{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,8,14]],"date-time":"2026-08-14T17:44:19Z","timestamp":1786729459760,"version":"build-2736575974"},"reference-count":50,"publisher":"American Chemical Society (ACS)","issue":"8","license":[{"start":{"date-parts":[[2022,7,22]],"date-time":"2022-07-22T00:00:00Z","timestamp":1658448000000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"name":"VLAG Graduate School, Wageningen University"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":[],"published-print":{"date-parts":[[2022,8,19]]},"abstract":"<jats:title>Abstract<\/jats:title>\n                  <jats:p>We studied the mechanistic and biological origins of anti-inflammatory poly-unsaturated fatty acid-derived N-acylethanolamines using synthetic bifunctional chemical probes of docosahexaenoyl ethanolamide (DHEA) and arachidonoyl ethanolamide (AEA) in RAW264.7 macrophages stimulated with 1.0 \u03bcg mL\u20131 lipopolysaccharide. Using a photoreactive diazirine, probes were covalently attached to their target proteins, which were further studied by introducing a fluorescent probe or biotin-based affinity purification. Fluorescence confocal microscopy showed DHEA and AEA probes localized in cytosol, specifically in structures that point toward the endoplasmic reticulum and in membrane vesicles. Affinity purification followed by proteomic analysis revealed peroxiredoxin-1 (Prdx1) as the most significant binding interactor of both DHEA and AEA probes. In addition, Prdx4, endosomal related proteins, small GTPase signaling proteins, and prostaglandin synthase 2 (Ptgs2, also known as cyclooxygenase 2 or COX-2) were identified. Lastly, confocal fluorescence microscopy revealed the colocalization of Ptgs2 and Rac1 with DHEA and AEA probes. These data identified new molecular targets suggesting that DHEA and AEA may be involved in reactive oxidation species regulation, cell migration, cytoskeletal remodeling, and endosomal trafficking and support endocytosis as an uptake mechanism.<\/jats:p>","DOI":"10.1021\/acschembio.1c00355","type":"journal-article","created":{"date-parts":[[2022,7,22]],"date-time":"2022-07-22T15:22:25Z","timestamp":1658503345000},"page":"2054-2064","source":"Crossref","is-referenced-by-count":6,"title":["PUFA-Derived\n                    <i>N<\/i>\n                    \u2011Acylethanolamide\nProbes Identify Peroxiredoxins and Small GTPases as Molecular Targets\nin LPS-Stimulated RAW264.7 Macrophages"],"prefix":"10.1021","volume":"17","author":[{"ORCID":"https:\/\/orcid.org\/0000-0002-1061-8352","authenticated-orcid":true,"given":"Ian-Arris","family":"de Bus","sequence":"first","affiliation":[{"name":"Wageningen University & Research , , Stippeneng 4 , ,","place":["Wageningen, The Netherlands, 6708 WE"]},{"name":"Wageningen University & Research , , Stippeneng 4 , ,","place":["Wageningen, The Netherlands, 6708 WE"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Antoine H. P.","family":"America","sequence":"additional","affiliation":[{"name":"Wageningen University & Research , , Droevendaalsesteeg 1 , ,","place":["Wageningen, The Netherlands, 6708 PB"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Norbert C. A.","family":"de Ruijter","sequence":"additional","affiliation":[{"name":"Wageningen University & Research , , Droevendaalsesteeg 1 , ,","place":["Wageningen, The Netherlands, 6708 PB"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-8106-0309","authenticated-orcid":true,"given":"Milena","family":"Lam","sequence":"additional","affiliation":[{"name":"Wageningen University & Research , , Stippeneng 4 , ,","place":["Wageningen, The Netherlands, 6708 WE"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-4483-5056","authenticated-orcid":true,"given":"Jasper W.","family":"van de Sande","sequence":"additional","affiliation":[{"name":"Wageningen University & Research , , Stippeneng 4 , ,","place":["Wageningen, The Netherlands, 6708 WE"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Mieke","family":"Poland","sequence":"additional","affiliation":[{"name":"Wageningen University & Research , , Stippeneng 4 , ,","place":["Wageningen, The Netherlands, 6708 WE"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Renger F.","family":"Witkamp","sequence":"additional","affiliation":[{"name":"Wageningen University & Research , , Stippeneng 4 , ,","place":["Wageningen, The Netherlands, 6708 WE"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-5773-8506","authenticated-orcid":true,"given":"Han","family":"Zuilhof","sequence":"additional","affiliation":[{"name":"Wageningen University & Research , , Stippeneng 4 , ,","place":["Wageningen, The Netherlands, 6708 WE"]},{"name":"Tianjin University , , 92 Weijin Road , ,","place":["Tianjin, People\u2019s Republic of China, 300072"]},{"name":"King Abdulaziz University , , ,","place":["Jeddah, Saudi Arabia, 21589"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Michiel G. J.","family":"Balvers","sequence":"additional","affiliation":[{"name":"Wageningen University & Research , , Stippeneng 4 , ,","place":["Wageningen, The Netherlands, 6708 WE"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-3659-2434","authenticated-orcid":true,"given":"Bauke","family":"Albada","sequence":"additional","affiliation":[{"name":"Wageningen University & Research , , Stippeneng 4 , ,","place":["Wageningen, The Netherlands, 6708 WE"]}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"316","published-online":{"date-parts":[[2022,7,22]]},"reference":[{"key":"2026081413082006000_cit1","doi-asserted-by":"publisher","first-page":"106351","DOI":"10.1016\/j.prostaglandins.2019.106351","article-title":"The role of\nn-3 PUFA-derived fatty acid derivatives and their oxygenated metabolites\nin the modulation of inflammation","volume":"144","author":"de\nBus","year":"2019","journal-title":"Prostag.\nOther Lipid Mediat."},{"key":"2026081413082006000_cit2","doi-asserted-by":"publisher","first-page":"106337","DOI":"10.1016\/j.prostaglandins.2019.106337","article-title":"Emerging class\nof omega-3 fatty acid\nendocannabinoids & their derivatives","volume":"143","author":"Watson","year":"2019","journal-title":"Prostag.\nOther Lipid Mediat."},{"key":"2026081413082006000_cit3","doi-asserted-by":"publisher","first-page":"352","DOI":"10.1111\/imm.12441","article-title":"Endocannabinoid signalling in innate\nand adaptive immunity","volume":"144","author":"Chiurchiu\u0300","year":"2015","journal-title":"Immunology"},{"key":"2026081413082006000_cit4","doi-asserted-by":"publisher","first-page":"1049","DOI":"10.1189\/jlb.3ru0115-021r","article-title":"Regulation of inflammation\nby cannabinoids, the endocannabinoids 2-arachidonoyl-glycerol and\narachidonoyl-ethanolamide, and their metabolites","volume":"97","author":"Turcotte","year":"2015","journal-title":"J. Leukoc. Biol."},{"key":"2026081413082006000_cit5","doi-asserted-by":"publisher","first-page":"284","DOI":"10.1016\/j.tips.2014.03.001","article-title":"COX-2-derived endocannabinoid\nmetabolites as novel\ninflammatory mediators","volume":"35","author":"Alhouayek","year":"2014","journal-title":"Trends Pharmacol."},{"key":"2026081413082006000_cit6","doi-asserted-by":"publisher","first-page":"1668","DOI":"10.1016\/j.cell.2015.05.045","article-title":"A Global Map of Lipid-Binding\nProteins and Their Ligandability in\nCells","volume":"161","author":"Niphakis","year":"2015","journal-title":"Cell"},{"key":"2026081413082006000_cit7","doi-asserted-by":"publisher","first-page":"588","DOI":"10.1124\/pr.110.003004","article-title":"International Union\nof Basic and Clinical Pharmacology. LXXIX. 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Sci."},{"key":"2026081413082006000_cit37","doi-asserted-by":"publisher","first-page":"280","DOI":"10.3390\/antiox9040280","article-title":"The Role of\nHydrogen Peroxide and Peroxiredoxins throughout\nthe Cell Cycle","volume":"9","author":"Heo","year":"2020","journal-title":"Antioxidants"},{"key":"2026081413082006000_cit38","doi-asserted-by":"publisher","first-page":"60","DOI":"10.14348\/molcells.2016.2341","article-title":"Multiple Roles\nof Peroxiredoxins in Inflammation","volume":"39","author":"Knoops","year":"2016","journal-title":"Mol. 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