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.

Fezza F., O.S. (2008). Characterization of biotin-anandamide, a novel tool for the visualization of anandamide accumulation. JOURNAL OF LIPID RESEARCH, 49(6), 1216-1223 [10.1194/jlr.M700486-JLR200].

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

FEZZA, FILOMENA;FINAZZI AGRO', ALESSANDRO;
2008

Abstract

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.
Pubblicato
Rilevanza internazionale
Articolo
Sì, ma tipo non specificato
Settore BIO/10
English
amine; anandamide; biotin; cannabinoid receptor; endocannabinoid; fatty acid amidase; n acylphosphatidylethanolamine; phospholipase D; protein; unclassified drug; vanilloid receptor; amide; arachidonic acid derivative; article; cellular distribution; chemical analysis; fluorescence microscopy; human; human cell; lipophilicity; priority journal; animal; cell line; fluorescent antibody technique; mass spectrometry; metabolism; mouse; nuclear magnetic resonance spectroscopy; Western blotting; Animals; Arachidonic Acids; Biotin; Blotting, Western; Cell Line; Fluorescent Antibody Technique; Magnetic Resonance Spectroscopy; Mass Spectrometry; Mice; Microscopy, Fluorescence; Polyunsaturated Alkamides; Receptors, Cannabinoid
Fezza F., O.S. (2008). Characterization of biotin-anandamide, a novel tool for the visualization of anandamide accumulation. JOURNAL OF LIPID RESEARCH, 49(6), 1216-1223 [10.1194/jlr.M700486-JLR200].
Fezza, F; Oddi, S; Di Tommaso, M; De Simone, C; Rapino, C; Pasquariello, N; Dainese, E; FINAZZI AGRO', A; Maccarrone, M
Articolo su rivista
File in questo prodotto:
Non ci sono file associati a questo prodotto.

I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.

Utilizza questo identificativo per citare o creare un link a questo documento: http://hdl.handle.net/2108/39172
Citazioni
  • ???jsp.display-item.citation.pmc??? 10
  • Scopus ND
  • ???jsp.display-item.citation.isi??? 21
social impact