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Current Medicinal Chemistry

Eiditor-in-Chief

ISSN (Print): 0929-8673
ISSN (Online): 1875-533X

Research Article

A Lipid Anchor Improves the Protective Effect of Ectoine in Inflammation

Author(s): A. Wedeking, N. Hagen-Euteneuer, M. Gurgui, R. Broere, G. Lentzen, R.H. Tolba, E. Galinski and G. van Echten-Deckert

Volume 21 , Issue 22 , 2014

Page: [2565 - 2572] Pages: 8

DOI: 10.2174/0929867321666131228222730

Price: $58

Abstract

Others and we have shown in several studies that the natural tetrahydropyrimidine ectoine protects mammalian cells and tissues against various stress factors including ischemia/reperfusion injury, UV-irradiation, and inflammation. Since little is known about the molecular mechanism of this protective effect, which was ascribed exclusively to an extracellular action of this small water-soluble molecule, we asked whether and how a hydrophobic anchor modulates the inflammation protective properties of ectoine. We therefore investigated the influence of ectoine and of its semi-synthetic derivative lauryl-ectoine on inflammation in RAW 264.7 macrophages and primary cultured rat intestinal smooth muscle (RISM) cells. Both, ectoine and lauryl-ectoine considerably decreased lipopolysaccharide (LPS)-induced interleukin (IL)- 1, IL-6, tumor necrosis factor (TNF)- α, and cyclooxygenase (COX)-2 gene expression in macrophages as well as TNF-α- induced IL-1, IL-6 and COX-2 expression in RISM cells. This reduction of inflammatory agents was accompanied on the one hand by a significant decrease of nuclear translocation of nuclear factor (NF)-κB and on the other hand by a reduction of cellular ceramide content. Interestingly, lauryl- ectoine was much more active exerting its effect at about 10-fold lower concentrations than its natural counterpart. Note that ectoine was almost completely recovered in the medium whereas lauryl-ectoine was found to be cell-associated. Together our data indicate that a lipid anchor considerably improves a possible preventive and/or therapeutic implementation of ectoine in inflammatory processes.

Keywords: Ectoine, ceramide, inflammation, lauryl-ectoine, lipophilicity, tumor necrosis factor alpha (TNF-α).


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