-induced mouse ear edema served as the principal in vivo model. The prostaglandin responses were found to be strongly dependent on the nature of the fatty acid part of the molecule. Polyunsaturated acid conjugates produced a marked increase in media levels of i15-deoxy-PGJ 2 with minimal effects on PGE production. It is reported in the literature that prostaglandin ratios in which the J series predominates over the E series promote the resolution of inflammatory conditions. Several of the elmiric acids tested here produced such favorable ratios suggesting that their potential antiinflammatory activity occurs via a novel mechanism of action. The ear edema assay results were generally in agreement with the prostaglandin assay findings indicating a connection between them.

The elmiric acids: Biologically active anandamide analogs

“…*i denotes immunoreactive. The data shown were previously reported in Burstein et al (2007). P<0.05 by ANOVA vs. the oil control.…”

“…Luminometer units are directly proportional to the number of metabolically active cells and are a measure of ATP levels. The data shown were previously reported in Burstein et al (2007). All of the ratio values greater than 20 are significant at the 95% confidence level when compared to the DMSO-LPS control by ANOVA.…”

“…The data presented here were previously reported in Burstein et al (2007). The values shown in this comparison represent the maximum response in each case.…”

“…Nevertheless, it provides a credible hypothesis on which to base future studies. The data shown were previously reported in Burstein et al (2007). The cells were treated with 1 and 10 uM elmiric acid whose identity is shown on the Y axis (designated as 1 or 10 on the Y axis).…”

Synthesis, Surface Active Properties and Cytotoxicity of Sodium <i>N</i>-Acyl Prolines

“…Based on in vitro and in vivo studies, amino acid-based surfactants may offer use in pharmaceutical, skin care and cosmetic applications due to their lower irritancy potential, less toxic and high biodegradability 41,42 . Lipoamino acids were used as potential anti-inflammatory agents 43 . Gopal et al 44 reported the cytotoxicity of series of N-sapienoyl C 16:1 amino acids and among those N-sapienoyl leucine exhibited the higher activity towards the selective tumor cell lines.…”