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J. Lipid Res.
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Originally published In Press as doi:10.1194/jlr.M700486-JLR200 on March 3, 2008

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Journal of Lipid Research, Vol. 49, 1216-1223, June 2008
Copyright © 2008 by American Society for Biochemistry and Molecular Biology

Characterization of biotin-anandamide, a novel tool for the visualization of anandamide accumulation

Filomena Fezza1,*,{dagger}, Sergio Oddi1,*,§, Monia Di Tommaso{dagger},§, Chiara De Simone*,{dagger}, Cinzia Rapino§, Nicoletta Pasquariello§, Enrico Dainese§, Alessandro Finazzi-Agrò{dagger} and Mauro Maccarrone2,*,§

* European Center for Brain Research/Istituto di Ricovero e Cura a Carattere Scientifico S. Lucia Foundation, Rome, Italy
{dagger} Department of Experimental Medicine and Biochemical Sciences, University of Rome Tor Vergata, Rome, Italy
§ Department of Biomedical Sciences, University of Teramo, Teramo, Italy

This study was partly supported by Fondazione TERCAS (Finanziamento 2005 to M.M.) and by the Ministero dell'Università e della Ricerca (PRIN 2006 to M.M.).

Published, JLR Papers in Press, March 3, 2008.

1 F. Fezza and S. Oddi contributed equally to this study.

2 To whom correspondence should be addressed. e-mail: mmaccarrone{at}unite.it

Anandamide (N-arachidonoylethanolamide; AEA) acts as an endogenous agonist of both cannabinoid and vanilloid receptors. During the last two decades, its metabolic pathways and biological activity have been investigated extensively and relatively well characterized. In contrast, at present, the effective nature and mechanism of AEA transport remain controversial and still unsolved issues. Here, we report the characterization of a biotinylated analog of AEA (b-AEA) that has the same lipophilicity of the parent compound. In addition, by means of biochemical assays and fluorescence microscopy, we show that b-AEA is accumulated inside the cells in a way superimposable on that of AEA. Conversely, b-AEA does not interact or interfere with the other components of the endocannabinoid system, such as type-1 and type-2 cannabinoid receptors, vanilloid receptor, AEA synthetase (N-acylphosphatidylethanolamine-hydrolyzing phospholipase D), or AEA hydrolase (fatty acid amide hydrolase). Together, our data suggest that b-AEA could be a very useful probe for visualizing the accumulation and intracellular distribution of this endocannabinoid.

Supplementary key words endocannabinoids • immunofluorescence • keratinocyte • transport • metabolism • skin


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