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Molecules 2017, 22(4), 616; doi:10.3390/molecules22040616

Anti-Inflammatory, Antioxidant and Crystallographic Studies of N-Palmitoyl-ethanol Amine (PEA) Derivatives

1
Department of Science, University of Basilicata, Viale dell′Ateneo Lucano 10, Potenza 85100, Italy
2
Department of Pharmacy, University of Salerno, Via Giovanni Paolo II n 132, Fisciano (SA) 84084, Italy
3
Institute for the Study of Nanostructured Materials, ISMN-CNR, Palermo, c/o Department of ChiBioFarAm, University of Messina, Vill. S. Agata, Viale F. Stagno d’Alcontres 31, Messina 98166, Italy
4
Department of Chemistry, University of Milano, Via Golgi 19, Milano 20133, Italy
5
Department of Pharmacy, Health and Nutritional Sciences, University of Calabria, Via Pietro Bucci, Arcavacata di Rende (CS) 87036, Italy
These authors contributed equally to the paper.
*
Authors to whom correspondence should be addressed.
Academic Editor: Derek J. McPhee
Received: 10 January 2017 / Revised: 3 April 2017 / Accepted: 5 April 2017 / Published: 11 April 2017
(This article belongs to the Section Medicinal Chemistry)
View Full-Text   |   Download PDF [4884 KB, uploaded 11 April 2017]   |  

Abstract

N-Palmitoyl-ethanolamine (PEA) is an anti-inflammatory component of egg yolk that is usually employed for the prevention of respiratory apparatus virus infection and then frequently used for its efficient anti-inflammatory and analgesic effects in experimental models of visceral, neuropathic, and inflammatory diseases. Nevertheless, data of its use in animal or human therapy are still scarce and further studies are needed. Herein, we report the biological evaluation of a small library of N-palmitoyl-ethanolamine analogues or derivatives, characterized by a protected acid function (either as palmitoyl amides or hexadecyl esters), useful to decrease their hydrolysis rate in vitro and prolong their biological activity. Two of these compounds—namely phenyl-carbamic acid hexadecyl ester (4) and 2-methyl-pentadecanoic acid (4-nitro-phenyl)-amide (5)—have shown good anti-inflammatory and antioxidant properties, without affecting the viability of J774A.1 macrophages. Finally, crystals suitable for X-ray analysis of compound 4 have been obtained, and its solved crystal structure is here reported. Our outcomes may be helpful for a rational drug design based on new PEA analogues/derivatives with improved biological properties. View Full-Text
Keywords: N-acyl-ethanolamines; N-palmitoyl-ethanolamine derivatives; biological evaluation of PEA derivatives; anti-inflammatory activity; antioxidant properties; crystallographic studies N-acyl-ethanolamines; N-palmitoyl-ethanolamine derivatives; biological evaluation of PEA derivatives; anti-inflammatory activity; antioxidant properties; crystallographic studies
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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Saturnino, C.; Popolo, A.; Ramunno, A.; Adesso, S.; Pecoraro, M.; Plutino, M.R.; Rizzato, S.; Albinati, A.; Marzocco, S.; Sala, M.; Iacopetta, D.; Sinicropi, M.S. Anti-Inflammatory, Antioxidant and Crystallographic Studies of N-Palmitoyl-ethanol Amine (PEA) Derivatives. Molecules 2017, 22, 616.

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